A Study of Comparative Chemical and Biological Activities of Alkylating Agents<sup>1</sup>

Bardos, Thomas J.; Datta-Gupta, N.; Hebborn, P.; Triggle, David J.

doi:10.1021/jm00326a006

Cited by 117 publications

(59 citation statements)

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“…The cytotoxicity of the new ureas (12a,b-22a,b) was determined in vitro against six cancer cell lines, namely, murine melanoma (B16), human colon adenocarcinoma (HT29), human chronic myelogenous leukemia (K-562), murine lymphocytotic leukemia (L1210), human estrogen-sensitive breast adenocarcinoma (MCF-7), and human bladder carcinoma (T24). The parent ureas from the first generation (23)(24)(25)(26)(27)(28)(29) were also tested as reference compounds. The results, expressed as IC 50 values, are reported in Tables 1 and 2. These data clearly showed an enantio dependence of the cytotoxic activity in the N′-(1-methyl-2-chloro)ethyl series (12a,b, 14a,b, 16a,b, 18a,b, and 20a,b-22a,b), the two isomers invariably differing in their IC 50 values.…”

Section: Resultsmentioning

confidence: 99%

A New Generation of N-Aryl-N‘-(1-alkyl-2-chloroethyl)ureas as Microtubule Disrupters: Synthesis, Antiproliferative Activity, and β-Tubulin Alkylation Kinetics

et al. 2003

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New N-aryl-N'-2-chloroethylureas (CEUs) with enhanced cytotoxicity were developed as antimitotic agents potentially useful in cancer chemotherapy. Highly potent CEUs were obtained by introduction of a branched alkylating chain, the N'-(1-methyl-2-chloro)ethyl group. Their cytotoxic activity was enantio-dependent and induced through specific alkylation of beta-tubulin, leading to microtubule disruption and mitotic arrest. Overall, the structural modifications of the CEUs described here significantly improved their kinetics of beta-tubulin alkylation. In this new series, CEUs 16a and 18a displayed particularly enhanced antiproliferative activity related to a faster reaction with beta-tubulin and merit further investigation as potential antitumor agents.

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Section: Resultsmentioning

confidence: 99%

A New Generation of N-Aryl-N‘-(1-alkyl-2-chloroethyl)ureas as Microtubule Disrupters: Synthesis, Antiproliferative Activity, and β-Tubulin Alkylation Kinetics

et al. 2003

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“…9 ' 15>18 " 21 To 45 ml of a refluxing solution of NBP (Merck p.a.) in 2-butanone 5 ml of a solution of the test compound (in 2-butanone) was added.…”

Section: Reaction With 4-(4-nitrobenzyl)pyridine (Nbp)mentioning

confidence: 99%

Quantitative correlation studies between the acute lethal toxicity of 15 organic halides to the guppy (Poecillah Reticulata) and chemical reactivity towards 4‐nitrobenzylpyridine

Hermens

Busser

Leeuwanch

et al. 1985

Toxicological & Environmental Chemistry

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The acute mortality (14-day LC50) to the guppy (Poecilia reticulata) of reactive organic halides was determined. These compounds were significantly more toxic than the non-reactive organic chemicals with unspecific toxicity. The 14-day LC50 of 15 compounds was correlated with hydrophobicity (P oct ) and a chemical reactivity parameter (reaction rate constants with 4-nitrobenzylpyridine). The quality of the QSAR with chemical reactivity as parameter was much better than of a QSAR with P oct

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“…A modified Bards method 6 ) differing in that 296 acetone solution of cyclohexylamine was used instead of N/IO-potassium hydroxide solution was a pplied to the spectrophotometric analysis of compound IV.…”

Section: Resultsmentioning

confidence: 99%

Study on the Correlation of Chemical Structure and Ovicidal Activities of 2-Bromoethylthiobenzenes

Ishida

Ida

Yamada

1967

Agricultural and Biological Chemistry

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Formation of a sulfonium-like intermediate was assumed in the hydrolysis of the 2-bromoethylthiobenzenes. A linear free energy relationship was found between the hydrolysis rate of a certain substituted 2-bromoethylthiobenzene and the molar fraction of water in the solvent. The effect of the substituent on the rate constant was attributed not only to the activation energy but also to the entropy change of activation. The negative p-value in the formation of the sulfonium-like intermediate in aqueous solution was comparable with that obtained in the p-a-rr analysis for ovicidal activity of the compounds.

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A Study of Comparative Chemical and Biological Activities of Alkylating Agents¹

Cited by 117 publications

References 0 publications

A New Generation of N-Aryl-N‘-(1-alkyl-2-chloroethyl)ureas as Microtubule Disrupters: Synthesis, Antiproliferative Activity, and β-Tubulin Alkylation Kinetics

A New Generation of N-Aryl-N‘-(1-alkyl-2-chloroethyl)ureas as Microtubule Disrupters: Synthesis, Antiproliferative Activity, and β-Tubulin Alkylation Kinetics

Quantitative correlation studies between the acute lethal toxicity of 15 organic halides to the guppy (Poecillah Reticulata) and chemical reactivity towards 4‐nitrobenzylpyridine

Study on the Correlation of Chemical Structure and Ovicidal Activities of 2-Bromoethylthiobenzenes

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A Study of Comparative Chemical and Biological Activities of Alkylating Agents1

Cited by 117 publications

References 0 publications

A New Generation of N-Aryl-N‘-(1-alkyl-2-chloroethyl)ureas as Microtubule Disrupters: Synthesis, Antiproliferative Activity, and β-Tubulin Alkylation Kinetics

A New Generation of N-Aryl-N‘-(1-alkyl-2-chloroethyl)ureas as Microtubule Disrupters: Synthesis, Antiproliferative Activity, and β-Tubulin Alkylation Kinetics

Quantitative correlation studies between the acute lethal toxicity of 15 organic halides to the guppy (Poecillah Reticulata) and chemical reactivity towards 4‐nitrobenzylpyridine

Study on the Correlation of Chemical Structure and Ovicidal Activities of 2-Bromoethylthiobenzenes

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A Study of Comparative Chemical and Biological Activities of Alkylating Agents¹