SYNTHESIS AND MICROBIOLOGICAL EVALUATION OF 1-(4-METHYL-6-NITRO-2H-BENZO[B] [1,4]THIAZINE-3(4H)-YLIDENE)HYDRAZINE-1,1-DIOXIDE DERIVATIVES

Authors

  • Monika Maheshwari Department of Pharmaceutical Chemistry, B N Institute of Pharmaceutical Sciences, Sevashram, Udaipur, Rajasthan, India.
  • Anju Goyal Department of Pharmaceutical Chemistry, B N Institute of Pharmaceutical Sciences, Sevashram, Udaipur, Rajasthan, India.

DOI:

https://doi.org/10.22159/ajpcr.2017.v10i9.19093

Keywords:

1, 4-Benzothiazines, Sulfones, Hydrazines, Antimicrobial activity

Abstract

 

 Objective: The objective of this work was to synthesize and evaluate antimicrobial properties of 1-(4-methyl-6-nitro-2H-benzo[b][1,4]thiazine- 3(4H)-ylidene)hydrazine-1,1-dioxide derivatives.

Methods: These new compounds were synthesized by methylation in 4-N and reacted with hydrazine derivatives and oxidized at the sulfur atom by 30% hydrogen peroxide to obtain sulfones. All the synthesized compounds were evaluated for antimicrobial activity using the disc diffusion method.

Results: The Fourier transform infrared, 1H nuclear magnetic resonance (NMR), 13CNMR, and mass studies confirm the synthesis of some new 1-(4-methyl- 6-nitro-2H-benzo[b][1,4]thiazine-3(4H)-ylidene)hydrazine-1,1-dioxide derivatives. Compound 6f showed the potent antimicrobial activity.

Conclusion: Result obtained in this research work clearly indicated that the compound 6f having methyl at 2 position and nitro groups at 2′ and 4′ position showed the most potent antimicrobial activity.

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References

Parai MK, Panda G. A covinient synthesis of chiral amino acid derived 3,4-dihydro-2H-benzo[b][1,4]thiazines and antibiotics levofloxacine. Tetrahedron Lett 2009;50:4703-5.

Fringuelli R, Schiaffella F, Utrilla Navarro MP, Milanese L, Santini C, Rapucci M, et al. 1,4-benzothiazine analogues and apoptosis: Structure-activity relationship. Bioorg Med Chem 2003;11(15):3245-54.

Hori M, Kataoka T, Shmizu H, Imai Y. Ring expansion reactions of benzothizolines to benzo thiazine. Chem Pharm Bull 1973;5:27.

Barange DK, Batchu VR, Gorja D, Pattabiraman VR, Tatini LK, Babu JM, et al. Rigioselective construction of six-membered fused heterocyclic rings via Pd/C-mediated C-C coupling followed by iodocyclization strategy: A new entry to 2H-1,2- benzothiazine-1,1-dioxides. Tetrahedron 2007;63:1775-89.

Bakavoli M, Nikpour M, Rahimizadeh M, Saberi MR, Sadeghian H. Design and synthesis of pyrimido[4,5-b][1,4]benzothiazine derivatives, as potent 15-lipoxygenase inhibitors. Bioorg Med Chem 2007;15(5):2120-6.

Dabholkar VV, Gavande RP. Synthesis of pyrazolyl 1,4-benzothiazine derivatives. Heteroletters 2011;1 Suppl 3:255-61.

Saadouni M, Gailane T, Baukhris S, Hassikou A, Habbadi N, Gailane T, et al. Regeoselective synthesis of new variety of 1,4-benzothiazines. Org Commun 2014;7(2):77-84.

Montis SD, Fattuoni C, Cadoni E, Cabiddu MG, Usai M, Cabiddu S. High yield synthesis of 4H-1,4-benzothiazine-1,1-dioxide derivatives. J Heterocycl Chem 2008;45:1445-9.

Schou SC, Hansen HC, Tangmose TM, Boonen HC, Worsaae A, Drabowski M, et al. Synthesis and pharmacological evaluation of 4H-1,4-benzothiazine-2-carbonitrile-1,1-dioxide and N-(2-cyanomethyl sulfonylphenyl)acylamide derivatives as potential activators of ATP sensitive potassium channels. Bioorg Med Chem 2005;13:141-55.

Guarda VL, Perrissin M, Thomasson F, Ximenes EA, Galdino SL, Pitta IR, et al. Synthesis and microbial activity of some 2H-benzo[1,4]thiazin-3-one derivatives. Heterocycl Commun 2000;6:49-54.

Souza AM, Guarda VL, Leite LF, Filho JM, Lima MC, Galdino SL, et al. On application of knoevenagel condensation for the synthesis of benzo thiazine compounds and structural study. Quim Nov 2006;29:1106-9.

Deshmukh MB, Mulik AR, Desal SD. Synthesis of some new 2-methyl-1,4-benzothiazine-3(1H)-one derivatives as potential vasodilators. Eur J Chem 2004;1:206-10.

Hamadi MY, Gupta R, Gupta RR. Synthesis and spectral investigations of fluorinated 4H-1,4-benzothiazines and their conversion into sulfones. J Fluorine Chem 1999;94:164-74.

Rathore BS, Kumar M. Synthesis of 7-chloro-5-trifluoromrthyl/7-fluoro/7-trifluoromethyl-4H-1,4-benzothiazines as antimicrobial agents. Bioorg Med Chem 2006;14:5678-82.

Maheshwari M, Goyal A. A review: Synthesis and medicinal importance of 1,4-benzothiazine analogous. Asian J Pharm Clin Res 2015;8:41-6.

Karthika C, Mohamed RK, Manivannan S. Phytochemical analysis and evaluation of anti-microbial potential of Senna alata Linn. Leaves extract. Asian J Pharm Clin Res 2016;9:253-7.

Maheshwari M, Goyal A. 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):178-82.

Gajbhiye A, Goel KK. Synthesis and anticonvulsant screening of N-aryl-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide derivative. Int J Pharm Pharm Sci 2013;5(1):220-2.

Published

01-09-2017

How to Cite

Maheshwari, M., and A. Goyal. “SYNTHESIS AND MICROBIOLOGICAL EVALUATION OF 1-(4-METHYL-6-NITRO-2H-BENZO[B] [1,4]THIAZINE-3(4H)-YLIDENE)HYDRAZINE-1,1-DIOXIDE DERIVATIVES”. Asian Journal of Pharmaceutical and Clinical Research, vol. 10, no. 9, Sept. 2017, pp. 348-52, doi:10.22159/ajpcr.2017.v10i9.19093.

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