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alpha-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives.
Bioorg Med Chem. 2010 Jan 01; 18(1):358-65.BM

Abstract

Series of 3,4- and 3,6-disubstituted chromenones including new chromenone derivatives were synthesized applying various synthetic strategies including Pechmann condensation, Knoevenagel condensation, Reimer-Tiemann reaction and Suzuki coupling in very good yields. Synthesized compounds (4a-z) were screened for in vitro alpha-glucosidase inhibitory and 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activities. Majority of compounds displayed varying degrees of alpha-glucosidase inhibitory and DPPH scavenging activity. Compound 4x emerged as the most potent alpha-glucosidase inhibitor in present series of compounds owing to the presence of 3-acetyl-6-(6-methoxy-3-pyridyl) group on chromenone; however, it could not display DPPH scavenging activity and was found to be mixed non-competitive type inhibitor of rat intestinal alpha-glucosidase. When tested in vivo for antihyperglycemic activity in starch loaded Wistar rats, it displayed significant antihyperglycemic property. This is the first report assigning rat intestinal alpha-glucosidase inhibitory property for this class of new chromenones and presents new family of compounds possessing alpha-glucosidase inhibitory activities and antihyperglycemic property. Compound 4x may serve as an interesting new compound for the development of therapeutics targeted against diet-induced hyperglycemia in diabetes.

Authors+Show Affiliations

Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500 607, India. chinarajuiict@yahoo.co.inNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19932027

Citation

Raju, B China, et al. "Alpha-Glucosidase Inhibitory Antihyperglycemic Activity of Substituted Chromenone Derivatives." Bioorganic & Medicinal Chemistry, vol. 18, no. 1, 2010, pp. 358-65.
Raju BC, Tiwari AK, Kumar JA, et al. Alpha-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives. Bioorg Med Chem. 2010;18(1):358-65.
Raju, B. C., Tiwari, A. K., Kumar, J. A., Ali, A. Z., Agawane, S. B., Saidachary, G., & Madhusudana, K. (2010). Alpha-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives. Bioorganic & Medicinal Chemistry, 18(1), 358-65. https://doi.org/10.1016/j.bmc.2009.10.047
Raju BC, et al. Alpha-Glucosidase Inhibitory Antihyperglycemic Activity of Substituted Chromenone Derivatives. Bioorg Med Chem. 2010 Jan 1;18(1):358-65. PubMed PMID: 19932027.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - alpha-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives. AU - Raju,B China, AU - Tiwari,Ashok K, AU - Kumar,J Ashok, AU - Ali,A Zehra, AU - Agawane,Sachin B, AU - Saidachary,G, AU - Madhusudana,K, Y1 - 2009/10/29/ PY - 2009/09/24/received PY - 2009/10/23/revised PY - 2009/10/24/accepted PY - 2009/11/26/entrez PY - 2009/11/26/pubmed PY - 2010/4/28/medline SP - 358 EP - 65 JF - Bioorganic & medicinal chemistry JO - Bioorg Med Chem VL - 18 IS - 1 N2 - Series of 3,4- and 3,6-disubstituted chromenones including new chromenone derivatives were synthesized applying various synthetic strategies including Pechmann condensation, Knoevenagel condensation, Reimer-Tiemann reaction and Suzuki coupling in very good yields. Synthesized compounds (4a-z) were screened for in vitro alpha-glucosidase inhibitory and 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activities. Majority of compounds displayed varying degrees of alpha-glucosidase inhibitory and DPPH scavenging activity. Compound 4x emerged as the most potent alpha-glucosidase inhibitor in present series of compounds owing to the presence of 3-acetyl-6-(6-methoxy-3-pyridyl) group on chromenone; however, it could not display DPPH scavenging activity and was found to be mixed non-competitive type inhibitor of rat intestinal alpha-glucosidase. When tested in vivo for antihyperglycemic activity in starch loaded Wistar rats, it displayed significant antihyperglycemic property. This is the first report assigning rat intestinal alpha-glucosidase inhibitory property for this class of new chromenones and presents new family of compounds possessing alpha-glucosidase inhibitory activities and antihyperglycemic property. Compound 4x may serve as an interesting new compound for the development of therapeutics targeted against diet-induced hyperglycemia in diabetes. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/19932027/alpha_Glucosidase_inhibitory_antihyperglycemic_activity_of_substituted_chromenone_derivatives_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(09)00982-1 DB - PRIME DP - Unbound Medicine ER -