4-n-bis(2-chloroethyl)aminobenzoic acid

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Description

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

Cross-References

ID Source	ID
PubMed CID	14356
CHEMBL ID	12293
SCHEMBL ID	766052
MeSH ID	M0163591

Synonyms (24)

Synonym
benzoic acid, p-[bis(2-chloroethyl)amino]-
nsc-26276
4-[bis(2-chloroethyl)amino]benzoic acid
wln: qvr dn2g2g
benzoic acid, 4-[bis(2-chloroethyl)amino]-
nsc26276
1141-37-3
benzoic acid nitrogen mustard
benzoic acid, p-(bis(2-chloroethyl)amino)-
brn 0988858
4-n-bis(2-chloroethyl)aminobenzoic acid
nsc 26276
4-(bis(2-chloroethyl)amino)benzoic acid
benzoic acid, 4-(bis(2-chloroethyl)amino)-
p-n,n-bis(2-chloroethyl)aminobenzoic acid
CHEMBL12293
kd3azx3r33 ,
unii-kd3azx3r33
4-[bis-(2-chloroethyl)amino] benzoic acid
SCHEMBL766052
DTXSID40150654
4-[bis(2-chloroethyl)amino] benzoic acid
p-(bis(2-chloroethyl)amino)benzoic acid
4-[bis-(2-chloroethyl)amino]benzoic acid

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

Bioassays (37)

