Compounds > 4-tert-butyl-(3-(2-chloroethyl)ureido)benzene
Page last updated: 2024-11-08

4-tert-butyl-(3-(2-chloroethyl)ureido)benzene

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Description

4-tert-butyl-(3-(2-chloroethyl)ureido)benzene: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID164059
CHEMBL ID146303
SCHEMBL ID598010
MeSH IDM0223901

Synonyms (18)

Synonym
118202-59-8
1-(4-tert-butylphenyl)-3-(2-chloroethyl)urea
tbceu
CHEMBL146303
AKOS005072690
n-[4-(tert-butyl)phenyl]-n'-(2-chloroethyl)urea
urea,n-(2-chloroethyl)-n'-[4-(1,1-dimethylethyl)phenyl]-
4-tert-butyl-(3-(2-chloroethyl)ureido)benzene
urea, n-(2-chloroethyl)-n'-(4-(1,1-dimethylethyl)phenyl)-
FA-0806
SCHEMBL598010
1-(4-(tert-butyl)phenyl)-3-(2-chloroethyl)urea
J-503212
mfcd00933173
DTXSID70152040
4-t-butyl-[3-(2-chloroethyl)ureido]benzene
1-[4-(tert-butyl)phenyl]-3-(2-chloroethyl)urea
CS-0329412
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (49)

