Synthesis, Crystal Structure, Antioxidant, and α-Glucosidase Inhibitory Activities of Methoxy-substituted Benzohydrazide Derivatives
- Authors: Prachumrat P.1, Kobkeatthawin T.1, Ruanwas P.1, Boonnak N.2, Laphookhieo S.3, Kassim M.B.4,5, Chantrapromma S.1
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Affiliations:
- Department of Chemistry, Faculty of Science
- Department of Basic Science and Mathematics, Faculty of Science
- Natural Products Research Laboratory, School of Science
- School of Chemical Sciences and Food Technology, Faculty of Science and Technology
- Fuel Cell Institute
- Issue: Vol 63, No 3 (2018)
- Pages: 405-411
- Section: Structure of Organic Compounds
- URL: https://journals.rcsi.science/1063-7745/article/view/192499
- DOI: https://doi.org/10.1134/S1063774518030227
- ID: 192499
Cite item
Abstract
Eight methoxy substituted at the benzylidene moiety benzohydrazide derivatives [R = 2-OCH3 (1), 3-OCH3 (2), 4-OCH3 (3), 2,3-(OCH3)2 (4), 3,4-(OCH3)2 (5), 2,4,5-(OCH3)3 (6), 2,4,6-(OCH3)3 (7), and 3,4,5-(OCH3)3 (8)] were synthesized and characterized by 1H NMR, FT-IR and UV-Vis spectroscopy. The crystal structure of 4 was determined by single crystal X-ray diffraction (sp. gr. Pbca, Z = 8). The molecule is slightly twisted with the dihedral angle between the two phenyl rings being 9.33(14)°. The methoxy group at the ortho position is twisted [C–O–C–C angle is–109.2(3)°] whereas the other at meta position is co-planar with the attached benzene ring. In the crystal packing, the molecules are linked into two-dimensional network parallel to the (001) plane by O–H···O, O–H···N, and N–H···O hydrogen bonds. Compounds 1–8 were evaluated for an antioxidant and α-glucosidase inhibitory activities and the results suggested that the −OCH3 substituent was ineffective for bioactivity enhancement.
About the authors
P. Prachumrat
Department of Chemistry, Faculty of Science
Email: suchada.c@psu.ac.th
Thailand, Hat-Yai
T. Kobkeatthawin
Department of Chemistry, Faculty of Science
Email: suchada.c@psu.ac.th
Thailand, Hat-Yai
P. Ruanwas
Department of Chemistry, Faculty of Science
Email: suchada.c@psu.ac.th
Thailand, Hat-Yai
N. Boonnak
Department of Basic Science and Mathematics, Faculty of Science
Email: suchada.c@psu.ac.th
Thailand, Muang
S. Laphookhieo
Natural Products Research Laboratory, School of Science
Email: suchada.c@psu.ac.th
Thailand, Chiang Rai
M. B. Kassim
School of Chemical Sciences and Food Technology, Faculty of Science and Technology; Fuel Cell Institute
Email: suchada.c@psu.ac.th
Malaysia, Selangor; Selangor
S. Chantrapromma
Department of Chemistry, Faculty of Science
Author for correspondence.
Email: suchada.c@psu.ac.th
Thailand, Hat-Yai