Design and synthesis of an indol derivative as antibacterial agent against Staphylococcus aureus

Hau Heredia Lenin, Figueroa Valverde Lauro, Rosas Nexticapa Marcela, Herrera Meza Socorro, López Ramos Maria, Díaz Cedillo Francisco, García Cervera Elodia, Pool Gómez Eduardo, Paat Estrella Josefa, Cauich Carrillo Regina, Euan Hau Saidy

Research output: Contribution to journalArticle

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Abstract

© 2017, Springer-Verlag Berlin Heidelberg. Several indole derivatives with antibacterial activity have been prepared using different protocols; however, some require special reagents and conditions. The aim of this study involved the synthesis of some indole derivatives using estrone and OTBS-estrone as chemical tools. The synthesis of the indole derivatives involves reactions such as follows: (1) synthesis of two indol derivatives (4 or 5) by reaction of estrone or OTBS-estrone with phenylhydrazine in medium acid; (2) reaction of 4 or 5 with 6-cloro-1-hexyne in medium basic to form two hexynyl-indol (7 or 8); (3) preparation of indol-propargylic alcohol derivatives (10 or 11) by reaction of benzaldehyde with 7 or 8 in medium basic; (4) synthesis of indol-aldehydes (12 or 13) via oxidation of 10 or 11 with DMSO; (5) synthesis of indeno-indol-carbaldehyde (15 or 16) via alkynylation/cyclization of 12 or 13 with hexyne in presence of copper(II); (6) preparation indeno-indol-carbaldehyde complex (19 or 20) via alkynylation/cyclization of 12 or 13 with 1-(hex-5-yn-1-yl)-2-phenyl-1H-imidazole. The antibacterial effect exerted by the indol-steroid derivatives against Streptococcus pneumoniae and Staphylococcus aureus bacteria was evaluated using dilution method and the minimum inhibitory concentration (MIC). The results showed that only the compound 19 inhibit the growth bacterial of S. aureus. In conclusion, these data indicate that antibacterial activity of 19 can be due mainly to functional groups involved in the chemical structure in comparison with the compounds studied.
Original languageAmerican English
Pages (from-to)159-177
Number of pages141
JournalJournal of Chemical Biology
DOIs
StatePublished - 1 Oct 2017

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Estrone
Staphylococcus aureus
Anti-Bacterial Agents
Derivatives
Cyclization
Microbial Sensitivity Tests
Berlin
Dimethyl Sulfoxide
Streptococcus pneumoniae
Aldehydes
Copper
Steroids
Alcohols
Bacteria
Functional groups
Dilution
Acids
Growth
indole
Oxidation

Cite this

Lenin, Hau Heredia ; Lauro, Figueroa Valverde ; Marcela, Rosas Nexticapa ; Socorro, Herrera Meza ; Maria, López Ramos ; Francisco, Díaz Cedillo ; Elodia, García Cervera ; Eduardo, Pool Gómez ; Josefa, Paat Estrella ; Regina, Cauich Carrillo ; Saidy, Euan Hau. / Design and synthesis of an indol derivative as antibacterial agent against Staphylococcus aureus. In: Journal of Chemical Biology. 2017 ; pp. 159-177.
@article{834e56094cf4458f9fe33485092638f5,
title = "Design and synthesis of an indol derivative as antibacterial agent against Staphylococcus aureus",
abstract = "{\circledC} 2017, Springer-Verlag Berlin Heidelberg. Several indole derivatives with antibacterial activity have been prepared using different protocols; however, some require special reagents and conditions. The aim of this study involved the synthesis of some indole derivatives using estrone and OTBS-estrone as chemical tools. The synthesis of the indole derivatives involves reactions such as follows: (1) synthesis of two indol derivatives (4 or 5) by reaction of estrone or OTBS-estrone with phenylhydrazine in medium acid; (2) reaction of 4 or 5 with 6-cloro-1-hexyne in medium basic to form two hexynyl-indol (7 or 8); (3) preparation of indol-propargylic alcohol derivatives (10 or 11) by reaction of benzaldehyde with 7 or 8 in medium basic; (4) synthesis of indol-aldehydes (12 or 13) via oxidation of 10 or 11 with DMSO; (5) synthesis of indeno-indol-carbaldehyde (15 or 16) via alkynylation/cyclization of 12 or 13 with hexyne in presence of copper(II); (6) preparation indeno-indol-carbaldehyde complex (19 or 20) via alkynylation/cyclization of 12 or 13 with 1-(hex-5-yn-1-yl)-2-phenyl-1H-imidazole. The antibacterial effect exerted by the indol-steroid derivatives against Streptococcus pneumoniae and Staphylococcus aureus bacteria was evaluated using dilution method and the minimum inhibitory concentration (MIC). The results showed that only the compound 19 inhibit the growth bacterial of S. aureus. In conclusion, these data indicate that antibacterial activity of 19 can be due mainly to functional groups involved in the chemical structure in comparison with the compounds studied.",
author = "Lenin, {Hau Heredia} and Lauro, {Figueroa Valverde} and Marcela, {Rosas Nexticapa} and Socorro, {Herrera Meza} and Maria, {L{\'o}pez Ramos} and Francisco, {D{\'i}az Cedillo} and Elodia, {Garc{\'i}a Cervera} and Eduardo, {Pool G{\'o}mez} and Josefa, {Paat Estrella} and Regina, {Cauich Carrillo} and Saidy, {Euan Hau}",
year = "2017",
month = "10",
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Lenin, HH, Lauro, FV, Marcela, RN, Socorro, HM, Maria, LR, Francisco, DC, Elodia, GC, Eduardo, PG, Josefa, PE, Regina, CC & Saidy, EH 2017, 'Design and synthesis of an indol derivative as antibacterial agent against Staphylococcus aureus', Journal of Chemical Biology, pp. 159-177. https://doi.org/10.1007/s12154-017-0173-0

