IJCRR - 7(14), July, 2015
Pages: 01-06
SYNTHESIS AND EVALUATION OF ANTIOXIDANT ACTIVITY (IN-VITRO) OF SOME N-PHTHALYL-[{(3-NITRO ANILINO)-4" ARYL SUBSTITUTED}]-1, 3, 4 THIADIAZOLES
Author: Pramilla Sah, Kuldeep Sen
Category: Healthcare
[Download PDF]
Abstract:
1, 3, 4- thiadiazoles are potential bioactive agents having the toxophoric N=C–S linkage. There are several isomers of thiadiazole, i.e.1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, and 1,3,4-thiadiazole. However 1, 3, 4-Thiadiazole is the main isomer of the thiadiazole series which has versatile pharmacological activities. Hence in this study we have synthesized some new substituted 1, 3, 4 thiadiazoles i.e. N-phthalyl-[{(3-nitro anilino)-4’’ aryl Substituted}]-1, 3, 4 thiadiazoles. The title compounds were prepared from N-phthayl-3-nitro anilino thiosemicarbazide by treating N-phthayl-3-nitro aniline with carbon disulphide,
ammonium hydroxide and hydrazine hydrate. The synthesized compounds were then evaluated for their in- vitro antioxidant activity by determining the reducing power and hydrogen peroxide scavenging potential. The results show that one derivative V2 (N-Phthalyl-[{(3’-nitro anilino)-5-(4’’-chloro phenyl)}]-1, 3, 4-thiadiazole) had the best redusing ability while V4 (N-Phthalyl-[{(3’- nitro anilino)-5- (4’’-bromo phenyl)}]-1, 3, 4-thiadiazole) was the strongest oxidant. The chemical structures of the synthesized compounds have been characterized by IR, 1HNMR and mass spectra.
Keywords: N-phthalyl, 1, 3, 4-thiadiazoles, Antioxidant activity
Citation:
Pramilla Sah, Kuldeep Sen. SYNTHESIS AND EVALUATION OF ANTIOXIDANT ACTIVITY (IN-VITRO) OF SOME N-PHTHALYL-[{(3-NITRO ANILINO)-4" ARYL SUBSTITUTED}]-1, 3, 4 THIADIAZOLES International Journal of Current Research and Review. 7(14), July, 01-06
References:
1. Mohan J, Rathee A. synthesis and antimicrobial activity of s-triazolo[3,4-b][1,3,4]thiadiazoles, s-triazolo[3,4-b] [1,3,4] thiadiazines and s-triazolo. Ind J Hetero Chem 2011; 21: 117-120.
2. Demirbas A, Sahin D, Demirbas N, and Karaoglu SA. Synthesis of some new 1,3,4-thiadiazol-2-ylmethyl-1,2,4-triazole derivatives and investigation of their antimicrobial activities. Euro J Med Chem 2009; 44(7): 2896–2903.
3. Hussain S, Sharma J, Amir, M. Synthesis and antimicrobial activities of 1,2,4-triazole and 1,3,4-thiadiazole derivatives of 5-amino-2-hydroxybenzoic acid. E-J. Chem 2008; 5(4):963–968.
4. Lamani RS, Shetty NS, Kambl RR, Khazi AM. Synthesis and antimicrobial studies of novel methylene bridged benzisoxazolyl imidazo[2,1-b][1,3,4]thiadiazole derivatives. Euro J Med Chem 2008; 44:2828–2833.
5. Chen CJ, Song BA, Yang S. et al., Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4- thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl1,3,4-oxadiazole derivatives. Bioorg Med Chem 2007;15: 3981–3989.
6. Jyothi C, Das AK, Pal P, Baidya M. synthesis and anti-inflammatory activities of some new substituted thiadiazolothieno- pyrimidinones. Indian J Hetero Chem 2007; 17: 191-192.
7. Karegoudar P, Prasad DJ, Ashok M, Mahalinga Poojary MB, Holla BS. Synthesis, antimicrobial and anti-inflammatory activities of some 1,2,4-triazolo[3,4-b][1,3,4] thiadiazoles and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines bearing trichlorophenyl moiety. Euro J Med Chem 2008; 43(4):808–815.
8. Goksen US, Kelekci NG, Goktas O. et. al., 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorg Med Chem 2007; 15(17): 5738–5751.
9. Behrouzi-Fardmoghadam M, Poorrajab F, Ardestani SK, Emami S, Shafiee A, Foroumadi A. Synthesis and in vitro anti-leishmanial activity of 1-[5-(5-nitrofuran-2-yl)-1,3,4- thiadiazol-2-yl]- and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines. Bioorg Med Chem 2008; 16(8): 4509–4515.
10. Wei MX, Feng L, Li XQ, Zhou XZ, Shao ZH, Shao H. Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing γ-butenolide moiety and preliminary evaluation of in vitro anticancer activity. Euro J Med Chem 2009;44 (8): 3340–3344.
11. Ibrahim DA. Synthesis and biological evaluation of 3,6-disubstituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives as a novel class of potential anti-tumor agents. Euro J Med Chem 2009;44:2776–2781.
12. Zhan P, Liu X, Fang Z, Li Z, Pannecouque C, Clercq ED. Synthesis and anti-HIV activity evaluation of 2-(4-(naphthalen-2-yl)-1,2,3-thiadiazol-5-ylthio)-N-acetamides as novel non-nucleoside HIV-1 reverse transcriptase inhibitors. Euro J Med Chem 2009; 44: 4648–4653.
13. Kus C, Kilcigil GA, Ozbey S. et al., Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class. Bioor Med Chem. 2008;16: 4294– 4303.
14. Cressier D, Prouillac C, Hernandez P. et al., Synthesis, antioxidant properties and radioprotective effects of new benzothiazoles and thiadiazoles. Bioorg Med Chem. 2009; 17(14): 5275–5284.
15. Foroumadi A, Rineh A, Emami S. et al., Synthesis and antiHelicobacter pylori activity of 5-(nitroaryl)-1,3,4-thiadiazoles with certain sulfur containing alkyl side chain, Bioorg Med Chem Lett. 2008; 18(11):3315–3320.
16. Sah P, Parmar S, Synthesis and Insecticidal Activity of Some New 2’-[1-Amino Methyl-{N-Alkyl phthalyl}- Benzimidazolo]-5’-(2’’/4’’/3’’/5’’-Aryl Substituted)-1’, 3’,4’-Thiadiazoles. Ultra Chem 2010:6(2):199-210.
17. Oyaizu M. Studies on product of browing reaction prepared from glucose amine. Jpn. J. Nutr 1986; 07: 307-315.
18. Ruch RT, Cheng SJ, Klaunig JE. Spin trapping of superoxide and hydroxyl radicals methods in enzymology 1984; 105: 198-209.
|