Studies on Chromene based 2, 6-disubstituted-Thiazolo [3,2-B] [1,2,4] Triazole derivatives: Synthesis and Biological Evaluation
In this study, a series of novel chromene based 2,6-disubstituted-thiazolo[3,2-b] [1,2,4] triazole derivatives (7a-g) were synthesized by condensing 5-substituted-1,2,4-traizole-thione (6a-g) using poly phosphoric acid through one pot reaction. The structure of new compounds was supported by 1H NMR, 13C NMR and MS data. The synthesized compounds were evaluated using writhing assays for analgesic and carrageenan-induced rat paw edema method for anti-inflammatory activities respectively. Some of the newly synthesized compounds 7c, 7f and 7g showed very good anti-inflammatory activity with 90.83%, 85.81% and 88.40% protection respectively along with low GI toxicity as compared to standard drug ibuprofen while compounds 7a, 7b, 7d and 7f showed highest analgesic activity with 52.54%, 54.02%, 56.76% and 52.45% protection among them compound 7d showed better protection than standard drug ibuprofen.
Keywords: thiazolo-triazoles, Chromene, Anti-inflammatory, Analgesic
2. Henriette G, Lorraine L, Bettina H, Clemence D, Kelly Dong, Irenej K, et al, Antivascular and antitumor evaluation of 2-amino-4-(3- bromo-4,5-dimethoxy-phenyl)-3-cyano-4H-chromenes, a novel series of anticancer agents, Mol Cancer Ther, 2004; 3(11):1375- 84.
3. Chetan BS, Nimesh MS, Manish PP, Ranjan GP, Microwave assisted synthesis of novel 4H-chromene derivatives bearing phenoxypyrazole and their antimicrobial activity assess, J Serb Chem Soc, 2012; 77:1–17.
4. Milan M, Mirjana M, Desanka B, Sanja M, Neda N, Vladimir M, et al, In vitro antioxidant of selected 4-Hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies, Int J Mol Sci, 2011;12(5):2822-2841.
5. Jie-Fei Cheng, Akira Ishikawa, Yoshinori Ono, Thomas Arrhenius, Alex Nadzan, Novel Chromene Derivatives as TNF-α Inhibitors, Bioorg Med Chem Lett, 2003; 13: 3647–3650 .
6. Suresh T, Arunima V, Atin K, Sandeep G, Prarthana VR, Ganesh RK, Novel chromeneimidazole derivatives as antifungal compounds: synthesis and in vitro evaluation, Acta Pol. Pharm, 2010; 67:423-427.
7. Nareshkumar Jain, Jiayi Xu , Ramesh MK ,Fuyong Du , Guo JianZhong , Emmanuel Pacia, et al, Identification and Structure−Activity Relationships of Chromene-Derived Selective Estrogen Receptor Modulators for Treatment of Postmenopausal Symptoms, J Med Chem, 2009; 52 (23):7544–7569.
8. Mori J, Iwashima M, Takeuchi M, Saito H, A synthetic study on antiviral and antioxidative chromene derivative, Chem Pharm Bull, 2006; 54(3):391-6.
9. Aliaa MK, Manal MK, Eman k Abd El-all and Heba AH Elshemy, Design and synthesis of substituted chromenes as potential anticancer agents, IJPRD, 2012; 4(3):310-322.
10. Denish CK, Hetal KP, Nilesh KG, Synthesis, characterization & anti-HIV activity of 4-Hydroxy-3-(5-methylisoxazol-3- yl)pyrano(3,2-C)chromene-2,5-dione, AJBPR, 2012; 2(2):126- 130.
11. Nimesh RK, Dhaval DH, Prashant TM, Saurabh KP, Synthesis and evaluation of in vitro antitubercular activity and antimicrobial activity of some novel 4H-chromeno[2,3-d]pyrimidine via 2- amino-4-phenyl-4H-chromene-3-carbonitriles, Med Chem Res, 2011; 20(7);854-864.
12. Nitin K, Sushil K, Himanshu G, Sharma PK, 3-Hydroxy-2- (substituted phenyl) -4H-chromen-4-one derivatives- synthesis, spectral characterization and pharmacological screening, WRJB, 2012; 1(1): 1-5.
13. Bhat MA, Siddiqui N, Khan SA, Synthesis of novel 3-(4-acetyl5H/methyl-5-substituted phenyl-4,5-dihydro-1,3,4-oxadiazol-2- yl)-2H-chromen-2-ones as potential anticonvulsant agents, Acta Pol Pharm, 2008; 65(2):235-39.
14. Indulatha VN, Gopal N, Jayakar B, Anti-inflammatory activity of newly synthesised N-[4’-Oxo-2’-(substituted aryl/heteryl)-thiazolidin-3’-yl]-3-carboxamido-2H-chromen-2-one derivatives, Int J ChemTech Res, 2011; 3(4):1930-1937.
15. Afshin Z Sara A, Selective COX-2 inhibitors: A review of their structure-activity relationships, Iran J Pharm Res, 2011; 10(4):655-683.
17. Thomas N, Zachariah SM, Pharmacological activities of chromene derivatives: An overview. Asian J Pharm. Clin. Res, 2013; 6(2):11-15.
18. Mathew V, Keshavayya J, Vaidya VP, Heterocyclic system containing bridgehead nitrogen atom: synthesis and pharmacological activities of some substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiaz-oles. Eur J Med Chem, 2006; 41:1048–1058.
19. Mathew V, Giles D, Keshavayya J, Vaidya VP, Studies on synthesis and pharmacological activities of 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and their dihydro analogues. Arch Pharm, 2009; 342:210–222.
20. Karthikeyan MS, Holla BS, Kulkuraya B, Kumari NS, Biological studies of some 2,4-dichloro-5-fluorophenyl containing triazolothiadiazoles, Monatshette fur chemie, 2007; 138:1309–1316.
21. Karegoudar P, Prasad DJ, Ashok M, Mahalinga M, Poojary B, Holla BS, Synthesis, antimicrobial and antiinflammatory activities of some 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 1,2,4-triazol-o[3,4-b][1,3,4]thiadiazines bearing trichloro phenyl moiety, Eur J Med Chem, 2008; 43:808–815.
22. Prasad DJ, Ashok M, Karegoudar P, Poojary B, Holla BS, Kumari NS, Synthesis and antimicrobial activities of some new triazolothiadiazoles bearing 4-methylthiobenzyl moiety, Eur J Med Chem, 2009; 44:551–557.
23. Winter CA, Risley ET, Nuss GW, Carrageenan-induced edema in hind paw of the rat as an assay for antiinflammatory drugs, Proc Soc Exp Biol Med, 1962; 3:544–547.
24. Collier HOJ, Dinneen C, Johnson CA, Schneider C, The abdominal constriction response and its suppression by analgesic drugs in the mouse, Br. J. Pharmacol. Chemother., 1968; 32(2):295-310.
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