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.
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.
Reaction of cyanoacetic acid hydrazide (1) with 4-methoxyacetophenone and 4-chlorobenzaldehyde (2a,b) afforded the corresponding 2-cyanoacetohydrazide derivatives (3a,b) respectively. The latter compounds were utilized as a key intermediate for the synthesis of new heterocyclic compounds. Newly synthesized compounds were characterized by elemental analyses and spectral data. The antitumor evaluation of some newly synthesized compounds was screened in vitro against human breast cancer cell line (MCF-7).
The reaction of imidazole-2-thione derivative 1 with 2-chloro-N-p-tolylacetamide afforded the corresponding 2-(1H-imidazol-2-ylthio)-N-p-tolylacetamide 2. Reaction compound 2 with different reagents such as p-chlorobenzaldehyde and p-chlorophenyl diazonium chloride afforded the corresponding arylidene derivative 3 and hydrazone derivative 6. Reactions of 2 with carbon disulfide in dimethylformamide (DMF) in one equivalent potassium hydroxide afforded intermediate potassium sulphide salt 8, which treatment with dilute hydrochloric acid and phenacyl bromide afforded the corresponding 2-[p-tolylcarbamoyl]ethanedithioic acid 9 and 3-[benzo-ylmethylthio]-N-p-tolyl-3-thioxo-propaneamide 10. While the reaction 2 with carbon disulphide in the presence of two equivalent potassium hydroxide in DMF gave non-isolated potassium salt 11, which was allowed to react with halogenated compounds namely ethyl chloroacetate and methyl iodide afforded the corresponding 3, 3-bis[(ethoxycarbonyl)methylthio]-N-p-tolylacrylamide 12 and 3,3bis-(methylthio)-N-p-tolylacrylamide 13 respectively. Reaction 2 with phenyl isothiocyanate in basic DMF yielded the intermediate potassium sulphide salt 18. Acidification 18 with dilute hydrochloric acid afforded the corresponding thiocarbamoyl derivative 19. Treatment of intermediate 18 with methyl iodide, phenacyl bromide and ethylchloroacetate afforded the 3-anilino-3-(methylthio)-N-p-tolylacrylamide 20, 2-(1,3-thiazol-2(3H)-ylidene)-N-p-tolylacetamide 21 and 2-(4-oxo-3phenyl-1,3-thiazolidin-2-ylidene)-N-p-tolylacetamide 22 respectively. The structure of the newly synthesized compounds has been confirmed by elemental analysis and spectra data. Synthesized compounds 2, 3, 6, 13, 15a, 15b, 17, 20, 21, 22 and 23 were screened for their antibacterial activities in vitro against Gram-positive (Staphylococcus aureus and Bacillus subtilis), Gram-negative (Pseudomonas aeuroginosa and Escherichia coli) and antifungal activities against (Aspergillus fumigates, Syncephalastrum racemosum, Geotrichum candidum and Candida albicans).
Reaction of 2-(quinolin-8-yloxy)acetohydrazide 1with phenyl isothiocyanate, carbon dsulphide, nitrous acid,active methylene compound and aromastic aldehydes afforded different heterocyclic compounds containing quinoline moiety 2-11. The structures of the new compounds confirmed by elemental analyses,spectroscopic measurements and chemical reactions.
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