Author(s): Vikas N. Telvekar, Krishna N. Mundlod, Ghanshyam B. Jadhav, Navnath T. Hatvate, Shrikant M. Ghodse


DOI: 10.5958/0974-360X.2020.00798.2   

Address: Vikas N. Telvekar1, Krishna N. Mundlod2*, Ghanshyam B. Jadhav2, Navnath T. Hatvate1, Shrikant M. Ghodse1
1Department of Pharmaceutical Sciences and Technology, Institute of Chemical Technology, Mumbai-400019. (Maharashtra) India.
2Department of Pharmaceutical Chemistry, MVP Samaj’s College of Pharmacy, Nashik - 422002. Dist - Nashik (Maharashtra) India.
*Corresponding Author

Published In:   Volume - 13,      Issue - 10,     Year - 2020

A novel series of 3-(4,5-dihydro-1H-pyrazol-3-yl)-4-hydroxy-2H-chromen-2-one derivatives was designed based on molecular hybridization technique. A series of 3-(1-benzoyl-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-4-hydroxy-2H-chromen-2-one derivatives (6a–6p) that incorporate a variety of substituents at the 2 and 4 position of the benzyl moiety have been synthesized. These compounds were evaluated for their antidiabetic activity against a-glucosidase and a-amylase. The biological screening indicates that these hybrid derivatives exhibited promising IC50 values in the range of 91.24µM -261.82µM and 85.03µM -237.78µM respectively. Two analogs, 6j and 6m have shown most potential activity against both a-glucosidase and a-amylase were identified as potent antidiabetic agents.

Cite this article:
Vikas N. Telvekar, Krishna N. Mundlod, Ghanshyam B. Jadhav, Navnath T. Hatvate, Shrikant M. Ghodse. Synthesis of Novel molecular hybrid 3-(4,5-dihydro-1H-pyrazol-3-yl)-4-hydroxy-2H-chromen-2-one derivatives and In Vitro α-glucosidase and α-amylase inhibitory activity. Research J. Pharm. and Tech. 2020; 13(10):4529-4534. doi: 10.5958/0974-360X.2020.00798.2

