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(S)-4-benzyl-3-((R)-2-((S)-(6-chloropyridin-3-yl)(hydroxy)methyl)hex-5-ynoyl)oxazolidin-2-one | 1190614-96-0

分子结构分类

有机化合物 - 有机杂环化合物 - 吡啶及其衍生物

中文名称

——

中文别名

——

英文名称

(S)-4-benzyl-3-((R)-2-((S)-(6-chloropyridin-3-yl)(hydroxy)methyl)hex-5-ynoyl)oxazolidin-2-one

英文别名

(4S)-4-benzyl-3-{(2R)-2-[(S)-(6-chloropyridin-3-yl)(hydroxy)methyl]hex-5-ynoyl}-1,3-oxazolidin-2-one；(4S)-4-benzyl-3-{(R)-2-[(S)-(6-chloropyridin-3-yl)(hydroxy)methyl]hex-5-ynoyl}-1,3-oxazolidin-2-one；(4S)-4-benzyl-3-[(2R)-2-[(S)-(6-chloropyridin-3-yl)-hydroxymethyl]hex-5-ynoyl]-1,3-oxazolidin-2-one

(S)-4-benzyl-3-((R)-2-((S)-(6-chloropyridin-3-yl)(hydroxy)methyl)hex-5-ynoyl)oxazolidin-2-one化学式

CAS

1190614-96-0

化学式

C₂₂H₂₁ClN₂O₄

mdl

——

分子量

412.873

InChiKey

CSPSGGVBGCKSLL-NLWGTHIKSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

634.4±55.0 °C(Predicted)
密度：

1.341±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

3.3
重原子数：

29
可旋转键数：

7
环数：

3.0
sp3杂化的碳原子比例：

0.32
拓扑面积：

79.7
氢给体数：

1
氢受体数：

5

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
——	(4S)-3-hex-5-ynoyl-4-benzyl-1,3-oxazolidin-2-one	1190614-95-9	C₁₆H₁₇NO₃	271.316

