NOVEL SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF THIAZINO-OXAZINE DERIVATIVES
Abstract
In the designing and synthesis of new heterocyclic compounds, containing two different pharmacophores, we have carried out new series of 3-(4-chlorophenyl)-4-methylidene-4,8-dihydro-2H,5H-1,3-thiazino[5,4-e]-1,3-oxazine-2,5,7(3H)-trione derivatives (5a-5k) in good yields from the cyclization of 5-[(1E)-N- (4-chlorophenyl) ethanimidoyl] -4-hydroxy- 2H-1,3- thiazine-2,6(3H)-dione derivatives (4a-4k) with triphosgene. All the synthesized compounds (5a-5k) were confirmed by spectral analysis. The synthesized compounds (5a-5k) were screened in vitro for their antibacterial activities against S. subtilis (gram positive) and E. coli. (gram negative) while antifungal activity against C. albicans by cup plate method. Some of the products of series were found to have quite good activities as compared to the standard drug streptomycin and flucanozole.
Keywords:
Thiazine, Oxazine, Triphosgene, Antibacterial and antifungal activity.DOI
https://doi.org/10.25004/IJPSDR.2018.100401References
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2. Prasad D, Kumar A, Shukla KP, Nath M. Design, synthesis and antimicrobial evaluation of novel 2-aryl-thiazolidin-4-one derivatives. Org Med Chem Lett. 2011; 1:4.
3. Goossens H. European Status of Resistance in Nosocomial Infections. Chemotherapy. 2005; 51: 177-181.
4. Mathew BP, Nath M. Recent approaches to antifungal therapy for invasive mycoses. Chem Med Chem. 2009; 4:310-323.
5. Temple C, Wheeler GP, Comber RN, Elliot RD, Montgomery JA. Synthesis of potential anticancer agents. Pyrido [4, 3-b][1, 4] oxazines and pyrido [4, 3-b][1, 4] thiazines . J Med Chem. 1983; 26: 1614-1619.
6. Malinka W, Kaczmarz M, Filipek B, Sepa J, Gold B. straight forward synthesis and structure of unprecedented iminium salts of dihydropyrido[3,2-e][1,3]thiazines. Farmaco. 2002; 57: 737-746.
7. Rathore SB, Rathore BS, Kumar M. Design and synthesis of 4H-1, 4-benzothiazines containing thiazole ring system for use as potential biopharmaceuticals. Res Chem Intermed. 2006; 32(7): 647-651.
8. El-Gaby SA, Saleh NM, Micky JA, Ammar Y, Mohamed AS. Biological Evolution of Some Novel Thiazol, Thiazolo[3,2-a]pyridine and Thiazolo[3,2:1,6] pyridine Derivatives containing Diphenyl Moiety As Antimicrobial Agents. Phosphorus Sulphur Silicon. 2006; 181: 1655-1663.
9. Kanagarajan V, Gopalakrishnan M. One-pot synthesis and in vitro microbiological evaluation of pyrimidinyl thiazolidinones catalyzed by activated fly ash in dry media. Pharm Chem J. 2011; 45(4):248-256.
10. Zhang LQ, Gun LP, Wei CX, Ding XQ, Quan ZS. Application and Mechanisms of Bacillus subtilis in Biological Control of Plant Disease Chem Pharm Bull. 2010; 58(3): 326-331.
11. Zebardast T, Zarghi A, Daraie B, Hedayati M, Dadrass OG. Design and synthesis of 3-alkyl-2-aryl-1,3-thiazinan-4-one derivatives as selective cyclooxygenase (COX-2) inhibitors. Bioorg Med Chem. 2009; 19: 3162-3165.
12. Tozkoparan B, Aktay G, Yesilada E, Synthesis of some 1,2,4-triazolo[3,2-b]-1,3-thiazine-7-ones with potential analgesic and anti-inflammatory activities. Farmaco. 2002; 57:145.
13. Barazarte A, Camacho J, Dominguez J, Lob OG, Gamboa N, Roderigues J, Capparelli MV. Synthesis, antimalarial activity, structure-activity relationship analysis of thieno- [3,2-b]benzothiazine S,S-dioxide analogs. J Bioorg Med Chem. 2008; 16: 3661-3674.
14. Kalirajan R, Kulshrestha V, Sankar S. Docking studies, synthesis, characterization of some novel oxazine substituted 9-anilinoacridine derivatives and evaluation for their antioxidant and anticancer activities as topoisomerase II inhibitors. Eur J Med Chem. 2012; 56: 217-224.
15. Fensome A, Bender R, Chopra R, Cohen J, Collins MK, Hudak V, Malakian K, Lochead S. Synthesis and structure-activity relationship of novel 6-aryl-1,4-dihydrobenzo[d][1,3]oxazine-2-thiones as progesterone receptor modulators leading to the potent and selective nonsteroidal progesterone receptor agonist tanaproget. J Med Chem. 2005; 48: 5092-5095.
16. Takasu K, Shimogama T, Satoh C, Kaiser M, Brun R, Ihara M. Synthesis and antimalarial property of orally active phenoxazinium salts. Med Chem Res. 2011; 20: 1147-1153.
17. Akhter M, Habibullah S, Hasan SM, Alam MM, Akhter N, Shaquiquzzaman M. Synthesis of some new 3,4-dihydro-2H-1,3-benzoxazines under microwave irradiation in solvent-free conditions and their biological activity. Medicinal Chemistry Research. 2011; 20(8):1147-1153.
18. Velikorodov AV, Urlyapova NG, Daudova AD. Synthesis and antimycobacterial activity of carbamate derivatives of 1,2-oxazine. Pharm Chem J 2006; 40(7):32-34.
19. Wael SI, Abou E, Hashem AI. Utilization of 2(3H)-Furanone Bearing a Pyrazolyl Side Chain for the Construction of a Variety of Thiazolidinone Derivatives. Med Chem Res. 2013; 22: 2005-2013.
20. Matralis AN, Katselou MG, Nikitakis A, Kourounakis AP. Novel Benzoxazine and Benzothiazine Derivatives as Multifunctional Antihyperlipidemic Agents.J Med Chem 2011; 54: 5583–5591.
21. Mathew BP, Kumar A, Sharma S, Shukla PK, Nath M. An eco-friendly synthesis and antimicrobial activities of dihydro-2H-benzo- and naphtho-1,3-oxazine derivatives. Eur J Med Chem .2010; 45:1502-1507.
Published
01-07-2018
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“NOVEL SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF THIAZINO-OXAZINE DERIVATIVES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 10, no. 4, July 2018, pp. 206-12, https://doi.org/10.25004/IJPSDR.2018.100401.
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How to Cite
“NOVEL SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF THIAZINO-OXAZINE DERIVATIVES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 10, no. 4, July 2018, pp. 206-12, https://doi.org/10.25004/IJPSDR.2018.100401.
