N-<(phenylmethoxy)carbonyl>-4(R)-methoxy-(S)-proline methyl ester | 96522-36-0

• 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
• 英文名称: N-<(phenylmethoxy)carbonyl>-4(R)-methoxy-(S)-proline methyl ester
• 英文别名: (2S,4R)-4-methoxypyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester；(2S,4R)-N-(benzyloxycarbonyl)-4-methoxy-2-(methoxycarbonyl)pyrrolidine；(1-Benzyloxycarbonyl-(4R)-methoxy-(2S)-pyrrolidinyl)carboxylic acid methyl ester；(2S, 4R)-4-Methoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester；1-O-benzyl 2-O-methyl (2S,4R)-4-methoxypyrrolidine-1,2-dicarboxylate
• CAS: 96522-36-0
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: GRYKIXJYTLTYIF-OLZOCXBDSA-N

物化性质

• 沸点：
  398.7±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-<(phenylmethoxy)carbonyl>-4(R)-methoxy-(S)-proline methyl ester 在 palladium on activated charcoal sodium hydroxide 、 水 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 生成 (2S,4R)-1-(叔丁氧羰基)-4-甲氧基吡咯烷-2-羧酸
  参考文献：
  名称：

  [EN] VLA-4 INHIBITOR
  [FR] INHIBITEUR DE VLA-4

  摘要：

  一种选择性抑制配体与α4β1整合素（VLA-4）结合的化合物；一种生产该化合物的方法；以及含有该化合物的药物。该化合物可由例如式（I）或其盐所代表。还提供了一种预防和/或治疗剂，其含有该化合物或盐作为主要成分，并对由细胞粘附引起的疾病具有有效性，例如炎症反应、自身免疫疾病、癌症转移、支气管哮喘、鼻塞、糖尿病、关节炎、牛皮癣、多发性硬化、炎症性肠道疾病和移植排斥反应等（在该式中，Y1代表芳基等；V1代表芳基等；R11至R14分别代表H、OH、卤素等）。

  公开号：

  WO2005121135A1
• 作为产物：
  描述：

  Cbz-L-羟脯氨酸 在 氯化亚砜 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 N-<(phenylmethoxy)carbonyl>-4(R)-methoxy-(S)-proline methyl ester
  参考文献：
  名称：

  Synthesis and pharmacological activity of angiotensin-converting enzyme inhibitors: N-(mercaptoacyl)-4-substituted-(S)-prolines

  摘要：

  The synthesis of a series of N-(mercaptoacyl)-4-substituted-(S)-prolines (2 and 3) is described. These compounds were evaluated in vitro for inhibition of angiotensin-converting enzyme (ACE), and selected compounds were evaluated in vivo for ACE inhibition. The most potent compounds in vitro are 108, 109, 111, 114, and 116, having relative potencies of 1.0, 1.0, 1.3, 1.1, and 2.6 as compared to the potency of captopril. The most potent compounds in vivo intravenously are 108, 111, 114, 116, 117, and 97.

  DOI：

  10.1021/jm00399a033

文献信息

• Indolyl-urea derivatives of thienopyridines useful as antiangiogenic agents, and methods for their use
  申请人：——

  公开号：US20040019065A1

  公开（公告）日：2004-01-29

  The invention relates to compounds represented by the formula I 1 and to prodrugs thereof, pharmaceutically acceptable salts or solvates of said compounds or said prodrugs, wherein X, R 1 and R 11 are as defined herein. The invention also relates to pharmaceutical compositions containing the compounds of formula I and to methods of treating hyperproliferative disorders in a mammal by administering the compounds of formula I.

  这项发明涉及由公式I表示的化合物，以及这些化合物的前药、药学上可接受的盐或溶剂，其中X、R1和R11如本文所定义。该发明还涉及含有公式I化合物的药物组合物，以及通过给予公式I化合物来治疗哺乳动物的过度增殖性疾病的方法。
• ANTI-INFLAMMATORY COMPOUND HAVING INHIBITORY ACTIVITY AGAINST MULTIPLE TYROSINE KINASES AND PHARMACEUTICAL COMPOSITION CONTAINING SAME
  申请人：Yang Beom-Seok

  公开号：US20130072482A1

  公开（公告）日：2013-03-21

  The present invention is for the anti-inflammatory compounds that have an inhibitory activity against protein tyrosine kinases and their pharmaceutical composition(s) containing the compound as the active ingredient. Since the compounds of the present invention can inhibit multiple protein kinases associated with inflammatory diseases and immune disorders, they are useful for their prevention or treatment.

