(R)-Butaprost, free acid

布塔前列素是前列腺素E2（PGE2）的结构类似物，对EP2受体亚型具有良好的选择性。Butaprost经常被用于药理学定义各种人类和动物组织和细胞的EP受体表达谱。1986年，Gardiner报告显示具有这种选择性活性的丁丙脯胺的差向异构体是C-16（R）-差向异构体时，引起了对丁丙脯胺结构的严重混淆。为了提高（R）-丁丙脯氨酸与前列腺素受体的结合亲和力，我们去除了（R）-丁丙脯氨酸甲酯，重建了天然C-1羧酸。前列腺素游离酸通常与它们的同源受体结合，其亲和力是相应酯衍生物亲和力的10到100倍。（R）-布 Butaprost is a structural analog of prostaglandin E2 (PGE2) with good selectivity for the EP2 receptor subtype. Butaprost has frequently been used to pharmacologically define the EP receptor expression profile of various human and animal tissues and cells . Serious confusion as to the structure of butaprost was generated by Gardiner in 1986,2 when he reported that the epimer of butaprost showing this selective activity was the C-16 (R)-epimer. In order to increase the binding affinity of (R)-butaprost for prostanoid receptors, we removed the methyl ester of (R)-butaprost and re-established the natural C-1 carboxylic acid. Prostaglandin free acids generally bind to their cognate receptors with 10 to 100 times the affinity of the corresponding ester derivative. The pharmacology of (R)-butaprost has not been carefully studied, but it is generally considered to be the less active C-16 epimer. (NOTE: In the Gardiner paper in the 1986 British Journal of Pharmacology, butaprost appears on page 46 where it is given the name TR 4979. The structure as drawn is incorrect, in that the author was using and referring to the more active C-16 epimer, which is actually 16(S). The structure on page 46 shows the structure as 16(R). It was not until the late 1990's that careful studies both in the US and Japan correctly identified the actual configuration of C-16 in the compound called butaprost is 16(S).

No numbering system information yet

No physical and chemical property information yet

No safety information yet

No production method and use information yet

No upstream information yet

No downstream information yet

No related product information yet