Design, synthesis, characterization and in vivo studies of some hydroxylated chalcone derivatives as hypoglycemic agents
Creators
- 1. Department of Applied Chemistry, Priyadarshini Bhagwati College of Engineering, Nagpur 440009, Maharashtra, India
- 2. Department of Pharmaceutical Chemistry, MET Institute of Pharmacy, Bhujbal Knowledge City, Nashik 422003, Maharashtra, India
- 3. Department of Chemistry, J. B. College of Science, Wardha 442001, Maharashtra, India
- 4. epartment of Pharmaceutical Chemistry, Dadasaheb Balpande College of Pharmacy, Nagpur 440037, Maharashtra, India
Description
Abstract:
Low molecular weight ligands (LMWL) have citadel reputation in the modulation of numerous therapeutic targets as a result of their smart uniqueness. The hydroxylated chalcone derivatives have been reported to be therapeutic agents owing to their capability to demonstrate multifarious pharmacological activities, however, their potential in lowering of blood glucose level is not yet explored fully. Corresponding aldehydes and acetophenones were made to react in an alcoholic basic medium to produce the desired chalcone scaffolds. The anti-hyperglycemic potentials of the derivatives were studied using the streptozotocin-induced diabetic rat model. Compounds 3d, 3f, 3g, 3h, and 3j demonstrated excellent anti-hyperglycemic activity. Chalcone 3d, having an ortho-methoxy substituent in B-ring, displayed the highest hypoglycemic potential with a 26.9% lowering of blood glucose level compared to standard acarbose which exhibited a 34.7% reduction. Compounds 3a, 3c, and 3e showed the lowest activity. The study revealed the potential of chalcone scaffolds in lessening the blood glucose level by 7.1% to 26.9%. The ortho-position was observed to be high opportunistic for inducing the hypoglycemia activity as compared to para-position and para-position is in turn advantageous to the meta-position. The role of various substituents in modulating this enzyme function was studied. The electron-donating groups were found to be effectual for modulation of the anti-diabetic target compared to electron-withdrawing groups.
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References
- Borikar SP, Kallewar NG, Mahapatra DK, Dumore NG, Danao KR. Combined flower decoction of Clitoria ternatea and Punica granatum expressed comparable hypoglycemic activity with that of metformin: In vivo study. Int J Pharm Sci Res 2017; 2(5): 4-7.
- aBorikar SP, Kallewar NG, Mahapatra DK, Dumore NG. Dried flower powder combination of Clitoria ternatea and Punica granatum demonstrated analogous anti-hyperglycemic potential as compared with standard drug metformin: In vivo study in Sprague Dawley rats. J Appl Pharm Sci 2018; 8(11): 75-79.
- Borikar SP, Kallewar NG, Mahapatra DK, Gupta RA, Dumore NG, Danao KR, Mahajan UN. Decoction of Andrographis paniculata whole plant and Gymnema sylvestre leaves demonstrated noteworthy hypoglycemic activity in Sprague Dawley rat. Phytopharmacol J 2018: 7(1): 84-87.
- Chhajed SS, Chaskar S, Kshirsagar SK, Haldar AGM, Mahapatra DK. Rational design and synthesis of some PPAR-γ agonists: substituted benzylideneamino-benzylidene-thiazolidine-2,4-diones. Comp Biol Chem 2017; 67: 260-265.
- Gangane PS, Kadam MM, Mahapatra DK, Mahajan NM, Mahajan UN. Design and formulating gliclazide solid dispersion immediate release layer and metformin sustained release layer in bilayer tablet for the effective postprandial management of diabetes mellitus. Int J Pharm Sci Res 2018; 9(9): 3743-3756.
- Godbole MD, Mahapatra DK, Khode PD. Fabrication and Characterization of Edible Jelly Formulation of Stevioside: A Nutraceutical or OTC Aid for the Diabetic Patients. Inventi Rapid Nutraceut 2017; 2017(2): 1-9.
- Kuhite NG, Padole CD, Amdare MD, Jogdand KR, Kathane LL, Mahapatra DK. Hippuric acid as the template material for the synthesis of a novel anti-diabetic 1,3,4-thiadiazole derivative. Indian J Pharm Biol Res 2017; 5(3): 42-45.
- Mahapatra DK, Asati V, Bharti SK. Chalcones and their therapeutic targets for the management of diabetes: structural and pharmacological perspectives. Eur J Med Chem 2015; 92: 839-865.
- aMahapatra DK, Bharti SK, Asati V. Anti-cancer chalcones: Structural and molecular target perspectives. Eur J Med Chem 2015; 98: 69-114.
- bMahapatra DK, Bharti SK, Asati V. Chalcone scaffolds as anti-infective agents: Structural and molecular target perspectives. Eur J Med Chem 2015; 101: 496-524.
- Mahapatra DK, Bharti SK. Therapeutic potential of chalcones as cardiovascular agents. Life Sci 2016; 148: 154-172.
- Mahapatra DK, Bharti SK, Asati V. Chalcone derivatives: Anti-inflammatory potential and molecular targets perspectives. Curr Top Med Chem 2017; 17(28): 3146-3169.
- aMahapatra DK, Chhajed SS, Shivhare RS. Development of Murrayanine-Chalcone hybrids: An effort to combine two privilege scaffolds for enhancing hypoglycemic activity. Int J Pharm Chem Anal 2017; 4(2): 30-34.
- Mahapatra DK, Dadure KM, Haldar AGM. Uracil substitution on a hippuric acid containing 1,3,4-thiadiazole scaffold: The exploration of the anti-hyperglycemic potential. Int J Med Sci Clin Res Rev 2018; 1(2): 1-4.
- Mahapatra DK, Bharti SK, Asati V. Recent perspectives of chalcone based molecules as protein tyrosine phosphatase 1B (PTP-1B) inhibitors. In: Mahapatra DK, Bharti SK, Editors. Medicinal Chemistry with Pharmaceutical Product Development. New Jersey: Apple Academic Press, 2019 (235-251 pp).