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Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group
ACS Medicinal Chemistry Letters ( IF 4.2 ) Pub Date : 2017-07-18 00:00:00 , DOI: 10.1021/acsmedchemlett.7b00212
Pierrik Lassalas 1 , Killian Oukoloff 2 , Vishruti Makani 3 , Michael James 3 , Van Tran 1 , Yuemang Yao 3 , Longchuan Huang 1 , Krishna Vijayendran 1 , Ludovica Monti 2 , John Q. Trojanowski 3 , Virginia M.-Y. Lee 3 , Marisa C. Kozlowski 1 , Amos B. Smith 1 , Kurt R. Brunden 3 , Carlo Ballatore 2
Affiliation  

The oxetane ring serves as an isostere of the carbonyl moiety, suggesting that oxetan-3-ol may be considered as a potential surrogate of the carboxylic acid functional group. To investigate this structural unit, as well as thietan-3-ol and the corresponding sulfoxide and sulfone derivatives, as potential carboxylic acid bioisosteres, a set of model compounds has been designed, synthesized, and evaluated for physicochemical properties. Similar derivatives of the cyclooxygenase inhibitor, ibuprofen, were also synthesized and evaluated for inhibition of eicosanoid biosynthesis in vitro. Collectively, the data suggest that oxetan-3-ol, thietan-3-ol, and related structures hold promise as isosteric replacements of the carboxylic acid moiety.

中文翻译:

评价Oxetan-3-ol,Thietan-3-ol及其衍生物作为羧酸官能团的生物等排体

氧杂环丁烷环充当羰基部分的等排物,表明氧杂环丁烷-3-醇可被认为是羧酸官能团的潜在替代物。为了研究该结构单元以及硫杂环丁-3-醇和相应的亚砜和砜衍生物作为潜在的羧酸生物等排体,已设计,合成并评估了一组模型化合物的理化性质。还合成了环氧合酶抑制剂布洛芬的类似衍生物,并评估了其在体外对类花生酸生物合成的抑制作用。总体而言,数据表明,氧杂环丁烷-3-醇,硫杂环丁烷-3-醇和相关结构有望作为羧酸部分的等排取代物。
更新日期:2017-07-19
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