Synthesis, Characterization and Biological Evaluation of Ammonium carboxylate salts of 1-[2-(2-tert-Butylcarbamoyl-Benzoylamino)-alkyl acyl]-Piperidine-4- Carboxylic Acid
Keywords:
Piperidine, Ammonium salts, Antibecterial, Antifungal.Abstract
A series of novel “Ammonium salt of piperidine-4-carboxylic acid coupled with several N-phthaloyl amino acids derivatives were synthesized, characterized, and evaluated for their antimicrobial as well as antifungal properties. These compounds were synthesized using DCC / HOBt coupling of piperidine-4-carboxylic acid methyl ester with N-phthaloyl amino acids followed by ring opening reaction using tert-butyl amine, the resulting ester derivatives were hydrolyzed using Sodium hydroxide, desired “Ammonium 1-[2-(2-tert-butylcarbamoyl-benzoylamino)-alkyl-acyl]- piperidine -4-carboxylate” derivatives were afforded by treatment of ammonia solution in methanol. These compounds synthesized were characterized using IR, NMR and Mass spectroscopy and screened for in vitro activity against S. aureus, E. coli, P. aeruginosa, S. typhimurium, F. oxysporum and A. alternata. Some of these compounds exhibited moderate to good activity, whereas some were found inactive, against pathogens being evaluated.
References
- Prentis R. A., Lis Y. and Walker S. R., (1988), Pharmaceutical innovation by the seven UK-owned pharmaceutical companies. British Journal of Clinical Pharmacology, 25, 387-396.
- Tessella Scientific Software Solutions, Automated Salts and Polymorph Screening. www.tessella.com/Services/CaseStudies/pdfs/e_GSK_ASAP.pdf. Accessed Dec. 15, 2006.
- Prakash K., Jieun R., Hyeongmin K., Iksoo K., Jeong T. K.,Hyunil K., Jae M. C., Gyiae Y. and Jaehwi L., (2014), Pharmaceutical particle technologies: An approach to improve drug solubility, dissolution and bioavailability, Asian journal of pharmaceutical sciences, 9, 304 -316.
- Patrick M., (2014), Principles of salt formation, UK Journal of Pharmaceutical and Biosciences, 2(4), 01-04.
- Kharatkar R. and Joshi K A., (2015), Synthesis, characterization and biological evaluation of novel 1-[2-(2-tert-butylcarbamoyl-benzoylamino)-alkyl acyl]-piperidine-4-carboxylic acid methyl ester, J Pharm Sci Bioscientific Res. 2015 5(6) 599-604.
- Abdel-Aziz A. A.,(2007), Novel and versatile methodology for synthesis of cyclic imides and evaluation of their cytotoxic, DNA binding, apoptotic inducing activities and molecular modeling study, European Journal of Medicinal Chemistry, 42(5), 614–626.
- Collin X, Robert J, Wielgosz G, et al•, New anti-inflammatory N-pyridinyl(alkyl)phthalimides acting as tumour necrosis factor-alpha production inhibitors, European Journal of Medicinal Chemistry, 2001; 36(7–8): 639–649.
- Zavyalov S. I, Dorofeeva OV, Rumyantseva EE, et al•, (2002). Synthesis of 2-aminothiazole derivatives, Pharmaceutical Chemistry Journal,2002; 36(8): 440–442.
- Cruickshank R, Duguid JP, Marmion BP and Swain RH, Medicinal Microbiology, Churchill Livingstone, London, Twelth Edition , 1975, 196-202.
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