Compounds > sn 23862
Page last updated: 2024-12-07

sn 23862

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Description

5-(N,N-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide: RN & structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID126690
CHEMBL ID281812
SCHEMBL ID2364159
MeSH IDM0205033

Synonyms (27)

Synonym
nsc-646392
nsc646392
5-[bis-2(chloro-ethyl)-amino]-2,4-dintro-benzamide
DB03228
CHEMBL281812 ,
sn-23862
5-[bis(2-chloroethyl)amino]-2,4-dinitrobenzamide
5-[bis-(2-chloro-ethyl)-amino]-2,4-dinitro-benzamide
5-(bis(2-chloroethyl)amino)-2,4-dinitrobenzamide
bdbm50004694
5-(n,n-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide
142439-61-0
eb8r4me372 ,
sn 23862
benzamide, 5-(bis(2-chloroethyl)amino-2,4-dinitro-
unii-eb8r4me372
benzamide,5-[bis(2-chloroethyl)amino]-2,4-dinitro-
DQMALWRRERBILB-UHFFFAOYSA-N
5-[n,n-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide
SCHEMBL2364159
DTXSID90162040
sn23862
5-(n, n-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide
benzamide, 5-(bis(2-chloroethyl)amino)-2,4-dinitro-
5-(bis-2(chloro-ethyl)-amino)-2,4-dintro-benzamide
Q27094157
PD007319

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" -450 mV by cyclic voltammetry) and were more toxic to hypoxic than aerobic UV4 cells."( Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells.
Cliffe, S; Denny, WA; Palmer, BD; Wilson, WR, 1992)		0.28
" Importantly, there was a highly significant linear relationship between cytotoxic potency and alkylating reactivity in both the aziridine and the mustard series, with the notable exception of 4, the 4-hydroxylamine of 1, which was 300-fold more toxic than predicted by this relationship."( Effect of nitroreduction on the alkylating reactivity and cytotoxicity of the 2,4-dinitrobenzamide-5-aziridine CB 1954 and the corresponding nitrogen mustard SN 23862: distinct mechanisms of bioreductive activation.
Denny, WA; Helsby, NA; Palmer, BD; Pruijn, FB; Wheeler, SJ; Wilson, WR; Yang, S, 2003)		0.52
" The metabolites that obtained from the reduction of nitro benzamide prodrugs (1-4) by Ssap-NtrB, showed differential cytotoxic effects, with none toxic for HUVEC cells, moderate toxic for Hep3B cells, but highly toxic for PC3 cells."( Prodrugs for Nitroreductase Based Cancer Therapy- 1: Metabolite Profile, Cell Cytotoxicity and Molecular Modeling Interactions of Nitro Benzamides with Ssap-NtrB.
Ay, M; Celik, A; Gungor, T; Kockar, F; Onder, FC; Tok, TT; Tokay, E; Yetis, G, 2018)		0.48
"Amongst all metabolites of prodrugs after Ssap-NtrB reduction, N-(2,4- dinitrophenyl)-4-nitrobenzamide (3) was efficient and toxic in PC3 cells as comparable as CB1954."( Prodrugs for Nitroreductase Based Cancer Therapy- 1: Metabolite Profile, Cell Cytotoxicity and Molecular Modeling Interactions of Nitro Benzamides with Ssap-NtrB.
Ay, M; Celik, A; Gungor, T; Kockar, F; Onder, FC; Tok, TT; Tokay, E; Yetis, G, 2018)		0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Putative nitroreductaseStaphylococcus saprophyticus subsp. saprophyticus ATCC 15305 = NCTC 7292Ki7.28005.96006.62007.2800AID1581901
Nitroreductase AEscherichia coli O157:H7IC50 (µMol)15.00000.89000.89000.8900AID208704
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (1)

Processvia Protein(s)Taxonomy
2,4,6-trinitrotoluene catabolic processOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
2,4,6-trinitrotoluene catabolic processOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
NAD(P)H dehydrogenase (quinone) activityOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
6,7-dihydropteridine reductase activityOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
FMN bindingOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
oxidoreductase activityOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
identical protein bindingOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
protein homodimerization activityOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
oxidoreductase activity, acting on other nitrogenous compounds as donors, with NAD or NADP as acceptorOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
cytosolOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
membraneOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
cytosolOxygen-insensitive NAD(P)H nitroreductaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (74)

Assay IDTitleYearJournalArticle
AID215296Aerobic cytotoxic activity was evaluated by the growth inhibition of UV4 aerobic cells1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis and hypoxia-selective cytotoxicity of a 2-nitroimidazole mustard.
