Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents

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Abstract

(1,4,5-Triphenylimidazol-2-yl-thio)butyric acid hydrazide (3) was obtained via alkylation of 1,4,5-triphenylimidazol-2- thiol (1) with ethylbromobutyrate, followed by addition of hydrazine hydrate. Treatment of acid hydrazide 3 with carbon disulfide in an ethanolic potassium hydroxide solution gave the intermediate potassium dithiocarbazinate salt, which was cyclized to 4-amino-5-[(1,4,5-triphenylimidazol- -2-yl)thiopropyl]-2H-1,2,4-triazole-3-thione (4) in the presence of hydrazine hydrate. Condensation of compound 3 with alkyl/arylisothiocyanate afforded the corresponding 1-[4-(1,4,5-triphenylimidazol-2-ylthio)butanoyl]-4-alkyl/arylthiosemicarbazides (5-7), which upon refluxing with sodium hydroxide, yielded the corresponding 1,2,4-triazole - -3-thiols 8-10. Under acidic conditions, compounds 4-6 were converted to aminothiadiazoles 11-13. Moreover, the series of Schiff bases 14-18 were synthesized from the condensation of compound 3 with different aromatic aldehydes. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral analyses. They were also preliminarily screened for their antimicrobial activity.

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  • 1. E. D. Weinber Antifungal Agents. Burger’s Medicinal Chemistry and Drug Discovery 5th ed. Wiley Interscience New York 1996 Vol. 2 pp. 637-652.

  • 2. U. Sahoo S. Biswal S. Sethy H. K. S. Kumar and M. Banerjee Imidazole and its biological activities: A review Asian J. Res. Chem. 5 (2012) 171-182.

  • 3. M. Mahdavi T. Akbarzadeh V. Sheibani M. Abbasi L. Firoozpour S. A. Tabatabaic A. Shafiee and A. Foroumadi Synthesis of two novel 3- amino- 5- [4- chloro- 2- phenoxyphenyl] - 4H- 1 2 4- triazoles with anticonvulsant activity Iranian J. Pharm. Res. 9 (2010) 265-269.

  • 4. O. Bekircan B. Kahveci and O. B. Ozgumus Synthesis of some N- alkoxycarbonyl- N’’- benzoylbenzamidrazones( p- toluamidrazones) and 1 3 5- trisubstituted 1 2 4- triazole derivatives from Nbenzoylimidates and their antimicrobial and anticancer screening studies Chin. J. Chem. 25 (2007) 1871-1877; DOI: 10.1002/cjoc.200790345.

  • 5. M. Hamdy A. Rahman and M. Hussein Synthesis of b-hydroxypropanoic acid derivatives as anti-inflammatory analgesic and antimicrobial agents Arch. Pharm. Chem. Life Sci. 339 (2006) 378-387; DOI: 10.1002/ardp.200600016.

  • 6. O. Bekircan M. Kucuk B. Kahveci and S. Kolaylı Convenient synthesis of fused heterocyclic 1 3 5- triazines from some N- acyl imidates and heterocyclic amines as anticancer and antioxidant agents Arch. Pharm. 338 (2005) 365-372; DOI: 10.1002/ardp.200400964.

  • 7. G. T. Zitouni Z. A. Kaplancıklı A. Ozdemir P. Chevallet H. B. Kandilci and B. Gumus Studies on 124-triazole derivatives as potential anti-inflammatory agents Arch. Pharm. Chem. Life Sci. 340 (2007) 586-590; DOI: 10.1002/ardp.200700134.

  • 8. B. Chai X. Qian S. Cao H. Liu and G. Song Synthesis and insecticidal activity of 124-triazole derivatives ARKIVOC ii (2003) 141-145.

  • 9. M. M. Ghorab S. G. Abdel-Hamide G. M. Ali and E. H. Shaurub Synthesis and insecticidal activity of some new 3- [4(3H) - quinazolinone- 2- yl) thiomethyl] - 1 2 4- triazole- 5- thiols Pestic. Sci. 48 (1996) 31-35; DOI: 10.1002/(SICI)1096-9063(199609)48.

  • 10. G. Turan-Zitouni Z. A. Kaplancıklı and A. Ozdemir Synthesis of some triazolylthioacetamidobenzofuran derivatives Farmaco 57 (2002) 573-578; DOI: 10.1016/S0014-827X(02)01250-8.

  • 11. M. Chen X.-F. Wang S.-S. Wang Y.-X. Feng F. Chen and C.-L. Yang Synthesis characterization and fungicidal activities of novel fluorinated 35-disubstituted-4H-124-triazol-4-amines J. Fluorine Chem. 135 (2012) 324 323-329; DOI: 10.1016/j.jfluchem.2011.12.015.

  • 12. A. Foroumadi S. Emami A. Hassanzadeh M. Rajaee K. Sokhanvar M. H. Moshafiand A. Shafiee Synthesis and antibacterial activity of N- (5- benzylthio- 1 3 4- thiadiazol- 2- yl) and N- (5- benzylsulfonyl-1 3 4- thiadiazol- 2- yl) piperazinyl quinolone derivatives Bioorg. Med. Chem. Lett. 15 (2005) 4488-4492; DOI: 10.1016/j.bmcl.2005.07.016.

  • 13. B. Modzelewska-Banachiewicz J. Banachiewicz A. Chodkowska E. Jagiello-Wojtowicz and L. Mazur Synthesis and biological activity of new derivatives of 3- (3 4- diaryl- 1 2 4- triazole- 5- yl) propenoic acid Eur. J. Med. Chem. 39 (2004) 873-877; DOI: 10.1016/j.ejmech.2004.07.002.

