Synthesis of 2,4-Disubstituted Thiazoles and Selenazoles as Potential Antifilarial and Antitumor Agents. 2. 2-Arylamido and 2-Alkylamido Derivatives of 2-Amino-4-(isothiocyanatomethyl)thiazole and 2-Amino-4-(isothiocyanatomethyl)selenazole

Yatendra Kumar; Rachel Green; Dean S. Wise; Linda L. Wotring; Leroy B. Townsend

doi:10.1021/jm00076a013

Synthesis of 2,4-Disubstituted Thiazoles and Selenazoles as Potential Antifilarial and Antitumor Agents. 2. 2-Arylamido and 2-Alkylamido Derivatives of 2-Amino-4-(isothiocyanatomethyl)thiazole and 2-Amino-4-(isothiocyanatomethyl)selenazole

Yatendra Kumar, Rachel Green, Dean S. Wise, Linda L. Wotring, Leroy B. Townsend

Research output: Contribution to journal › Article › peer-review

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Abstract

The synthesis of a series of 2-arylamido and 2-alkylamido derivatives of 2-amino-4-(isothiocyanatomethyl)thiazole and 2-amino-4-(isothiocyanatomethyl)selenazole is described. In vitro antiproliferative evaluations were carried out using L1210 cells. The 2-(alkylamido)thiazole derivatives were moderately antiproliferative, with IC₅₀'s of 4–8 µM. A significant increase in activity was obtained for the arylamido derivatives, with IC₅₀'s of 0.2–1 µM. The results obtained for the selenazoles were similar to those for the thiazoles. 2-Benzamido-4-(isothiocyanatomethyl)-thiazole (19) was found to be a potent inhibitor of GMP synthetase. None of the compounds prepared in this study demonstrated antifilarial activity.

Original language	English (US)
Pages (from-to)	3849-3852
Number of pages	4
Journal	Journal of medicinal chemistry
Volume	36
Issue number	24
DOIs	https://doi.org/10.1021/jm00076a013
State	Published - 1993
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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Kumar, Y., Green, R., Wise, D. S., Wotring, L. L., & Townsend, L. B. (1993). Synthesis of 2,4-Disubstituted Thiazoles and Selenazoles as Potential Antifilarial and Antitumor Agents. 2. 2-Arylamido and 2-Alkylamido Derivatives of 2-Amino-4-(isothiocyanatomethyl)thiazole and 2-Amino-4-(isothiocyanatomethyl)selenazole. Journal of medicinal chemistry, 36(24), 3849-3852. https://doi.org/10.1021/jm00076a013

Synthesis of 2,4-Disubstituted Thiazoles and Selenazoles as Potential Antifilarial and Antitumor Agents. 2. 2-Arylamido and 2-Alkylamido Derivatives of 2-Amino-4-(isothiocyanatomethyl)thiazole and 2-Amino-4-(isothiocyanatomethyl)selenazole. / Kumar, Yatendra; Green, Rachel; Wise, Dean S. et al.
In: Journal of medicinal chemistry, Vol. 36, No. 24, 1993, p. 3849-3852.

Research output: Contribution to journal › Article › peer-review

Kumar, Y, Green, R, Wise, DS, Wotring, LL & Townsend, LB 1993, 'Synthesis of 2,4-Disubstituted Thiazoles and Selenazoles as Potential Antifilarial and Antitumor Agents. 2. 2-Arylamido and 2-Alkylamido Derivatives of 2-Amino-4-(isothiocyanatomethyl)thiazole and 2-Amino-4-(isothiocyanatomethyl)selenazole', Journal of medicinal chemistry, vol. 36, no. 24, pp. 3849-3852. https://doi.org/10.1021/jm00076a013

Kumar Y, Green R, Wise DS, Wotring LL, Townsend LB. Synthesis of 2,4-Disubstituted Thiazoles and Selenazoles as Potential Antifilarial and Antitumor Agents. 2. 2-Arylamido and 2-Alkylamido Derivatives of 2-Amino-4-(isothiocyanatomethyl)thiazole and 2-Amino-4-(isothiocyanatomethyl)selenazole. Journal of medicinal chemistry. 1993;36(24):3849-3852. doi: 10.1021/jm00076a013

Kumar, Yatendra ; Green, Rachel ; Wise, Dean S. et al. / Synthesis of 2,4-Disubstituted Thiazoles and Selenazoles as Potential Antifilarial and Antitumor Agents. 2. 2-Arylamido and 2-Alkylamido Derivatives of 2-Amino-4-(isothiocyanatomethyl)thiazole and 2-Amino-4-(isothiocyanatomethyl)selenazole. In: Journal of medicinal chemistry. 1993 ; Vol. 36, No. 24. pp. 3849-3852.

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abstract = "The synthesis of a series of 2-arylamido and 2-alkylamido derivatives of 2-amino-4-(isothiocyanatomethyl)thiazole and 2-amino-4-(isothiocyanatomethyl)selenazole is described. In vitro antiproliferative evaluations were carried out using L1210 cells. The 2-(alkylamido)thiazole derivatives were moderately antiproliferative, with IC50's of 4–8 µM. A significant increase in activity was obtained for the arylamido derivatives, with IC50's of 0.2–1 µM. The results obtained for the selenazoles were similar to those for the thiazoles. 2-Benzamido-4-(isothiocyanatomethyl)-thiazole (19) was found to be a potent inhibitor of GMP synthetase. None of the compounds prepared in this study demonstrated antifilarial activity.",

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AU - Townsend, Leroy B.

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N2 - The synthesis of a series of 2-arylamido and 2-alkylamido derivatives of 2-amino-4-(isothiocyanatomethyl)thiazole and 2-amino-4-(isothiocyanatomethyl)selenazole is described. In vitro antiproliferative evaluations were carried out using L1210 cells. The 2-(alkylamido)thiazole derivatives were moderately antiproliferative, with IC50's of 4–8 µM. A significant increase in activity was obtained for the arylamido derivatives, with IC50's of 0.2–1 µM. The results obtained for the selenazoles were similar to those for the thiazoles. 2-Benzamido-4-(isothiocyanatomethyl)-thiazole (19) was found to be a potent inhibitor of GMP synthetase. None of the compounds prepared in this study demonstrated antifilarial activity.

AB - The synthesis of a series of 2-arylamido and 2-alkylamido derivatives of 2-amino-4-(isothiocyanatomethyl)thiazole and 2-amino-4-(isothiocyanatomethyl)selenazole is described. In vitro antiproliferative evaluations were carried out using L1210 cells. The 2-(alkylamido)thiazole derivatives were moderately antiproliferative, with IC50's of 4–8 µM. A significant increase in activity was obtained for the arylamido derivatives, with IC50's of 0.2–1 µM. The results obtained for the selenazoles were similar to those for the thiazoles. 2-Benzamido-4-(isothiocyanatomethyl)-thiazole (19) was found to be a potent inhibitor of GMP synthetase. None of the compounds prepared in this study demonstrated antifilarial activity.

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Synthesis of 2,4-Disubstituted Thiazoles and Selenazoles as Potential Antifilarial and Antitumor Agents. 2. 2-Arylamido and 2-Alkylamido Derivatives of 2-Amino-4-(isothiocyanatomethyl)thiazole and 2-Amino-4-(isothiocyanatomethyl)selenazole

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