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Mini-Reviews in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Mini-Review Article

Antimicrobial Activities of Various Thiazine Based Heterocyclic Compounds: A Mini-Review

Author(s): Mohammad Asif*, Mohd. Imran and Abida

Volume 19, Issue 2, 2022

Published on: 29 June, 2021

Page: [166 - 172] Pages: 7

DOI: 10.2174/1570193X18666210629102447

Price: $65

Abstract

Heterocyclic compounds play a vital role in the development of novel compounds because of their diverse pharmacological activities. Thiazine is a six-membered heterocyclic moiety. Various thiazine derivatives were synthesized or isolated from natural sources like plants and animals. Thiazine derivatives have varieties of pharmacological activities such as antimicrobial, antibacterial, antifungal, antiviral, anti-inflammatory, anticoagulant, anticancer, antihypertensive, and other useful biological as well as chemical applications. In the therapy of antimicrobial infections, new antimicrobial agents are needed because current antimicrobials have developed drug resistance. So, we discussed some thiazine derivatives, which exhibited antimicrobial activity.

Keywords: Heterocyclic, thiazine derivatives, antimicrobial agents, biologically active compounds, organic chemistry, alkaloids.

Graphical Abstract

[1]
Gupta, R.R.; Kumar, M.; Gupta, V. Heterocyclic Chemistry; Springer-Verlag: Germany, 1998, Vol. 1, .
[http://dx.doi.org/10.1007/978-3-642-72276-9]
[2]
Gupta, R.R.; Kumar, M.; Gupta, V. Heterocyclic Chemistry; Springer-Verlag: Germany, 1999, Vol. 2, .
[http://dx.doi.org/10.1007/978-3-662-07757-3]
[3]
Sharma, P.K.; Kaur, G. A review on antimicrobial activities of important thiazines based heterocycles. Drug Invention Today, 2017, 9(3), 23-25.
[4]
Sharma, P.K.; Kumar, M. Regioselective one-pot synthesis of 5-chloro-3-methyl-8-trifluoromethyl-4H-1,4-benzothiazines. Hetrocycl. Comm., 2009, 15(2), 127-133.
[5]
Sharma, P.K.; Kaur, G. Antibacterial, antifungal and antioxidant activities of substituted pyrazolylbenzothiazines. Der Pharm. Lett, 2016, 8(11), 79-82.
[6]
Sharma, P.K.; Makkar, R. A review: Thiazines derivatives treated as potential antimicrobial agents. Asian J. Pharm. Clin. Res., 2017, 10(1), 43-46.
[http://dx.doi.org/10.22159/ajpcr.2017.v10i1.115467]
[7]
Maheshwari, M. Synthesis and anti-microbial activity of 1-(6-nitro-2H-benzo[b][1,4] thiazine-3(4h)-ylidene)hydrazine-1, 1-dioxide derivatives. Int. J. Pharm. Pharm. Sci., 2016, 8(10), 178-182.
[http://dx.doi.org/10.22159/ijpps.2016v8i10.13673]
[8]
Sharma, P.K.; Kaur, C. Antifungal, antibacterial and antioxidant activities of substituted morpholinylbenzothiazine. Der Pharm. Lett., 2016, 8(11), 140-142.
[9]
Prakash, N.; Ingarsal, N. A novel bromonaphthyl based 2-amino-1, 3-thiazines: Synthesis, characterization with in vitro antimicrobial screening research. J. Chem. Sci., 2015, 5(7), 8-11.
[10]
Sharma, P.K.; Kumar, M. Synthesis of bioactive substituted pyrazolylbenzothiazinones. Res. Chem. Intermed., 2015, 41(9), 6141-6148.
[http://dx.doi.org/10.1007/s11164-014-1727-1]
[11]
Sharma, P.K. Antimicrobial activities of substituted 2-aminobenzothiazoles. J. Chem. Pharm. Res., 2015, 7(3), 819-822.
[12]
Sharma, P.K. Morpholinylbenzothiazine consider as bioactive compound. Der Pharm. Lett., 2016, 8(4), 86-90.
[13]
Sharma, P.K. Synthesis and antimicrobial activities of substituted phenylthioureas. J. Chem. Pharm. Res., 2015, 7(2), 133-139.
