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
A series of novel 2-aryl 1 -4-bromothiophenes (2a-f), biarylthiophenes with non-identical aryl groups (3a-e) and biarylthiophenes with identical aryl groups (4a-f) were synthesized in moderate to excellent yields by using different arylboronic acids in a Suzuki-Miyaura cross-coupling reaction. The experimental results showed that the use of K 2 CO 3 as base resulted in moderate yields compared with that of good yields obtained upon using K 3 PO 4 . The highest yield obtained using K 3 PO 4 was 82% for 2, 4-bis (4-chlorophenyl) thiophene (4d). The synthesized compounds in the present study were examined for their biofilm inhibition and hemolysis assay. Among all compounds 2, 4-bis (4-methoxyphenyl) thiophene (4b) was found to strongly inhibit the formation of bacterial biofilm against E. coli. The compound 4b exhibited higher inhibition (80.92%) compared with the standard Rifampicin with 97.43% inhibition. The compound 2, 4-bis (4-chlorophenyl) thiophene (4d) displayed strong anti-biofilm activity with its ability to prevent the formation of Pasteurell amultocida biofilm at the percent inhibition of 74.53%. In addition, 2f showed the highest percentage hemolysis 16.0% compared with that of the standard Triton-X-100. 3
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