175733-64-9Relevant academic research and scientific papers
Cell cycle disruption and apoptotic activity of 3-aminothiazolo[3,2-a]benzimidazole-2-carbonitrile and its homologues
Sarhan, Abdelwareth A.O.,Al-Dhfyan, Abdullah,Al-Mozaini, Maha A.,Adra, Chaker N.,Aboul-Fadl, Tarek
, p. 2689 - 2694 (2010)
3-Aminothiazolo[3,2-a]benzimidazole-2-carbonitrile (2) was prepared and upon hydrolysis using concentrated sulfuric acid or phosphoric acid resulted in the corresponding 3-aminothiazolo[3,2-a]benzimidazole-2-carboxamide derivative (3). Cyclization of the 2 using acetic anhydride or formic acid gave the corresponding pyrimido[4′,5′:4,5]thiazolo[3,2-a]benzimidazol-4(3H)-one (5) in good yields. Acetylation of 2 with acetic anhydride in pyridine afforded N-acetylaminothiazolo[3,2-a]benzimidazole-2-carbonitrile (6). In vitro antiproliferative activities of synthesized compounds were investigated at The National Cancer Institute (NCI), USA, according to their applied protocol. Compound 6 revealed significant antiproliferative activity, however, weak activity was shown by the other derivatives. Cell cycle disruption and apoptotic activity of 6 were studied, interestingly, 6 has the ability to arrest G2/M phase and it can induce apoptosis in time dependant manner.
Synthesis and Reactions of 3-Aminothiazolobenzimidazole-2-carbonitrile
Sarhan, A. A. O.,El-Shenef, H. A. H.,Mahmoud, A. M.
, p. 116 - 135 (2007/10/03)
3-Aminothiazolobenzimidazole-2-carbonitrile was prepared and allowed to react with aromatic aldehydes, formamide and formic acid to give the corresponding arylmethylidenes 4a-d, pyrimidine 5 and pyrimidinone 6 respectively. 6 was alkylated with alkyl halides and the N-alkyl derivatives 9a-b were obtained.Acetylation of 3 afforded the N-acetyl derivative 10, which cyclized to the pyrimidinone 11.Compound 11 was also prepared independently by several methods.On alkylation of 11 by using EtOH/ AcONa or EtOH/KOH the N-alkyl derivatives 12a-d were obtained.Hydrolysis of 3 with EtOH/KOH or EtOH/NH2NH2 gave the benzimidazole-2-thiol 1.Furthermore, condensation of 3 with triethylorthoformate gave the ethoxymethylideneamino derivative 14.Interaction of 14 with different amines afforded the derivatives 15, 16 and 17a-c in good yield.Reaction of 3 with H3PO4 or H2SO4 afforded the corresponding amide derivative 18. - Keywords: Thiazolobenzimidazole; alkylation; acetylation; cyclization; condensation; hydrolysis
