Synthesis and evaluation of antimicrobial activity of cyclic imides derived from phthalic and succinic anhydrides
Abstract
Cyclic imides are a group of compounds which have valuable biological properties including cytotoxic, anti-inflammatory, antibacterial and antifungal activities. In this study, succinic and phthalic anhydrides were treated with glycinamide in pyridine to yield the corresponding amic acids. These amic acids underwent ring closure with acetic anhydride and anhydrous sodium acetate to form cyclic imides. In another procedure, succinic and phthalic anhydrides upon reaction with 2-amino-benzylamine in pyridine gave the corresponding cyclic imides. The imides were screened for their antimicrobial activities against three types of bacteria and one type of fungi. Phthalimide derived from benzylamine exhibited remarkable antimicrobial activity against E. coli.
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Marulasiddaiah R, Kalkhambkar RG, Kulkarni MV. Synthesis and Biological Evaluation of Cyclic Imides with Coumarins and Azacoumarins. Open J Med Chem. 2012,2:89-97.
PATIL M.M. RAJPUT S.S. Succinimides: synthesis , reaction, and biological activity. Int J Pharm Pharm Sci. 2014,6(11): 8-14.
Dhivare RS, Rajput SS. Synthesis and antimicrobial activity of five membered cyclic imide derivatives of mono, di and tri substituted aromatic amines and napthyl amine. World J Pharm Sci. 2015;4(6):1650-1658.
Al-Majidi SMH, Ahmad MR, Kareem Khan A. Synthesis and characterization of novel 1,8-Naphthalimide derivatives containing 1,3-oxazoles, 1,3-thiazoles, 1,2,4-triazoles as antimicrobial agents. J Al-Nahrain Uni. 2013;16(4):55-66.
Al-Azzawi AA, Hassan AS. Synthesis and preliminary evaluation of antimicrobial activity of new sulfonamido and acetamido cyclic imides linked to benzothiazole moiety K. J Pharm Sci. 2011,2:59-80.
Tozato Prado SR, Cechinel-Filho V, Campos-Buzzi F, Correa R, Correia Suter Cadena SM, Martinelli de Oliveira MB. Biological evaluation of some selected cyclic imides: Mitochondrial effects and in vitro cytotoxicity. Z Naturforsch. 2004;59c: 663D672.
Gayoso CW, Lima EO, Souza EL, Filho VC, Trajano VN, Pereira FO, Lima IO. Antimicrobial effectiveness of maleimides on fungal strains isolated from onychomycosis. Brazilian Archives of Bio & Tech. 2006, 49(4): 661-664.
Sortino M, Filho VC, Corre R, Zacchino S. N-Phenyl and N-phenylalkyl-maleimides acting against Candida spp.: Time-to-kill, stability, interaction with maleamic acids. Bioorg Med Chem. 2008;16: 560–568.
Dhivare RS, Rajput SS. Microwave assisted solvent free synthesis and antifungal evaluation of 3, 5-bis-(4-hydroxy-3-methoxybenzylidene)-nphenyl-piperidine-2, 6-dione derived from N-phenyl glutarimides. Int J Chem Tech Res. 2016,9(3):325-331.
Guri D, QingPeng W, HuiZhen Z, YiYi Z, Song LVJ, ChengHe Z. A series of naphthalimide azoles: design, synthesis and bioactive evaluation as potential antimicrobial agents. Sci China Chem. 2013;56(7):952–969.
Khalil AEG, Berghot MA, Gouda MA. Synthesis and study of some new N-substituted imide derivatives as potential antibacterial agents. Chem paper. 2010;64(5):637-644.
AL- Azzawi AM, Al-Obiadi KKH. Synthesis and antimicrobial screening of new BisSchiff bases and their acetyl oxadiazole azetidinone derivatives from pyromellitic diimid. Int J Res Pharm & Chem. 2016,6(1):1-8.
Dhivare RS, Rajput SS. Synthesis and antimicrobial evaluation of some novel bis-heterocyclic chalcones from cyclic imides under microwave irradiation. Chem Sci Rev Lett. 2015,4(15):937-944.
Sultana K, Khan NH, Shahid K. Synthesis, characterization and In Vitro antibacterial evaluation of Sn, Sb, and Zn coordination complexes of 2-(2-methoxyphenyl)-1H-isoindole-1, 3(2h)-dione. Int J Pharm Sci Rev Res. 2014;28(2):1-5.
Yunesa JA, Cardosob AA, Yunesc RA, Corread R, Campos-Buzzid F, Cechinel Filhod V. Antiproliferative effects of a series of cyclic imides on primary endothelial cells and a leukemia cell line. Z Naturforsch. 2008;63c:675-680.
Campos-Buzzid F, Corread R, Souzaa MM, Yunes RA, Nunes RJ,Cechinel-Filho V. Studies on new cyclic imides obtained from aminophenazone with analgesic properties. Arzneim.-Forsch./Drug Res. 2002;52,6:455-461.
Al-Azzawi AM. Synthesis, characterization and evaluation of antibacterial activity of several new 3,4-dimethyl maleimides and 1,8-naphthalimides containing 1,3,4-xadiazole ring. J Al-Nahrain Uni Sci. 2011;14(1):15-29.
Abdel-Aziz AAM. Novel and versatile methodology for synthesis of cyclic imides and evaluation of their cytotoxic, DNA binding, apoptotic inducing activities and molecular modeling study. Eur J Med Chem: 2007;42:614-626.
Bakhta MF, Shahar Yar M, Abdel-Hamid SG, Qasoumi SIA, Samad A. Molecular properties prediction, synthesis and antimicrobial activity of some newer oxadiazole derivatives. Eur J Med Chem. 2010;45:5862-5869.
Al-Azzawi AM, Hamd AS. Synthesis and antimicrobial screening of new naphthalimides linled to oxadiazole, thiadiazole and triazole cycles. Int J Res Pharm & Chem. 2014,4(2):283-290.
Shaki H, Khosravi A, Gharanjig K, Mahboubi A. Synthesis and biological properties of novel cationic fluorescent dye. Int J Tec Res & App. 2015;29: 103-106.
Kumari G, Singh RK. Green synthesis, antibacterial activity, and SAR of some novel naphthalimides and allylidenes. Med Chem Res. 2015;24:171–181.
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