Abstract
A series of (3-phenyl-5-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanones was synthesized by condensing suitably substituted chalcones, i.e., 3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-ones, and isoniazid in acetic acid. The structure of newly synthesized compounds has been established on the basis of analytical and spectral data. The new compounds were screened for antimicrobial activity and most of them showed good activity comparable with that of standard drugs ciprofloxacin and fluconazole. Compounds containing methoxy group showed high antimicrobial activity.
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Abdel-Hafez ESMN, Abuo-Rahma G, El-D AA, Abdel-Aziz M, Radwan MF, Farag HH (2009) Design, synthesis and biological investigation of certain pyrazole-3-carboxylic acid derivatives as novel carriers for nitric oxide. Bioorg Med Chem 17:3829–3837
Acharya BN, Saraswat D, Tiwari M, Shrivastava AK, Ghorpade R, Bapna S, Kaushik MP (2010) Synthesis and antimalarial evaluation of 1,3,5-trisubstituted pyrazolines. Eur J Med Chem 45:430–438
Ali MA, Shaharyar M, Siddiqui AA, Sriram D, Yogeeswari P, Clercq ED (2007) Synthesis and anti-HIV activity of N1-nicotinoyl-3-(4′-hydroxy-3′-methylmrthylphenyl)-5-[substituted phenyl]-2-pyrazolones. Acta Pol Pharma Drug Res 63:435–439
Argyrou A, Jin L, Siconilfi-Baez L, Angeletti RH, Blanchard JS (2006) Proteome-wide profiling of isoniazid targets in mycobacterium tuberculosis. Biochemistry 45:13947–13953
Bailey DM, Hansen PE, Hlavac AG, Baizman ER, Pearl J, Defelice AF, Feigenson ME (1985) 3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants. J Med Chem 28:256–260
Cheng H, Lundy DeMello KM, Li J, Sakya SM, Ando K, Kawamura K, Kato T, Rafka RJ, Jaynes BH, Ziegler CB, Stevens R, Lund LA, Mann DW, Kilroy C, Haven ML, Nimz EL, Dutra JK, Li C, Minich ML, Kolosko NL, Petras C, Silivia AM, Seibel SB (2006) Synthesis and SAR of heteroaryl-phenyl-substituted pyrazole derivatives as highly selective and potent canine COX-2 inhibitors. Bioorg Med Chem Lett 16:2076
Chowdhury MA, Abdellatif KRA, Dong Y, Das D, Suresh MR, Knaus EE (2008) Synthesis of celecoxib analogs that possess a N-hydroxypyrid-2(1H)one 5-lipoxygenase pharmacophore: Biological evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity. Bioorg Med Chem Lett 18:6138–6141
Daffé M, Draper P (1998) The envelope layers of mycobacteria with reference to their pathogenicity. Adv Microb Physiol 39:131–203
Delaine T, Genisson VB, Meunier B, Bernadou J (2007) Synthesis of the isonicotinoylnicotinamide scaffolds of the naturally occurring isoniazid−NAD(P) adducts. J Org Chem 72:675–678
Foye WO, Lemke TL, Williams DA (1995) Principles of medicinal chemistry, 4th edn. B.I. Waverly Pvt Ltd, New Delhi, pp 768–769, 806–811
Jagrat M, Behera J, Yabanoglu S, Ercan A, Ucar G, Sinha BN, Sankaran V, Basu A, Jayaprakash V (2011) Pyrazoline based MAO inhibitors: synthesis, biological evaluation and SAR studies. Bioorg Med Chem Lett. doi:10.1016/j.bmcl.2011.05.057
Janus SL, Magdif AZ, Erik BP, Claus N (1999) Synthesis of triazenopyrazole derivatives as potential inhibitors of HIV-1. Monatsh Chem 130:1167–1173
Jeong TS, Kim KS, Kim JR, Cho KY, Lee S (2004) Novel 3,5-diaryl pyrazolines and pyrazole as low-density lipoprotein (LDL) oxidation inhibitor. Bioorg Med Chem Lett 14:2719–2723
Johnsson K, King DS, Schultz PG (1995) Studies on the mechanism of action of isoniazid and ethionamide in the chemotherapy of tuberculosis. J Am Chem Soc 117:5009–5010
Kumar P (2009) Solid state oxidative aromatization of Hantzsch 1,4-dihydropyridines to pyridines using iodobenzene diacetate or hydroxy(tosyloxy)iodobenzene. Chin J Chem 27:1487–1491
Kumar P, Kumar A (2010) An expeditious synthesis of isoxazoline using cetyltrimethylammonium cerium nitrate: a phase transferring oxidative 1,3-dipolar cycloaddition. Chin Chem Lett 21:1287–1290
Kumar A, Chawla A, Jain S, Kumar P, Kumar S (2011a) 3-Aryl-2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxy]-phenyl}-acrylic acid alkyl ester: synthesis and antihyperglycemic evaluation. Med Chem Res 20:678–686