  • 14. N. Solak and S. Rollas Synthesis and antituberculosis activity of 2- (aryl /alkylamino) - 5- (4- aminophenyl) - 1 3 4- thiadiazoles and their Schiff bases ARKIVOC xii (2006) 173-181; DOI: 10.3998/ ark.5550190.0007.c20.

  • 15. S. Schenone C. Brullo O. Bruno F. Bondavalli A. Ranise W. Filippelli B. Rinaldi A. Capuano and G. Falcone New 1 3 4- thiadiazole derivatives endowed with analgesic and anti- inflammatory activities Bioorg. Med. Chem. 14 (2006) 1698-1705; DOI: 10.1016/j.bmc.2005.10.064.

  • 16. S. Rollas N. Gulerman and H. Erdeniz Synthesis and antimicrobial activity of some new hydrazones of 4- fluorobenzoic acid hydrazide and 3- acetyl- 2 5- disubstituted- 1 3 4- oxadiazolines Farmaco 57 (2002) 171-174; DOI: 10.1016/S0014-827X(01)01192-2.

  • 17. T. R. Bal B. Anand P. Yogeeswari and D. Sriram Synthesis and evaluation of anti- HIV activity of isatin b- thiosemicarbazone derivatives Bioorg. Med. Chem. Lett. 15 (2005) 4451-4455; DOI: 10.1016/j. bmcl.2005.07.046.

  • 18. S. N. Pandeya D. Sriram G. Nath and E. De Clercq Synthesis antibacterial antifungal and anti- HIV activities of Schiff and Mannich bases derived from isatin derivatives and N- [4- (4’- chlorophenyl) thiazol- 2- yl] thiosemicarbazide Eur. J. Pharm. Sci. 9 (1999) 25-31; DOI: 10.1016/S0928-0987(99)00038-X.

  • 19. S. N. Pandeya D. Sriram G. Nath and E. De Clercq Synthesis antibacterial antifungal and anti- HIV evaluation of Schiff and Mannich bases of isatin and its derivatives with triazole Arzneim. Forsch. 50 (2000) 55-59.

  • 20. S. M. Sondhi M. Dinodia and A. Kumar Synthesis anti- inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives Bioorg. Med. Chem. 14 (2006) 4657-4663; DOI: 10.1016/j.bmc.2006.02.014.

  • 21. M. R. Maurya S. Agarwal M. Abid A. Azam C. Bader M. Ebel and D. Rehder Synthesis characterization reactivity and in vitro antiamoebic activity of hydrazone based oxovanadium(IV) oxovanadium(V) and m- bis(oxo) bis{oxovanadium(V) } complexes Dalton Trans. (2006) 937-947; DOI: 10.1039/B512326G.

  • 22. E. S. H. El Ashry A. A. Kassem H. Abdel-Hamid F. F. Louis Sh. A. N. Khattab and M. R. Aouad Synthesis of 4- amino- 5- (3- chloro- 2- benzothienyl) - 3- mercapto- 1 2 4- triazolo[3 4- b][1 3 4] thiadiazoles and triazolo[3 4 b] [1 3 4] thiadiazines under classical and microwave conditions ARKIVOC xiv (2006) 119-132.

  • 23. A. H. K. Sharba R. H. Al-Bayati N. Rezki and M. R. Aouad Synthesis of thiadiazoles and 1 2 4- triazoles derived from cyclopropane dicarboxylic acid Molecules 10 (2005) 1153-1160; DOI: 10.3390/10091153.

  • 24. M. R. Aouad N. Rezki M. Kasmi L. Aouad and M. A. Rezki Synthesis characterization and evaluation of antimicrobial activity of some novel 1 2 4- triazoles and 1 3 4- thiadiazoles bearing imidazole nucleus Heterocycles 85 (2012) 1141-1154; DOI: 10.3987/COM-12-12456.

  • 25. European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society of Clinical Microbiology and Infectious Diseases (ESCMID) Determination of Minimum Inhibitory Concentrations (MICs) of Antibacterial Agents by Agar Dilution Clin. Microbiol. Infect. (Suppl. 6) (2000) 509-515; DOI: 10.1046/j.1469-0692.2000.00142.x.

  • 26. National Committee for Clinical Laboratory Standards Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. Approved Standard M7-A5 5th ed. NCCLS Wayne 2000.

  • 27. E. S. H. El Ashry N. Rashed L. F. Awad E. Ramadan S. M. Abdel-Maggeed and N. Rezki MAOS versus conventional synthesis of 4 5- di- and 3 4 5- triphenylimidazole- 2- thione and their derivatives ARKIVOC vii (2007) 30-40.

  • 28. H. Kumar S. A. Javed S. A. Khan and M. Amir 134-Oxadiazole/thiadiazole and 124-triazole derivatives of biphenyl-4-yloxy acetic acid: synthesis and preliminary evaluation of biological properties Eur. J. Med. Chem. 43 (2008) 2688-2698; DOI: 10.1016/j.ejmech.2008.01.039.

  • 29. N. Galic B. Peric B. Kojic-Prodic and Z. Cimerman Structural and spectroscopic characteristics of aroylhydrazones derived from nicotinic acid hydrazide J. Mol. Struct. 559 (2001) 187-194; DOI: 10.10.1016/S0022-2860(00)00703-1.

  • 30. V. Klimesova L. Zahajska K. Waisser J. Kaustova and U. Mollmann Synthesis and antimycobacterial activity of 1 2 4- triazole 3- benzylsulfanyl derivatives Farmaco 59 (2004) 279-288; DOI: 10.1016/j.farmac.2004.01.006.

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