Dhanaja Kotte, Kumaraswamy Gullapelli, Brahmeshwari Gavaji, Ramchander Merugu, Ravichander Maroju, Muralikrishna Patwari
Dhanaja Kotte1, Kumaraswamy Gullapelli2*, Brahmeshwari Gavaji1, Ramchander Merugu3, Ravichander Maroju2, Muralikrishna Patwari4
1Department of Chemistry, Kakatiya University, Warangal, India - 506009.
2Department of Chemistry, Mahatma Gandhi Institute of Technology, Hyderabad, India - 500075.
3Department of Biochemistry, Mahatma Gandhi University, Nalgonda, India, 508254.
4Department of Chemistry, Chaitanya Bharathi Institute of Technology, Hyderabad, India, 500075.
Volume - 13,
Issue - 10,
Year - 2020
A series of new triazinane-2-thiones and imino thiazolidinone-4-ones were synthesized from 2-acetyl benzimidazole (1). Treatment of compound 1 with urea in the presence of I2 furnishes compound (2), which on reaction with Aryl isothiocyanateaffords the compound (3), which undergoes Cyclic condensation of classical Mannich amino methylation of compound 3with formaldehyde and methyl amine produces corresponding triazinane -2-thiones (4), whereas cyclic condensation of compound 3 with cholroacetic acid to furnish the corresponding iminothiazolidinones-4-ones(5).the chemical structures of the newly synthesized compounds have been characterized on the basis of spectral (IR,1HNMR and Mass) and analytical data. The title compounds were evaluated for their anti-inflammatory activity and molecular docking studies. The docking studies are supporting anti-inflammatory activity exhibiting high inhibition constant and binding energy.
Cite this article:
Dhanaja Kotte, Kumaraswamy Gullapelli, Brahmeshwari Gavaji, Ramchander Merugu, Ravichander Maroju, Muralikrishna Patwari. An Efficient Synthesis, Anti inflammatory activity and Molecular Docking Studies of new Triazinanes and Iminothiazolidinones. Research J. Pharm. and Tech. 2020; 13(10):4743-4750. doi: 10.5958/0974-360X.2020.00836.7
1. Jingpei H, Huawen H, Min Z, Xiaohong H, Min C, Dongchu C, Jinwen L, Guifeng, X, Yang W, and Zhongliu W. A mini review of the synthesis of poly-1,2,3-triazole-basedfunctionalmaterials. RSCAdv.2017; 7: 2281-87. DOI: 10.1039/C6RA 27012C.
2. Arjmand F, Mohani B and Ahmad S. Synthesis, antibacterial, antifungal activity and interaction of CT-DNA with a new benzimidazole derived Cu (II) complex. Eur. J Med. Chem. 2005: 4: 1103-10. DOI:10.1016/j.ejmech.2005.05.005.
3. Galal SA, Abdelsamie AS, Rodriguez ML and Kerwin SM and El Diwani H.I. Synthesis and studying the antitumor activity of novel 5-(2-methylbenzimidazol-5-yl)-1,3,4- oxadiazole-2(3H)-thiones. Eur. J. Chem. 2010; 1: 67-72. DOI: 10.5155 / eurjchem.1.2.67-72.1
4. Wardakhan WW, Samir EM, El-Arab EE. Synthesis and cytotoxicity of novel thiophene, pyran and pyridine derivatives. Bull. Chem. Soc. Ethiop 2018; 32: 259-70. DOI: 10.4314/ bcse. v32i2.7
5. Gullapelli K, Thupurani M, Brahmeshwari G. Synthesis and anti bacterial activityof2-(4-aminophenyl) benzimidazole based pyrimidine derivatives. Int J Pharm Biol Sci 2014; 5:682–90.
6. John A. Joule. Natural Products Containing Nitrogen Heterocycles Some Highlights 1990- 2015. Advances in Heterocyclic Chemistry 2016:119: 81-06. DOI: 10.1016/ bs. aihch.2015.10.005.
7. Rajiv D, Suman Shrivastava, Sonwane SK, and Srivastava SK. Pharmacological Significance of Synthetic Heterocycles Scaffold. A Review, Advan. Biol. Res 2011; 5 (3): 120-144, 2011.
8. Nguyen PT, Baldeck. JD, Olsson J, Marquis RE. Antimicrobial actions of benzimidazole against oral streptococci. Oral Microbiol Immunol 2005:93–00.DOI:10.1111/j.1399-302X.2004.00197.x.
9. Hasan K, Riza D, Nihat S, Gunal S. Synthesis of some benzimidazole derivatives and their antibacterial and antifungal activities. Asian J Chem 2009; 21:6181–89.
10. Dixit S, Kumar Sharma P, Kaushik N. Synthesis of novel benzimidazole derivatives: as potent analgesic agent. Med Chem Res 2013; 22: 900–04. DOI: 10.1007/s00044-012-0083-1.
11. Gulapelli K, Brahmeshwari G, Ravichander M, Uma K. Synthesis, antibacterial and molecular docking studies of new benzimidazole derivatives. Egyptian J. Basic Appl. Sci2017; 4; 303-09. DOI: 10.1016/j.ejbas.2017.09.002.
12. Chunhui Z, Jaeki M, Zhigang L, Anne Y, Heather D, Tian G, Young-T Ch and Neville R. K. Synthesis and biological evaluation of novel 1,3,5-triazine derivatives as antimicrobial agents. Bio Org and Med Chem Lett 2008;18(2) :1308–1311. DOI: 10.1016/ j.bmcl. 2008 .01.031.