AID1595314Substrate activity at Escherichia coli nitroreductase nfsB assessed as Kcat using NADH as cofactor at 0 to 800 mM in Tris-Cl buffer at pH 7.5 by spectrophotometric method2019European journal of medicinal chemistry, Jun-01, Volume: 171PRODRUGS FOR NITROREDUCTASE BASED CANCER THERAPY- 2: Novel amide/Ntr combinations targeting PC3 cancer cells.
AID1595315Substrate activity at Escherichia coli nitroreductase nfsB assessed as Km using NADH as cofactor in Tris-Cl buffer at pH 7.5 by spectrophotometric method2019European journal of medicinal chemistry, Jun-01, Volume: 171PRODRUGS FOR NITROREDUCTASE BASED CANCER THERAPY- 2: Novel amide/Ntr combinations targeting PC3 cancer cells.
AID280589Selectivity ratio of IC50 for WiDr NTR-ve cells to IC50 for WiDr NTRneo cells2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID280592Selectivity ratio of IC50 for Skov3 NTR-ve cells to IC50 for Skov3 NTRneo cells2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID208701TE50 is termed as Bystander effect evaluated in T78-1 and T79-A3 cell lines1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
Mustard prodrugs for activation by Escherichia coli nitroreductase in gene-directed enzyme prodrug therapy.
AID280579Stability in alpha MEM at 37 degC after 24 hrs2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID715661Prodrug conversion in Tris-HCl buffer assessed as Staphylococcus saprophyticus ATCC 15305 Ssap-NtrB-mediated reduction by steady state kinetics analysis2012Bioorganic & medicinal chemistry, Jun-01, Volume: 20, Issue:11
An unusually cold active nitroreductase for prodrug activations.
AID280578Solubility in alpha MEM2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID228298CT10 ratio defined as ratio of CT10 (air) to that of CT10 (nitrogen))1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells.
AID9640Compound was tested for aerobic growth inhibition against AA8 cells after 4 hr of exposure1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 14. Synthesis and hypoxic cell cytotoxicity of regioisomers of the hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID280594Clonogenic survival of 97% V79 NTRoua cells in co-cultures with 3% V79 NTRpuro cells after 5 hrs by MCL assay2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID227233Tested for hypersensitivity factor which is the ratio of cytotoxicities against drug induced hypoxic UV4 cells and chinese hamster ovary fibroblast line AA81994Journal of medicinal chemistry, Jul-08, Volume: 37, Issue:14
Hypoxia-selective antitumor agents. 9. Structure-activity relationships for hypoxia-selective cytotoxicity among analogues of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID67622Potency in clonogenic assay defined by Hypersensitivity factor calculated for AA8 cells versus EMT6 cells [IC50(AA8)/IC50 (EMT6)]1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 14. Synthesis and hypoxic cell cytotoxicity of regioisomers of the hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID280598Toxicity in ip dosed CD1 nude mouse in DMA/PEG2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID1595319Substrate activity at Staphylococcus saprophyticus nitroreductase assessed as ratio of Kcat/Km using NADPH as cofactor in presence of Tris-Cl buffer at pH 7.5 by spectrophotometric method2019European journal of medicinal chemistry, Jun-01, Volume: 171PRODRUGS FOR NITROREDUCTASE BASED CANCER THERAPY- 2: Novel amide/Ntr combinations targeting PC3 cancer cells.