Kumar P, Kumar S, Husain K, Kumar A (2011b) An efficient synthesis of pyrazole chalcones under solvent free conditions at room temperature. Chin Chem Lett 22:37–40
Lorian V (1986) Antibiotics in laboratory medicine, 2nd edn. Williams & Wilkins, London, p 116
Manna K, Agrawal YK (2009) Microwave assisted synthesis of new indophenazine 1,3,5-trisubstruted pyrazoline derivatives of benzofuran and their antimicrobial activity. Bio Med Chem Lett 19:2688–2692
Marrakchi H, Laneelle G, Quémard A (2000) InhA, a target of the antituberculous drug isoniazid, is involved in a mycobacterial fatty acid elongation system, FAS-II. Microbiology 146:289–296
McFarland J (1907) Nephelometer: an instrument for estimating the number of bacteria in suspension used for calculating the opsonic index and for vaccines. J Am Med Assoc 49:1176–1178
Michon V, Du Penhoat CH, Tombret F, Gillardin JM, Lepagez F, Berthon L (1995) Preparation, structural analysis and anticonvulsant activity of 3- and 5-aminopyrazole N-benzoyl derivatives. Eur J Med Chem 30:147–155
NCCLS (2000) Method for dilution antimicrobial susceptibility test for bacteria that grow aerobically approved standard, 5th edn. National Committee for Clinical Laboratory Standards, Villanova, PA
Nguyen M, Claparols C, Bernadou J, Meunier B (2002) Is the isonicotinoyl radical generated during activation of isoniazid by MnIII-pyrophosphate? C. R. Chimie 5:325–330
Ozdemir Z, Kandilci HB, Gumusel B, Alıs UC, Bilgin AA (2007) Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. Eur J Med Chem 42:373–379
Prasad YR, Rao AL, Prasoona L, Murali K, Kumar PR (2005) Synthesis and antidepressant activity of some 1,3,5-triphenyl-2-pyrazolines and 3-(2″-hydroxy naphthalen-1″-yl)-1,5-diphenyl-2-pyrazolines. Bioorg Med Chem Lett 15:5030–5034
Quémard A, Dessen A, Sugantino M, Jacobs WR Jr, Sacchetini JC, Blanchard JS (1996) Binding of catalase-peroxidase-activated isoniazid to wild-type and mutant mycobacterium tuberculosis enoyl-ACP reductases. J Am Chem Soc 118:1561–1562
Shaharyar M, Abdullah MM, Bakht MA, Majeed J (2010) Pyrazoline bearing benzimidazoles: search for anticancer agent. Eur J Med Chem 45:114–119
Sharma PK, Kumar S, Kumar P, Kaushik P, Kaushik D, Dhingra Y, Aneja KR (2010) Synthesis and biological evaluation of some pyrazolylpyrazolines as anti-inflammatory-antimicrobial agents. Eur J Med Chem 45:2650–2655
Sridhar R, Perumal PT, Etti S, Shanmugam G, Ponnuswamy MN, Prabavathy VR, Mathivanan N (2004) Design, synthesis and anti-microbial activity of 1H-pyrazole carboxylates. Bioorg Med Chem Lett 14:6035–6040
Sriram D, Yogeeshwari P (2008) Medicinal chemistry, 2nd edn. Pearson Education, Dorling Kindersley, Noida, pp 329–333
Tewari AK, Mishra A (2001) Synthesis and anti-inflammatory activities of N4,N5-disubstituted-3-methyl-1H-pyrazolo[3,4-c]pyridazines. Bioorg Med Chem 9:715
Turan-Zitouni G, Chevallet P, Kilic FS, Erol K (2000) Synthesis of some thiazolyl-pyrazoline derivatives and preliminary investigation of their hypotensive activity. Eur J Med Chem 35:635–641
Wiley RH, Wiley P (1964) Pyrazolones, pyrazolidones and derivatives. Wiley, New York
Xia Y, Dong ZW, Zhao BX, Ge X, Meng N, Shin DS, Miao JY (2007) Synthesis and structure–activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide derivatives as potential agents against A549 lung cancer cells. Bioorg Med Chem 15:6893–6899
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Financial support by UGC, New Delhi, is gratefully acknowledged. Thanks to Mr Ashwani Kumar, GJUST-Hisar, for his valuable suggestions for carrying out antimicrobial activity.
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Kumar, S., Meenakshi, Kumar, S. et al. Synthesis and antimicrobial activity of some (3-phenyl-5-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanones: new derivatives of 1,3,5-trisubstituted pyrazolines. Med Chem Res 22, 433–439 (2013). https://doi.org/10.1007/s00044-012-0045-7
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DOI: https://doi.org/10.1007/s00044-012-0045-7