高效合成 apricoxib（CS-706），一种选择性环氧化酶-2 抑制剂，并评估其对炎症性乳腺癌细胞中前列腺素 E2 生成的抑制作用。
Efficient synthesis of apricoxib, CS-706, a selective cyclooxygenase-2 inhibitor, and evaluation of inhibition of prostaglandin E2 production in inflammatory breast cancer cells.
机构信息
Department of Experimental Therapeutics, M D Anderson Cancer Center, 1862 East Road, Houston, TX 77054-3005, USA.
出版信息
Bioorg Med Chem Lett. 2011 Oct 15;21(20):6071-3. doi: 10.1016/j.bmcl.2011.08.050. Epub 2011 Aug 19.
Abstract
An efficient synthesis of apricoxib (CS-706), a selective cyclooxygenase inhibitor, was developed using copper catalyzed homoallylic ketone formation from methyl 4-ethoxybenzoate followed by ozonolysis to an aldehyde, and condensation with sulfanilamide. This method provided multi-gram access of aprocoxib in good yield. Apricoxib exhibited potency equal to celecoxib at inhibition of prostaglandin E2 synthesis in two inflammatory breast cancer cell lines.
摘要
高效合成昔布类环氧化酶抑制剂——昔布（CS-706），采用铜催化的烯丙基酮形成法，从 4-乙氧基苯甲酸甲酯出发，接着进行臭氧氧化生成醛，再与磺胺缩合。该方法可提供多克级 apricoxib，收率良好。昔布在两种炎症性乳腺癌细胞系中抑制前列腺素 E2 合成的效力与塞来昔布相当。
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