AID280623Antitumor activity against human 100% WiDr NTRneo tumor cells injected in CD1 nude mouse assessed as growth delay at 200 umol/kg, ip in DMA/PEG2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID215298Compound was tested for the concentration required to reduce cell survival under hypoxic conditions, using the cell line UV4 in the clonogenic assay.1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 14. Synthesis and hypoxic cell cytotoxicity of regioisomers of the hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID280586Selectivity ratio of IC50 for EMT6 NTR-ve cells to IC50 forEMT6 NTRpuro cells2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID1581871Substrate activity at Escherichia coli nitroreductase nfsB assessed as Kcat upto 1 mM using NADH as cofactor in sodium phosphate buffer at pH 7.5 incubated for 5 mins by RP-HPLC2020European journal of medicinal chemistry, Feb-01, Volume: 187Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer.
AID9839Growth inhibition of aerobic chinese hamster ovary fibroblast AA8 cell line using an exposure time of 18 hours1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells.
AID233558The ratio of C10 values in air and N2 using UV4 cell line.1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 14. Synthesis and hypoxic cell cytotoxicity of regioisomers of the hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID1595317Substrate activity at Staphylococcus saprophyticus nitroreductase assessed as Kcat using NADPH as cofactor in presence of Tris-Cl buffer at pH 7.5 by spectrophotometric method2019European journal of medicinal chemistry, Jun-01, Volume: 171PRODRUGS FOR NITROREDUCTASE BASED CANCER THERAPY- 2: Novel amide/Ntr combinations targeting PC3 cancer cells.
AID715662Prodrug conversion in Tris-HCl buffer assessed as Staphylococcus saprophyticus ATCC 15305 Ssap-NtrB-mediated reduction after 30 mins by HPLC analysis2012Bioorganic & medicinal chemistry, Jun-01, Volume: 20, Issue:11
An unusually cold active nitroreductase for prodrug activations.
AID1595320Substrate activity at Escherichia coli nitroreductase nfsB assessed as ratio of Kcat/Km up to 80 mM using NADH as cofactor relative to CB1954/NfsB2019European journal of medicinal chemistry, Jun-01, Volume: 171PRODRUGS FOR NITROREDUCTASE BASED CANCER THERAPY- 2: Novel amide/Ntr combinations targeting PC3 cancer cells.
AID715667Activity of Staphylococcus saprophyticus ATCC 15305 Ssap-NtrB assessed as residual activity measured for 10 mins at 15 degC by spectrophotometric analysis2012Bioorganic & medicinal chemistry, Jun-01, Volume: 20, Issue:11
An unusually cold active nitroreductase for prodrug activations.
AID1581893Substrate activity at Staphylococcus saprophyticus nitroreductase NtrB assessed as ratio of Kcat/Km using NADPH as cofactor in Tris-Cl buffer at pH 7.5 incubated for 30 mins by HPLC analysis relative to CB1954/NfsB2020European journal of medicinal chemistry, Feb-01, Volume: 187Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer.
AID215462Hypoxic selectivity was measured as product of concentration and exposure time needed to reduce cell survival to 10% of control using UV4 cells at 10e6 /mL in the clonogenic assay1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells.
AID280583Selectivity ratio of IC50 for V79 NTR-ve cells to IC50 for V79 NTRpuro cells2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID280580Partition coefficient at pH 7.4 by shake-flask method2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID228299The ratio of the cytotoxicities against UV4 cell line in the air and N2 was measured using clonogenic assay1994Journal of medicinal chemistry, Jul-08, Volume: 37, Issue:14
Hypoxia-selective antitumor agents. 9. Structure-activity relationships for hypoxia-selective cytotoxicity among analogues of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID280615Antitumor activity against mixed human 10% WiDr NTRneo/ 90% WiDr tumor cells injected in CD1 nude mouse assessed as growth delay at 200 umol/kg, ip in DMA/PEG2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID147403Catalytic constant determined to activate by FMN-dependent nitroreductase enzyme from Escherichia coli B (NTR)2000Journal of medicinal chemistry, Oct-05, Volume: 43, Issue:20
Crystal structure of FMN-dependent nitroreductase from Escherichia coli B: a prodrug-activating enzyme.
