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茚地那韦

茚地那韦

CAS号：150378-17-9

英文名：indinavir

分子式

C36H47N5O4

熔点

150-153ºC

密度

1.25 g/cm3

分子量

613.789

沸点

877.9ºC at 760 mmHg

溶解度

信号词

危险品标志

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化合物简介

Indinavir is a member of the novel hydroxyaminopentane amide class of HIV-1 protease inhibitors. Indinavir is used as an antiviral.

基本信息

中文名称

茚地那韦

英文名称

indinavir

中文别名

[1(1S,2R),5(S)]-2,3,5-三去氧-N-(2,3-二氢-2-羟基.1H-茚-1-基)-5-[2-[[(1,1-二甲基乙基)氨基]羰基]-4-(3-吡啶基甲基)-1-哌嗪基]-2-(苯基甲基)-D-赤式-戊酰胺、吲地纳韦

英文别名

Indinavir、N-[2(R)-hydroxy-1(S)-indanyl]-5-{[2(S)-tert-butylaminocarbonyl]-4-(3-pyridylmethyl)piperazino}-4(S)-hydroxy-2(R)-phenylmethylpentanamide、(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tertbutyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide、(1(1S,2R),5(S))-2,3,5-Trideoxy-N-(2,3-dihydro-2-hydroxy-1H-inden-1-yl)-5-(2-(((1,1-dimethylethyl)amino)carbonyl)-4-(3-pyridinylmethyl)-1-piperazinyl)-2-(phenylmethyl)-D-erythro-pentonamide、(1(1S,2R)5(S))-2,3,5-TRIDEOXY-N-(2,3-DIHYDRO-2HYDROXY-1H-INDEN-1-YI)

CAS号

150378-17-9

分子式

C36H47N5O4

分子量

613.789

精确质量

613.363

PSA

118.03

LOGP

3.5245

编号系统

UNII

9MG78X43ZT

物化性质

密度

1.25 g/cm3

沸点

877.9ºC at 760 mmHg

熔点

150-153ºC

闪点

484.7ºC

折射率

1.636

蒸汽压

0mmHg at 25°C

生产方法及用途

生产方法

在-50℃下，将弱碱Lithium hexamethyl disilazide(LHS)加到化合物(I)和(S)-(+)-脱水甘油醇甲苯磺酸酯(Ⅱ)的溶液中，然后升温至-25℃，反应可得72%收率的化合物(Ⅲ)。(Ⅲ)和化合物(Ⅳ)在异丙醇(IPA)中回流缩合，再加入6mol/L盐酸脱去N上的保护基，得到化合物(V)。最后和3-吡啶羧酰氯反应，即得产物，收率71%以化合物(Ⅲ)计。

用途

本品为抗病毒药。为一种新奇的羟基氨基戊烷酰胺类HIV-1蛋白酶抑制剂，用于治疗艾滋病。

合成路线

3-氯甲基吡啶盐酸盐

3-氯甲基吡啶盐酸盐

[1(1S,2R),5(S)]-2,3,5-三脱氧-N-(2,3-二氢-2-羟基-1H-茚-1-基)-5-[2-[(叔丁基氨基)甲酰]-1-哌嗪基]-2-(苯基甲基)-D-赤式-戊酰胺

[1(1S,2R),5(S)]-2,3,5-三脱氧-N-(2,3-二氢-2-羟基-1H-茚-1-基)-5-[2-[(叔丁基氨基)甲酰]-1-哌嗪基]-2-(苯基甲基)-D-赤式-戊酰胺

茚地那韦

上游原料

共找到28个上游原料 >

吡嗪-2-甲酰氯

吡嗪-2-甲酰氯

3-氯甲基吡啶盐酸盐

3-氯甲基吡啶盐酸盐

tert-butyl (S)-4-((2S,4R)-4-benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-2H-indeno[1,2-d]oxazol-3(3aH)-yl)-2-hydroxy-5-oxopentyl)-3-(tert-butylcarbamoyl)piperazine-1-carboxylate

tert-butyl (S)-4-((2S,4R)-4-benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-2H-indeno[1,2-d]oxazol-3(3aH)-yl)-2-hydroxy-5-oxopentyl)-3-(tert-butylcarbamoyl)piperazine-1-carboxylate

dihydro-5(S)-(((tert-butyldimethylsilyl)oxy)methyl)-3(R)-(phenylmethyl)-3(2H)-furanone

dihydro-5(S)-(((tert-butyldimethylsilyl)oxy)methyl)-3(R)-(phenylmethyl)-3(2H)-furanone

(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one

(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one

2-吡嗪叔丁酰胺

2-吡嗪叔丁酰胺

上游原料

吡嗪-2-甲酰氯 3-氯甲基吡啶盐酸盐 tert-butyl (S)-4-((2S,4R)-4-benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-2H-indeno[1,2-d]oxazol-3(3aH)-yl)-2-hydroxy-5-oxopentyl)-3-(tert-butylcarbamoyl)piperazine-1-carboxylate dihydro-5(S)-(((tert-butyldimethylsilyl)oxy)methyl)-3(R)-(phenylmethyl)-3(2H)-furanone (5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one 2-吡嗪叔丁酰胺 (1R,2S)-1-氨基-2-茚满醇 2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid (3aS,8aR)-3-(4,5-脱水-2,3-二脱氧-2-(苯基甲基)-D-赤式-戊酮基)-3,3a,8,8a-四氢-2,2-二甲基-2H-茚并[1,2-d]恶唑 2-甲酸吡嗪 (S)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-pent-4-en-1-one (S)-5-羟甲基二氢呋喃-2-酮 (3aS,8aR)-2,2-dimethyl-3-(3-phenylpropanoyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazole dihydro-5(S)-(hydroxymethyl)-3(R)-(phenylmethyl)-3(2H)-furanone N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-[(tert-butyldimethylsilyl)oxy]-5-[1-[4-[(1,1-dimethylethoxy)carbonyl]-2(S)-(N-tert-butylcarbamoyl)piperazinyl]]pentanamide [1(1S,2R),5(S)]-2,3,5-三脱氧-N-(2,3-二氢-2-羟基-1H-茚-1-基)-5-[2-[(叔丁基氨基)甲酰]-1-哌嗪基]-2-(苯基甲基)-D-赤式-戊酰胺 (S)-4-N-Boc-哌嗪-2-甲酸 (S)-4-叔丁氧羰基-1-苄氧羰基-2-哌嗪羧酸 4-叔丁氧羰基-2(S)-哌嗪叔丁酰胺 3-氯甲基吡啶 dihydro-5(S)-[[4-[(1,1-dimethylethoxy)carbonyl]-2(S)-(N-tert-butylcarbamoyl)piperazinyl]methyl]-3(R)-(phenylmethyl)-3(2H)-furanone dihydro-5(S)-[[[(trifluoromethyl)sulfonyl]oxy]methyl]-3(R)-(phenylmethyl)-3(2H)-furanone N-tert-butyl-4-((1,1-dimethylethoxy)carbonyl)-1-((phenylmethyl)carbonyl)piperazine-2(S)-carboxamide (2R,4S)-2-benzyl-5-chloro-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-2H-indeno[1,2-d]oxazol-3(3aH)-yl)-4-hydroxypentan-1-one (2R,4S)-2-benzyl-5-((S)-4-(tert-butoxycarbonyl)-2-(tert-butylcarbamoyl)piperazin-1-yl)-4-hydroxypentanoic acid 叔-丁基(3S)-3-(叔-丁基氨基甲酰)-4-[[(2S)-环氧乙烷-2-基]甲基]哌嗪-1-羧酸酯 3-吡啶甲醛