Reaction 1H-indole-3-carboxaldhyde 1 with thiosemicarbazide derivatives to give thiosemicarbazone derivatives 2a,b. Cyclization of thiosemicarbazone 2a with HCl, Ac 2 O, phenacyl bromides and chloroacetic acid afforded the corresponding 1,2,4-triazole-3-thiol derivative 3, diacetyl derivative 4 and 1,3-thiazole derivative 5 and 1,3-thiazolidin-4-ones derivative 6 respectively. Compound 6 undergoes a series of heterocyclization reactions to give new heterocyclic compounds. The structure of the newly synthesized compounds had been confirmed by elemental analysis and spectra data. The some newly synthesized compounds were evaluated for in vitro cytotoxic activity against three human cancer cell lines, including human liver cancer (HepG2), human colon cancer (HT-29) and human breast cancer (MCF-7) using MTT assay.
Novel fused pyrans were synthesized from the reaction of the tetrahydropyran-4-one with arylidine malononitriles. Different fused pyran derivatives were obtained from the mentioned reaction depending on type of catalyst used and type of energy used. Reactions were carried out under silent and ultrasonic conditions. In general, it was found that sometimes ultrasound irradiations change the reaction path in comparing with silent condition. In addition to improvement in reaction times, the products were obtained in high yields and their structures were determined by elemental analyses, spectral data.
Reaction of indole-3-carboxaldehydes 4 with hydrazine derivatives and different substituted acid hydrazides afforded the corresponding hydrazine derivatives 5a-c and acid hydrazide derivatives 7-11 respectively. Condensation of indole-3-carboxaldehydes 4 with phenacyl bromide and thiourea gives 1,3-thiazol-2-amine derivative 18. On the other hand, reaction 4 with 3-acetylchromene-2-one afforded chalcone derivative 19. Compound 4 undergoing Knoevenagel condensation with cyanoacetamide, ethyl cyanoacetate, benzimidazol-2-ylacetonitrile, rhodanine-3-acetic acid, 2,3-dihydropyrimidin-4-one derivative and 2,4-dihydropyrazol-3-one afforded the compounds 20a,b, 22, 23, 27 and 28 respectively. The structure of the newly synthesized compounds has been confirmed by elemental analysis and spectra data. The antimicrobial activities of the some newly synthesized compounds were measured and showed that most of them have high activities.
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