Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.

Novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives were synthesized and characterized by using spectral techniques like IR, (1)H NMR, (13)C NMR, COSY, DEPT, and GC-MS. All these compounds were screened for anti-fungal, anti-bacterial and anti-oxidant activity. Cyclohexenone derivatives, in general, showed better anti-fungal and anti-bacterial activity than parent chalcones. Whereas, all the Indazole derivatives showed very good anti-oxidant activity and some were also found to be active as anti-bacterial agent. Among the screened compounds, 15 was found to be most active as anti-fungal agent (against Rhizoctonia solani, LC(50) = 2.36 μg mL(-1)), 15b was found to be most active anti-bacterial agent (against Klebsiella pneumonia, MIC = 24.68 μg mL(-1)) and 14b emerged as most active anti-oxidant (IC(50) = 19.81 μg mL(-1)).

[1]  V. Padmavathi,et al.  AN EFFICIENT SYNTHESIS OF 6,8-DIARYLCARBAZOLES VIA FISCHER INDOLE CYCLIZATIONS , 1999 .

[2]  A. Loupy Solvent-free Reactions , 1999 .

[3]  G. G. Stokes "J." , 1890, The New Yale Book of Quotations.

[4]  M. Taheri,et al.  Preparation of 4,6-Diarylindazole Derivatives in Ionic Liquid under Solvent-free Conditions , 2010 .

[5]  Z. Nowakowska A review of anti-infective and anti-inflammatory chalcones. , 2007, European journal of medicinal chemistry.

[6]  I. Karaman,et al.  Screening of Biological Activities of a Series of Chalcone Derivatives against Human Pathogenic Microorganisms , 2010, Chemistry & biodiversity.

[7]  Avelino Corma,et al.  Inorganic Solid Acids and Their Use in Acid-Catalyzed Hydrocarbon Reactions , 1995 .

[8]  A. Schmidt,et al.  Recent Advances in the Chemistry of Indazoles , 2008 .

[9]  Peter O. Krutzik,et al.  Increasing rates of reaction: microwave-assisted organic synthesis for combinatorial chemistry. , 2002, Journal of combinatorial chemistry.

[10]  C. Khobragade,et al.  Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents. , 2009, Bioorganic & medicinal chemistry.

[11]  J. Tierney,et al.  Microwave assisted organic synthesis-a review , 2001 .

[12]  Remo Guidieri Res , 1995, RES: Anthropology and Aesthetics.

[13]  Paul Knochel,et al.  Comprehensive organic synthesis , 2014 .

[14]  W. Oh,et al.  Chalcones as novel influenza A (H1N1) neuraminidase inhibitors from Glycyrrhiza inflata. , 2011, Bioorganic & medicinal chemistry letters.

[15]  Atul Kumar,et al.  Synthesis of chalcones and flavanones using Julia–Kocienski olefination , 2010 .

[16]  V. Arán,et al.  Pharmacological properties of indazole derivatives: recent developments. , 2005, Mini reviews in medicinal chemistry.

[17]  Abhishek Sharma,et al.  Reinvestigation of structure-activity relationship of methoxylated chalcones as antimalarials: synthesis and evaluation of 2,4,5-trimethoxy substituted patterns as lead candidates derived from abundantly available natural β-asarone. , 2010, European journal of medicinal chemistry.

[18]  Melissa L. Golden,et al.  Ferrocenyl chalcones versus organic chalcones: a comparative study of their nematocidal activity. , 2011, Bioorganic & medicinal chemistry.

[19]  P. Misra,et al.  Ring Closure Reactions of Chalcones Using Microwave Technology , 1999 .

[20]  V. Padmavathi,et al.  Synthesis of Annelated 1,2,3-Selena- or -Thia-diazoles , 1998 .

[21]  C. Khobragade,et al.  Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents. , 2010, Bioorganic & medicinal chemistry.

[22]  V. Padmavathi,et al.  Synthesis of Some Fused Pyrazoles and Isoxazoles , 2000 .

[23]  D. Hadjipavlou-Litina,et al.  Natural and synthetic 2'-hydroxy-chalcones and aurones: synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity. , 2009, Bioorganic & medicinal chemistry.

[24]  V. Padmavathi,et al.  CYCLOHEXENONE CARBOXYLATES. A VERSATILE SOURCE FOR FUSED ISOXAZOLES AND PYRAZOLES , 2001 .

[25]  D. Hadjipavlou-Litina,et al.  Chalcones and their potential role in inflammation. , 2008, Mini reviews in medicinal chemistry.

[26]  A. Abdel-Rahman,et al.  Synthesis and Antimicrobial Evaluation of Some Chalcones and Their Derived Pyrazoles, Pyrazolines, Isoxazolines, and 5,6-Dihydropyrimidine-2-(1H)-thiones , 2007 .

[27]  N. Lawrence,et al.  Potent antimitotic and cell growth inhibitory properties of substituted chalcones. , 1998, Bioorganic & medicinal chemistry letters.

[28]  Fumio Toda,et al.  SOLID STATE ORGANIC CHEMISTRY : EFFICIENT REACTIONS, REMARKABLE YIELDS, AND STEREOSELECTIVITY , 1995 .

[29]  Jean-Louis Luche,et al.  Microwave activation in phase transfer catalysis , 1999 .

[30]  D. Batovska,et al.  Trends in utilization of the pharmacological potential of chalcones. , 2010, Current clinical pharmacology.

[31]  José Elguero,et al.  Theoretical estimation of the annular tautomerism of indazoles , 2005 .

[32]  A. Saxena,et al.  Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agents. , 2005, Bioorganic & medicinal chemistry letters.

[33]  R. Kumar,et al.  Synthesis, antimicrobial evaluation and QSAR analysis of novel nalidixic acid based 1,2,4-triazole derivatives. , 2011, European journal of medicinal chemistry.

[34]  T. Shah,et al.  Synthesis and antibacterial studies of some novel isoxazoline derivatives , 2007 .

[35]  C. Kunick,et al.  A new Heck reaction modification using ketone Mannich bases as enone precursors: parallel synthesis of anti-leishmanial chalcones. , 2008, Bioorganic & medicinal chemistry letters.

[36]  P. Perjési,et al.  Activation of oxidative stress response by hydroxyl substituted chalcones and cyclic chalcone analogues in mitochondria , 2010, FEBS letters.

[37]  M. Gopalakrishnan,et al.  Synthesis and characterization of 4,6-diaryl-4,5-dihydro-2H-indazol-3-ols and 4,6-diaryl-2-phenyl-4,5-dihydro-2H-indazol-3-ols — a new series of fused indazole derivatives , 2008 .

[38]  Herbert O. House,et al.  Modern Synthetic Reactions , 1972 .

[39]  R. P. Pandey,et al.  Microwave synthesis and antifungal evaluations of some chalcones and their derived diaryl-cyclohexenones , 2010, Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes.

[40]  M. Saraste,et al.  FEBS Lett , 2000 .