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Molecules 2015, 20(9), 16566-16581; doi:10.3390/molecules200916566

Benzofuranyl Esters: Synthesis, Crystal Structure Determination, Antimicrobial and Antioxidant Activities

1
X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia
2
Department of Engineering Chemistry, Alva’s Institute of Engineering & Technology, Visvesvaraya Technological University, Mijar, Moodbidri 574225, Karnataka, India
3
Department of Sugar Technology & Chemistry, University of Mysore, Sir M. V. PG Center, Tubinakere, Mandya 571402, Karnataka, India
4
Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Perak Campus, Jalan Universiti, Bandar Barat, Kampar 31900, Malaysia
5
School of Biological Sciences, Universiti Sains Malaysia, Penang 11800, Malaysia
6
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 21 July 2015 / Revised: 14 August 2015 / Accepted: 17 August 2015 / Published: 11 September 2015
(This article belongs to the Section Molecular Diversity)
View Full-Text   |   Download PDF [1772 KB, uploaded 11 September 2015]   |  

Abstract

A series of five new 2‐(1‐benzofuran‐2‐yl)‐2‐oxoethyl 4-(un/substituted)benzoates 4(ae), with the general formula of C8H5O(C=O)CH2O(C=O)C6H4X, X = H, Cl, CH3, OCH3 or NO2, was synthesized in high purity and good yield under mild conditions. The synthesized products 4(ae) were characterized by FTIR, 1H-, 13C- and 1H-13C HMQC NMR spectroscopic analysis and their 3D structures were confirmed by single-crystal X-ray diffraction studies. These compounds were screened for their antimicrobial and antioxidant activities. The tested compounds showed antimicrobial ability in the order of 4b < 4a < 4c < 4d < 4e and the highest potency with minimum inhibition concentration (MIC) value of 125 µg/mL was observed for 4e. The results of antioxidant activities revealed the highest activity for compound 4e (32.62% ± 1.34%) in diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, 4d (31.01% ± 4.35%) in ferric reducing antioxidant power (FRAP) assay and 4a (27.11% ± 1.06%) in metal chelating (MC) activity. View Full-Text
Keywords: benzofuran; spectroscopic analysis; antimicrobial; antioxidant; XRD; substituent benzofuran; spectroscopic analysis; antimicrobial; antioxidant; XRD; substituent
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Kumar, C.S.C.; Then, L.Y.; Chia, T.S.; Chandraju, S.; Win, Y.-F.; Sulaiman, S.F.; Hashim, N.S.; Ooi, K.L.; Quah, C.K.; Fun, H.-K. Benzofuranyl Esters: Synthesis, Crystal Structure Determination, Antimicrobial and Antioxidant Activities. Molecules 2015, 20, 16566-16581.

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