Synthesis and Antimycobacterial Activity of some 2-(4-Aminophenyl)-5-Substitutedamino-1,3,4-thiadiazole Derivatives and Their Coupling Products

Volume: 20 Number: 2 February 2, 2016
EN TR

Synthesis and Antimycobacterial Activity of some 2-(4-Aminophenyl)-5-Substitutedamino-1,3,4-thiadiazole Derivatives and Their Coupling Products

Abstract

In the present study, several 2-(4-aminophenyl)-5-substitutedamino-1,3,4-thiadiazoles (2a-l) and their coupling products, 2,3,4-pentanetrione-3-[4-(5-alkyl/arylamino-1,3,4-thiadiazole-2-yl)phenyl]hydrazones (3a-j) were synthesized in good yields and characterized by UV,  IR, 1H-NMR, mass and elemental analysis. The compounds were evaluated for their in vitro antimycobacterial  activity  against Mycobacterium tuberculosis H37Rv. Antitubercular activity of the synthesized compounds was determined in vitro using the BACTEC 460 Radiometric System against Mycobacterium tuberculosis H37Rv at 6.25 mg/mL. The antimycobacterial data of screened compounds indicated  that 2-(4-aminophenyl)-5-(4-chlorophenyl)amino-1,3,4-thiadiazole demonstra-ted the highest inhibition  (2f ).

 

Keywords

References

  1. 2015 World Health Organization (WHO) Global Tuberculosis Report; http://www.who.int/tb/publications/global_report/gtbr15_main_text.pdf
  2. Hasan R. Drug resistant tuberculosis: Challenges of urbanization. Int J Mycobacteriol 2014; 3: 79–81.
  3. Matteelli A, Roggi A, Carvalho AC. Extensively drug-resistant tuberculosis: epidemiology and management. Clin Epidemiol 2014; 6: 111-8.
  4. Brigden G, Hewison C, Varaine F. New developments in the treatment of drug-resistant tuberculosis: clinical utility of bedaquiline and delamanid. Infect Drug Resist 2015; 30(8): 367-78.
  5. Wong EB, Cohen KA, Bishai WR. Rising to the challenge: new therapies for tuberculosis. Trends Microbiol 2013; 21(9): 493-501.
  6. Poce G, Cocozza M, Consalvi S, Biava M. SAR analysis of new anti-TB drugs currently in pre-clinical and clinical development. Eur J Med Chem 2014; 86: 335-51.
  7. Foroumadi A, Soltani F, Moshafi MH, Ashraf-Askari R. Synthesis and in vitro antibacterial activity of some N-(5-aryl-1,3,4-thiadiazole-2-yl)piperazinyl quinolone derivatives. Farmaco 2003; 58: 1023-8.
  8. Foroumadi A, Kargar Z, Sakhteman A, Sharifzadeh Z, Feyzmohammadi R, Kazemi M, Shafiee A. Synthesis and antimycobacterial activity of some alkyl [5-(nitroaryl)-1,3,4-thiadiazol-2-ylthio]propionates. Bioorg Med Chem 2006; 16: 1164–7.

Details

Primary Language

English

Subjects

-

Journal Section

-

Authors

Sevim Rollas This is me

Publication Date

February 2, 2016

Submission Date

December 22, 2015

Acceptance Date

-

Published in Issue

Year 2016 Volume: 20 Number: 2

APA
Karakuş, S., & Rollas, S. (2016). Synthesis and Antimycobacterial Activity of some 2-(4-Aminophenyl)-5-Substitutedamino-1,3,4-thiadiazole Derivatives and Their Coupling Products. Marmara Pharmaceutical Journal, 20(2), 199-206. https://doi.org/10.12991/mpj.20162013533
AMA
1.Karakuş S, Rollas S. Synthesis and Antimycobacterial Activity of some 2-(4-Aminophenyl)-5-Substitutedamino-1,3,4-thiadiazole Derivatives and Their Coupling Products. J Res Pharm. 2016;20(2):199-206. doi:10.12991/mpj.20162013533
Chicago
Karakuş, Sevgi, and Sevim Rollas. 2016. “Synthesis and Antimycobacterial Activity of Some 2-(4-Aminophenyl)-5-Substitutedamino-1,3,4-Thiadiazole Derivatives and Their Coupling Products”. Marmara Pharmaceutical Journal 20 (2): 199-206. https://doi.org/10.12991/mpj.20162013533.
EndNote
Karakuş S, Rollas S (February 1, 2016) Synthesis and Antimycobacterial Activity of some 2-(4-Aminophenyl)-5-Substitutedamino-1,3,4-thiadiazole Derivatives and Their Coupling Products. Marmara Pharmaceutical Journal 20 2 199–206.
IEEE
[1]S. Karakuş and S. Rollas, “Synthesis and Antimycobacterial Activity of some 2-(4-Aminophenyl)-5-Substitutedamino-1,3,4-thiadiazole Derivatives and Their Coupling Products”, J Res Pharm, vol. 20, no. 2, pp. 199–206, Feb. 2016, doi: 10.12991/mpj.20162013533.
ISNAD
Karakuş, Sevgi - Rollas, Sevim. “Synthesis and Antimycobacterial Activity of Some 2-(4-Aminophenyl)-5-Substitutedamino-1,3,4-Thiadiazole Derivatives and Their Coupling Products”. Marmara Pharmaceutical Journal 20/2 (February 1, 2016): 199-206. https://doi.org/10.12991/mpj.20162013533.
JAMA
1.Karakuş S, Rollas S. Synthesis and Antimycobacterial Activity of some 2-(4-Aminophenyl)-5-Substitutedamino-1,3,4-thiadiazole Derivatives and Their Coupling Products. J Res Pharm. 2016;20:199–206.
MLA
Karakuş, Sevgi, and Sevim Rollas. “Synthesis and Antimycobacterial Activity of Some 2-(4-Aminophenyl)-5-Substitutedamino-1,3,4-Thiadiazole Derivatives and Their Coupling Products”. Marmara Pharmaceutical Journal, vol. 20, no. 2, Feb. 2016, pp. 199-06, doi:10.12991/mpj.20162013533.
Vancouver
1.Sevgi Karakuş, Sevim Rollas. Synthesis and Antimycobacterial Activity of some 2-(4-Aminophenyl)-5-Substitutedamino-1,3,4-thiadiazole Derivatives and Their Coupling Products. J Res Pharm. 2016 Feb. 1;20(2):199-206. doi:10.12991/mpj.20162013533

.