Pyrazine Associated Novel 1,2,4-Triazolo Thiadazines: Synthesis, Characterization and as Antibacterial Agents

Chandra Sekhara Reddi Maddireddi; Uma Devi  Parimi; Sreenivasa Reddy Bhimi Reddy; Satyanarayana Reddy Mandapati

doi:10.14233/ajchem.2016.20011

Issue

Vol. 28 No. 11 (2016): Vol 28 Issue 11

Issue Published : August 10, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Pyrazine Associated Novel 1,2,4-Triazolo Thiadazines: Synthesis, Characterization and as Antibacterial Agents

https://doi.org/10.14233/ajchem.2016.20011

Chandra Sekhara Reddi Maddireddi

Department of Chemistry, GITAM Institute of Science, GITAM University, Gandhi Nagar, Rushikonda, Visakhapatnam-530 045, India

Uma Devi Parimi

Department of Chemistry, GITAM Institute of Science, GITAM University, Gandhi Nagar, Rushikonda, Visakhapatnam-530 045, India

Sreenivasa Reddy Bhimi Reddy

Department of Chemistry, GITAM Institute of Science, GITAM University, Gandhi Nagar, Rushikonda, Visakhapatnam-530 045, India

Satyanarayana Reddy Mandapati

Department of Chemistry, GITAM Institute of Science, GITAM University, Gandhi Nagar, Rushikonda, Visakhapatnam-530 045, India

Corresponding Author(s) : Chandra Sekhara Reddi Maddireddi

csreddimelpl@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 11 (2016): Vol 28 Issue 11
Article Published : August 11, 2016

Abstract

5-(5-Methyl-pyrazin-2-yl)-[1,3,4]-oxadiazole-2-thiol (4) has been synthesized form the starting material 5-methyl-2-pyrazinecarboxylic acid (1) on esterification with ethanol and condensation with hydrazine hydrate followed by cyclization with carbon disulfide. Compound 4 further converted into the next intermediate, 4-amino-5-(5-methyl-pyrazin-2-yl)-4H-[1,2,4]-triazole-2-thiol (5) when reacts with hydrazine hydrate. Finally, the target compounds, 3-(5-methyl-pyrazin-2-yl)-6-aryl-7H-[1,2,4]-triazole-[3,4-b][1,3,4]-thiadazine (6a-g) have been synthesized successfully from the condensation reaction performed using compound 5 and a variety of phenacyl bromides. The chemical structures of all the newly synthesized intermediates and products were confirmed by IR, ¹H NMR, mass spectral studies and elemental analysis. Additionally all the target compounds have been screened for antibacterial activity.

Keywords

1,2,4-Triazolo thiadiazines Pyrazine Antibacterial activity

Reddi Maddireddi, C. S., Parimi, U. D., Bhimi Reddy, S. R., & Mandapati, S. R. (2016). Pyrazine Associated Novel 1,2,4-Triazolo Thiadazines: Synthesis, Characterization and as Antibacterial Agents. Asian Journal of Chemistry, 28(11), 2453–2456. https://doi.org/10.14233/ajchem.2016.20011

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References

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References

S. Sharma, S. Gangal, A. Rauf and M. Zahin, Arch. Pharm. Chem. Life Sci., 341, 714 (2008); doi:10.1002/ardp.200800005.

G. Turan-Zitouni, Z.A. Kaplancikli, M.T. Yildiz, P. Chevallet and D. Kaya, Eur. J. Med. Chem., 40, 607 (2005); doi:10.1016/j.ejmech.2005.01.007.

L. Zahajska, V. Klimesova, J. Koci, K. Waisser and J. Kaustova, Arch. Pharm. Pharm. Med. Chem, 337, 549 (2004); doi:10.1002/ardp.200400899.

B. Tozkoparan, E. Kupeli, E. Yesilada and M. Ertan, Bioorg. Med. Chem., 15, 1808 (2007); doi:10.1016/j.bmc.2006.11.029.

L. Labanauskas, E. Udrenaite, P. Gaidelis and A. Brukstus, IL Farmaco, 59, 255 (2004); doi:10.1016/j.farmac.2003.11.002.

B. Shivarama Holla, B. Veerendra, M.K. Shivananda and B. Poojary, Eur. J. Med. Chem., 38, 759 (2003); doi:10.1016/S0223-5234(03)00128-4.

A.S.A. Almasirad, M. Tabatabai, A. Faizi, N. Kebriaeezadeh, A. Mehrabi, A. Dalvandi and A. Shafiee, Bioorg. Med. Chem. Lett., 14, 6057 (2004); doi:10.1016/j.bmcl.2004.09.072.

M.T. Abdel-Aal, W.A. El-Sayed, S.M. El-Kosy and E.S.H. El-Ashry, Arch. Pharm. Chem. Life Sci., 341, 307 (2008); doi:10.1002/ardp.200700154.

B. Chai, X. Qian, S. Cao, H. Liu and G. Song, ARKIVOC, 141 (2003); doi:10.3998/ark.5550190.0004.216.

A. Varvaresou, T. Siatra-Papastaikoudi, A. Tsotinis, A. Tsantili-Kakoulidou and A. Vamvakides, IL Farmaco, 53, 320 (1998); doi:10.1016/S0014-827X(98)00024-X.

National Committee for Clinical Laboratory Standards (NCCLS), Nat. Comm. Clin. Lab. Stands, Villanova, p. 242 (1982).

Issue

Vol. 28 No. 11 (2016): Vol 28 Issue 11

Pyrazine Associated Novel 1,2,4-Triazolo Thiadazines: Synthesis, Characterization and as Antibacterial Agents

Corresponding Author(s) : Chandra Sekhara Reddi Maddireddi

Abstract

Keywords

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