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One Pot Selective Arylation of 2-Bromo-5-Chloro Thiophene; Molecular Structure Investigation via Density Functional Theory (DFT), X-ray Analysis, and Their Biological Activities

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Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan
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Department of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, Abbottabad 22060, Pakistan
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H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
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Departments of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia
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Center of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia
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The Patent Office, Karachi 75270, Pakistan
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Department of Crop Science, Faculty of Agriculture, 43400 UPM Serdang, Selangor, Malaysia
*
Authors to whom correspondence should be addressed.
Academic Editor: Abihijit Chatterjee
Int. J. Mol. Sci. 2016, 17(7), 912; https://doi.org/10.3390/ijms17070912
Received: 7 April 2016 / Accepted: 13 May 2016 / Published: 28 June 2016
(This article belongs to the Section Physical Chemistry, Theoretical and Computational Chemistry)
Synthesis of 2,5-bisarylthiophenes was accomplished by sequential Suzuki cross coupling reaction of 2-bromo-5-chloro thiophenes. Density functional theory (DFT) studies were carried out at the B3LYP/6-31G(d, p) level of theory to compare the geometric parameters of 2,5-bisarylthiophenes with those from X-ray diffraction results. The synthesized compounds are screened for in vitro bacteria scavenging abilities. At the concentration of 50 and 100 μg/mL, compounds 2b, 2c, 2d, 3c, and 3f with IC50-values of 51.4, 52.10, 58.0, 56.2, and 56.5 μg/mL respectively, were found most potent against E. coli. Among all the synthesized compounds 2a, 2d, 3c, and 3e with the least values of IC50 77, 76.26, 79.13 μg/mL respectively showed significant antioxidant activities. Almost all of the compounds showed good antibacterial activity against Escherichia coli, whereas 2-chloro-5-(4-methoxyphenyl) thiophene (2b) was found most active among all synthesized compound with an IC50 value of 51.4 μg/mL. All of the synthesized compounds were screened for nitric oxide scavenging activity as well. Frontier molecular orbitals (FMOs) and molecular electrostatic potentials of the target compounds were also studied theoretically to account for their relative reactivity View Full-Text
Keywords: 2-bromo-5-chloro thiophenes; Suzuki coupling; density functional theory (DFT); antibacterial; antioxidant 2-bromo-5-chloro thiophenes; Suzuki coupling; density functional theory (DFT); antibacterial; antioxidant
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Rasool, N.; Kanwal, A.; Rasheed, T.; Ain, Q.; Mahmood, T.; Ayub, K.; Zubair, M.; Khan, K.M.; Arshad, M.N.; M. Asiri, A.; Zia-Ul-Haq, M.; Jaafar, H.Z.E. One Pot Selective Arylation of 2-Bromo-5-Chloro Thiophene; Molecular Structure Investigation via Density Functional Theory (DFT), X-ray Analysis, and Their Biological Activities. Int. J. Mol. Sci. 2016, 17, 912.

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