86-75-9Relevant articles and documents
Synthesis and mechanistic studies of quinolin-chlorobenzothioate derivatives with proteasome inhibitory activity in pancreatic cancer cell lines
Hu, Shuai,Jin, Yi,Liu, Yanghan,Ljungman, Mats,Neamati, Nouri
, p. 884 - 895 (2018/09/29)
Inhibition of proteasome activity blocks the degradation of dysfunctional proteins and induces cancer cell death due to cellular stress. Thus, proteasome inhibitors represent an attractive class of anticancer agents, and bortezomib, carfilzomib and ixazomib have been FDA-approved to treat multiple myeloma. However, cancer cells acquire resistance to these inhibitors through point mutations in the proteasome catalytic subunit or induction of alternative compensatory mechanisms. In this study, we identified a quinolin-chlorobenzothioate, QCBT7, as a new proteasome inhibitor showing cytotoxicity in a panel of cancer cell lines. QCBT7 is a more stable derivative of quinoline-8-thiol that targets the regulatory subunit instead of the catalytic subunit of the proteasome. QCBT7 caused the accumulation of ubiquitylated proteins in the cancer cells, indicating its proteasome inhibitory activity. Additionally, QCBT7 increased the expression of a set of genes (PFKFB4, CHOP, HMOX1 and SLC7A11) at both nascent RNA and protein levels, similarly to the known proteasome inhibitors MG132 and ixazomib. Together, QCBT7 induces proteasome inhibition, hypoxic response, endoplasmic reticulum stress and glycolysis, finally leading to cell death. Importantly, we have identified PFKFB4 as a potential biomarker of proteasome inhibitors that can be used to monitor treatment response.
Solid-Phase Benzoylation of Phenols and Alcohols in Microwave Reactor: An Ecofriendly Protocol
Chakraborty, Suchandra,Saha, Ahana,Basu, Kaushik,Saha, Chandan
supporting information, p. 2331 - 2343 (2015/10/12)
An efficient solid-phase benzoylation of phenols and alcohols was developed under microwave irradiation. A stoichiometric amount of benzoyl chloride was sufficient to carry out the reaction. This benzoylation features short reaction time, good yields, and easy workup procedures. Furthermore, the scope of the reaction was extended to prepare 3,5-dinitrobenzoyl derivatives of alcohols.
Copper-mediated ortho-nitration of (hetero)arenecarboxylates
Katayev, Dmitry,Pfister, Kai F.,Wendling, Timo,Goossen, Lukas J.
supporting information, p. 9902 - 9905 (2014/08/18)
Various (hetero)arenecarboxylic acids were converted to the corresponding Daugulis amides and nitrated selectively in the ortho-position in the presence of [CuNO3(PPh3)2] and AgNO2 at 50 °C. A microwave-assisted saponification allows regenerating the carboxylate group within minutes, which may then be removed tracelessly by protodecarboxylation, or substituted by aryl- or alkoxy-groups via decarboxylative cross-coupling.