Assay IDTitleYearJournalArticle
AID342589Antiproliferative activity against human MCF7 cells after 48 hrs by sulforhodamine B method2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Selective alkylation of beta(II)-tubulin and thioredoxin-1 by structurally related subsets of aryl chloroethylureas leading to either anti-microtubules or redox modulating agents.
AID101660Dose required to inhibit cell growth was determined against MDA-MB-231 cell line of human non-hormone dependent breast carcinoma2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID331421Effect on thioredoxin-1 nuclear translocation in human M21 cells at 30 uM after 24 hrs by Western blot analysis2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Cycloalkyl-substituted aryl chloroethylureas inhibiting cell cycle progression in G0/G1 phase and thioredoxin-1 nuclear translocation.
AID342492Growth inhibition of human HT29 cells after 48 hrs by sulforhodamine B assay2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Aromatic 2-chloroethyl urea derivatives and bioisosteres. Part 2: Cytocidal activity and effects on the nuclear translocation of thioredoxin-1, and the cell cycle progression.
AID96155In vitro cytotoxic activity required to inhibit human chronic myelogenous leukemia K-562 cell line2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
A new generation of N-aryl-N'-(1-alkyl-2-chloroethyl)ureas as microtubule disrupters: synthesis, antiproliferative activity, and beta-tubulin alkylation kinetics.
AID342590Antiproliferative activity against human M21 cells after 48 hrs by sulforhodamine B method2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Selective alkylation of beta(II)-tubulin and thioredoxin-1 by structurally related subsets of aryl chloroethylureas leading to either anti-microtubules or redox modulating agents.
AID342599Inhibition of nuclear translocation of thioredoxin-1 from cytosol in human M21 cells at 2 times GI50 after 16 hrs by immunocytofluorescence2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Selective alkylation of beta(II)-tubulin and thioredoxin-1 by structurally related subsets of aryl chloroethylureas leading to either anti-microtubules or redox modulating agents.
AID331402Cell cycle arrest in human MCF7 cells assessed as increase in G0/G1 phase accumulation at 25 uM after 16 hrs by FACS analysis2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Cycloalkyl-substituted aryl chloroethylureas inhibiting cell cycle progression in G0/G1 phase and thioredoxin-1 nuclear translocation.
AID232851Alkylating activity by using 4-(4-nitrobenzyl)-pyridine(NBP) colorimetric assay2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID331396Antiproliferative activity against human HT29 cells2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Cycloalkyl-substituted aryl chloroethylureas inhibiting cell cycle progression in G0/G1 phase and thioredoxin-1 nuclear translocation.
AID342503Cell cycle arrest in human MCF7 cells assessed as G2/M phase accumulation at 2 times GI50 after 24 hrs by flow cytometry2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Aromatic 2-chloroethyl urea derivatives and bioisosteres. Part 2: Cytocidal activity and effects on the nuclear translocation of thioredoxin-1, and the cell cycle progression.
AID288696Growth inhibition of human MCF7 cells after 48 hrs2007Bioorganic & medicinal chemistry, Jul-01, Volume: 15, Issue:13
Alkylation potency and protein specificity of aromatic urea derivatives and bioisosteres as potential irreversible antagonists of the colchicine-binding site.
AID342495Inhibition of nuclear translocation of thioredoxin 1 in human M21 cells at 50 uM after 18 hrs by immunocytochemistry2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Aromatic 2-chloroethyl urea derivatives and bioisosteres. Part 2: Cytocidal activity and effects on the nuclear translocation of thioredoxin-1, and the cell cycle progression.
AID102024Dose to inhibit cell growth determined against LoVo cell line of human adenocarcinoma2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID47684Dose required to inhibit cell growth was determined against CHO cell line2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID342494Growth inhibition of human MCF7 cells after 48 hrs by sulforhodamine B assay2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Aromatic 2-chloroethyl urea derivatives and bioisosteres. Part 2: Cytocidal activity and effects on the nuclear translocation of thioredoxin-1, and the cell cycle progression.
AID342493Growth inhibition of human M21 cells after 48 hrs by sulforhodamine B assay2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Aromatic 2-chloroethyl urea derivatives and bioisosteres. Part 2: Cytocidal activity and effects on the nuclear translocation of thioredoxin-1, and the cell cycle progression.
AID232855Glutathione activity was measured after incubation with a conc. of 500 uM2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID75442Glutathione reductase activity was measured after incubation with a conc. of 500 uM2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID331397Antiproliferative activity against human M21 cells2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Cycloalkyl-substituted aryl chloroethylureas inhibiting cell cycle progression in G0/G1 phase and thioredoxin-1 nuclear translocation.
AID45591Cytotoxic activity on colchicine-resistant CHO-VV 3-2 cell line expressing mutated tubulin2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
A new generation of N-aryl-N'-(1-alkyl-2-chloroethyl)ureas as microtubule disrupters: synthesis, antiproliferative activity, and beta-tubulin alkylation kinetics.
AID342497Inhibition of nuclear translocation of thioredoxin 1 in human M21 cells at 10 uM after 18 hrs by immunocytochemistry2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Aromatic 2-chloroethyl urea derivatives and bioisosteres. Part 2: Cytocidal activity and effects on the nuclear translocation of thioredoxin-1, and the cell cycle progression.
AID85435Dose required to inhibit cell growth was determined against HT-29 cell line of human adenocarcinoma2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID84447In vitro cytotoxic activity required to inhibit human colon adenocarcinoma HT-29 cell line2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
A new generation of N-aryl-N'-(1-alkyl-2-chloroethyl)ureas as microtubule disrupters: synthesis, antiproliferative activity, and beta-tubulin alkylation kinetics.
AID208528In vitro cytotoxic activity required to inhibit human bladder carcinoma T24 cell line2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
A new generation of N-aryl-N'-(1-alkyl-2-chloroethyl)ureas as microtubule disrupters: synthesis, antiproliferative activity, and beta-tubulin alkylation kinetics.
AID98729In vitro cytotoxic activity required to inhibit murine lymphocytotic leukemia L1210 cell line2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
A new generation of N-aryl-N'-(1-alkyl-2-chloroethyl)ureas as microtubule disrupters: synthesis, antiproliferative activity, and beta-tubulin alkylation kinetics.
AID342596Induction of beta2-tubulin alkylation in human M21 cells at 2 times GI50 after 48 hrs by Western blot analysis2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Selective alkylation of beta(II)-tubulin and thioredoxin-1 by structurally related subsets of aryl chloroethylureas leading to either anti-microtubules or redox modulating agents.
AID104074In vitro cytotoxic activity required to inhibit human estrogen-sensitive breast adenocarcinoma MCF-7 cell line2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
A new generation of N-aryl-N'-(1-alkyl-2-chloroethyl)ureas as microtubule disrupters: synthesis, antiproliferative activity, and beta-tubulin alkylation kinetics.