[14]
Sharma, P.K. Synthesis and antimicrobial studies of fused hetero cycles pyrimidobenzothiazoles. J. Chem. Pharm. Res., 2015, 7(1), 710-714.
[15]
Sharma, P.K. Antibacterial, antifungal and antioxidant activities of substituted 4H-1, 4-benzothiazines. Pharma Chem., 2016, 8(11), 156-159.
[16]
Deshmukh, R. Synthesis, structural study and biological evaluation of 1,3-thiazine. Der Chem. Sin., 2015, 6(3), 59-63.
[17]
Ali, T.E.; El-Kazak, A.M. Synthesis and antimicrobial activity of some new 1,3-thiazoles, 1,3,4-thiadiazoles, 1, 2, 4-triazoles. Eur. J. Chem., 2015, 1(1), 6-11.
[http://dx.doi.org/10.5155/eurjchem.1.1.6-11.12]
[18]
Yamanouchi, K.; Yamada, S. An efficient one-pot synthesis of pyrimido[2,1-b][1,3] thiazine derivatives by reaction of avtivated acetylene, thiourecils and isocyanides. J. Mol. Struct., 2015, 1083, 450-459.
[19]
Babu, K.; Pitchai, P. Synthesis and microbial studies of novel 1, 3-thiazine compounds bearing schiff base moiety. Pharma Chem., 2015, 7(10), 89-92.
[20]
Ghoneim, A.A.; Ragab, I. Cycloaddition involving activated isothiocyanate: Synthesis and antimicrobial activities of thiazine, pyrimidine and pyridine derivatives. Inter. J. Chem. Pharm. Sci., 2015, 3(4), 1637-1342.
[21]
Prakash, N.; Ingarsal, N. An efficient synthesis with antimicrobial screening of N-methyl derivative of 4-(2-bromonaphthalen-6-yl)-6-aryl-6H-1,3-thiazin-2-amines. Pharma Chem., 2015, 7(10), 246-250.
[22]
Ghoneim, A.A.; Bdelaziz, S. Synthesis and antimicrobial activities of some thieno [3, 2-d] [1, 3] thiazine nucleosides derivatives. Eur. J. Chem., 2014, 5(3), 397-401.
[http://dx.doi.org/10.5155/eurjchem.5.3.397-401.999]
[23]
Czarny, A.; Zaczyńska, E.; Jeleń, M.; Zimecki, M.; Pluta, K.; Morak-Młodawska, B.; Artym, J.; Kocięba, M. Antimicrobial properties of substituted quino[3,2-b]benzo[1,4]thiazines. Pol. J. Microbiol., 2014, 63(3), 335-339.
[http://dx.doi.org/10.33073/pjm-2014-044] [PMID: 25546944]
[24]
Beena, K.P. Synthesis, characterization and evaluation of some 1, 3 thiazine derivatives as possible antimicrobial agents. Am. J. Pharm. Tech. Res., 2013, 3(4), 2249-3387.
[25]
Rathod, A.K. Microwave-assisted synthesis of some new benzothiazines derivatives and their antimicrobial activity. Int. J. Pharm. Sci. Rev. Res., 2013, 18(2), 47-49.
[26]
Ganorkar, R.P.; Parhate, R. Synthesis, characterization and antibacterial activities of some new bromo/nitro 1,3-thiazenes. Rasayan J. Chem., 2013, 6, 65.
[27]
Suloeva, M.; Yure, E.; Petrova, E.; Gutcaits, M. Synthesis and antimicrobial activity of new triazolopyridinyl phenothiazines. Chem. Heterocycl. Compd., 2001, 37, 872.
[http://dx.doi.org/10.1023/A:1012455709358]
[28]
Didwagh, S.S.; Piste, P.B.; Burungale, A.S.; Nalawade, A.M. Synthesis and antimicrobial evaluation of novel 3-(4, 6-diphenyl-6H-1,3-thiazin-2-yl)-2-(4-methoxyphenyl) thiazolidin-4-one derivatives. J. Appl. Pharm. Sci., 2013, 3(11), 122.
[29]
Damanjit, C.S. Synthesis and biological evaluation of 1,3-thiazines-A review. Pharmacophore, 2013, 4(3), 70-88.
[30]
Dabholkar, V.V.; Karekar, A.; Shinde, N.B.; Naik, P. Novel Spiro oxazoles containing triazolothiadiazines, thiadiazines and thiazines-Synthesis, characterization and biological evaluation. J. Chem. Biol. Phys. Sci., 2013, 3(3), 1690-1696.
[31]
Jupudi, S.; Rao, P.V. An overview on versatile molecule: 1, 3-thiazines. Asian J. Res. Pharm. Sci., 2013, 3(4), 170-177.
