-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】
　　　　　　[3S-[3R*[E(1S*,2S*,4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*]]-4-[[[[4-[2-[1,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,21,23,24,25,26,26a-Docosahydro-5,19-dihydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-1,7,20,21-tetraoxo-8-(2-propenyl)-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosin-3-yl]-1-propenyl]-2-methoxycyclohexyl]oxy]carbonyl]amino]benzeneacetic acid methyl ester

【CA登记号】170146-86-8

【分子式】C₂₈H₂₀ClNO₄

【分子量】469.9289

【开发单位】Yamanouchi (Originator)

【药理作用】Benign Prostatic Hyperplasia Therapy, RENAL-UROLOGIC DRUGS, Steroid 5alpha-Reductase Inhibitors

合成路线1

The acylation of 5-(benzyloxy)indole (I) with ethyl chloroformate produced the N-(ethoxycarbonyl)indole (II), which was debenzylated by transfer hydrogenolysis with ammonium formate in the presence of Pd/C to afford the 5-hydroxyindole (III). Condensation of (III) with 3-chloro-4-fluorobenzonitrile (IV) produced the diaryl ether (V). Then, basic hydrolysis of the cyano and ethoxycarbonyl groups of (V) gave the benzoic acid derivative (VI). Finally, N-alkylation of the indole ring of (VI) with 4-phenoxybenzyl bromide (VII) furnished the title compound.

参考文献中间体

【1】 Mase, T.; Inami, H.; Hara, H.; Fujii, M; Oritani, H.; Koutoku, H.; Igarashi, S.; A novel class of inhibitors for human steroid 5alpha-reductase: Synthesis and biological evaluation of indole derivatives. II. Chem Pharm Bull 2000, 48, 3, 382.

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)	30840	5-Benzyloxyindole; benzyl 1H-indol-5-yl ether; 5-(benzyloxy)-1H-indole	1215-59-4	C₁₅H₁₃NO	详情	详情
(II)	51275	ethyl 5-(benzyloxy)-1H-indole-1-carboxylate		C₁₈H₁₇NO₃	详情	详情
(III)	51276	ethyl 5-hydroxy-1H-indole-1-carboxylate		C₁₁H₁₁NO₃	详情	详情
(IV)	51277	3-Chloro-4-fluorobenzonitrile	117482-84-5	C₇H₃ClFN	详情	详情
(V)	51278	ethyl 5-(2-chloro-4-cyanophenoxy)-1H-indole-1-carboxylate		C₁₈H₁₃ClN₂O₃	详情	详情
(VI)	51279	3-chloro-4-(1H-indol-5-yloxy)benzoic acid		C₁₅H₁₀ClNO₃	详情	详情
(VII)	51280	1-(bromomethyl)-4-phenoxybenzene; 4-(bromomethyl)phenyl phenyl ether		C₁₃H₁₁BrO	详情	详情

Extended Information