![]() | Only 14 pages are availabe for public view |
Abstract The synthesis of N-acylbenzotriazoles and their potential in a number of organic transformations are reviewed. A novel and efficient synthesis of N-acylbenzotriazoles (Ia-m, IIa, Va, VIa, VIIa, VIIIc and Xa) from the corresponding carboxylic acids and tosyl chloride is discussed. This methodology is used for the synthesis of Vorinostate (SAHA) III, new N-acyl derivatives of Cephalexin (IXa-k’) and N-(3-nicotinamidobenzoyl) aminoacids (XIa-m). The antibacterial activities of N-acylcephalexins were evaluated against Staphylococcus aureus (ATCC 6538), Paenibacillus polymyxa (ATCC, 842), Escherichia coli (ATCC 10536) and Pseudomonas aeruginosa (ATCC 27853). N-(3,4,5-Trimethoxybenzoyl)cephalexin (IXb) and N-Cbz-Trp-cephalexin (IXg) exhibited a broader spectrum antibacterial activity. Cytotoxicity of N-(3-nicotinamidobenzoyl)amino acids (XIa-m) was tested against breast (MCF-7), colon (HCT-116) and prostate carcinoma (DU145 and PC3) cell lines. Compounds XIh, XIj, and XIk showed cytotoxic activities higher than 5-Fluorouracil (5-FU) against breast carcinoma cell line (MCF-7) and higher than 5-FU and Imatinib incase of colon carcinoma cell line. Most of the synthesized compounds XIa-m exhibited good cytotoxic activity against prostate carcinoma cell lines DU-145 and PC3. |