International Journal of Modern Science and Technology
International Journal of Modern Science and Technology, 1(4), 2016, Pages 121-128.
Microwave Assisted Synthesis, Characterization and Biological studies on 1,3,4-Thiadiazinan-5-one derivatives
S. Srinivasan, R. Girija
Department of Chemistry, Queen Mary’s College (Autonomous), Chennai, India.
Heterocyclic compounds play an important role as the main sources of lead molecules of agrochemicals. The 1,3,4-thiadiazinan-5-one nucleus is one of the most important and well known heterocyclic nuclei, which is a common and integral feature of a variety of natural products and medicinal agents. To find the novel lead compounds with various biological activities a series of thiadiazinan-5-one were rationally designed and synthesized. In this study an effort is made to synthesize 1,3,4-Thiadiazinan-5-one derivatives through the condensation reaction of Aryl aldehydes, substituted hydrazine derivatives and thioacetic acid using green solvent which is an efficient, green and facile three-component reaction. Using this method, 80% yield of thiadiazinan-5-one was obtained, while in conventional method, the yield only exceeded upto 50%. The chemical structures of the synthesized compounds were characterized by considering the data of their elemental analysis as well as their spectral data using, FT-IR, 1H-NMR, 13C-NMR and Mass spectra. The compounds are found to possess good biological activity. Especially, compounds were bearing the sulfur and nitrogen atoms showed activity than those bearing the oxygen atom.
Keywords: Microwave; Aryl aldehyde; Thioacetic acid; Hydrazine; Antimicrobial activity.
- Hunasha RD, Satyanarayana D. One pot synthesis of 3-(substituted phenoxymethyl)-6-phenyl/substituted phenoxymethyl-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole derivatives as antimicrobial agents. International Journal of Pharma and Bio Sciences 3 (2012) 183-192.
- Ritter SK. EPA analysis suggests green success. Chemical Engineering News 79 (2001) 27-34.
- Moghanian H, Ebrahimi A. Three Component, One pot synthesis of amido- alkyl napthols using polyphosphate ester under solvent free conditions. Journal of Saudi Chemical Society 2 (2014) 165-168.
- Nalini V, Girija R. Synthesis and characterization and biological studies of 9-aryl substituted acridinedione derivatives by Hantzsh condensation. International journal of current research 5 (2013) 3076-3081.
- Sanjeeva Reddy Ch, Sanjeeva Rao L, Sunitha B, Nagaraj A. Synthesis and antibacterial activity of N-Substituted-[1,2,4] triazoles and 1,2,4-triazole [3,4-b] [1,3,4] thiadiazines. Indian Journal of Chemistry 54B (2015) 1283-1289.
- Deohate PP. Synthesis, structural study and biological activity of bridgehead nitrogen containing Triazolo-thiadiazine derivatives. Chemical Science Transactions 2 (2013) 556-560.
- Kharate RM, Deohate PP, Beard BN. Synthesis structural study and antimicrobial screening of bridgehead nitrogen containing 1,8, bis-thiadiazino-triazolyl-octanes. Der Pharma Chemical 4 (2012) 2434-2437.
- Deohate PP. Synthesis, structural study and biological activity of bridgehead nitrogen containing Triazolo-thiadiazine heterocycles. Der Pharma Chemical, 4 (2012) 2042-2046.
- Mathew V, Keshavayya J, Vaidya VP. Heterocyclic system containing bridgehead nitrogen atom: synthesis and pharmacological activites of some substituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles, European Journal of Medicinal Chemistry, 9 (2006) 1048-1058.
- Mathew V, Keshavayya J, Vaidya VP, Giles D. Studies on synthesis and pharmacological activities of 3,6-disubstituted-1,2,4-triazolo[3,4-b]1,3,4-thiadiazoles and their dihydro analogies. European Journal of Medicinal Chemistry 6 (2007) 823-840.
- Demirbas N, Demirbas A, Karaoglu SA, Celik E. Synthesis and antimicrobial activities of some new [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles and [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazines. ARKIVOC, 1 (2005) 75-91.
- Kirankumar M, Sunitha K, Bhupathi Reddy K, Jayanthkumar M. Shobha Rani N, Mohan R, Vijayakumar B. Synthesis and biological evaluation of new 10-(6-substituted-[1,2,4]-triazolo-[3,4-b] [1,3,4] thiadiazol-3-ylmethyl)-3-nitro-10H-phenoxazine and 10-(6-substituted -7H-[1,2,4]-triazolo-[3,4-b][1,3,4]-thiaiazol-3-yl methyl)-3-nitro-10H-phenoxazine. World Journal of Pharmacy and Pharmaceutical Sciences 2 (2013) 5284-5295.
- Sridhara AM, Venugopala Reddy KR, Keshavayya J, Chdanda B. Synthesis and antimicrobial activity of pthalazine substituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles and 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines. Der Pharma Chemical 2 (2010) 201-211.
- Siddiqui MT, Comrie MH. Antituberculosis agents. V: α-[5-(5-nitro-2-furyl)-1,3,4-oxadiazol-2-ylthio] acethydrazide and related compounds. Journal of Pharmaceutical Sciences 6 (1991) 548-550.
- Venkata S, Rao C, Rajeswar RV. One-Pot synthesis of 1,3,4-Thiadiazin-5-yl-chromen-2-one Derivatives via Three-Component Reaction. Synthetic Communications 42 (2012) 1454–1460.
- Schro der J, Henke A, Wenzel H, Brandstetter H, Stammler HG, Stammler A, Pfeiffer WD, Tschesche H. Structure-based design and synthesis of potent matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold. J Med Chem 44 (2001) 3231–3243.
- Sugawara H, Endoh M. Enantiomer EMD 57439 antagonizes the Ca2þ sensitizing effect of (þ)-enantiomer EMD 57033 on diastolic function but not on systolic function in rabbit ventricular cardiomyocytes. Jpn J Pharmacol 80 (1999) 55–65.
- Himmel HM, Amos GJ, Wettwer E, Ravens U. Effects of the calcium sensitizer [þ]-EMD 60263 and its enantiomer-EMD 60264 on cardiac ionic currents of guinea pig and rat ventricular myocytes. J Cardiovasc Pharmacol 33 (1999) 301-308.
- Milan C, Valentina Pavic, Maja Molnar, Bojansarkanj, Elizabeta Has-Schon. 2Design and synthesis of some new 1,3,4-thiadiazines with coumarin moieties and their antioxidative and antifungal activity. Molecules 19 (2014) 1163-1177.
- Sarkanj B, Molnar M, Cacic M, Gille L. 4-Methyl-7-hydroxycoumarin antifungal and antioxidant activity enhancement by substitution with thiosemicarbazide and thiazolidinone moieties. Food Chem 139 (2013) 488-495.
- Novikova AP, Perova NM, Chupakhin ON. Synthesis and properties of functional derivatives of 1,3,4-thiadiazines and condensed systems based on these compounds. Khim Geterot Soedin 11(1991) 1443-1457.