<abstract xml:lang="en" xmlns="http://www.w3.org/1999/xhtml">A series of 1-(<italic>N</italic>-substituted-1<italic>H-</italic>indol-3-yl)-3-arylprop-2-ene-1-ones (<bold>2a, b-4a, b</bold>) were prepared and allowed to react with urea, thiourea or guanidine to give pyrimidine derivatives <bold>5a, b-13a, b</bold>. Reaction of <bold>2a, b-4a, b</bold> with ethyl acetoacetate in the presence of a base gave cyclohexanone derivatives <bold>14a, b-16a, b</bold>. Reaction of the latter compounds with hydrazine hydrate afforded indazole derivatives <bold>17a, b-19a, b</bold>. On the other hand, reaction of <bold>2a, b-4a, b</bold> with some hydrazine derivatives, namely hydrazine hydrate, acetyl hydrazine, phenylhydrazine and benzylhydrazine hydrochloride, led to the formation of pyrazole derivatives <bold>20a, b-31a, b</bold>. Moreover, reaction of <bold>2a, b-4a, b</bold> with hydroxylamine hydrochloride gave isoxazole derivatives <bold>32a, b-34a, b</bold>. The newly synthesized compounds were tested for their antimicrobial activity and showed that 4-(<italic>N</italic>-ethyl-1<italic>H</italic>-indol-3-yl)-6-(<italic>p</italic>-chlorophenyl)-pyrimidine-2-amine (<bold>11b</bold>) was the most active of all the test compounds towards <italic>Candida albicans</italic> compared to the reference drug cycloheximide. Eighteen new compounds, namely pyrimidin-2(1<italic>H</italic>)-ones <bold>5a, b-7a, b</bold>, pyrimidin-2(1<italic>H</italic>)-thiones <bold>8a, b-10a, b</bold> and pyrimidin-2-amines <bold>11a, b-13a, b</bold> derivatives, were tested for their <italic>in vitro</italic> antiproliferative activity against HEPG2, MCF7 and HCT-116 cancer cell lines. 4-(<italic>N</italic>-ethyl-1<italic>H</italic>-indol-3-yl)-6-(<italic>p</italic>-methoxyphenyl)-pyrimidin-2-amine (<bold>11a)</bold> was found to be highly active with <italic>IC</italic>50 of 0.7 μmol L-1.</abstract>

A series of 1-(N-substituted-1H-indol-3-yl)-3-arylprop-2-ene-1-ones (2a, b-4a, b) were prepared and allowed to react with urea, thiourea or guanidine to give pyrimidine derivatives 5a, b-13a, b. Reaction of 2a, b-4a, b with ethyl acetoacetate in the presence of a base gave cyclohexanone derivatives 14a, b-16a, b. Reaction of the latter compounds with hydrazine hydrate afforded indazole derivatives 17a, b-19a, b. On the other hand, reaction of 2a, b-4a, b with some hydrazine derivatives, namely hydrazine hydrate, acetyl hydrazine, phenylhydrazine and benzylhydrazine hydrochloride, led to the formation of pyrazole derivatives 20a, b-31a, b. Moreover, reaction of 2a, b-4a, b with hydroxylamine hydrochloride gave isoxazole derivatives 32a, b-34a, b. The newly synthesized compounds were tested for their antimicrobial activity and showed that 4-(N-ethyl-1H-indol-3-yl)-6-(p-chlorophenyl)-pyrimidine-2-amine (11b) was the most active of all the test compounds towards Candida albicans compared to the reference drug cycloheximide. Eighteen new compounds, namely pyrimidin-2(1H)-ones 5a, b-7a, b, pyrimidin-2(1H)-thiones 8a, b-10a, b and pyrimidin-2-amines 11a, b-13a, b derivatives, were tested for their in vitro antiproliferative activity against HEPG2, MCF7 and HCT-116 cancer cell lines. 4-(N-ethyl-1H-indol-3-yl)-6-(p-methoxyphenyl)-pyrimidin-2-amine (11a) was found to be highly active with IC50 of 0.7 μmol L-1.

Synthesis, antimicrobial and anti-cancer activities of some new <italic>N</italic>-ethyl, <italic>N</italic>-benzyl and <italic>N</italic>-benzoyl-3-indolyl heterocycles

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

Pharmacognosy Department, National Research Centre, Cairo, Egypt

Department of Chemistry, Faculty of Science (Girls), Al-Azhar University, Cairo, Egypt

Acta Pharmaceutica

Synthesis, antimicrobial and anti-cancer activities of some new -ethyl, -benzyl and -benzoyl-3-indolyl heterocycles

A series of 1-(N-substituted-1H-indol-3-yl)-3-arylprop-2-ene-1-ones (2a, b-4a, b) were prepared and allowed to react with urea, thiourea or guanidine to give...

Synthesis, antimicrobial and anti-cancer activities of some new N-ethyl, N-benzyl and N-benzoyl-3-indolyl heterocycles

Publié en ligne: 28 juin 2012

Pages: 157 - 179

DOI: https://doi.org/10.2478/v10007-012-0020-3

Mots clés
-supstituirani-3-indolilkalkoni, heterociklički spojevi, antimikrobno djelovanje, antitumorsko djelovanje

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