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Relevant academic research and scientific papers

Visible-light induced copper(i)-catalyzed oxidative cyclization of: O -aminobenzamides with methanol and ethanol via HAT

The use of the in situ generated ligand-copper superoxo complex absorbing light energy to activate the alpha C(sp3)-H of MeOH and EtOH via the hydrogen atom transfer (HAT) process for the synthesis of quinazolinones by oxidative cyclization of alcohols with o-aminobenzamide has been investigated. The synthetic utility of this protocol offers an efficient synthesis of a quinazolinone intermediate for erlotinb (anti-cancer agent) and 30 examples were reported.

Synthesis, In Vitro Antiproliferative Activity, and In Silico Studies of New Anilinoquinazoline Derivatives as Potential AntitumorAgents

Abstract: A series of anilinoquinazoline derivatives with modification on the 2nd carbon of the aniline ring has been synthesized and characterized. The compounds have been tested for their in vitro antiproliferative activity against three NSCLC cell lines, including A549, H1650 and H1975. One of the products has demonstrated the highest IC50 value against A549 (17.60 ± 1.70 μM), surpassing the standard drug, gefitinib (34.32 ± 1.30 μM), another one has exhibited IC50 value against H1975 (9.75 ± 1.06 μM), surpassing gefitinib (31.12 ± 0.38 μM). The best performing derivatives in the antiproliferative assay have been selected for further in silico study for investigating their plausible binding mode in different EGFR kinases through molecular docking and molecular dynamics simulations.

Microwave assisted partial synthesis of enantiomerically pure s-ispinesib - A case study

Ispinesib, a quinazolinone derivative, is the first candidate that has entered clinical trials aimed at developing novel KSP inhibitors. It was discovered by Cytokinetics in a high-throughput screening effort followed by lead optimization of the identified KSP inhibitors. The synthetic route, which involved eleven steps, was problematic with an overall yield of only about 8%. Later a new synthetic strategy was developed which involved the introduction of the chiral center in the very first step using an enantiomerically pure amino acid which led to the synthesis of enantiomerically pure quinazolinones nucleus. Following this route, the yield rose to about 40 % together with a reduction in the manufacturing cost. Present study is the first ever reinvestigation of the partial synthesis of enantiomerically pure ispinesib under microwave irradiation by optimizing the reaction conditions for two bottleneck steps of the synthesis of ispinesib via two routes. The aim of study was to reduce the reaction time and the number of steps and then scale-up the microwave synthesis to synthesize multigrams of ispinesib by using continuous flow processing approach. Route 1 involves the synthesis of quinazolinone core under MW irradiation in a one-pot, two-step reaction sequence using D-valine while Route 2 takes into account N-alkylation of D-valine methyl ester via reductive amination prior to the formation of quinazolinone nucleus.