DeVries V G, Largis E E, Miner T G, Shepherd R G, Upeslacis J
J Med Chem. 1983 Oct;26(10):1411-21. doi: 10.1021/jm00364a011.
The synthesis of a series of analogues in which the alkyl group of cetaben is substituted with various functional groups or replaced entirely by a functionalized alkanoyl moiety is described. Also reported are the syntheses of branched-chain (alkylamino)benzoic acids in which branching is specifically localized at the terminus of the alkyl chain. Structure-activity relationships of these compounds, both as hypolipidemic agents and as inhibitors of the enzyme fatty acyl-CoA:cholesterol acyltransferase (ACAT), are discussed. Certain compounds were specifically synthesized to test the hypothesis that groups located near the terminus of the alkyl chain of cetaben might retard metabolic degradation of the molecule and, thus, enhance biological activity. Some of these (48-50) were found to be the most active analogues synthesized.
本文描述了一系列类似物的合成，其中西他苯的烷基被各种官能团取代或完全被功能化的烷酰基部分取代。还报道了支链（烷基氨基）苯甲酸的合成，其中支链特定地位于烷基链的末端。讨论了这些化合物作为降血脂剂和酶脂肪酰基辅酶A：胆固醇酰基转移酶（ACAT）抑制剂的构效关系。专门合成了某些化合物以检验这样的假设，即位于西他苯烷基链末端附近的基团可能会延缓分子的代谢降解，从而增强生物活性。其中一些化合物（48 - 50）被发现是合成的最具活性的类似物。