AID342501Cell cycle arrest in human MCF7 cells assessed as MG0/G1 phase accumulation at 2 times GI50 after 24 hrs by flow cytometry2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Aromatic 2-chloroethyl urea derivatives and bioisosteres. Part 2: Cytocidal activity and effects on the nuclear translocation of thioredoxin-1, and the cell cycle progression.
AID331420Effect on thioredoxin-1 nuclear translocation in human M21 cells at 25 uM after 24 hrs by Western blot analysis2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Cycloalkyl-substituted aryl chloroethylureas inhibiting cell cycle progression in G0/G1 phase and thioredoxin-1 nuclear translocation.
AID154140Dose required to inhibit cell growth was determined against P388D1 cell line of murine lymphocytotic leukemia2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID94466Dose required to inhibit cell growth was determined against K562 cell line of chronic myelogenous leukemia2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID45590Cytotoxic activity on paclitaxel-resistant CHO-TAX 5-6 cell line expressing mutated tubulin2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
A new generation of N-aryl-N'-(1-alkyl-2-chloroethyl)ureas as microtubule disrupters: synthesis, antiproliferative activity, and beta-tubulin alkylation kinetics.
AID323933Antiproliferative activity against human HT29 cells2008Bioorganic & medicinal chemistry, Feb-15, Volume: 16, Issue:4
A comparative molecular field and comparative molecular similarity indices analyses (CoMFA and CoMSIA) of N-phenyl-N'-(2-chloroethyl)ureas targeting the colchicine-binding site as anticancer agents.
AID342502Cell cycle arrest in human MCF7 cells assessed as S phase accumulation at 2 times GI50 after 24 hrs by flow cytometry2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Aromatic 2-chloroethyl urea derivatives and bioisosteres. Part 2: Cytocidal activity and effects on the nuclear translocation of thioredoxin-1, and the cell cycle progression.
AID342591Antiproliferative activity against human HT29 cells after 48 hrs by sulforhodamine B method2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Selective alkylation of beta(II)-tubulin and thioredoxin-1 by structurally related subsets of aryl chloroethylureas leading to either anti-microtubules or redox modulating agents.
AID342593Cell cycle arrest in human MCF7 cells assessed as accumulation at S phase at 2 times GI50 after 24 hrs by flow cytometry2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Selective alkylation of beta(II)-tubulin and thioredoxin-1 by structurally related subsets of aryl chloroethylureas leading to either anti-microtubules or redox modulating agents.
AID342594Cell cycle arrest in human MCF7 cells assessed as accumulation at G2/M phase at 2 times GI50 after 24 hrs by flow cytometry2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Selective alkylation of beta(II)-tubulin and thioredoxin-1 by structurally related subsets of aryl chloroethylureas leading to either anti-microtubules or redox modulating agents.
AID331405Cell cycle arrest in human MCF7 cells assessed as increase in S phase accumulation at 25 uM after 16 hrs by FACS analysis2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Cycloalkyl-substituted aryl chloroethylureas inhibiting cell cycle progression in G0/G1 phase and thioredoxin-1 nuclear translocation.
AID331408Cell cycle arrest in human MCF7 cells assessed as increase in G2/M phase accumulation at 25 uM after 16 hrs by FACS analysis2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Cycloalkyl-substituted aryl chloroethylureas inhibiting cell cycle progression in G0/G1 phase and thioredoxin-1 nuclear translocation.
AID101796Beta tubulin alkylation activity in MDA-MB-231 cells2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID39124In vitro cytotoxic activity required to inhibit murine melanoma B16 cell line2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
A new generation of N-aryl-N'-(1-alkyl-2-chloroethyl)ureas as microtubule disrupters: synthesis, antiproliferative activity, and beta-tubulin alkylation kinetics.
AID342592Cell cycle arrest in human MCF7 cells assessed as accumulation at G0/G1 phase at 2 times GI50 after 24 hrs by flow cytometry2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Selective alkylation of beta(II)-tubulin and thioredoxin-1 by structurally related subsets of aryl chloroethylureas leading to either anti-microtubules or redox modulating agents.
AID288695Growth inhibition of human M21 cells after 48 hrs2007Bioorganic & medicinal chemistry, Jul-01, Volume: 15, Issue:13
Alkylation potency and protein specificity of aromatic urea derivatives and bioisosteres as potential irreversible antagonists of the colchicine-binding site.
AID96470Dose required to inhibit cell growth was determined against L1210 cell line of murine lymphocytotic leukemia2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID101655DNA damages caused in MDA-MB-231 cells after 2 hr compound exposure to 400 uM concentration2001Journal of medicinal chemistry, Mar-01, Volume: 44, Issue:5
Antimitotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of N-aryl-N'-(2-chloroethyl)ureas as new selective alkylating agents.
AID45411Cytotoxic activity on wild type CHO10001 cell line expressing mutated tubulin2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
A new generation of N-aryl-N'-(1-alkyl-2-chloroethyl)ureas as microtubule disrupters: synthesis, antiproliferative activity, and beta-tubulin alkylation kinetics.
AID288694Growth inhibition of human HT29 cells after 48 hrs2007Bioorganic & medicinal chemistry, Jul-01, Volume: 15, Issue:13
Alkylation potency and protein specificity of aromatic urea derivatives and bioisosteres as potential irreversible antagonists of the colchicine-binding site.
AID331398Antiproliferative activity against human MCF7 cells2008Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12
Cycloalkyl-substituted aryl chloroethylureas inhibiting cell cycle progression in G0/G1 phase and thioredoxin-1 nuclear translocation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (27.27)18.2507
2000's8 (72.73)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: 12.08

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 Index12.08 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.64 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.08)

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%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		2.0310sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
urea
pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.		1.9910isourea;
monocarboxylic acid amide;
one-carbon compound		Daphnia magna metabolite;
Escherichia coli metabolite;
fertilizer;
flour treatment agent;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
carmustine
Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.		210N-nitrosoureas;
organochlorine compound		alkylating agent;
antineoplastic agent
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.		210aromatic amine;
monocarboxylic acid;
nitrogen mustard;
organochlorine compound;
tertiary amino compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent
colchicine
(S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.		2.9540alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen
vinblastine
[no description available]		2.4420
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.9540taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
1,2-distearoyllecithin
[no description available]		1.9910
1-methylpropyl-2-imidazolyl disulfide
1-methylpropyl-2-imidazolyl disulfide: a thioredoxin inhibitor with antineoplastic activity		2.4420imidazoles
vinblastine sulfate
[no description available]		2.0410
ceu 98
[no description available]		3.4170
phosphatidylcholines
Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.		1.99101,2-diacyl-sn-glycero-3-phosphocholine
ConditionIndicatedRelationship StrengthStudiesTrials