Synthesis, antityrosinase activity of curcumin analogues, and crystal structure of (1E,4E)-1,5-bis(4-ethoxyphenyl)penta-1,4-dien-3-one
- Authors: Chantrapromma S.1, Ruanwas P.1, Boonnak N.2, Chantrapromma K.3, Fun H.4,5
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Affiliations:
- Department of Chemistry, Faculty of Science
- Department of Basic Science and Mathematics, Faculty of Science
- Faculty of Science and Technology
- X-ray Crystallography Unit, School of Physics
- Department of Pharmaceutical Chemistry, College of Pharmacy
- Issue: Vol 61, No 7 (2016)
- Pages: 1081-1085
- Section: Structure of Organic Compounds
- URL: https://journals.rcsi.science/1063-7745/article/view/190502
- DOI: https://doi.org/10.1134/S1063774516070051
- ID: 190502
Cite item
Abstract
Five derivatives of curcumin analogue (R = OCH2CH3 (1), R = N(CH3)2 (2), R = 2,4,5-OCH3 (3), R = 2,4,6-OCH3 (4), and R = 3,4,5-OCH3 (5)) were synthesized and characterized by 1H NMR, FT-IR and UV–Vis spectroscopy. The synthesized derivatives were screened for antityrosinase activity, and found that 4 and 5 possess such activity. The crystal structure of 1 was determined by single crystal X-ray diffraction: monoclinic, sp. gr. P21/c, a = 17.5728(15) Å, b = 5.9121(5) Å, c = 19.8269(13) Å, β = 121.155(5)°, Z = 4. The molecule 1 is twisted with the dihedral angle between two phenyl rings being 15.68(10)°. In the crystal packing, the molecules 1 are linked into chains by C−H···π interactions and further stacked by π···π interactions with the centroid–centroid distance of 3.9311(13) Å.
About the authors
S. Chantrapromma
Department of Chemistry, Faculty of Science
Author for correspondence.
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, Songkhla
K. Chantrapromma
Faculty of Science and Technology
Email: suchada.c@psu.ac.th
Thailand, Songkhla
H.-K. Fun
X-ray Crystallography Unit, School of Physics; Department of Pharmaceutical Chemistry, College of Pharmacy
Email: suchada.c@psu.ac.th
Malaysia, Pulau, Penang; Riyadh