Cytotoxicity and utility of 1-indanone in the synthesis of some new heterocycles.
Benzo[d]imidazole 3 and 1,2,4-triazin-5(2H)-one 6 were prepared by the reaction of starting ethyl (3-hydroxy-1H-inden-2-yl)(oxo)-acetate 2 with o-phenylenediamine and thiosemicarbazide respectively. Reaction of 1,4-dihydro-1-phenylindeno[1,2-c]pyrazole-3-carbohydrazide 8 with phenylisothiocyanate gave thiosemicarbazide 9, and its reaction with chloroacetic acid or phenacylbromides led to the formation of thiazolidinone-4-one 10 or 1,3-thiazoles 12a, b. The reactivity of hydrazide 8 towards fluorinated aldehyde, phthalic anhydride, and hydrazonoyl chlorides 15a, b was studied to give fluorinated hydrazones, imide bis-hydrazones 13-16. The newly synthesized compounds were screened for their cytotoxic activities and compounds 6, 8, 9 and 10 were found the most potentially cytotoxic. The detailed synthesis, spectroscopic and biological data are reported.
Hegazi
Bahira
B
Applied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt.
Mohamed
Hanan Ahmed
HA
Dawood
Kamal Mohamed
KM
Badria
Farid Abdel-Rahem
FA
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007189:Indans / Q000138:chemical synthesis / Q000737:chemistry*; D009369:Neoplasms / Q000188:drug therapy; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D053778:Thiazolidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014227:Triazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000970:Antineoplastic Agents; D001562:Benzimidazoles; D006571:Heterocyclic Compounds; D006835:Hydrazones; D007189:Indans; D013844:Thiazoles; D053778:Thiazolidines; D014227:Triazines; C013352:indacrinone; C031000:benzimidazole