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

• Published in: International journal of molecular sciences 2016-07, Vol.17 (7), p.912-912
• Main Authors: Rasool, Nasir, Kanwal, Aqsa, Rasheed, Tehmina, Ain, Quratulain, Mahmood, Tariq, Ayub, Khurshid, Zubair, Muhammad, Khan, Khalid Mohammed, Arshad, Muhammad Nadeem, M Asiri, Abdullah, Zia-Ul-Haq, Muhammad, Jaafar, Hawa Z E
• Format: Article
• Language: English
• Subjects: 2-bromo-5-chloro thiophenes; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; antibacterial; antioxidant; Biological activity; Chemical synthesis; Density; density functional theory (DFT); Escherichia coli; Escherichia coli - drug effects; Microbial Sensitivity Tests; Molecular Structure; Suzuki coupling; Thiophenes - chemistry; Thiophenes - pharmacology; X-Ray Diffraction
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms17070912

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.