1.    Ripsin CM, Kang H, Urban RJ. Management of blood glucose in type 2 diabetes mellitus. Am. Fam. Phys. 2009; 79 (1): 29–36.
2.    Saeed A, Channar PA, Larik FA, Jabeen F, Muqadar U, Saeed S, Florke U, Ismail H, Dilshad E, Mirza B. Design, synthesis, molecular docking studies of organotin-drug derivatives as multi-target agents against antibacterial, antifungal, α-amylase, α-glucosidase and butyrylcholinesterase. Inorg. Chim. Acta. 2017; 464: 204–213.
3.    Cai CY, Rao L, Rao Y, Guo JX, Xiao ZZ, Cao JY, Huang ZS, Wang B. Analogues of xanthones—Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates. Eur. J. Med. Chem. 2017; 130: 51–59.
4.    Arshad N, Perveen F, Saeed A, Channar PA, Farooqi SI, Larik FA, Ismail H, Mirza B. Spectroscopic, molecular docking and structural activity studies of (E)-N′-(substituted benzylidene/methylene) isonicotinohydrazide derivatives for DNA binding and their biological screening. J. Mol. Struct. 2017; 1139: 371–380.
5.    Chaudhry F, Naureen S, Huma R, Shaukat A, Al-Rashida M, Asif NAM, Munawar MA, Khan MA. In search of new α-glucosidase inhibitors: Imidazolylpyrazole derivatives. Bioorg. Chem. 2017; 71: 102–109.
6.    Noreen T, Taha M, Imran S, Chigurupati S, Rahim F, Selvaraj M, Ismail NH, Mohammad, JI, Ullah H, Nawaz F. Synthesis of alpha amylase inhibitors based on privileged indole scaffold. Bioorg. Chem. 2017; 72: 248–255.
7.    Balan K, Perumal P, Sundarabaalaji N, Palvannan T. Synthesis, molecular modeling and biological evaluation of novel 2-allyl amino 4-methyl sulfanyl butyric acid as α-amylase and α-glucosidase inhibitor. J. Mol. Struct. 2015; 1081: 62–68.
8.    Saeed A, Bosch A, Bettiol M, Nossa González DL, Erben MF, Lamberti Y. Novel Guanidine Compound against Multidrug-Resistant Cystic Fibrosis-Associated Bacterial Species. Molecules 2018; 23: 1158.
9.    Chakraborty I, Sathish Kumar SR, Bhaskara Rao KV. Exploration of α- amylase Inhibitor producing marine actinobacteria and evaluation of its antioxidant and antimicrobial activities –In vitro study. Research J. Pharm. and Tech. 2013; 6(8): 889-893.
10.    Kato E, Iwano N, Yamada A, Kawabata J. Synthesis and α-amylase inhibitory activity of glucose–deoxynojirimycin conjugates. Tetrahedron letter. 2011; 67: 7692–7702
11.    Patel BD, Bhadada SV, Ghate MD. synthesis and anti-diabetic activity of triazolotriazine derivatives as dipeptidyl peptidase-4 (DPP-4) inhibitors. Bioorg. Chem. 2017; 72: 345–358
12.    Lakshman KD, Rao KNV, Bindu M, Sathis KD, David B. 2 Alpha-Glucosidase Inhibitory Activities of Wrightia tinctoria Roxb and Schrebera swietenoides Roxb Bark Extract. Research J. Pharmacology and Pharmacodynamics; 2011; 3(1): 22-24
13.    K. Ishwar Bhat, Apoorva A, Abhishek Kumar, Pankaj Kumar. Synthesis and Antioxidant Activity of Some New Coumarin Incorporated 4-Thiazolidinone Derivatives. Research J. Pharm. and Tech 2018; 11(12): 5408-5412.
14.    Abhishek K, Shetty P, Amrutha CL, Derin RV, Ashlin B. Synthesis and Antimicrobial Evaluation of Some Novel Derivatives of Coumarin Moiety. Research J. Pharm. and Tech. 2016; 9(5): 545-548.
15.    Abhishek K, Pankaj K, Jean SP, Bhashini, Akshata. Synthesis and Antimicrobial Evaluation of Some new Coumarinyl Schiff Base Derivatives. Research J. Pharm. and Tech 2018; 11(11): 4946-4948.
16.    Sandhu S, Bansal Y, Silakari O, Bansal G. Coumarin hybrids as novel therapeutic agents. Bioorg. Med. Chem. 2014; 22: 3806–3814.
17.    Pisani L, Farina R, Catto M, Iacobazzi RM, Nicolotti O, Cellamare S, Mangiatordi GF, Denora N, Soto-Otero R, Siragusa L, Altomare CD, Carotti A. J. Med. Chem. 2016; 59: 6791–6806.
18.    Dwivedi AP, Kumar S, Varshney V, Singh AB, Srivastava AK, Sahu DP. Synthesis and antihyperglycemic activity of novel N-acyl-2-arylethylamines and N-acyl-3-coumarylamines. Bioorg. Med. Chem. Lett. 2008; 18: 2301–2305.
19.    B. C. Revanasiddappa, M. Vijay Kumar, Prashanth Nayak, Ajmal Roshan Ali, M. S. Jisha. Synthesis, Antibacterial and Antifungal Evaluation of Novel Pyrazoline Derivatives. Research J. Pharm. and Tech. 2017; 10(5): 1481-1484.
20.    Pankaj Kumar, Abhishek Kumar, Prashant Nayak, Jean Sandra pinto, Brynish D’Souza. Synthesis and Antimicrobial Evaluation of some Novel Pyrazoline Incorporated Pyrrole Derivatives. Research J. Pharm. and Tech. 2018; 11(6): 2460-2462.
21.    Anand N, Jaiswal N, Pandey SK, Srivastava AK, Tripathi RP. Application of click chemistry towards an efficient synthesis of 1,2,3-1H-triazolyl glycohybrids as enzyme inhibitors. Carbohydr. Res. 2011; 346: 16–25.
22.    Kishore K., Sharma RSK, Chanti BP, M. Sreenivasa Rao, K. Durga Prasadu, D. Ravi Kumar Synthesis, characterization and pharmacological evaluation of novel spiro heterocyclic compounds as anti-diabetic agents. Asian J. Research Chem. 2017; 10(3):393-398.
23.    Ishwar Bhat, Apoorva A, Abhishek Kumar, Pankaj Kumar. Synthesis and Antidiabetic Evaluation of Some New Coumarin Coupled 4-Thiazolidinone Derivatives. Research J. Pharm. and Tech. 2019; 12(11): 5215-5218.
24.    Trivedi JC, Bariwal JB, Upadhyay KD, Naliapara YT, Joshi S K, Pannecouque, CC, Clercqd ED, Shah A K. Improved and rapid synthesis of new coumarinyl chalcone derivatives and their antiviral activity. Tetrahedron Letters. 2007; 48: 8472–8474.
25.    Abdelhafez OM, Amin KM, Batran RZ, Maher TJ, Nada SA, Sethumadhavan S. Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives. Bioorganic and Medicinal Chemistry. 2010; 18: 3371–3378.
26.    Sahoo A, Yabanoglu SB, Sinha N, Ucar G, Basu A, Jayaprakash V. Towards development of selective and reversible pyrazoline based MAO-inhibitors: Synthesis, biological evaluation and docking studies. Bioorganic and Medicinal Chemistry Letters. 2010; 20: 132–136.
27.    Guang-cheng W, Ya-ping P, Zhen-zhen X, Jing W, Ming C. Synthesis, α-glucosidase inhibition and molecular docking studies of novel thiazolidine-2,4-dione or rhodanine derivatives. Med. Chem. Commun. 2017; 8:1477-1484.
28.    Hatem AA, Nor Azman NI, Rohaya A, El‑Hassane A, Mohamed M, Rashad A. Synthesis, biological activity and molecular docking of new tricyclic series as α‑glucosidase inhibitors. BMC Chemistry. 2019; 13: 52.
29.    Parvin K, Meenakshi D, Kulbir K, Jayant S, Sunil K, Hitender S. Synthesis of novel inhibitors of α-amylase based on the thiazolidine-4-one skeleton containing a pyrazole moiety and their configurational studies. Med. Chem. Commun. 2017; 8: 1468.
30.    Vasudev Pai, Rudraprabhu V. Savadi, Anant Bhandarkar. In-Vitro Alpha-Amylase Inhibition Action of Isolated Phytoconstituent in Zanthoxylum rhetsa (Roxb) Bark. Research J. Pharm. and Tech. 2011; 4(7): 1147-1150.

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