Synthesis, structure combined with conformational analysis, biological activities and docking studies of bis benzylidene cyclohexanone derivatives
Joint Authors
Lutfi, Jihad
al-Tamani, al-Sayyid H.
Sulayman, Said M.
Said, Muhammad M.
al-Ashri, al-Sayyid H.
Barakat, Asim
Source
Journal of Saudi Chemical Society
Issue
Vol. 21, Issue 5 (31 Jul. 2017), pp.619-632, 14 p.
Publisher
Publication Date
2017-07-31
Country of Publication
Saudi Arabia
No. of Pages
14
Main Subjects
Pharmacy, Health & Medical Sciences
Chemistry
Topics
Abstract EN
We report the synthesis and biological evaluation of bis benzylidne cyclohexanone derivatives 2,6-di(4-fluorobenzylidene)cyclohexanone 3a and (2E,6E)-2,6-bis({[4-(trifluoromethyl) phenyl]methylidene})cyclohexanone 3b.
Compound 3b crystallized in the monoclinic space group P21/n with unit cell parameters a= 29.3527(12) A ˚ , b=8.3147(3) A ˚ , c = 32.7452(14) A ˚ , b = 112.437(2), and V = 7386.8(5) A ˚ 3, Z = 16, and Rint = 0.072 at T = 100 K.
The asymmetric unit contains four independent molecules, each of which has slight differences in the bond lengths and angles.
One non-classical C11D–H11F F3A hydrogen bond connects the molecules.
Density functional theory was used to optimize the structures and calculate the natural charges, dipole moments, frontier molecular orbitals, and NMR and UV–Vis spectroscopic properties, which are discussed and compared with the experimental data.
The synthetic derivatives were evaluated for a-glucosidase inhibitory activity, and we found that compound 3a (IC50 =96.3 ± 0.51 lM) is a potent a-glucosidase inhibitor, showing superior activity to the standard drug acarbose (IC50= 841± 1.73 lM).
Compound 3b (IC50= 7.92 ± 1.3 lg/mL) was found to be a potent antileishmanial compound, especially compared to the antileishmanial drugs pentamidine (IC50= 5.09 ± 0.04 lM) and amphotericine B (IC50 =0.29 ± 0.05 lg/mL).
In addition, 3a and
American Psychological Association (APA)
Lutfi, Jihad& Said, Muhammad M.& al-Ashri, al-Sayyid H.& al-Tamani, al-Sayyid H.& Sulayman, Said M.& Barakat, Asim. 2017. Synthesis, structure combined with conformational analysis, biological activities and docking studies of bis benzylidene cyclohexanone derivatives. Journal of Saudi Chemical Society،Vol. 21, no. 5, pp.619-632.
https://search.emarefa.net/detail/BIM-781835
Modern Language Association (MLA)
Lutfi, Jihad…[et al.]. Synthesis, structure combined with conformational analysis, biological activities and docking studies of bis benzylidene cyclohexanone derivatives. Journal of Saudi Chemical Society Vol. 21, no. 5 (Jul. 2017), pp.619-632.
https://search.emarefa.net/detail/BIM-781835
American Medical Association (AMA)
Lutfi, Jihad& Said, Muhammad M.& al-Ashri, al-Sayyid H.& al-Tamani, al-Sayyid H.& Sulayman, Said M.& Barakat, Asim. Synthesis, structure combined with conformational analysis, biological activities and docking studies of bis benzylidene cyclohexanone derivatives. Journal of Saudi Chemical Society. 2017. Vol. 21, no. 5, pp.619-632.
https://search.emarefa.net/detail/BIM-781835
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references : p. 631-632
Record ID
BIM-781835