AID1595318Substrate activity at Staphylococcus saprophyticus nitroreductase assessed as Km using NADPH as cofactor in presence of Tris-Cl buffer at pH 7.5 by spectrophotometric method2019European journal of medicinal chemistry, Jun-01, Volume: 171PRODRUGS FOR NITROREDUCTASE BASED CANCER THERAPY- 2: Novel amide/Ntr combinations targeting PC3 cancer cells.
AID9489Inhibition of growth under aerobic conditions in AA8 cells1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 14. Synthesis and hypoxic cell cytotoxicity of regioisomers of the hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID1581879Substrate activity at Escherichia coli nitroreductase nfsB assessed as Km upto 1 mM using NADH as cofactor in sodium phosphate buffer at pH 7.5 incubated for 5 mins by RP-HPLC2020European journal of medicinal chemistry, Feb-01, Volume: 187Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer.
AID229968IC50 ratio for NR-positive and NR-negative cell lines1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
Mustard prodrugs for activation by Escherichia coli nitroreductase in gene-directed enzyme prodrug therapy.
AID226470Hypersensitivity factor was defined as the ratio of IC50(AA8) to IC50(UV4)1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells.
AID280585Antiproliferative activity against mouse EMT6 NTRpuro cells after 18 hrs2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID215305Cytotoxicity in a growth inhibition assay against aerobic cultures of UV4 cells was determined1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID9486Aerobic cytotoxicity was assessed in a growth inhibition assay using log phase cultures of the chinese hamster ovary fibroblast line AA81994Journal of medicinal chemistry, Jul-08, Volume: 37, Issue:14
Hypoxia-selective antitumor agents. 9. Structure-activity relationships for hypoxia-selective cytotoxicity among analogues of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID715477Ratio of apparent Kcat to apparent Km for Staphylococcus saprophyticus ATCC 15305 Ssap-NtrB-mediated reduction by steady state kinetics analysis2012Bioorganic & medicinal chemistry, Jun-01, Volume: 20, Issue:11
An unusually cold active nitroreductase for prodrug activations.
AID715464Activity of Staphylococcus saprophyticus ATCC 15305 Ssap-NtrB assessed as residual activity measured for 10 mins at 3 degC by spectrophotometric analysis2012Bioorganic & medicinal chemistry, Jun-01, Volume: 20, Issue:11
An unusually cold active nitroreductase for prodrug activations.
AID1581885Substrate activity at Escherichia coli nitroreductase nfsB assessed as ratio of Kcat/Km upto 1 mM using NADH as cofactor in sodium phosphate buffer at pH 7.5 incubated for 5 mins by RP-HPLC2020European journal of medicinal chemistry, Feb-01, Volume: 187Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer.
AID215299Tested for the product of drug concentration and exposure time required to reduce UV4 cell survival under hypoxic condition by clonogenic assay1994Journal of medicinal chemistry, Jul-08, Volume: 37, Issue:14
Hypoxia-selective antitumor agents. 9. Structure-activity relationships for hypoxia-selective cytotoxicity among analogues of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID9679Aerobic cytotoxic activity was evaluated by the growth inhibition of AA8 (chinese hamster) aerobic cells1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis and hypoxia-selective cytotoxicity of a 2-nitroimidazole mustard.
AID1581901Binding affinity to Staphylococcus saprophyticus nitroreductase NtrB2020European journal of medicinal chemistry, Feb-01, Volume: 187Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer.
AID280599Clonogenic survival of V79 NTRoua cells after 5 hrs by MCL assay2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID21950Solubility (alpha-MEM culture medium, containing 5% fetal calf serum)1994Journal of medicinal chemistry, Jul-08, Volume: 37, Issue:14
Hypoxia-selective antitumor agents. 9. Structure-activity relationships for hypoxia-selective cytotoxicity among analogues of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID280601Antitumor activity against mixed mouse EMT6/EMT6 NTRpuro cells injected in CD1 nude mouse assessed as cell kill at 200 umol/kg, ip in DMA/PEG after 18 hrs2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID280584Antiproliferative activity against mouse wild type EMT6 NTR-ve cells after 18 hrs2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID208702Cytotoxicity in T78-1 (NR-negative) cell lines1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
Mustard prodrugs for activation by Escherichia coli nitroreductase in gene-directed enzyme prodrug therapy.
