Synthesis, spectral characterization, and in vitro antibacterial and antifungal activities of novel 1,3-thiazine-2-amines comprising morpholine nucleus

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 25, Issue 6, 2010, Pages 756-764

  Thanusu, J ^a   Kanagarajan, V ^a   Gopalakrishnan, M ^a  

^a ANNAMALAI UNIVERSITY   (India)

Author keywords

Antibacterial activity; Antifungal activity; Morpholino thiazines; Synthesis; Thiourea

Indexed keywords

4 (4 MORPHOLINOPHENYL) 6 (3 NITROPHENYL) 6H 1,3 THIAZIN 2 AMINE; 4 (4 MORPHOLINOPHENYL) 6 PHENYL 6H 1,3 THIAZIN 2 AMINE; 6 (3 CHLOROPHENYL) 4 (4 MORPHOLINOPHENYL) 6H 1,3 THIAZIN 2 AMINE; 6 (3 FLUOROPHENYL) 4 (4 MORPHOLINOPHENYL) 6H 1,3 THIAZIN 2 AMINE; 6 (4 BROMOPHENYL) 4 (4 MORPHOLINOPHENYL) 6H 1,3 THIAZIN 2 AMINE; 6 (4 CHLOROPHENYL) 4 (4 MORPHOLINOPHENYL) 6H 1,3 THIAZIN 2 AMINE; 6 (4 FLUOROPHENYL) 4 (4 MORPHOLINOPHENYL) 6H 1,3 THIAZIN 2 AMINE; 6 (4 METHOXYPHENYL) 4 (4 MORPHOLINOPHENYL) 6H 1,3 THIAZIN 2 AMINE; 6 (4 METHYLPHENYL) 4 (4 MORPHOLINOPHENYL) 6H 1,3 THIAZIN 2 AMINE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; THIAZINAMIUM; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; BACILLUS SUBTILIS; BACTERIAL STRAIN; DRUG SYNTHESIS; ESCHERICHIA COLI; MUCOR; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; RHIZOPUS; STAPHYLOCOCCUS AUREUS; VIBRIO CHOLERAE;

AMINES; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACILLALES; DRUG DESIGN; FUNGI; GRAM-NEGATIVE BACTERIA; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MORPHOLINES; THIAZINES;

BACTERIA (MICROORGANISMS); MUCOR; RHIZOPUS; STAPHYLOCOCCUS AUREUS; VIBRIO CHOLERAE;

EID: 78149451803     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756360903389898     Document Type: Article

References (30)

