《Structure-based discovery of novel 4-(2-fluorophenoxy)quinoline derivatives as c-Met inhibitors using isocyanide-involved multicomponent reactions》 was published in European Journal of Medicinal Chemistry in 2020. These research results belong to Nan, Xiang; Li, Hui-Jing; Fang, Sen-Biao; Li, Qin-Ying; Wu, Yan-Chao. Formula: C5H13NO2 The article mentions the following:
In this study, two novel series of 6,7-dimethoxy-4-(2-fluorophenoxy)quinoline derivatives containing α-acyloxycarboxamide I [R1 = Me, n-Pr, t-Bu, cyclohexyl, phenyl; R2 = cyclopentyl, 2-thienyl, Ph, etc.] or α-acylaminoamide II [R3 = H, n-Bu, Ph, etc.] scaffolds were designed, synthesized and evaluated for their in-vitro biol. activities against c-Met kinase and four cancer cell lines (H460, HT-29, MKN-45 and MDA-MB-231). Most of the target compounds I and II exhibited moderate to significant potency and possessed selectivity for H460 and HT-29 cancer cell lines. The preliminary structure-activity relationships indicated that α-acyloxycarboxamide or α-acylaminoamide as 5-atom linker contributed to the antitumor potency. Among these compounds, compound I [R1 = t-Bu, R2 = 4-fluorophenyl] (c-Met IC50 = 2.43 nM, a multitarget tyrosine kinase inhibitor) exhibited the most potent inhibitory activities against H460, HT-29 and MDA-MB-231 cell lines with IC50 of 0.14 ± 0.03μM, 0.20 ± 0.02μM and 0.42 ± 0.03μM, which were 1.7-, 1.3- and 1.6-fold more active than foretinib, resp. In addition, concentration-dependent assay and time-dependent assay indicated compound I [R1 = t-Bu, R2 = 4-fluorophenyl] inhibited the proliferation of H460 cell in a time and concentration dependent manner. Moreover, docking studies revealed the common mode of interaction with the c-Met binding site, suggesting that compound I [R1 = t-Bu, R2 = 4-fluorophenyl] is a potential candidate for cancer therapy deserving further study. After reading the article, we found that the author used N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5Formula: C5H13NO2)
N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Formula: C5H13NO2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem