Open Access
Subscription Access
Open Access
Subscription Access
Synthesis and Biological Evaluation of Novel R1, R2 Substituted 2-(4-((2-(4-alkoxyphenyl)-5-methyloxazol-4-yl)Methyl)-1-alkyl-5-methyl-1h-pyrazol-3-yloxy)-6-(Hydroxymethyl)Tetrahydro-2h-pyran-3,4,5-triol Having Anti Diabetic Activity
Subscribe/Renew Journal
The synthesis and biological evaluation of novel pyrazole based heterocycles attached to sugar moiety lead to creating a new molecular frame work. Nine new compounds were synthesized by reacting ethyl 2-((2-(4-methoxyphenyl)-5-methyloxazol-4-yl) methyl)-3-oxobutanoate derivatives (9a-9c) with different alkyl hydrazines to give various substituted 4-((2-(4-methoxyphenyl)-5-methyloxazol-4-yl) methyl)-5-methyl-1H-pyrazol-3-ol derivatives (10 a-10i) which in turn were reacted with bromoglucose (3)to yield R1, R2 substituted 2-(4-((2-(4-alkoxyphenyl)-5-methyloxazol-4-yl)methyl)-1-alkyl-5-methyl-1H-pyrazol-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (12a-12i). The chemical structures of the synthesized compounds were characterized by means of IR, Mass and NMR spectroscopy. The compounds were screened for anti-diabetic activity by urinary glucose excretion method (UGE). Among the compounds tested, 12f, 12h and12i have exhibited moderate anti-diabetic activity as that of standard drug, remogliflozin. These compounds can be further exploited to get the potent lead compound.
Keywords
Pyrazoles, glucoacetate, Alkylhydrazines, Oxazoles, Mass and NMR spectra, Anti diabetic activity.
Subscription
Login to verify subscription
User
Font Size
Information
- Desai KG, Desai KR. Green route for the heterocyclization of 2-mercaptobenzimidazole into β-lactum segment derivatives containing –CONH– bridge with benzimidazole: Screening in vitro antimicrobial activity with various microorganisms. Bioorg Med Chem, 2006;14(24):8271–9.
- Y.P S, A T, R D, R As. Rational Design, Synthesis And Computational Structureactivity Relationship Of Novel 3-(4-Chlorophenyl)-5-(3-Hydroxy-4-Ethoxyphenyl)-4,5-Dihydro-1h-Pyrazole-1-Carboxamide. Iranian J Biotech, 2009;7(3):166–78.
- Wiley JL, Jefferson REG, Grier MC, Mahadevan A, Razdan RK, Martin BR. Novel Pyrazole Cannabinoids: Insights into CB1 Receptor Recognition and Activation. The J of Phar and exp ther,2000; 296(3):103-1022.
- Thore SN, Gupta AS.Synthesis of Fluorinated Pyrazolone Compounds. Orient J Chem, 2010;26(2):613–6.
- Prathap KJ, Himaja M, Mali SV, Munirajasekhar D. Synthesis of New (Pyrazol-3-yl)-1,3,4-oxadiazole Derivatives by Unexpected Aromatization During Oxidative Cyclization of 4,5-Dihydro-1H-pyrazole-3-carbohydrazones and Their Biological Activities. J Heterocycl Chem, 2014;51(3):726–32.
- Mansour AK, Eid MM, Khalil NSAM. Synthesis and Reactions of Some New Heterocyclic Carbohydrazides and Related Compounds as Potential Anticancer Agents. Molecules, 2003;8(10):744–55.
- Bhatia MS, Ingale KB, Choudhari PB, Zarekar BE, Bhatia NM,. Sherikar AS. 3D QSAR: Exploring Influence of Parameters of Pyrazoline Analogues on Resistant Strains of Staphylococcus aureus. Int J of Drug Desand Dis,2010; 1(1): 41-48.
- Morita Y, Matsumura E, Okabe T, Shibata M, Sugiura M, Ohe T, et al. Biological Activity of Tropolone. Biol Pharm Bull, 2003;26(10):1487–90.
- Jebaseelan S. Identification of Phytochemical Constituents within the rhizome extract of Costusspeciosus (koen) using Gas Chromatography-Mass Spectrometry (GC-MS) Analysis and In vitro Anti Diabetic Activity. Research J. Pharm. and Tech, 2019; 12(2):812-816.
- Singh K, Kumari S, Gupta YK. Synthesis and Antimicrobial Activity of New Pyrazoles and Chalcones Derived from Cyclic Imides. Research J. Pharm. and Tech, 2017; 10(12): 4483-4488.
- Yadav AK, Mehdi M, Fatima T. Synthesis, Characterization and AntimicrobialActivity of Some new 1,4 Diaryl-3-Methyl-6-Imino-4,7-Dihydro-1,3-Thiazino (5,4-d) Pyrazoles. Asian J. Research Chem, 2018; 11(2):217-220.
- Vijay NB, Gopinath S. Khansole, Jaman A. Angulwar, Sunil S, et al.. One Pot, Four-Component for the Synthesis of Pyrano Pyrazole Derivatives using TBAHS as Green Catalyst and their Biological Evaluation. Asian J. Research Chem, 2017; 10(6):745-749.
- Marupati S, Laxminarayana E, RameshM, RamchanderM, Venkat ReddyP. Microwave assisted facile synthesis of 5-Aryl-5, 6-dihydro-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(4H)-ones and docking for anti-inflammatory activity. Asian J. Research Chem, 2017; 10(4):593-596.
- Freddy HH, Azadkumar SS. Syntheses of Biologically active 1-[2-(1,3-Dimethyl-2,6-Dioxo-1,2,3,6-Tetrahydro-Purin-7-Yl)-Acetyl]-3-(Substituted Phenyl)-1H-Pyrazole-4-Carbaldehyde. Asian J. Research Chem, 2012; 5(7): 827-830.
- Ashok GG, Nawathye VV, Dalavi DB, Upadhyaya DJ,. Thorat BR, Yamgar RS. Synthesis and Characterization of Hydrazones, Pyrazoles and Pyrazolones from 8-Amino-6-Chloro Coumarine. Asian J. Research Chem, 2011; 4(10):1621-1624.
- Ouyang G, Cai X-J, Chen Z, Song B-A, Bhadury PS, Yang S, et al. Synthesis and Antiviral Activities of Pyrazole Derivatives Containing an Oxime Moiety. J Agric Food Chem, 2008;56(21):10160–7.
- el-Sabbagh OI, Baraka MM, Ibrahim SM, Pannecouque C, Andrei G, Snoeck R, et al. Synthesis and antiviral activity of new pyrazole and thiazole derivatives. Eur J Med Chem, 2009;44(9):3746–53.
- Hassan SY. Synthesis, antibacterial and antifungal activity of some new pyrazoline and pyrazole derivatives. Mol Basel Switz, 2013;18(3):2683–711.
- Sun J, Zhou Y. Synthesis and Antifungal Activity of the Derivatives of Novel Pyrazole Carboxamide and Isoxazolol Pyrazole Carboxylate. Molecules, 2015;20(3):4383–94.
Abstract Views: 151
PDF Views: 0