  本发明涉及具有抑制蛋白酪氨酸激酶活性的抗炎化合物及其含有该化合物作为活性成分的药物组合物。由于本发明的化合物可以抑制与炎症性疾病和免疫紊乱相关的多种蛋白激酶，因此它们对于预防或治疗这些疾病是有用的。
• VLA-4 INHIBITOR
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1757602A1

  公开（公告）日：2007-02-28

  An object of the present invention is to provide a compound which selectively inhibits binding of a ligand and α4β1 integrin (VLA-4), a process for producing the compound, and a medicament containing the compound. A compound represented by the formula (I) etc. orasaltthereof, a process for producing the compound or a salt thereof, a medicament containing the compound or a salt thereof, as well as a preventive and/or a therapeutic agent for a disease caused by cell adhesion, for example, inflammatory reaction, autoimmune disease, cancer metastasis, bronchial asthma, nasal obstruction, diabetes, arthritis, psoriasis, multiple sclerosis, inflammatory bowel disease and rejection reaction at transplantation, containing the compound or a salt thereof as a primary component. [wherein Y1 represents a divalent aryl group etc. , V1 represents an aryl group etc., and R11 to R14 represent H, OH or a halogen atom etc.]

  本发明的一个目的是提供一种化合物，该化合物选择性地抑制配体与α4β1整合素（VLA-4）的结合，以及包含该化合物的药物的制备过程。化合物的结构如公式（I）所示，或其盐，制备该化合物或其盐的过程，包含该化合物或其盐的药物，以及作为细胞粘附引起的疾病（例如炎症反应、自身免疫疾病、癌症转移、支气管哮喘、鼻阻塞、糖尿病、关节炎、银屑病、多发性硬化症、炎症性肠病和移植排斥反应等）的预防和/或治疗剂，包含该化合物或其盐作为主要成分。【其中Y1代表双价芳基等，V1代表芳基等，R11至R14代表H、OH或卤素原子等】
• New Optically Active 4-Alkoxyprolinol Ethers Derived from trans-4-Hydroxy-L-proline
  作者：Nora M. Friedemann、Astrid Eustergerling、Udo Nubbemeyer

  DOI：10.1002/ejoc.201101156

  日期：2012.2

  (2S,4R)-trans-4-Hydroxy-L-proline has been used as thechiral-pool source in the efficient syntheses of optically active protected 4-hydroxyprolinols. After N-acyl protection andester formation, the first ether moiety was introduced maintaining the chiral centre adjacent to the ester. Then, reduction of the ester delivered the corresponding carbinol, which had to be alkylated selectively to avoid side

  (2S,4R)-trans-4-Hydroxy-L-proline 已被用作手性池源，用于有效合成光学活性保护的 4-羟基脯氨醇。N-酰基保护和酯形成后，引入第一个醚部分，保持与酯相邻的手性中心。然后，酯的还原产生相应的甲醇，必须选择性地将其烷基化以避免与 N-保护基团发生副反应。最后，去除 N-酰基官能团以生成显示定义取代模式的目标甲基和叔丁基醚。如此形成的旋光4-烷氧基脯氨醇醚可用作生物活性化合物中的核心片段或用作合适起始材料中的稳定手性辅助亚单元。
• ANTI-INFLAMMATORY COMPOUND HAVING INHIBITORY ACTIVITY AGAINST MULTIPLE TYROSINE KINASES, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME
  申请人：Korea Institute of Science and Technology

  公开号：EP2578590A2

  公开（公告）日：2013-04-10

  The present invention is for the anti-inflammatory compounds that have an inhibitory activity against protein tyrosine kinases and their pharmaceutical composition(s) containing the compound as the active ingredient. Since the compounds of the present invention can inhibit multiple protein kinases associated with inflammatory diseases and immune disorders, they are useful for their prevention or treatment.

  本发明涉及对蛋白酪氨酸激酶具有抑制活性的抗炎化合物及其含有该化合物作为活性成分的药物组合物。由于本发明的化合物可抑制与炎症性疾病和免疫紊乱有关的多种蛋白激酶，因此可用于预防或治疗这些疾病。