AID280587Antiproliferative activity against human wild type WiDr NTR-ve cells after 18 hrs2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID715470Prodrug conversion in sodium phosphate buffer using NAD(P)H as cofactor assessed as Bacillus amyloliquefaciens CAMR 0454 ywrO-mediated reduction by steady state kinetics analysis2012Bioorganic & medicinal chemistry, Jun-01, Volume: 20, Issue:11
An unusually cold active nitroreductase for prodrug activations.
AID208704Cytotoxicity in T79-A3 (NR-positive) cell lines1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
Mustard prodrugs for activation by Escherichia coli nitroreductase in gene-directed enzyme prodrug therapy.
AID1581878Substrate activity at Staphylococcus saprophyticus nitroreductase NtrB assessed as Km using NADPH as cofactor in Tris-Cl buffer at pH 7.5 incubated for 30 mins by HPLC analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer.
AID200280Aerobic cytotoxic activity was evaluated by the growth inhibition of SKOV (human ovarian cancer line) aerobic cells1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis and hypoxia-selective cytotoxicity of a 2-nitroimidazole mustard.
AID1581872Substrate activity at Staphylococcus saprophyticus nitroreductase NtrB assessed as Kcat using NADPH as cofactor in Tris-Cl buffer at pH 7.5 incubated for 30 mins by HPLC analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer.
AID215468Growth inhibition of aerobic chinese hamster ovary fibroblast UV4 cells using an exposure time of 18 hours1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells.
AID280581Antiproliferative activity against chinese hamster wild-type V79 NTR-ve cells after 18 hrs2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID227212Ratio of the cytotoxicities against drug induced aerobic Walker cells and chinese hamster ovary fibroblast line AA81994Journal of medicinal chemistry, Jul-08, Volume: 37, Issue:14
Hypoxia-selective antitumor agents. 9. Structure-activity relationships for hypoxia-selective cytotoxicity among analogues of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID280582Antiproliferative activity against chinese hamster V79 NTRpuro cells after 18 hrs2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID280593Clonogenic survival of 3% V79 NTRpuro cells in co-cultures with 97% V79 NTRoua after 5 hrs by MCL assay2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID1581892Substrate activity at Escherichia coli nitroreductase nfsB assessed as ratio of Kcat/Km upto 1 mM using NADH as cofactor in sodium phosphate buffer at pH 7.5 incubated for 5 mins by RP-HPLC relative to CB1954/NfsB2020European journal of medicinal chemistry, Feb-01, Volume: 187Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer.
AID1595321Substrate activity at Staphylococcus saprophyticus nitroreductase assessed as ratio of Kcat/Km up to 80 mM using NADH as cofactor relative to CB1954/NfsB2019European journal of medicinal chemistry, Jun-01, Volume: 171PRODRUGS FOR NITROREDUCTASE BASED CANCER THERAPY- 2: Novel amide/Ntr combinations targeting PC3 cancer cells.
AID226469Hypersensitivity factor is the ratio of IC50 against AA8 to that against UV4.1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID1581886Substrate activity at Staphylococcus saprophyticus nitroreductase NtrB assessed as ratio of Kcat/Km using NADPH as cofactor in Tris-Cl buffer at pH 7.5 incubated for 30 mins by HPLC analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer.
AID280591Antiproliferative activity against human Skov3 NTRneo cells after 18 hrs2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID215303Potency in clonogenic assay, defined by hypersensitivity factor calculated for UV4 cells versus AA8 cells [IC50(AA8)/IC50(UV4)]1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 14. Synthesis and hypoxic cell cytotoxicity of regioisomers of the hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID280590Antiproliferative activity against human wild type Skov3 NTR-ve cells after 18 hrs2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID280588Antiproliferative activity against human WiDr NTRneo cells after 18 hrs2007Journal of medicinal chemistry, Mar-22, Volume: 50, Issue:6
Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.
