SYNTHESIS AND ANTI-MICROBIAL ACTIVITY OF 1-(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 road, Udaipur, Rajasthan, India, 313001
  • Anju Goyal Department of Pharmaceutical Chemistry, B N Institute of Pharmaceutical Sciences, Sevashram road, Udaipur, Rajasthan, India, 313001.

DOI:

https://doi.org/10.22159/ijpps.2016v8i10.13673

Keywords:

1, 4-Benzothiazines, Sulfones, Hydrazines, Anti-microbial activity

Abstract

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

Methods: These new compounds were synthesized by reaction of 2H-benzo[b][1,4]thiazin-3(4H)-one 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 FTIR, 1HNMR, 13CNMR and Mass studies confirms the synthesis of some new 1-(6-nitro-2H-benzo[b][1,4]thiazine-3(4H)-ylidene) hydrazine-1,1-dioxide derivatives. Compound 5f showed potent antimicrobial activity whereas compounds 5c and 5e showed moderate antimicrobial activity.

Conclusion: Result obtained in this research work clearly indicated that the compound 5f having methyl at 2 position and nitro groups at 2′ and 4′ position showed the most potent antimicrobial activity.

 

Downloads

Download data is not yet available.

References

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

Dabholkar VV, Gavande RP. Synthesis and biological evaluation of oxadiazolyl-1,4-benzothiazines. Rasayan J Chem 2010;3:655-9.

Parai MK, Panda GA. A convenient synthesis of chiral amino acid derived 3, 4-dihydro-2H-benzo[b][1,4]thiazines and antibiotic levofloxacin. Tetrahedron lett 2009;50:4703-5.

Bakovoli 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;15:2120-6.

Maheshwari M, Yadav M, Pathak D. Synthesis and anti-inflammatory activity of some newer N-(substituted-phenyl)-2H/4H-benzo [b] [1, 4] thiazn-3-amines. Indian J Heterocyclic Chem 2010;20:145-8.

Gupta S, Ajmera N, Meena P, Gautam N, Kumar A, Gautam DC. Synthesis and biological evaluation of new 1,4-thiazine containing heterocyclic compounds. Jordan J Chem 2009; 4:209-21.

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.

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 Heterocyclic Chem 2008;45:1445-9.

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

Karthika C, Mohamed RK, Manivannan S. Phytochemical analysis and evaluation of the antimicrobial potential of Senna alata linn. leaves extract. Asian J Pharm Clin Res 2016;9:253-7.

Hussain M, Khan MRU, Raza SM, Aziz A, Bakhsh H, Majeed A. Assessment of antimicrobial potential of Delbergia sisso against eight pathogenic bacteria-an in vitro study. Int J Pharm Sci 2014;4:702-6.

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

Guarda VLM, Perrissin M, Thomasson F, Ximenes EA, Galdino SL, Pitta IR, et al. Synthesis and microbial activity of some 4-butyl-2H-benzo[1,4]thiazin-3-one derivatives. Farmaco 2001;56:689-93.

Guarda VLM, 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. Heterocyclic Commun 2000;6:49-54.

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

Souza AMA, Guarda VLM, Leite LFCC, Filho JMB, Lima MCA, Galdino SL, et al. On application of knoevenagel condensation for the synthesis of benzothiazine compounds and structural study. Quim Nova 2006;29:1106-9.

Qiyun F, Junzhong L, Nin L, Shaotong Z. The structure of hydrazine crystal and its antibacterial activities. Rom Biotechnol Lett 2012;17:7552-63.

Published

2016-10-01

How to Cite

Maheshwari, M., and A. Goyal. “SYNTHESIS AND ANTI-MICROBIAL ACTIVITY OF 1-(6-NITRO-2H-BENZO[b][1,4]THIAZINE-3(4H)-YLIDENE)HYDRAZINE-1,1-DIOXIDE DERIVATIVES”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 8, no. 10, Oct. 2016, pp. 178-82, doi:10.22159/ijpps.2016v8i10.13673.

Issue

Section

Original Article(s)