[32]
Govindan, S. Synthesis, characterization and biological studies of some 3, 5-diaryl-tetrahydro-N-formyl-1, 4-thiazine-1, 1-dioxide. J. Chem. Pharm. Res., 2013, 5(1), 99-103.
[33]
Valliappan, R. Synthesis, characterization and biological studies of some 3, 5-diaryltetrahydro-N-ethoxycarbonyl-1, 4-thiazine-1, 1-dioxide. J. Appl. Chem., 2013, 2(2), 137-142.
[34]
Ram, S.G.; Parhate, V.V. Synthesis, charecterization and antibacterial activities of some new bromo/nitro 1, 3-thiazines. Rasayan J. Chem., 2013, 6, 65-67.
[35]
Rathore, M.M.; Rajput, P.R. Synthesis and antimicrobial activities of some bromo-substituted-1, 3-thiazines. Int. J. Res. Pharm. Biomed. Sci., 2013, 4, 59-62.
[36]
Gahtori, P.; Ghosh, S.K. Design, synthesis and SAR exploration of hybrid 4-chlorophenylthiazolyl-s-triazine as potential antimicrobial agents. J. Enzyme Inhib. Med. Chem., 2012, 27(2), 281-293.
[http://dx.doi.org/10.3109/14756366.2011.587418] [PMID: 21657948]
[37]
Sharma, P.K.; Kumar, M.; Vats, S. Synthesis and antimicrobial activity of morpholinyl/piperazinylbenzothiazines. Med. Chem. Res., 2012, 21(8), 2072-2078.
[http://dx.doi.org/10.1007/s00044-011-9732-z]
[38]
Farooque, H.; Zulfequar, H. Synthesis and antimicrobial screening of some 1,3-thiazines. J. Chem. Pharm. Res., 2012, 4, 2263-2267.
[39]
Banda, G.; Hipparagi, S.M.; Ramjith, U.S.; Jacob, C.M. The synthesis of thiazine derivatives of fluoro, chloro benzimidazole by the microwave induced reaction and screened for their antibacterial and analgesic activity. Inter. J. Res. Pharm. Sci., 2012, 2(3), 146-158.
[40]
Gayathri, B.; Jacob, C.M. Microwave assisted synthesis of fluoro, chloro 2-substituted benzimidazole thiazine derivatives for antibacterial and analgesic activities. Inter. J. Res. Pharm. Sci., 2012, 2(3), 146-158.
[41]
Haider, F.H. Synthesis and anti-microbial screening of some 1, 3 thiazine derivatives. J. Chem. Pharm. Res., 2012, 4(4), 2263-2267.
[42]
Kruithof, A.; Ploeger, M.L.; Janssen, E.; Helliwell, M.; de Kanter, F.J.; Ruijter, E.; Orru, R.V. Multicomponent synthesis of 3,6-dihydro-2H-1,3-thiazine-2-thiones. Molecules, 2012, 17(2), 1675-1685.
[http://dx.doi.org/10.3390/molecules17021675] [PMID: 22318323]
[43]
Dipansu, G.S.; Mander, B.P. Synthesis, characterization and biological evaluation of some novel 4, 6-disubstituted-1, 3-thiaizne derivatives for their antibacterial activity. Inter. J. Health Pharm. Sci., 2012, 1(1), 27-33.
[44]
Naushad, E.; Panugonda, R. Synthesis of N-nitroso-2, 6-dicarboxy-3, 5 diaryltetrahydro-1, 4 thiazine-1, 1 dioxides. Med. Chem. Res., 2012, 21, 2056-2063.
[http://dx.doi.org/10.1007/s00044-011-9729-7]
[45]
Elarfi, M.J.; Al-Difa, H.A. Synthesis of oxazine, thiazine and isoxazole and their antibacterial activities. Sci. Rev. Chem. Comm., 2012, 2(2), 103-107.
[46]
Shweta, S.; Deepika, Y. Synthesis and biological activity of phenothiazine derivatives. Int. J. Res. Ayurveda Pharm., 2011, 2(4), 1130-1137.
[47]
Bhangale, L.P.; Sawant, R.L.; Wadekar, J.B. Topliss modified approach for design and synthesis of 1, 3 thiazines as antimicrobials. Inter. J. Drug Design Dis, 2011, 2, 637-641.
[48]
Balenkova, E.S.; Nenajdenko, V.G. Preparation of α,β-unsaturated trifluoromethyl ketones and their application in the synthesis of heterocycles. ARKIVOC, 2011, 1, 246-328.
[49]
Kumar, B.K.; Devi, K.V.; Gupta, P.R.; Kranthi, G.; Ramakrishna, C.; Sankaraiah, P.; Kumar, C.S. Synthesis and biological evaluation of different thiazine derivatives. J. Pharm. Res., 2011, 4(1), 274-275.
