Synthesis and Antimicrobial activites of some Antipyrine-Triazole-Conazoles

Starting from antipyrine-triazole moiety some new kind of conazoles were synthesized. The synthesized compounds were screened for their antimicrobial activities against some test microorganisms. Among them compound 3 which is an reduction product of compound 2 showed very good antitubercular activity against Mycobacterium smegmatis compared with Streptomycin standard drug. Also among the conazoles compound 4b and 4c showed good antitubercular activity.

Keywords:

Antipyrine, Azole Conazole,

PDF

___

[1] Sun S, Lou H, Gao Y, Fan P, Ma B, Ge W, et al. Liquid chromatography–tandem mass spectrometric method for the analysis of fluconazole and evaluation of the impact of phenolic compounds on the concentration of fluconazole in Candida albicans. Journal of Pharmaceutical and Biomedical Analysis 2004;34:1117–24. https://doi.org/10.1016/j.jpba.2003.11.013.
[2] Verreck G, Six K, Van den Mooter G, Baert L, Peeters J, Brewster ME. Characterization of solid dispersions of itraconazole and hydroxypropylmethylcellulose prepared by melt extrusion—part I. International Journal of Pharmaceutics 2003;251:165–74. https://doi.org/10.1016/S0378-5173(02)00591-4.
[3] Abastabar M, Al-Hatmi AMS, Vafaei Moghaddam M, de Hoog GS, Haghani I, Aghili SR, et al. Potent Activities of Luliconazole, Lanoconazole, and Eight Comparators against Molecularly Characterized Fusarium Species. Antimicrob Agents Chemother 2018;62:e00009-18, /aac/62/5/e00009-18.atom. https://doi.org/10.1128/AAC.00009-18.
[4] Rostom SAF, Shalaby MA, El-Demellawy MA. Polysubstituted pyrazoles, part 5.11For part 4: see Ref. [18]. Synthesis of new 1-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents. European Journal of Medicinal Chemistry 2003;38:959–74. https://doi.org/10.1016/j.ejmech.2003.08.003.
[5] Turan-Zitouni G, Kaplancikli ZA, Erol K, Kiliç FS. Synthesis and analgesic activity of some triazoles and triazolothiadiazines. Il Farmaco 1999;54:218–23. https://doi.org/10.1016/S0014-827X(99)00016-6.
[6] Kolavi G, Hegde V, Khazi I ahmed, Gadad P. Synthesis and evaluation of antitubercular activity of imidazo[2,1-b][1,3,4]thiadiazole derivatives. Bioorganic & Medicinal Chemistry 2006;14:3069–80. https://doi.org/10.1016/j.bmc.2005.12.020.
[7] Shivarama Holla B, Sarojini BK, Sooryanarayana Rao B, Akberali PM, Suchetha Kumari N, Shetty V. Synthesis of some halogen-containing 1,2,4-triazolo-1,3,4-thiadiazines and their antibacterial and anticancer screening studies — Part I. Il Farmaco 2001;56:565–70. https://doi.org/10.1016/S0014-827X(01)01094-1.
[8] Narendra Sharath Chandra JN, Sadashiva CT, Kavitha CV, Rangappa KS. Synthesis and in vitro antimicrobial studies of medicinally important novel N-alkyl and N-sulfonyl derivatives of 1-[bis(4-fluorophenyl)-methyl]piperazine. Bioorganic & Medicinal Chemistry 2006;14:6621–7. https://doi.org/10.1016/j.bmc.2006.05.064.
[9] Dixit PP, Patil VJ, Nair PS, Jain S, Sinha N, Arora SK. Synthesis of 1-[3-(4-benzotriazol-1/2-yl-3-fluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-3-substituted-thiourea derivatives as antituberculosis agents. European Journal of Medicinal Chemistry 2006;41:423–8. https://doi.org/10.1016/j.ejmech.2005.12.005.
[10] Abu-Elmaati, T.M., Reactions with Heterocyclic Amines: New Routes fort he Synthesis of Novel Azolo{1,5-α]Pyrimidine, some Pyridine, Pyran and Pyrazole Derivatives Containing The Antipyrine Moiety. Acta Chimica Slovenica 2002; 49; 721-732.
[11] El Sayed MT, El-Sharief MAMSh, Zarie ES, Morsy NM, Elsheakh AR, Voronkov A, et al. Design, synthesis, anti-inflammatory activity and molecular docking of potential novel antipyrine and pyrazolone analogs as cyclooxygenase enzyme (COX) inhibitors. Bioorganic & Medicinal Chemistry Letters 2018;28:952–7. https://doi.org/10.1016/j.bmcl.2018.01.043.
[12] Bansal T, Singh M, Mishra G, Talegaonkar S, Khar RK, Jaggi M, et al. Concurrent determination of topotecan and model permeability markers (atenolol, antipyrine, propranolol and furosemide) by reversed phase liquid chromatography: Utility in Caco-2 intestinal absorption studies. Journal of Chromatography B 2007;859:261–6. https://doi.org/10.1016/j.jchromb.2007.09.025.
[13] El-Ghamaz NA, Ghoneim MM, El-Sonbati AZ, Diab MA, El-Bindary AA, Abd El-Kader MK. Synthesis and optical properties studies of antipyrine derivatives thin films. Journal of Saudi Chemical Society 2017;21:S339–48. https://doi.org/10.1016/j.jscs.2014.03.010
[14] Bayrak, H., Cebeci, Y. U., Karaoğlu, S. A. Synthesis of Novel Antipyrine Derivatives Possessing Excellent Antimicrobial Activities, ChemistrySelect 2019;6;12906-12908. https://doi.org/10.1002/slct.201902376
[15] Woods GL, Clinical and Laboratory Standards Institute (Wayne P. Susceptibility testing of mycobacteria, nocardiae, and other aerobic actinomycetes: approved standard. Wayne: Clinical and Laboratory Standards Institute; 2011.