(R)-2-(2-Chloro-acetyl)-pyrrolidine-1-carboxylic acid benzyl ester | 741703-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-(2-Chloro-acetyl)-pyrrolidine-1-carboxylic acid benzyl ester
• 英文别名: benzyl (2R)-2-(2-chloroacetyl)pyrrolidine-1-carboxylate
• CAS: 741703-34-4
• 化学式: C₁₄H₁₆ClNO₃
• 分子量: 281.739
• InChiKey: GREQVDCAJBXYQL-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-(2-Chloro-acetyl)-pyrrolidine-1-carboxylic acid benzyl ester 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 生成 1-Pyrrolidinecarboxylic acid, 2-oxiranyl-, phenylmethyl ester, (2R)-
  参考文献：
  名称：

  Discovery of novel 1-arylmethyl pyrrolidin-2-yl ethanol amines as calcium-sensing receptor antagonists

  摘要：

  A 3D quantitative structure-activity relationship study for inhibition of calcium-sensing receptor in the aryloxypropanolamine series predicted that these molecules adopt a U-shaped conformation with pi-stacking between the two aromatic rings. This hypothesis led to the discovery of novel l-arylmethyl pyrrolidin-2-yl ethanol amines capable of antagonizing the calcium-sensing receptor with potency comparable to that of NPS-2143. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.095
• 作为产物：
  描述：

  (R)-benzyl 2-(2-diazoacetyl)pyrrolidine-1-carboxylate 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 (R)-2-(2-Chloro-acetyl)-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Discovery of pyrazolthiazoles as novel and potent inhibitors of bacterial gyrase

  摘要：

  Bacterial DNA gyrase is an attractive target for the investigation of new antibacterial agents. Inhibitors of the GyrB subunit, which contains the ATP-binding site, are described in this communication. Novel, substituted 5-(1H-pyrazol-3-yl)thiazole compounds were identified as inhibitors of bacterial gyrase. Structure-guided optimization led to greater enzymatic potency and moderate antibacterial potency. Data are presented for the demonstration of selective enzyme inhibition of Escherichia coli GyrB over Staphylococcus aureus GyrB.

  DOI：

  10.1016/j.bmcl.2010.03.052

文献信息

• [EN] NOVEL 2-SUBSTITUTED CYCLIC AMINES AS CALCIUM SENSING RECEPTOR MODULATORS<br/>[FR] NOUVEAUX AMINES CYCLIQUES SUBSTITUES EN POSITION 2 COMME MODULATEURS DU RECEPTEUR DE DETECTION DE CALCIUM
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2004069793A3

  公开（公告）日：2005-01-20
• Discovery of pyrazolthiazoles as novel and potent inhibitors of bacterial gyrase
  作者：Steven M. Ronkin、Michael Badia、Steve Bellon、Anne-Laure Grillot、Christian H. Gross、Trudy H. Grossman、Nagraj Mani、Jonathan D. Parsons、Dean Stamos、Martin Trudeau、Yunyi Wei、Paul S. Charifson

  DOI：10.1016/j.bmcl.2010.03.052

  日期：2010.5

  Bacterial DNA gyrase is an attractive target for the investigation of new antibacterial agents. Inhibitors of the GyrB subunit, which contains the ATP-binding site, are described in this communication. Novel, substituted 5-(1H-pyrazol-3-yl)thiazole compounds were identified as inhibitors of bacterial gyrase. Structure-guided optimization led to greater enzymatic potency and moderate antibacterial potency. Data are presented for the demonstration of selective enzyme inhibition of Escherichia coli GyrB over Staphylococcus aureus GyrB.
• Discovery of novel 1-arylmethyl pyrrolidin-2-yl ethanol amines as calcium-sensing receptor antagonists
  作者：Ashvinikumar V. Gavai、Roy J. Vaz、Amarendra B. Mikkilineni、Jacques Y. Roberge、Yalei Liu、R. Michael Lawrence、James R. Corte、Wu Yang、Mark Bednarz、John K. Dickson、Zhengping Ma、Ramakrishna Seethala、Jean H.M. Feyen

  DOI：10.1016/j.bmcl.2005.08.095

  日期：2005.12

  A 3D quantitative structure-activity relationship study for inhibition of calcium-sensing receptor in the aryloxypropanolamine series predicted that these molecules adopt a U-shaped conformation with pi-stacking between the two aromatic rings. This hypothesis led to the discovery of novel l-arylmethyl pyrrolidin-2-yl ethanol amines capable of antagonizing the calcium-sensing receptor with potency comparable to that of NPS-2143. (c) 2005 Elsevier Ltd. All rights reserved.