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(2R,5S)-tert-butyl-2-((R)-((tert-butyldimethylsilyl)oxy)(6-chloropyridin-3-yl)methyl)-5-(4-(methoxycarbonyl)benzyl)pyrrolidine-1-carboxylate	1269429-14-2	C₃₀H₄₃ClN₂O₅Si	575.22
——	(2S,5S)-tert-butyl 2-((R)-((tert-butyldimethylsilyl)oxy)(6-chloropyridin-3-yl)methyl)-5-(4-nitrobenzyl)pyrrolidine-1-carboxylate	1190615-05-4	C₂₈H₄₀ClN₃O₅Si	562.181
——	tert-butyl (2R,5R)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(6-chloropyridin-3-yl)methyl]-5-(4-nitrobenzyl)pyrrolidine-1-carboxylate	1190615-07-6	C₂₈H₄₀ClN₃O₅Si	562.181
——	tert-butyl (2R,5S)-2-[(R)hydroxy(pyridin-3-yl)methyl]-5-(4-{[(2S)-2-(methylamino)propanoyl]amino}benzyl)pyrrolidine-1-carboxylate	1190615-35-0	C₂₆H₃₆N₄O₄	468.596
——	tert-butyl (2S,5R)-2-(4-{[(2S)-2-aminopropanoyl]amino}benzyl)-5-[(R)-hydroxy(pyridin-3-yl)methyl]pyrrolidine-1-carboxylate	1190615-33-8	C₂₅H₃₄N₄O₄	454.569
——	(2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate	1190615-16-7	C₂₂H₂₉N₃O₃	383.491
——	(2S,5R)-tert-butyl-2-(4-aminobenzyl)-5-((R)-((tert-butyldimethylsilyl) oxy)(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate	1190615-04-3	C₂₈H₄₃N₃O₃Si	497.753
——	tert-butyl (2R,5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridine-3-yl)methyl]pyrrolidine-1-carboxylate	1190615-06-5	C₂₈H₄₃N₃O₃Si	497.753
——	(2R,5S)-tert-butyl-2-((R)-((tert-butyldimethylsilyl)oxy)(pyridin-3-yl)methyl)-5-(4-(methoxycarbonyl)benzyl)pyrrolidine-1-carboxylate	1269429-18-6	C₃₀H₄₄N₂O₅Si	540.775
——	tert-butyl (2S,5R)-2-(4-amino-3-bromobenzyl)-5-[(R)-hydroxy(pyridin-3-yl)methyl]pyrrolidine-1-carboxylate	1190615-22-5	C₂₂H₂₈BrN₃O₃	462.387
——	tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(1-oxidopyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate	1269615-53-3	C₃₀H₄₄N₂O₆Si	556.775
——	tert-butyl (2R,5S)-2-[(R)-[6-(tert-butylamino)pyridin-3-yl]{[tert-butyl(dimethyl)silyl]oxy}methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate	1269615-35-1	C₃₄H₅₃N₃O₅Si	611.897
——	4-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-[6-(tert-butylamino)pyridin-3-yl](hydroxy)methyl]pyrrolidin-2-yl}methyl)benzoic acid	1269615-37-3	C₂₇H₃₇N₃O₅	483.608
——	tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridin-3-yl)methyl]-5-(4-{[(2R)-2-pyridin-2-ylpropanoyl]amino}benzyl)pyrrolidine-1-carboxylate	1190615-44-1	C₃₆H₅₀N₄O₄Si	630.903
——	tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridin-3-yl)methyl]-5-(4-{[(2S)-2-pyridin-2-ylpropanoyl]amino}benzyl)pyrrolidine-1-carboxylate	1190615-45-2	C₃₆H₅₀N₄O₄Si	630.903
——	4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(6-chloropyridin-3-yl)-6-(4-nitrophenyl)-5-oxohexan-2-yl)carbamate	1190615-02-1	C₃₂H₄₀ClN₃O₇Si	642.224
——	4-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}{6-[(2-phenylpropan-2-yl)amino]pyridin-3-yl}methyl]pyrrolidin-2-yl}methyl)benzoic acid	1269615-31-7	C₃₈H₅₃N₃O₅Si	659.941
——	tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}{6-[(2-phenylpropan-2-yl)amino]pyridin-3-yl}methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate	1269615-32-8	C₃₉H₅₅N₃O₅Si	673.968
——	methyl 4-[(5R,6R)-6-{[tert-butyl(dimethyl)silyl]oxy}-6-(6-chloropyridin-3-yl)-5-({[(4-methoxybenzyl)oxy]carbonyl}amino)hex-1-yn-1-yl]benzoate	1269429-12-0	C₃₄H₄₁ClN₂O₆Si	637.248
——	4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(6-chloropyridin-3-yl)hex-5-yn-2-yl)carbamate	1190614-94-8	C₂₆H₃₅ClN₂O₄Si	503.113
——	4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(6-chloropyridin-3-yl)-6-(4-nitrophenyl)hex-5-yn-2-yl)carbamate	1190615-01-0	C₃₂H₃₈ClN₃O₆Si	624.209

反应信息

作为反应物：

描述：

(S)-4-benzyl-3-((R)-2-((S)-(6-chloropyridin-3-yl)(hydroxy)methyl)hex-5-ynoyl)oxazolidin-2-one 在 2,6-二甲基吡啶、水、双氧水、 sodium hydroxide 作用下，以四氢呋喃、二氯甲烷为溶剂，反应 34.0h，生成 (R)-2-((S)-(6-chloropyridin-3-yl)((trimethylsilyl)oxy)methyl)hex-5-ynoic acid

参考文献：

名称：

[EN] NOVEL PYRROLIDINE DERIVED BETA 3 ADRENERGIC RECEPTOR AGONISTS
[FR] NOUVEAUX AGONISTES DE RÉCEPTEURS ADRÉNERGIQUES BÊTA 3 DÉRIVÉS DE PYRROLIDINE

摘要：

本发明提供了式(I)的化合物，其药物组成物以及使用该化合物在治疗或预防由β3-肾上腺素受体激活介导的疾病的方法。

公开号：

WO2011025774A1
作为产物：

描述：

(4S)-3-hex-5-ynoyl-4-benzyl-1,3-oxazolidin-2-one 在甲醇、三乙胺、三氟乙酸、 magnesium chloride 作用下，以乙酸乙酯为溶剂，反应 77.0h，生成 (S)-4-benzyl-3-((R)-2-((S)-(6-chloropyridin-3-yl)(hydroxy)methyl)hex-5-ynoyl)oxazolidin-2-one

参考文献：

名称：

[EN] NOVEL PYRROLIDINE DERIVED BETA 3 ADRENERGIC RECEPTOR AGONISTS
[FR] NOUVEAUX AGONISTES DE RÉCEPTEURS ADRÉNERGIQUES BÊTA 3 DÉRIVÉS DE PYRROLIDINE

