Design and synthesis of two indol-steroid derivatives

L. Figueroa-Valverde, F. Díaz-Cedillo, E. García-Cervera, E. Pool Gómez, M. Rosas-Nexticapa, M. López-Ramos

Research output: Contribution to journalArticle

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Abstract

In this study two new indol-steroid derivatives were synthesized. The first stage involves the synthesis of 17-(2-amino-thiazol-5-yl)- 10,13-dimethyl-1,2-6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (3) by the reaction of progesterone with thiourea using I2 as catalyst. The second stage was achieved by reaction of a brucine derivative with the compound 3 to form the compound N-(2,3-dimethoxystrychnidin-10-ylenamino)-N'-[10,13-dimethyl-17(2-amino-thiazol-5-yl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17- tetradecahydro-cyclopenta-[a]phenanthren-3-ylidene]-ethane-1,2-diamine using boric acid as catalyst. The third stage was achieved by reaction of compound 3 with brucine to form 10,13-dimethyl-17-[2-(2,3-dimethoxy-strychnidin-10-ylideneamino)-thiazol-5-yl]- 1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-onausing boric acid as catalyst. The structure of compounds obtained was confirmed by spectrometry data.
Original languageAmerican English
Pages (from-to)4959-4962
Number of pages4
JournalAsian Journal of Chemistry
DOIs
StatePublished - 1 Jan 2014

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ethylenediamine
Steroids
Derivatives
Catalysts
Thiourea
Spectrometry
Progesterone
boric acid
brucine

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Figueroa-Valverde, L., Díaz-Cedillo, F., García-Cervera, E., Gómez, E. P., Rosas-Nexticapa, M., & López-Ramos, M. (2014). Design and synthesis of two indol-steroid derivatives. Asian Journal of Chemistry, 4959-4962. https://doi.org/10.14233/ajchem.2014.16268
Figueroa-Valverde, L. ; Díaz-Cedillo, F. ; García-Cervera, E. ; Gómez, E. Pool ; Rosas-Nexticapa, M. ; López-Ramos, M. / Design and synthesis of two indol-steroid derivatives. In: Asian Journal of Chemistry. 2014 ; pp. 4959-4962.
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abstract = "In this study two new indol-steroid derivatives were synthesized. The first stage involves the synthesis of 17-(2-amino-thiazol-5-yl)- 10,13-dimethyl-1,2-6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (3) by the reaction of progesterone with thiourea using I2 as catalyst. The second stage was achieved by reaction of a brucine derivative with the compound 3 to form the compound N-(2,3-dimethoxystrychnidin-10-ylenamino)-N'-[10,13-dimethyl-17(2-amino-thiazol-5-yl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17- tetradecahydro-cyclopenta-[a]phenanthren-3-ylidene]-ethane-1,2-diamine using boric acid as catalyst. The third stage was achieved by reaction of compound 3 with brucine to form 10,13-dimethyl-17-[2-(2,3-dimethoxy-strychnidin-10-ylideneamino)-thiazol-5-yl]- 1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-onausing boric acid as catalyst. The structure of compounds obtained was confirmed by spectrometry data.",
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Figueroa-Valverde, L, Díaz-Cedillo, F, García-Cervera, E, Gómez, EP, Rosas-Nexticapa, M & López-Ramos, M 2014, 'Design and synthesis of two indol-steroid derivatives', Asian Journal of Chemistry, pp. 4959-4962. https://doi.org/10.14233/ajchem.2014.16268

Design and synthesis of two indol-steroid derivatives. / Figueroa-Valverde, L.; Díaz-Cedillo, F.; García-Cervera, E.; Gómez, E. Pool; Rosas-Nexticapa, M.; López-Ramos, M.

In: Asian Journal of Chemistry, 01.01.2014, p. 4959-4962.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Design and synthesis of two indol-steroid derivatives

AU - Figueroa-Valverde, L.

AU - Díaz-Cedillo, F.

AU - García-Cervera, E.

AU - Gómez, E. Pool

AU - Rosas-Nexticapa, M.

AU - López-Ramos, M.

PY - 2014/1/1

Y1 - 2014/1/1

N2 - In this study two new indol-steroid derivatives were synthesized. The first stage involves the synthesis of 17-(2-amino-thiazol-5-yl)- 10,13-dimethyl-1,2-6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (3) by the reaction of progesterone with thiourea using I2 as catalyst. The second stage was achieved by reaction of a brucine derivative with the compound 3 to form the compound N-(2,3-dimethoxystrychnidin-10-ylenamino)-N'-[10,13-dimethyl-17(2-amino-thiazol-5-yl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17- tetradecahydro-cyclopenta-[a]phenanthren-3-ylidene]-ethane-1,2-diamine using boric acid as catalyst. The third stage was achieved by reaction of compound 3 with brucine to form 10,13-dimethyl-17-[2-(2,3-dimethoxy-strychnidin-10-ylideneamino)-thiazol-5-yl]- 1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-onausing boric acid as catalyst. The structure of compounds obtained was confirmed by spectrometry data.

AB - In this study two new indol-steroid derivatives were synthesized. The first stage involves the synthesis of 17-(2-amino-thiazol-5-yl)- 10,13-dimethyl-1,2-6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (3) by the reaction of progesterone with thiourea using I2 as catalyst. The second stage was achieved by reaction of a brucine derivative with the compound 3 to form the compound N-(2,3-dimethoxystrychnidin-10-ylenamino)-N'-[10,13-dimethyl-17(2-amino-thiazol-5-yl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17- tetradecahydro-cyclopenta-[a]phenanthren-3-ylidene]-ethane-1,2-diamine using boric acid as catalyst. The third stage was achieved by reaction of compound 3 with brucine to form 10,13-dimethyl-17-[2-(2,3-dimethoxy-strychnidin-10-ylideneamino)-thiazol-5-yl]- 1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-onausing boric acid as catalyst. The structure of compounds obtained was confirmed by spectrometry data.

U2 - 10.14233/ajchem.2014.16268

DO - 10.14233/ajchem.2014.16268

M3 - Article

SP - 4959

EP - 4962

JO - Asian Journal of Chemistry

JF - Asian Journal of Chemistry

SN - 0970-7077

ER -

Figueroa-Valverde L, Díaz-Cedillo F, García-Cervera E, Gómez EP, Rosas-Nexticapa M, López-Ramos M. Design and synthesis of two indol-steroid derivatives. Asian Journal of Chemistry. 2014 Jan 1;4959-4962. https://doi.org/10.14233/ajchem.2014.16268