Assay ID	Title	Year	Journal	Article
AID1132020	Antitumor activity against rat Walker 256 cells allografted in rat	1978	Journal of medicinal chemistry, Jan, Volume: 21, Issue:1	Structure-activity relationships in antitumor aniline mustards.
AID1421496	Cytotoxicity against human LO2 cells assessed as decrease in cell viability after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Oct-05, Volume: 158	Synthesis of scutellarein derivatives with antiproliferative activity and selectivity through the intrinsic pathway.
AID1383599	Selectivity index, ratio of IC50 for human LO2 cells to IC50 for human Bel7402 cells	2018	European journal of medicinal chemistry, Apr-25, Volume: 150	Novel hybrids of brefeldin A and nitrogen mustards with improved antiproliferative selectivity: Design, synthesis and antitumor biological evaluation.
AID1421495	Antiproliferative activity against human Bel7402 cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Oct-05, Volume: 158	Synthesis of scutellarein derivatives with antiproliferative activity and selectivity through the intrinsic pathway.
AID24282	Chemical half-life in percholate at 37 degree was determined	1994	Journal of medicinal chemistry, Jul-22, Volume: 37, Issue:15	Novel prodrugs of alkylating agents derived from 2-fluoro- and 3-fluorobenzoic acids for antibody-directed enzyme prodrug therapy.
AID1393842	Antiproliferative activity against human HL60 cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Feb-25, Volume: 146	Novel enmein-type diterpenoid hybrids coupled with nitrogen mustards: Synthesis of promising candidates for anticancer therapeutics.
AID1777556	Antiproliferative activity against human MCF7 cells assessed as inhibition of cell proliferation measured after 72 hrs by CCK-8 assay	2021	Bioorganic & medicinal chemistry, 09-01, Volume: 45	Design and synthesis of β-carboline derivatives with nitrogen mustard moieties against breast cancer.
AID1421494	Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Oct-05, Volume: 158	Synthesis of scutellarein derivatives with antiproliferative activity and selectivity through the intrinsic pathway.
AID1465329	Antiproliferative activity against human PC3 cells treated for 24 hrs measured after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22	Design and synthesis of novel nitrogen mustard-evodiamine hybrids with selective antiproliferative activity.
AID1777558	Cytotoxicity against human MCF-10A cells assessed as inhibition of cell proliferation measured after 72 hrs by CCK-8 assay	2021	Bioorganic & medicinal chemistry, 09-01, Volume: 45	Design and synthesis of β-carboline derivatives with nitrogen mustard moieties against breast cancer.
AID1777557	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition of cell proliferation measured after 72 hrs by CCK-8 assay	2021	Bioorganic & medicinal chemistry, 09-01, Volume: 45	Design and synthesis of β-carboline derivatives with nitrogen mustard moieties against breast cancer.
AID1393843	Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Feb-25, Volume: 146	Novel enmein-type diterpenoid hybrids coupled with nitrogen mustards: Synthesis of promising candidates for anticancer therapeutics.
AID102183	Inhibitory concentration was evaluated against colorectal tumar cell line LoVo	1996	Journal of medicinal chemistry, Mar-01, Volume: 39, Issue:5	New mustard prodrugs for antibody-directed enzyme prodrug therapy: alternatives to the amide link.
AID1185080	Antiproliferative activity against human MCF7 cells assessed as growth inhibition after 72 hrs by MTT assay	2014	ACS medicinal chemistry letters, Jul-10, Volume: 5, Issue:7	Novel hybrids of natural oridonin-bearing nitrogen mustards as potential anticancer drug candidates.
AID1465331	Antiproliferative activity against human THP1 cells treated for 24 hrs measured after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22	Design and synthesis of novel nitrogen mustard-evodiamine hybrids with selective antiproliferative activity.
AID1185082	Antiproliferative activity against human MGC803 cells assessed as growth inhibition after 72 hrs by MTT assay	2014	ACS medicinal chemistry letters, Jul-10, Volume: 5, Issue:7	Novel hybrids of natural oridonin-bearing nitrogen mustards as potential anticancer drug candidates.
AID91909	The compound was tested for cytotoxicity against human JAR, choriocarcinoma cell line.	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Novel prodrugs which are activated to cytotoxic alkylating agents by carboxypeptidase G2.
AID1383594	Antiproliferative activity against human HL60 cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Apr-25, Volume: 150	Novel hybrids of brefeldin A and nitrogen mustards with improved antiproliferative selectivity: Design, synthesis and antitumor biological evaluation.
AID1185079	Antiproliferative activity against human K562 cells assessed as growth inhibition after 72 hrs by MTT assay	2014	ACS medicinal chemistry letters, Jul-10, Volume: 5, Issue:7	Novel hybrids of natural oridonin-bearing nitrogen mustards as potential anticancer drug candidates.
AID1393846	Antiproliferative activity against human LO2 cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Feb-25, Volume: 146	Novel enmein-type diterpenoid hybrids coupled with nitrogen mustards: Synthesis of promising candidates for anticancer therapeutics.
AID1185088	Cytotoxicity against human L02 cells by MTT assay	2014	ACS medicinal chemistry letters, Jul-10, Volume: 5, Issue:7	Novel hybrids of natural oridonin-bearing nitrogen mustards as potential anticancer drug candidates.
AID1393847	Selectivity index, ratio of IC50 for human LO2 cells to IC50 for human Bel7402 cells	2018	European journal of medicinal chemistry, Feb-25, Volume: 146	Novel enmein-type diterpenoid hybrids coupled with nitrogen mustards: Synthesis of promising candidates for anticancer therapeutics.
AID101135	The compound was tested for cytotoxicity against human LS174T,colorectal cell line.	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Novel prodrugs which are activated to cytotoxic alkylating agents by carboxypeptidase G2.
AID1383598	Antiproliferative activity against human LO2 cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Apr-25, Volume: 150	Novel hybrids of brefeldin A and nitrogen mustards with improved antiproliferative selectivity: Design, synthesis and antitumor biological evaluation.
AID1465330	Antiproliferative activity against human HepG2 cells treated for 24 hrs measured after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22	Design and synthesis of novel nitrogen mustard-evodiamine hybrids with selective antiproliferative activity.
AID1465332	Antiproliferative activity against human HL60 cells treated for 24 hrs measured after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22	Design and synthesis of novel nitrogen mustard-evodiamine hybrids with selective antiproliferative activity.
AID1383595	Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Apr-25, Volume: 150	Novel hybrids of brefeldin A and nitrogen mustards with improved antiproliferative selectivity: Design, synthesis and antitumor biological evaluation.
AID1185087	Anticancer activity against human Bel7402 cells assessed as growth inhibition by MTT assay	2014	ACS medicinal chemistry letters, Jul-10, Volume: 5, Issue:7	Novel hybrids of natural oridonin-bearing nitrogen mustards as potential anticancer drug candidates.
AID1060756	Antitumor activity against mouse B16F10 cells xenografted in C57BL/6 mouse assessed as reduction of tumor size at 100 ug administered as intratumorally for 3 days	2014	European journal of medicinal chemistry, Jan, Volume: 71	Synthesis and analysis of activity of a potential anti-melanoma prodrug with a hydrazine linker.
AID1393845	Antiproliferative activity against human Bel7402/5-FU cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Feb-25, Volume: 146	Novel enmein-type diterpenoid hybrids coupled with nitrogen mustards: Synthesis of promising candidates for anticancer therapeutics.
AID1383597	Antiproliferative activity against human Bel7402/5-FU cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Apr-25, Volume: 150	Novel hybrids of brefeldin A and nitrogen mustards with improved antiproliferative selectivity: Design, synthesis and antitumor biological evaluation.
AID1421493	Antiproliferative activity against human A549 cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Oct-05, Volume: 158	Synthesis of scutellarein derivatives with antiproliferative activity and selectivity through the intrinsic pathway.
AID1383596	Antiproliferative activity against human Bel7402 cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Apr-25, Volume: 150	Novel hybrids of brefeldin A and nitrogen mustards with improved antiproliferative selectivity: Design, synthesis and antitumor biological evaluation.
AID1465333	Antiproliferative activity against human PBMC treated for 24 hrs measured after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22	Design and synthesis of novel nitrogen mustard-evodiamine hybrids with selective antiproliferative activity.
AID1132021	Toxicity in rat allografted with rat Walker 256 cells	1978	Journal of medicinal chemistry, Jan, Volume: 21, Issue:1	Structure-activity relationships in antitumor aniline mustards.
AID1185081	Antiproliferative activity against human Bel7402 cells assessed as growth inhibition after 72 hrs by MTT assay	2014	ACS medicinal chemistry letters, Jul-10, Volume: 5, Issue:7	Novel hybrids of natural oridonin-bearing nitrogen mustards as potential anticancer drug candidates.
AID1393844	Antiproliferative activity against human Bel7402 cells after 72 hrs by MTT assay	2018	European journal of medicinal chemistry, Feb-25, Volume: 146	Novel enmein-type diterpenoid hybrids coupled with nitrogen mustards: Synthesis of promising candidates for anticancer therapeutics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (15.38)	18.7374
1990's	4 (30.77)	18.2507
2000's	0 (0.00)	29.6817
2010's	6 (46.15)	24.3611
2020's	1 (7.69)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.92

