Acyclic retinoid, Polyprenoic acid, NK-333, NIK-333, E-5166, -Drug Synthesis Database

【结构式】

【药物名称】Acyclic retinoid, Polyprenoic acid, NK-333, NIK-333, E-5166

【化学名称】(2E,4E,6E,10E)-3,7,11,15-Tetramethyl-2,4,6,10,14-hexadecapentaenoic acid
　　　　　　4,5-Didehydrogeranylgeranoic acid

【CA登记号】81485-25-8, 80370-67-8 (no stereochemistry)

【分子式】C₂₀H₃₀O₂

【分子量】302.4609

【开发单位】Eisai (Originator), Nikken Chemicals (Not Determined)

【药理作用】Chemopreventive Agents, Oncolytic Drugs, Apoptosis Inducers, Retinoid RARbeta Ligands, Retinoid RXRalpha Ligands, Retinoids

合成路线1

The Wittig condensation of 6,10,14-trimethylpentadeca-3,5,9,13-tetraen-2-one (I) with triethyl phosphonoacetate (II) by means of NaH in refluxing hexane gives ethyl 3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoate (III), which is then hydrolyzed with KOH in hot isopropanol.

参考文献中间体

【1】 Yamatsu, I.; Tagaya, O.; Abe, S.; Abe, K.; Suzuki, K.; Yamada, K.; Suzuki, T.; Inai, Y.; Suzuki, Y. (Eisai Co., Ltd.); 3,7,11,15-Tetramethyl-2,4,6,10,14-hexadecapentaenoic acid. BE 888290; US 4917829 .
【2】 Katoh, Y.; et al. (Eisai Co., Ltd.); Method for treatment of inflammation. EP 0107188; JP 59073516 .
【3】 Prous, J.; Castaner, J.; E-5166. Drugs Fut 1986, 11, 7, 562.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	24564	(3E,5E,9E)-6,10,14-trimethyl-3,5,9,13-pentadecatetraen-2-one		C₁₈H₂₈O	详情	详情
(II)	10019	Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate	867-13-0	C₈H₁₇O₅P	详情	详情
(III)	24566	ethyl (2E,4E,6E,10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoate		C₂₂H₃₄O₂	详情	详情

Extended Information