AID9643Cytotoxicity in a growth inhibition assay against aerobic cultures of AA8 cells was determined1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide.
AID215295Concentration required to reduce cell survival tunder hypoxic conditions using the UV4 aerobic cells1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis and hypoxia-selective cytotoxicity of a 2-nitroimidazole mustard.
AID1595316Substrate activity at Escherichia coli nitroreductase nfsB assessed as ratio of Kcat/Km using NADH as cofactor in Tris-Cl buffer at pH 7.5 by spectrophotometric method2019European journal of medicinal chemistry, Jun-01, Volume: 171PRODRUGS FOR NITROREDUCTASE BASED CANCER THERAPY- 2: Novel amide/Ntr combinations targeting PC3 cancer cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's9 (45.00)18.2507
2000's7 (35.00)29.6817
2010's3 (15.00)24.3611
2020's1 (5.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.31

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.31 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index4.35 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.31)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
xanthenes
Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.		2.3920xanthene
4-nitroaniline
[no description available]		1.9810nitroanilinebacterial xenobiotic metabolite
azomycin
azomycin: RN given refers to parent cpd with specified locant; structure		1.9910C-nitro compound;
imidazoles		antitubercular agent
aniline mustard
Aniline Mustard: Alkylating anti-neoplastic agent.		4.08150
flavone acetic acid
flavone acetic acid: structure given in first source		6.9810
tretazicar
tretazicar: minor descriptor (75-84); on-line & Index Medicus search AZIRIDINES (75-84)		4.1150
vadimezan
vadimezan : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 5,6-dimethyl-9-oxoxanthen-4-yl group.		2.3920monocarboxylic acid;
xanthones		antineoplastic agent
n-((n,n-dimethylamino)ethyl)-5-(n,n-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide
N-((N,N-dimethylamino)ethyl)-5-(N,N-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide: RN & structure given in first source		3.0950
nitrofurazone
Nitrofurazone: A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial WOUNDS AND INJURIES and skin infections. Nitrofurazone has also been administered orally in the treatment of TRYPANOSOMIASIS.. nitrofurazone : A semicarbazone resulting from the formal condensation of semicarbazide with 5-nitrofuraldehyde. A broad spectrum antibacterial drug, although with little activity against Pseudomonas species, it is used as a local application for burns, ulcers, wounds and skin infections.		2.0710
pr-104a
PR-104A: 3,5-dinitrobenzamide nitrogen mustard, an alkyating antineoplastic; PR-104A is the corresponding alcohol of PR104		2.6320
dicumarol
Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.		2.0110hydroxycoumarinanticoagulant;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
Hsp90 inhibitor;
vitamin K antagonist
flavin mononucleotide
Flavin Mononucleotide: A coenzyme for a number of oxidative enzymes including NADH DEHYDROGENASE. It is the principal form in which RIBOFLAVIN is found in cells and tissues.		2.4420
tirapazamine
Tirapazamine: A triazine derivative that introduces breaks into DNA strands in hypoxic cells, sensitizing tumor cells to the cytotoxic activity of other drugs and radiation.. tirapazamine : A member of the class of benzotriazines that is 1,2,4-benzotriazine carrying an amino substituent at position 3 and two oxido substituents at positions 1 and 4.		1.9810aromatic amine;
benzotriazines;
N-oxide		antibacterial agent;
antineoplastic agent;
apoptosis inducer
ConditionIndicatedRelationship StrengthStudiesTrials
Anoxemia
[description not available]		01.9810
Hypoxia
Sub-optimal OXYGEN levels in the ambient air of living organisms.		01.9810
Cancer of Prostate
[description not available]		02.2510
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.2510
Benign Neoplasms
[description not available]		02.6930
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.6930
Experimental Mammary Neoplasms
[description not available]		01.9810
Experimental Neoplasms
[description not available]		0210