(2S,3R,4S)-2-<(L-4-thiazolylalanyl)amino>-1-cyclohexyl-3,4-dihydroxy-6-methylheptane | 136010-43-0

分子结构分类

有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物

中文名称

——

中文别名

——

英文名称

(2S,3R,4S)-2-<(L-4-thiazolylalanyl)amino>-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

英文别名

H-3-thiazol-4-yl-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane；4-thiazolylalaninyl amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane；(2S,3R,4S)-2-[(L-4-thiazolylalanyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane；(2S)-2-amino-N-[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]-3-(1,3-thiazol-4-yl)propanamide

(2S,3R,4S)-2-<(L-4-thiazolylalanyl)amino>-1-cyclohexyl-3,4-dihydroxy-6-methylheptane化学式

CAS

136010-43-0

化学式

C₂₀H₃₅N₃O₃S

mdl

——

分子量

397.582

InChiKey

XSFMACOYUXXLDH-CADBVGFASA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

644.1±55.0 °C(Predicted)
密度：

1.160±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

3.3
重原子数：

27
可旋转键数：

10
环数：

2.0
sp3杂化的碳原子比例：

0.8
拓扑面积：

137
氢给体数：

4
氢受体数：

6

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	N-(tert-butoxycarbonyl)-4-thiazolylalaninyl amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane	136010-42-9	C₂₅H₄₃N₃O₅S	497.7

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(2S,3R,4S)-2-<amino>-1-cyclohexyl-3,4-dihydroxy-6-methylheptane	140903-55-5	C₃₆H₄₉N₃O₄S	619.869
——	(1R,2R,3R)-N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-2-ethyl-3-(morpholine-4-carbonyl)cyclopropane-1-carboxamide	140903-50-0	C₃₁H₅₀N₄O₆S	606.827
——	(1S,2R,3S)-N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-2-ethyl-3-(morpholine-4-carbonyl)cyclopropane-1-carboxamide	141042-04-8	C₃₁H₅₀N₄O₆S	606.827
——	(1R,2S,3R)-N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-2-ethyl-3-(morpholine-4-carbonyl)cyclopropane-1-carboxamide	141041-97-6	C₃₁H₅₀N₄O₆S	606.827
——	(1S,2S,3S)-N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-2-ethyl-3-(morpholine-4-carbonyl)cyclopropane-1-carboxamide	141042-00-4	C₃₁H₅₀N₄O₆S	606.827
——	(1S,2S,3S)-N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-2-(2-methylpropyl)-3-(morpholine-4-carbonyl)cyclopropane-1-carboxamide	141042-01-5	C₃₃H₅₄N₄O₆S	634.881
——	(1S,2R,3S)-N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-2-(2-methylpropyl)-3-(morpholine-4-carbonyl)cyclopropane-1-carboxamide	141042-05-9	C₃₃H₅₄N₄O₆S	634.881
——	(1R,2S,3R)-N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-2-(2-methylpropyl)-3-(morpholine-4-carbonyl)cyclopropane-1-carboxamide	141041-98-7	C₃₃H₅₄N₄O₆S	634.881
——	(1R,2R,3R)-N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-2-(2-methylpropyl)-3-(morpholine-4-carbonyl)cyclopropane-1-carboxamide	140903-51-1	C₃₃H₅₄N₄O₆S	634.881
——	(S)-N-[(S)-1-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-2-morpholin-4-yl-3-phenyl-propionamide	——	C₃₃H₅₀N₄O₅S	614.85
——	(2S,3R,4S)-2-<-3-(4-thiazolyl)-L-alanyl>amino>-1-cyclohexyl-3,4-dihydroxy-6-methylheptane	140926-08-5	C₃₅H₅₂N₄O₆S	656.887
——	(S)-2-Benzyl-N-[(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-4-morpholin-4-yl-4-oxo-butyramide	141115-19-7	C₃₅H₅₂N₄O₆S	656.887
——	(2R)-2-benzyl-N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-N'-methyl-N'-(2-pyridin-2-ylethyl)butanediamide	——	C₃₉H₅₅N₅O₅S	705.962
——	(1S,2S,3S)-2-Benzyl-3-(morpholine-4-carbonyl)-cyclopropanecarboxylic acid [(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-amide	141042-03-7	C₃₆H₅₂N₄O₆S	668.898
——	(1R,2S,3R)-2-Benzyl-3-(morpholine-4-carbonyl)-cyclopropanecarboxylic acid [(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-amide	141042-57-1	C₃₆H₅₂N₄O₆S	668.898
——	(1R,2R,3R)-2-Benzyl-3-(morpholine-4-carbonyl)-cyclopropanecarboxylic acid [(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-amide	140903-53-3	C₃₆H₅₂N₄O₆S	668.898
——	(1S,2R,3S)-2-Benzyl-3-(morpholine-4-carbonyl)-cyclopropanecarboxylic acid [(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-amide	141042-07-1	C₃₆H₅₂N₄O₆S	668.898
——	(2S,3R,4S)-2-<carbonyl>-3-(4-thiazoyl)-L-alanyl>amino>-1-cyclohexyl-3,4-dihydroxy-6-methylheptane	140903-52-2	C₃₅H₅₀N₄O₆S	654.871
——	(1S,2S,3S)-2-(Morpholine-4-carbonyl)-3-phenyl-cyclopropanecarboxylic acid [(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-amide	141042-02-6	C₃₅H₅₀N₄O₆S	654.871
——	(1R,2R,3S)-2-(Morpholine-4-carbonyl)-3-phenyl-cyclopropanecarboxylic acid [(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-amide	141041-99-8	C₃₅H₅₀N₄O₆S	654.871
——	(1S,2S,3R)-2-(Morpholine-4-carbonyl)-3-phenyl-cyclopropanecarboxylic acid [(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-amide	141042-06-0	C₃₅H₅₀N₄O₆S	654.871
(2S)-N-[1-[[(2S,3R,4S)-1-环己基-3,4-二羟基-6-甲基庚烷-2-基]氨基]-1-氧代-3-(1,3-噻唑-4-基)丙-2-基]-2-[(4-甲基哌嗪-1-基)磺酰基甲基]-3-苯丙酰胺	zankiren	138742-43-5	C₃₅H₅₅N₅O₆S₂	705.984

反应信息

作为反应物：

描述：

(2S,3R,4S)-2-<(L-4-thiazolylalanyl)amino>-1-cyclohexyl-3,4-dihydroxy-6-methylheptane 在 N-甲基吗啉、 1-羟基苯并三唑、盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺、三氟乙酸作用下，以二氯甲烷、 N,N-二甲基甲酰胺为溶剂，反应 19.5h，生成 3-Amino-N-[(S)-1-[(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethylcarbamoyl]-2-(4-methoxy-phenyl)-ethyl]-3-methyl-butyramide

参考文献：

名称：

Studies directed toward the design of orally active renin inhibitors. 1. Some factors influencing the absorption of small peptides

摘要：

A systematic evaluation of structure-absorption relationships using a high throughput intraduodenal rat screening model has led to the delineation of a set of structural parameters that appear to govern bioavailability in a series of peptide-based renin inhibitors. Optimum structures, exemplified by 25 and 41, incorporated a single, solubilizing substituent at the C- or N-terminus combined with a lipophilic P2-site residue. Both inhibitors gave unprecedented plasma drug levels upon intraduodenal administration to monkeys, and the calculated bioavailability for 41 (14 +/- 4%) is the highest reported for any peptidic renin inhibitor.

DOI：

10.1021/jm00056a005
作为产物：

描述：

(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane