<abstract xml:lang="en" xmlns="http://www.w3.org/1999/xhtml"><p>Starting from 1-benzyl- (<bold>2a</bold>) and 1-benzoyl-3-bromoacetyl indoles (<bold>2b</bold>) new heterocyclic, 2-thioxoimidazolidine (<bold>4a, b</bold>), imidazolidine-2,4-dione (<bold>5a, b</bold>), pyrano(2,3-<italic>d</italic>)imida-zole (<bold>8a, b</bold> and <bold>9a, b</bold>), 2-substituted quinoxaline (<bold>11a, b-17a, b</bold>) and triazolo(4,3-<italic>a</italic>)quinoxaline derivatives (<bold>18a, b</bold> and <bold>19a, b</bold>) were synthesized and evaluated for their antimicrobial and anticancer activities. Antimicrobial activity screening performed with concentrations of 0.88, 0.44 and 0.22 μg mm<sup>-2</sup> showed that 3-(1-substituted indol-3-yl)quinoxalin-2(1<italic>H</italic>)ones (<bold>11a, b</bold>) and 2-(4-methyl piperazin-1-yl)-3-(1-substituted indol-3-yl) quinoxalines (<bold>15a, b</bold>) were the most active of all the tested compounds towards <italic>P. aeruginosa, B. cereus</italic> and <italic>S. aureus</italic> compared to the reference drugs cefotaxime and piperacillin, while 2-chloro-3-(1-substituted indol-3-yl)quinoxalines (<bold>12a, b</bold>) were the most active against C. <italic>albicans</italic> compared to the reference drug nystatin. On the other hand, 2-chloro-3-(1-benzyl indol-3-yl) quinoxaline <bold>12a</bold> display potent efficacy against ovarian cancer xenografts in nude mice with tumor growth suppression of 100.0 ± 0.3 %.</p></abstract>

Starting from 1-benzyl- (2a) and 1-benzoyl-3-bromoacetyl indoles (2b) new heterocyclic, 2-thioxoimidazolidine (4a, b), imidazolidine-2,4-dione (5a, b), pyrano(2,3-d)imida-zole (8a, b and 9a, b), 2-substituted quinoxaline (11a, b-17a, b) and triazolo(4,3-a)quinoxaline derivatives (18a, b and 19a, b) were synthesized and evaluated for their antimicrobial and anticancer activities. Antimicrobial activity screening performed with concentrations of 0.88, 0.44 and 0.22 μg mm-2 showed that 3-(1-substituted indol-3-yl)quinoxalin-2(1H)ones (11a, b) and 2-(4-methyl piperazin-1-yl)-3-(1-substituted indol-3-yl) quinoxalines (15a, b) were the most active of all the tested compounds towards P. aeruginosa, B. cereus and S. aureus compared to the reference drugs cefotaxime and piperacillin, while 2-chloro-3-(1-substituted indol-3-yl)quinoxalines (12a, b) were the most active against C. albicans compared to the reference drug nystatin. On the other hand, 2-chloro-3-(1-benzyl indol-3-yl) quinoxaline 12a display potent efficacy against ovarian cancer xenografts in nude mice with tumor growth suppression of 100.0 ± 0.3 %.

Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivatives

Chemistry Department of Natural Compounds, National Research Centre, Cairo, Egypt

Chemistry Department of Natural and Microbial Products, National Research Centre, Cairo, Egypt

Univeterinary Research Unit, Pharmaceutical Company, Cairo, Egypt

Acta Pharmaceutica

Starting from 1-benzyl- (2a) and 1-benzoyl-3-bromoacetyl indoles (2b) new heterocyclic, 2-thioxoimidazolidine (4a, b), imidazolidine-2,4-dione (5a, b),...

Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivatives

Pubblicato online: 13 mar 2010

Pagine: 55 - 71

DOI: https://doi.org/10.2478/v10007-010-0004-0

Parole chiave
2-klor-3-(1-benzil)kinoksalini, 2-klor-3-(1-benzoilindol-3-il)kinoksalini, antimikrobno djelovanje, antitumorsko djelovanje

This content is open access.

Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivatives

Pubblicato online: 13 mar 2010

Pagine: 55 - 71

DOI: https://doi.org/10.2478/v10007-010-0004-0

Parole chiave2-klor-3-(1-benzil)kinoksalini, 2-klor-3-(1-benzoilindol-3-il)kinoksalini, antimikrobno djelovanje, antitumorsko djelovanje

This content is open access.

Parole chiave
2-klor-3-(1-benzil)kinoksalini, 2-klor-3-(1-benzoilindol-3-il)kinoksalini, antimikrobno djelovanje, antitumorsko djelovanje