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.

Metric	This Compound (vs All)
Research Demand Index	11.92 (24.57)
Research Supply Index	2.64 (2.92)
Research Growth Index	4.56 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (11.92)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	13 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	2.38	2	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
chlorambucil Chlorambucil: A nitrogen mustard alkylating agent used as antineoplastic for chronic lymphocytic leukemia, Hodgkin's disease, and others. Although it is less toxic than most other nitrogen mustards, it has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (Merck Index, 11th ed). chlorambucil : A monocarboxylic acid that is butanoic acid substituted at position 4 by a 4-[bis(2-chloroethyl)amino]phenyl group. A chemotherapy drug that can be used in combination with the antibody obinutuzumab for the treatment of chronic lymphocytic leukemia.	3.42	7	aromatic amine; monocarboxylic acid; nitrogen mustard; organochlorine compound; tertiary amino compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	3.08	4	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
sarkolysin [no description available]	1.95	1	monocarboxylic acid
4-aminobenzoic acid para-Aminobenzoates: Benzoic acids, salts, or esters that contain an amino group attached to carbon number 4 of the benzene ring structure.. 4-aminobenzoate : An aromatic amino-acid anion that is the conjugate base of 4-aminobenzoic acid.	2.38	2	aminobenzoate; aromatic amino-acid anion	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
chlornaphazin chlornaphazin: structure	1.95	1	naphthalenes
aniline mustard Aniline Mustard: Alkylating anti-neoplastic agent.	1.95	1
phenacid phenacid: RN given refers to parent cpd; structure	2.37	2
hydroxyaniline mustard hydroxyaniline mustard: structure; RN given refers to parent cpd	2.37	2
phenylenediamine mustard phenylenediamine mustard: RN given refers to parent cpd	2.37	2
4-((2-chloroethyl) (2-mesyloxyethyl)amino)benzoic acid 4-((2-chloroethyl) (2-mesyloxyethyl)amino)benzoic acid: structure given in first source	2.39	2
4-((2-chloroethyl)(2-mesyloxyethyl)amino)benzoylglutamic acid 4-((2-chloroethyl)(2-mesyloxyethyl)amino)benzoylglutamic acid: structure in first source	2.39	2
4-n-bis(2-chloroethyl)aminobenzoylglutamic acid 4-N-bis(2-chloroethyl)aminobenzoylglutamic acid: structure given in first source	2.67	3
evodiamine [no description available]	2.15	1	beta-carbolines
scutellarin scutellarin: see scutellarein for aglycone. scutellarin : The glycosyloxyflavone which is the 7-O-glucuronide of scutellarein.	2.17	1	glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antineoplastic agent; proteasome inhibitor
melphalan Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.	2.97	4	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
brefeldin a [no description available]	2.17	1	macrolide antibiotic	Penicillium metabolite
3-hydroxymethyl-beta-carboline 3-hydroxymethyl-beta-carboline: antagonizes anticonvulsant & anxiolytic actions of diazepam at doses which do not elicit overt behavioral effects in mice	2.31	1	beta-carbolines

Condition	Relationship Strength	Studies
Carcinoma 256, Walker A transplantable carcinoma of the rat that originally appeared spontaneously in the mammary gland of a pregnant albino rat, and which now resembles a carcinoma in young transplants and a sarcoma in older transplants. (Stedman, 25th ed)	1.95	1
Leukemia L 1210 [description not available]	1.95	1
Experimental Leukemia [description not available]	1.95	1
Colorectal Cancer [description not available]	1.99	1
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	1.99	1
B16 Melanoma [description not available]	2.1	1
Benign Neoplasms [description not available]	2.17	1
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.	2.17	1
Choriocarcinoma A malignant metastatic form of trophoblastic tumors. Unlike the HYDATIDIFORM MOLE, choriocarcinoma contains no CHORIONIC VILLI but rather sheets of undifferentiated cytotrophoblasts and syncytiotrophoblasts (TROPHOBLASTS). It is characterized by the large amounts of CHORIONIC GONADOTROPIN produced. Tissue origins can be determined by DNA analyses: placental (fetal) origin or non-placental origin (CHORIOCARCINOMA, NON-GESTATIONAL).	1.97	1

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