Synthesis, anticancer and antimicrobial evaluation of new benzofuran based derivatives: PI3K inhibition, quorum sensing and molecular modeling study was written by El-Khouly, Omar A.;Henen, Morkos A.;El-Sayed, Magda A.-A.;Shabaan, Mona I.;El-Messery, Shahenda M.. And the article was included in Bioorganic & Medicinal Chemistry in 2021.Reference of 638-07-3 The following contents are mentioned in the article:
A new series of benzofuran derivatives , e.g., I [R = CH2CO2Et, Ph, 4-MeC6H4, etc.] and II [R1 = Ph, 4-ClC6H4, 3-MeC6H4, etc.], were designed and synthesized. All synthesized compounds were evaluated for anticancer activity against hepatocellular carcinoma (HePG2), mammary gland breast cancer (MCF-7), epithelioid carcinoma cervix cancer (Hela) and human prostate cancer (PC3). Compounds I [R = Me, CH2CO2Et, Ph] showed the highest activity toward the four cell lines with an IC50 range of 8.49-16.72μM, 6.55-13.14μM and 4-8.99μM resp. in comparison to DOX (4.17-8.87μM). Phosphatidylinositol-3-kinases (PI3K) inhibition was evaluated against the most active anticancer compounds I [R = Me, CH2CO2Et, Ph]. Compounds I [R = Me, CH2CO2Et, Ph] showed good inhibitory activity against PI3Kα with IC50 values 4.1, 7.8, and 20.5μM, resp. in comparison to 6.18μM for the reference compound LY294002. In addition, activity of compounds I [R = CH2CO2Et, Ph] on cell cycle arrest and induction of apoptosis in different phases of MCF-7 cells were assessed and detected pre-G1 apoptosis and cell growth arrest at G2/M. Also, both extrinsic and intrinsic apoptosis in MCF-7 cells induced by compounds I [R = CH2CO2Et, Ph]. Mol. docking, binding affinity surface mapping and contact preference of the synthesized compounds I [R = Me, CH2CO2Et, Ph] against PI3K were estimated and studied computationally using mol. operating environment software (MOE) and showed good interaction with essential residues for inhibition Val851. In addition, antimicrobial activity was evaluated against gram pos. isolates as Staphylococcus aureus and Bacillus cereus, gram neg. isolate as Escherichia coli, Pseudomonas aeruginosa and antifungal potential against Candida albicans. Compound II [R1 = 3-MeC6H4] showed outstanding anti Gram-pos. activity with MIC values 8 and 256μg/mL in Staphylococcus aureus and Bacillus cereus resp. Also, compounds II [R1 = 4-MeC6H4, 3-MeC6H4, 4-NO2C6H4] and 2-(4-methoxyphenyl)-2-oxoethyl (E)-2-(1-(benzofuran-2-yl)ethylidene)hydrazine-1-carbodithioate showed good anti Gram-neg. activity with MIC value 512μg/mL for all compounds In addition, the state-of-art quorum sensing (QS) inhibiting effects were detected using Chromobacterium violaceum and compounds I [R = Me, CH2CO2Et, 4-MeC6H4, benzofuran-2-yl] and (E)-1-(benzofuran-2-yl)-3-(dimethylamino)prop-2-en-1-one showed good QS inhibition (3, 3, 5, 2, and 7 mm). This study involved multiple reactions and reactants, such as Ethyl 4-chloro-3-oxobutanoate (cas: 638-07-3Reference of 638-07-3).
Ethyl 4-chloro-3-oxobutanoate (cas: 638-07-3) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications.While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.Reference of 638-07-3
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics