Original scientific paper

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

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

ESLAM REDA EL-SAWY ; Chemistry Department of Natural Compounds, National Research Centre, Cairo, Egypt
ADEL HAMED MANDOUR ; Chemistry Department of Natural Compounds, National Research Centre, Cairo, Egypt
KHALED MAHMOUD ; Pharmacognosy Department, National Research Centre, Cairo, Egypt
INAS EZZ-ELDIN ISLAM ; Department of Chemistry, Faculty of Science (Girls), Al-Azhar University, Cairo, Egypt
HEBA MOHAMED ABO-SALEM ; Chemistry Department of Natural Compounds, National Research Centre, Cairo, Egypt

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, phenyl- hydrazine 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.

Keywords

N-substituted-3-indolylchalcones; heterocycles; antimicrobial activity; anti-cancer activity

Hrčak ID:

78871

URI

https://hrcak.srce.hr/78871

Publication date:

30.6.2012.

Article data in other languages: croatian

Visits: 2.536 *