Synthesis, Crystal Structure, Antioxidant, and α-Glucosidase Inhibitory Activities of Methoxy-substituted Benzohydrazide Derivatives

P. Prachumrat, T. Kobkeatthawin, P. Ruanwas, N. Boonnak, S. Laphookhieo, Mohammad Kassim, S. Chantrapromma

Research output: Contribution to journalArticle

1 Citation (Scopus)

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–HO, O–HN, and N–HO 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.

Original languageEnglish
Pages (from-to)405-411
Number of pages7
JournalCrystallography Reports
Volume63
Issue number3
DOIs
Publication statusPublished - 1 May 2018

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Glucosidases
antioxidants
Antioxidants
Crystal structure
Derivatives
crystal structure
Molecules
rings
Dihedral angle
synthesis
Bioactivity
Benzene
Ultraviolet spectroscopy
dihedral angle
molecules
Hydrogen bonds
benzene
Nuclear magnetic resonance
Single crystals
hydrogen bonds

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

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Synthesis, Crystal Structure, Antioxidant, and α-Glucosidase Inhibitory Activities of Methoxy-substituted Benzohydrazide Derivatives. / Prachumrat, P.; Kobkeatthawin, T.; Ruanwas, P.; Boonnak, N.; Laphookhieo, S.; Kassim, Mohammad; Chantrapromma, S.

In: Crystallography Reports, Vol. 63, No. 3, 01.05.2018, p. 405-411.

Research output: Contribution to journalArticle

Prachumrat, P. ; Kobkeatthawin, T. ; Ruanwas, P. ; Boonnak, N. ; Laphookhieo, S. ; Kassim, Mohammad ; Chantrapromma, S. / Synthesis, Crystal Structure, Antioxidant, and α-Glucosidase Inhibitory Activities of Methoxy-substituted Benzohydrazide Derivatives. In: Crystallography Reports. 2018 ; Vol. 63, No. 3. pp. 405-411.
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