[50]
Sharma, P.K.; Fogla, A. Synthesis and antimicrobial activity of structurally flexible heterocycles with the 1, 4-thiazine heterosystem. Res. Chem. Intermed., 2011, 37(8), 1103-1111.
[http://dx.doi.org/10.1007/s11164-011-0320-0]
[51]
Rathod, S.P.; Rajput, P.R. Synthesis and antibacterial activities of chloro-substituted-1, 3-thaizines. Rasayan J. Chem., 2010, 3(2), 363-367.
[52]
Kadhim, M.A. Synthesis and chemical characterization of some novel azachalcones compounds and evaluation of their biological activity. J. Univ. Anbar. Pure. Sci., 2010, 4(3), 40-43.
[53]
Yavari, I.; Hossaini, Z.Ph. 3P-mediated one-pot synthesis of functionalized 3, 4-dihydro-2H-1, 3-thiazines from N, N′-dialkylthioureas and activated acetylenes in water. Monatsh Chem. Chem. Mon., 2010, 141(2), 229-232.
[http://dx.doi.org/10.1007/s00706-009-0247-y]
[54]
Suresh, C.H.; Jayaveera, K.N. Synthesis of 4-(2′-substituted benzothiazoles)-5-mercapto-3-(substituted)-1, 2, 4-traizole derivatives for possible antimicrobiological activities. Res. J. Pharm. Biol. Chem. Sci., 2010, 1(4), 635-640.
[55]
Gudadhe, S.K. Iodo flavonoid in the synthesis of heterocyclic compounds. Amravati Univ. J., 2010, 3, 363-367.
[56]
Vyas, R.; Choudhary, P.; Sharma, H.; Varma, B.L. Synthesis and antimicrobial activity of thiazine derivative. Indian J. Heterocycl. Chem., 2008, 17, 237-239.
[57]
Thanusu, J.; Kanagarajan, V.; Gopalakrishnan, M. Synthesis, spectral characterization, and in vitro antibacterial and antifungal activities of novel 1,3-thiazine-2-amines comprising morpholine nucleus. J. Enzyme Inhib. Med. Chem., 2010, 25(6), 756-764.
[http://dx.doi.org/10.3109/14756360903389898] [PMID: 20590407]
[58]
Abbas, E.M.; Farghaly, T.A. Synthesis, reactions, and biological activity of 1, 4- benzothiazine derivatives. Monatsh. Chem. Chem. Mon., 2010, 141(6), 661-667.
[http://dx.doi.org/10.1007/s00706-010-0312-6]
[59]
Sharma, P.K.; Kumar, M. Synthesis and antimicrobial activity of 2H-pyrimido[2,1-b] benzothiazol-2-ones. Res. Chem. Intermed., 2010, 36(8), 985-993.
[http://dx.doi.org/10.1007/s11164-010-0211-9]
[60]
Gupta, S.; Ajmera, N.; Meena, P.; Gautam, N.; Kumar, A.; Gautam, D.C. Synthesis and antimicrobial activity of thiazine derivatives. Jordan J. Chem., 2009, 4, 209.
[61]
Matysiak, J. Synthesis, antiproliferative and antifungal activities of some 2-(2,4-dihydroxyphenyl)-4H-3,1-benzothiazines. Bioorg. Med. Chem., 2006, 14(8), 2613-2619.
[http://dx.doi.org/10.1016/j.bmc.2005.11.053] [PMID: 16377195]
[62]
Rathore, B.S.; Kumar, M. Synthesis of 7-chloro-5-trifluoro-methyl/7-fluoro/7-trifluoromethyl-4H-1,4-benzothiazines as anti-microbial agents. Bioorg. Med. Chem., 2006, 14(16), 5678-5682.
[http://dx.doi.org/10.1016/j.bmc.2006.04.009] [PMID: 16650998]
[63]
Macchiarulo, A.; Costantino, G.; Fringuelli, D.; Vecchiarelli, A.; Schiaffella, F.; Fringuelli, R. 1,4-Benzothiazine and 1,4-benzoxazine imidazole derivatives with antifungal activity: a docking study. Bioorg. Med. Chem., 2002, 10(11), 3415-3423.
[http://dx.doi.org/10.1016/S0968-0896(02)00263-8] [PMID: 12213454]
[64]
Fringuelli, R.; Schiaffella, F.; Vecchiarelli, A. Antifungal and immunomodulating activities of 1,4-benzothiazine azole derivatives. review J. Chemother., 2001, 13(1), 9-14.
[http://dx.doi.org/10.1179/joc.2001.13.1.9] [PMID: 11233807]

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