Design and synthesis of an indol derivative as antibacterial agent against Staphylococcus aureus. / Lenin, Hau Heredia; Lauro, Figueroa Valverde; Marcela, Rosas Nexticapa; Socorro, Herrera Meza; Maria, López Ramos; Francisco, Díaz Cedillo; Elodia, García Cervera; Eduardo, Pool Gómez; Josefa, Paat Estrella; Regina, Cauich Carrillo; Saidy, Euan Hau.

In: Journal of Chemical Biology, 01.10.2017, p. 159-177.

Research output: Contribution to journalArticle

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T1 - Design and synthesis of an indol derivative as antibacterial agent against Staphylococcus aureus

AU - Lenin, Hau Heredia

AU - Lauro, Figueroa Valverde

AU - Marcela, Rosas Nexticapa

AU - Socorro, Herrera Meza

AU - Maria, López Ramos

AU - Francisco, Díaz Cedillo

AU - Elodia, García Cervera

AU - Eduardo, Pool Gómez

AU - Josefa, Paat Estrella

AU - Regina, Cauich Carrillo

AU - Saidy, Euan Hau

PY - 2017/10/1

Y1 - 2017/10/1

N2 - © 2017, Springer-Verlag Berlin Heidelberg. Several indole derivatives with antibacterial activity have been prepared using different protocols; however, some require special reagents and conditions. The aim of this study involved the synthesis of some indole derivatives using estrone and OTBS-estrone as chemical tools. The synthesis of the indole derivatives involves reactions such as follows: (1) synthesis of two indol derivatives (4 or 5) by reaction of estrone or OTBS-estrone with phenylhydrazine in medium acid; (2) reaction of 4 or 5 with 6-cloro-1-hexyne in medium basic to form two hexynyl-indol (7 or 8); (3) preparation of indol-propargylic alcohol derivatives (10 or 11) by reaction of benzaldehyde with 7 or 8 in medium basic; (4) synthesis of indol-aldehydes (12 or 13) via oxidation of 10 or 11 with DMSO; (5) synthesis of indeno-indol-carbaldehyde (15 or 16) via alkynylation/cyclization of 12 or 13 with hexyne in presence of copper(II); (6) preparation indeno-indol-carbaldehyde complex (19 or 20) via alkynylation/cyclization of 12 or 13 with 1-(hex-5-yn-1-yl)-2-phenyl-1H-imidazole. The antibacterial effect exerted by the indol-steroid derivatives against Streptococcus pneumoniae and Staphylococcus aureus bacteria was evaluated using dilution method and the minimum inhibitory concentration (MIC). The results showed that only the compound 19 inhibit the growth bacterial of S. aureus. In conclusion, these data indicate that antibacterial activity of 19 can be due mainly to functional groups involved in the chemical structure in comparison with the compounds studied.

AB - © 2017, Springer-Verlag Berlin Heidelberg. Several indole derivatives with antibacterial activity have been prepared using different protocols; however, some require special reagents and conditions. The aim of this study involved the synthesis of some indole derivatives using estrone and OTBS-estrone as chemical tools. The synthesis of the indole derivatives involves reactions such as follows: (1) synthesis of two indol derivatives (4 or 5) by reaction of estrone or OTBS-estrone with phenylhydrazine in medium acid; (2) reaction of 4 or 5 with 6-cloro-1-hexyne in medium basic to form two hexynyl-indol (7 or 8); (3) preparation of indol-propargylic alcohol derivatives (10 or 11) by reaction of benzaldehyde with 7 or 8 in medium basic; (4) synthesis of indol-aldehydes (12 or 13) via oxidation of 10 or 11 with DMSO; (5) synthesis of indeno-indol-carbaldehyde (15 or 16) via alkynylation/cyclization of 12 or 13 with hexyne in presence of copper(II); (6) preparation indeno-indol-carbaldehyde complex (19 or 20) via alkynylation/cyclization of 12 or 13 with 1-(hex-5-yn-1-yl)-2-phenyl-1H-imidazole. The antibacterial effect exerted by the indol-steroid derivatives against Streptococcus pneumoniae and Staphylococcus aureus bacteria was evaluated using dilution method and the minimum inhibitory concentration (MIC). The results showed that only the compound 19 inhibit the growth bacterial of S. aureus. In conclusion, these data indicate that antibacterial activity of 19 can be due mainly to functional groups involved in the chemical structure in comparison with the compounds studied.

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