135467-69-5Relevant articles and documents
A Catalyst-Controlled Aerobic Coupling of ortho-Quinones and Phenols Applied to the Synthesis of Aryl Ethers
Huang, Zheng,Lumb, Jean-Philip
, p. 11543 - 11547 (2016)
ortho-Quinones are underutilized six-carbon-atom building blocks. We herein describe an approach for controlling their reactivity with copper that gives rise to a catalytic aerobic cross-coupling with phenols. The resulting aryl ethers are generated in high yield across a broad substrate scope under mild conditions. This method represents a unique example where the covalent modification of an ortho-quinone is catalyzed by a transition metal, creating new opportunities for their utilization in synthesis.
Selective Inhibitors of Human Liver Carboxylesterase Based on a β-Lapachone Scaffold: Novel Reagents for Reaction Profiling
Hatfield, M. Jason,Chen, Jingwen,Fratt, Ellie M.,Chi, Liying,Bollinger, John C.,Binder, Randall J.,Bowling, John,Hyatt, Janice L.,Scarborough, Jerrod,Jeffries, Cynthia,Potter, Philip M.
supporting information, p. 1568 - 1579 (2017/03/08)
Carboxylesterases (CEs) are ubiquitous enzymes that are responsible for the metabolism of xenobiotics, including drugs such as irinotecan and oseltamivir. Inhibition of CEs significantly modulates the efficacy of such agents. We report here that β-lapachone is a potent, reversible CE inhibitor with Ki values in the nanomolar range. A series of amino and phenoxy analogues have been synthesized, and although the former are very poor inhibitors, the latter compounds are highly effective in modulating CE activity. Our data demonstrate that tautomerism of the amino derivatives to the imino forms likely accounts for their loss in biological activity. A series of N-methylated amino derivatives, which are unable to undergo such tautomerism, were equal in potency to the phenoxy analogues and demonstrated selectivity for the liver enzyme hCE1. These specific inhibitors, which are active in cell culture models, will be exceptionally useful reagents for reaction profiling of esterified drugs in complex biological samples.
Synthesis and anti-inflammatory evaluations of β-lapachone derivatives
Tseng, Chih-Hua,Cheng, Chih-Mei,Tzeng, Cherng-Chyi,Peng, Shin-I,Yang, Chiao-Li,Chen, Yeh-Long
, p. 523 - 531 (2013/02/25)
β-Lapachone (β-LAPA), a natural product from the lapacho tree in South America, is a potential chemotherapeutic agent that exhibit a wide variety of pharmacological effects such as anti-virus, anti-parasitic, anti-cancer, and anti-inflammatory activities.
