Synthesis, Crystal Structure, Antioxidant, and α-Glucosidase Inhibitory Activities of Methoxy-substituted Benzohydrazide Derivatives
- Prince of Songkla University, Department of Chemistry, Faculty of Science (Thailand)
- Thaksin University, Department of Basic Science and Mathematics, Faculty of Science (Thailand)
- Mae Fah Luang University, Natural Products Research Laboratory, School of Science (Thailand)
- Universiti Kebangsaan, School of Chemical Sciences and Food Technology, Faculty of Science and Technology (Malaysia)
Eight methoxy substituted at the benzylidene moiety benzohydrazide derivatives [R = 2-OCH{sub 3} (1), 3-OCH{sub 3} (2), 4-OCH{sub 3} (3), 2,3-(OCH{sub 3}){sub 2} (4), 3,4-(OCH{sub 3}){sub 2} (5), 2,4,5-(OCH{sub 3}){sub 3} (6), 2,4,6-(OCH{sub 3}){sub 3} (7), and 3,4,5-(OCH{sub 3}){sub 3} (8)] were synthesized and characterized by {sup 1}H 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 −OCH{sub 3} substituent was ineffective for bioactivity enhancement.
- OSTI ID:
- 22758239
- Journal Information:
- Crystallography Reports, Vol. 63, Issue 3; Other Information: Copyright (c) 2018 Pleiades Publishing, Inc.; Country of input: International Atomic Energy Agency (IAEA); ISSN 1063-7745
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
SUPERCONDUCTIVITY AND SUPERFLUIDITY
37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ANTIOXIDANTS
BENZENE
FOURIER TRANSFORM SPECTROMETERS
GLUCOSIDASE
HYDROGEN
HYDROGEN 1
INFRARED SPECTRA
MOLECULES
MONOCRYSTALS
NUCLEAR MAGNETIC RESONANCE
ORTHORHOMBIC LATTICES
RINGS
SPECTROSCOPY
SYNTHESIS
TWO-DIMENSIONAL SYSTEMS
X-RAY DIFFRACTION