13. Brzozowski Z, Saczewski F and Gdaniec M. Synthesis, structural characterization and antitumor activity of novel 2,4-diamino-1,3,5-triazine derivatives. Eur. J. Med. Chem. 2000; 35:1053–64, (2000). DOI: 10.1016/S0223-5234(00)01194-6.
14. Jian Liu, Qun Zeng, Yalin Zhang, and Chaoyang Zhang. Limited-Sample Coarse-Grained Strategy and Its Applications to Molecular Crystals: Elastic Property Prediction and Nano indentation Simulations of 1,3,5-Trinitro-1,3,5-triazinane. J. Phys. Chem. C 2016; 120:15198−208. DOI: 10.1021/jp9624865.
15. Hsiao-Fan Ch, Shang-Jung Y, Zhen-Han T, Wen-Yi H, Ting-C W and Ken-Tsung W. 1,3,5-Triazine derivatives as new electron transport–type host materials for highly efficient green phosphorescent OLED. J Mater Chem 2009;19: 8112–18. DOI:10.1039/B913423A.
16. Ziemowit P, Marta D, Olivier M, Rémi M, Piotr M, Marek S, Katarzyna M and Frédéric P. Linear and Third-1 Order Nonlinear Optical Properties of Novel Triazobenzene-1, 3, 5-triazinane-2,4, 6-triones (Isocyanurates) Derivatives. Chem Plus Chem, 2017; 82: 1372.DOI: 10.1002/cplu.201700396
17. Vicini P, Geronikaki A, Anastasia K, Incerti M, Zani F. Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-thiazolidinones. Bioorg. Med. Chem. 2006; 14: 3859-64.DOI: 10.1016/j.bmc.2006.01.043.
18. Gullapelli K and G. Brahmeshwari. Synthesis and antifungal activity of 3-(4-(4-(1H) benzo[d] imidazole 2-yl) phenylamino) thiazol-2-yl)-2-phenyl thiazolidin-4-one derivatives. Int. J. Chem. Sci 2014;12(3): 885-93.
19. Singh S P, Parmar S S, Raman K and Stenberg VI. Chemistry and biological activity of thiazolidinones. Chem. Rev1981; 81: 175-203. DOI: 10.1021/ cr000 42a003.
20. Kasmi-Mir S, Djafri A, Paquin L, Hamelin J and Rahmouni M. One-Pot Synthesis of 5-Arylidene-2-Imino-4-Thiazolidinones under Microwave Irradiation. Molecules. 2006; 11: 97. DOI: 10.3390/11080597.
21. Rosaria O, Rosanna M, Maria Letizia B and Giuseppe B. 5-Arylidene-2-imino-4-thiazolidinones: Design and synthesis of novel anti-inflammatory agents. Bioorg. Med. Chem. 2005; 13: 4243–52. DOI: 10.1016 / j.bmc. 2005.04.058.
22. Firouz M M and Leila H.A Novel Synthesis of Some 2-Imino-4-thiazolidinone Derivatives. J. Heterocyclic Chem2007;44: 35-38.
23. Souad KM, Ayada D, Ludovic P, Jack Hamelin and Mustapha R. One-Pot Synthesis of 5-Arylidene-2-Imino-4-Thiazolidinones under Microwave Irradiation. Molecules 2006; 11: 597-02. DOI: 10.3390/11080597.
24. Havaldar F H and Mishra SKJ. Synthesis of some azetidin-2-ones and thiazolidin-4-ones as potential antimicrobial agents. Indian J. Heterocycl Chem. 2004; 13:197- 200.
25. Zask A, Jirkovsky I, Nowicki JW and Mc Caleb ML. synthesis and antihyperglycemic activity of novel 5-(naphthalenylsulfonyl)-2,4- thiazolidinediones. J. Med. Chem. 1990 ; 33 (5): 1418-23. DOI:10.1021/jm00167a022.
26. Appalanaidu K, Rajesh K, Dadmal T L, Vishnu Sravan B , Ravindra MK , Chitta Ranjan P. Synthesis and biological evaluation of novel 2-imino-4- thiazolidinone derivatives as potent anti-cancer agents. Bioorg. Med. Chem. Lett.2016; 26:5361–68. DOI: 10.1016/j.bmcl.2016.08.013.
27. Chavan A A and Pai NR .Synthesis and antimicrobial screening of 5-arylidene-2-imino-4-thiazolidinones. ARKIVOC. 2007; (xvi): 148.
28. Brahmeshwari G, Kishore G . Synthesis and antimicrobial activity of benzimidazolyl oxazolyl thiazolidin-4-ones and azetidin -2-ones. Indian J Chem 2018, 57B, 1042-1050
29. Sangita Ch, Priyanka Ch, Protapaditya D, Bhattacharya S. Evaluation of Anti-inflammatory Effect of Ashwagandha: A Preliminary Study in vitro. Pharmacognosy Journal. 2012;4: 47-49.
30. Bikadi Z, Demko L and Hazai E. Functional and structural characterization of a protein based on analysis of its hydrogen bonding network by hydrogen bonding plot, Arch. Biochem. Biophys. 2007; 461: 225-34. Arch. Biochem. Biophys.2007; 461: 225.