Compounds > n-((n,n-dimethylamino)ethyl)-5-(n,n-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide
Page last updated: 2024-12-07

n-((n,n-dimethylamino)ethyl)-5-(n,n-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide

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Description

N-((N,N-dimethylamino)ethyl)-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 CID132429
CHEMBL ID45575
MeSH IDM0205035

Synonyms (8)

Synonym
142439-63-2
n-((n,n-dimethylamino)ethyl)-5-(n,n-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide
debcadb
benzamide, 5-(bis(2-chloroethyl)amino)-n-(2-(dimethylamino)ethyl)-2,4-dinitro-
5-(bis(2-chloroethyl)amino)-n-(2-(dimethylamino)ethyl)-2,4-dinitrobenzamide
CHEMBL45575
DTXSID50162041
5-[bis(2-chloroethyl)amino]-n-[2-(dimethylamino)ethyl]-2,4-dinitrobenzamide

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (36)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
AID215294Concentration required to 10% of controls reduce cell survival under 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.
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.
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.
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.
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.
AID200279Aerobic 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.
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.
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.
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.
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.
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.
AID9476Compound was tested for the concentration required to reduce cell survival under hypoxic conditions, using the cell line AA8 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.
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.
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.
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.
AID233557The ratio of C10 values in air and N2 using AA8 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.
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.
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.
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.
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.
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (80.00)18.2507
2000's1 (20.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.40

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 Index12.40 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.20 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.40)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
4-nitroaniline
[no description available]		1.9810nitroanilinebacterial xenobiotic metabolite
aniline mustard
Aniline Mustard: Alkylating anti-neoplastic agent.		1.9810
tretazicar
tretazicar: minor descriptor (75-84); on-line & Index Medicus search AZIRIDINES (75-84)		2.6930
sn 23862
5-(N,N-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide: RN & structure given in first source		3.0950
ConditionIndicatedRelationship StrengthStudiesTrials