摘要：

本发明提供了式(I)的化合物，其药物组成物以及使用该化合物在治疗或预防由β3-肾上腺素受体激活介导的疾病的方法。

公开号：

WO2011025774A1

点击查看最新优质反应信息

文献信息

[EN] NOVEL BETA 3 ADRENERGIC RECEPTOR AGONISTS<br/>[FR] NOUVEAUX AGONISTES DU RÉCEPTEUR BÊTA 3 ADRÉNERGIQUE

申请人：MERCK SHARP & DOHME

公开号：WO2011137054A1

公开（公告）日：2011-11-03

The present invention provides compounds of Formula (I), pharmaceutical compositions thereof, and methods of using the same in the treatment or prevention of diseases mediated by the activation of b3-adrenoceptor.

本发明提供了式(I)的化合物，其药物组成物以及在治疗或预防由b3-肾上腺素受体激活介导的疾病中使用这些化合物的方法。
[EN] HYDROXYMETHYL PYRROLIDINES AS BETA 3 ADRENERGIC RECEPTOR AGONISTS<br/>[FR] HYDROXYMÉTHYLPYRROLIDINES EN TANT QU'AGONISTES DE RÉCEPTEUR BÊTA-3-ADRÉNERGIQUE

申请人：MERCK & CO INC

公开号：WO2009123870A1

公开（公告）日：2009-10-08

The present invention provides compounds of Formula I, pharmaceutical compositions thereof, and method of using the same in the treatment or prevention of diseases mediated by the activation of β3-adrenoceptor.

本发明提供了式I的化合物，其药物组成物以及使用该化合物在治疗或预防由β3-肾上腺素受体激活介导的疾病的方法。
NOVEL PYRROLIDINE DERIVED BETA 3 ADRENERGIC RECEPTOR AGONISTS

申请人：Edmondson Scott D.

公开号：US20120157432A1

公开（公告）日：2012-06-21

The present invention provides compounds of Formula (I), pharmaceutical compositions thereof, and method of using the same in the treatment or prevention of diseases mediated by the activation of β3-adrenoceptor.

本发明提供公式（I）的化合物、其制药组合物以及使用该化合物治疗或预防通过激活β3-肾上腺素受体介导的疾病的方法。
HYDROXYMETHYL PYRROLIDINES AS BETA 3 ADRENERGIC RECEPTOR AGONISTS

申请人：Berger Richard

公开号：US20110028461A1

公开（公告）日：2011-02-03

The present invention provides compounds of Formula I, pharmaceutical compositions thereof, and method of using the same in the treatment or prevention of diseases mediated by the activation of β3-adrenoceptor.

本发明提供了I式化合物，其药物组成物以及使用该组成物的方法，用于治疗或预防通过激活β3肾上腺素受体介导的疾病。
Design, Synthesis, and Evaluation of Conformationally Restricted Acetanilides as Potent and Selective β<sub>3</sub>Adrenergic Receptor Agonists for the Treatment of Overactive Bladder

作者：Christopher R. Moyes、Richard Berger、Stephen D. Goble、Bart Harper、Dong-Ming Shen、Liping Wang、Alka Bansal、Patricia N. Brown、Airu S. Chen、Karen H. Dingley、Jerry Di Salvo、Aileen Fitzmaurice、Loise N. Gichuru、Amanda L. Hurley、Nina Jochnowitz、Randall R. Miller、Shruty Mistry、Hiroshi Nagabukuro、Gino M. Salituro、Anthony Sanfiz、Andra S. Stevenson、Katherine Villa、Beata Zamlynny、Mary Struthers、Ann E. Weber、Scott D. Edmondson

DOI：10.1021/jm4017224

日期：2014.2.27

A series of conformationally restricted acetanilides were synthesized and evaluated as beta(3)-adrenergic receptor agonists (beta(3)-AR) for the treatment of overactive bladder (OAB). Optimization studies identified a five-membered ring as the preferred conformational lock of the acetanilide. Further optimization of both the aromatic and thiazole regions led to compounds such as 19 and 29, which have a good balance of potency and selectivity. These compounds have significantly reduced intrinsic clearance compared to our initial series of pyridylethanolamine beta(3)-AR agonists and thus have improved unbound drug exposures. Both analogues demonstrated dose dependent beta(3)-AR mediated responses in a rat bladder hyperactivity model.