1. Koketsu M, Tanaka K, Takenaka Y, Kwong CD, Ishihara H. Synthesis of 1,3- thiazine derivatives and their evaluation as potential antimycobacterial agents. Eur J Pharm Sci 2002;15:307-10.
2. Kai H, Morioka Y, Tomida M, Takahashi T, Hattori M, Hanasaki K, et al. 2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 2: Orally bioavailable compounds. Bioorg Med Chem Lett 2007;17:3925-9. (Pubitemid 46920938)
3. Kai H, Morioka Y, Murashi T, Morita K, Shinonome S, Nakazato H, et al. 2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 1: Discovery of CB2 receptor selective compounds. Bioorg Med Chem Lett 2007;17:4030-4. (Pubitemid 46920922)
4. Barros-García FJ, Bernalte-García A, Lozano-Vila AM, Luna-Giles F, Pariente JA, Pedrero-Marín R, et al. Synthesis, structural characterization and influence on the phagocytic activity of human neutrophils of thiazoline and thiazine derivative ligands and their zinc(II) complexes. J Inorg Biochem 2006; 100:1861-1870
5. Galanski ME, Erker T, Handler N, Lemmens-Gruber R, Kamyar M, Studenik CR. Studies on the chemistry of thienoanellated O,N- and S,Ncontaining heterocycles. Part 30: Synthesis and pharmacological properties of thieno[2,3-b][1,4]thiazines with potential vasopressin receptor antagonistic activity. Bioorg Med Chem 2006;14:826-36.
6. Malinka W, Kaczmarz M, Filipek B, Sapa J, Glod B. Preparation of novel derivatives of pyridothiazine-1,1-dioxide and their CNS and antioxidant properties. Farmaco 2002;57:737-46.
7. 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; 57:145-52.
8. Loiseau PM, Mettey Y, Vierfond JM. Antifilarial and trypanocidal properties of phenothiazines and related polycyclics as new lead structures. Int J Parasitol 1996;26:1115-17.
9. Das J, Robl JA, Reid JA, Chong-Qing Sun, Misra RN, Brown BR, et al. Dual metalloprotease inhibitors. IV. Utilization of thiazepines and thiazines as constrained peptidomimetic surrogates in mercaptoacyl dipeptides. Bioorg Med Chem Lett 1994;4:2193-8.
10. Skiles JW, Suh JT, Williams BE, Menard PR, Barton JN, Love B, et al. Angiotensin-converting enzyme inhibitors: new orally active 1,4- thiazepine-2,5-diones, 1,4-thiazine-2,5-diones, and 1,4-benzothiazepine- 2,5-diones possessing antihypertensive activity. J Med Chem 1986;29:784-96.
11. 13C NMR spectra of N-substituted morpholines. Eur Pat Appl (1989); EP 334146:28. Chem Abstr 1989;112:178999.
12. Hale JJ, Mills SG, MacCross M, Dorn CP, Finke PE, Budhu RJ, et al. Phosphorylated morpholine acetal human neurokinin-1 receptor antagonists as water-soluble prodrugs. J Med Chem 2000;43:1234-7.
13. Fisher MH, Wyvratt MJ. Morpholine derivatives compositions and uses. US Patent (1991); 5077290:10. Chem Abstr 1991;116:214513.
14. Avramova P, Danchev N, Buyukliev R, Bogoslovova T. Synthesis, toxicological, and pharmacological assessment of derivatives of 2-aryl-4-(3- arylpropyl)morpholines. Arch Pharm 1998;331:342-6.
15. Dorn CP, Hale JJ, MacCross M, Mills SG. Morpholine compounds are prodrugs useful as tachykinin receptor antagonists. US Patent (1997); 5691336:82. Chem Abstr 1997;128:48231.
16. Varma RS, Prakash R, Khan MM, Ali A. 4-Phenyl morpholines as potent antimicrobial agents. Indian Drugs 1986;23:345-9.
17. Misra VS, Singh S, Agarwal R, Chaudhary KC. Substituted morpholines derivatives as potent anti-inflammators. J Chem Soc Pak 1981;3:209-11
18. Agarwal R, Chaudhary KC, Misra VS. Substituted morpholines compounds possessing central nervous system activities. J Chem Soc Pak 1984;6:308-10.
19. Barret GC, Kane VV, Lowe G. Studies related to cephalosporin C. Part I. 3-Hydroxy- and 3-amino-furan-2(5H)-ones. J Chem Soc 1964:783-7.
20. Calaycay JR, Kelly TM, MacNaul KL, McCauley ED, Qi H, Grant SK, et al.Expression and immunoaffinity purification of human inducible nitric-oxide synthase. Inhibition studies with 2-amino-5,6-dihydro-4H- 1,3-thiazine. J Biol Chem 1996;271:28212-19.
21. McCurnin DM, Bassert JM. Clinical Textbook for Veterinary Technicians, 5th ed. Philadelphia, PA: Saunders, 2002.
22. Tandon VK, Maurya HK, Yadav DB, Tripathi A, Kumar M, Shukla PK. Naphtho[2,3-b][1,4]-thiazine-5,10-diones and 3-substituted-1,4-dioxo- 1,4-dihydronaphthalen-2-yl-thioalkanoate derivatives: synthesis and biological evaluation as potential antibacterial and antifungal agents. Bioorg Med Chem Lett 2006;16:5883-7.
23. Parks LW. Metabolism of sterols in yeast. CRC Crit Rev Microbiol 1978;6:301-41.
24. Gopalakrishnan M, Sureshkumar P, Thanusu J, Kanagarajan V. Design, synthesis, characterization, antibacterial and antifungal activities of novel class of 5,7-diaryl-4,4-dimethyl-4,5,6,7-tetrahydropyridino[3,4-d]-1,2,3- selenadiazoles. J Enzyme Inhib Med Chem 2008;23:347-51.
25. Gopalakrishnan M, Thanusu J, Kanagarajan V, Govindaraju R. Design, synthesis and in vitro microbiological evaluation of 6,6-dimethyl-7,9-diaryl- 1,2,4,8-tetraazaspiro[4.5]decan-3-thiones - a new series of "tailor- made" compounds. J Enzyme Inhib Med Chem 2009;24:406-12.
26. Gopalakrishnan M, Thanusu J, Kanagarajan V. Synthesis and biological evaluation of 5,7-diaryl-4,4-dimethyl-4,5,6,7-tetrahydropyridino[3,4-d]- 1,2,3-thiadiazoles. Med Chem Res 2007;16:392-401.
27. Gopalakrishnan M, Sureshkumar P, Thanusu J, Kanagarajan V, Govindaraju R, Jayasri G. A convenient "one-pot" synthesis and in vitro microbiological evaluation of novel 2,7-diaryl-[1,4]-diazepan-5-ones. J Enzyme Inhib Med Chem 2007;22:709-15.
28. Gopalakrishnan M, Sureshkumar P, Thanusu J, Kanagarajan V. Synthesis, spectral analysis, antibacterial and antifungal activities of some 4,6-diaryl- 4,5-dihydro-3-hydroxy-2[H]-indazole - a novel fused indazole derivative. J Enzyme Inhib Med Chem 2008;23:974-9.
29. Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J. Design, "one-pot" synthesis, characterization, antibacterial and antifungal activities of novel 6-aryl-1,2,4,5-tetrazinan-3-thiones in dry media. J Sulfur Chem 2007;28:383-92.
30. Dhar MH, Dhar MM, Dhawan BN, Mehrotra BN, Ray C. Screening of Indian plants biological activity. Part I. Indian J Exp Biol 1968;6:232-47.