(2S,4R)-1-苯甲基2-甲基4-羟基哌啶-1,2-二甲酸基酯 | 403503-37-7

• 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: (2S,4R)-1-苯甲基2-甲基4-羟基哌啶-1,2-二甲酸基酯
• 英文名称: (2S,4R)-1-benzyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate
• 英文别名: methyl 1-benzyloxycarbonyl-cis-4-hydroxy-(S)-pipecolate；(2S,4R)-4-hydroxypipecolic acid methyl ester；benzyl cis-4-hydroxy-2-methoxycarbonylpiperidine-1-carboxylate；1-O-benzyl 2-O-methyl (2S,4R)-4-hydroxypiperidine-1,2-dicarboxylate
• CAS: 403503-37-7
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: UZYUNWAMEQIRQH-OLZOCXBDSA-N

物化性质

• 沸点：
  436.1±45.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1-苯甲基2-甲基4-羟基哌啶-1,2-二甲酸基酯 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到1-O-benzyl 2-O-methyl (2S,4S)-4-fluoropiperidine-1,2-dicarboxylate
  参考文献：
  名称：

  Stereoselective syntheses of 4-fluoro- and 4,4-difluoropipecolic acids

  摘要：

  Stereoselective syntheses of 4-fluoro- and 4,4-difluoropipecolic acids starting from Z-protected 4-hydroxy- and 4-oxopipecolates via fluorodehydroxylation and fluorodeoxygenation are described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01660-4
• 作为产物：
  描述：

  N-CBZ--L-烯丙基甘氨酸 在 氯化亚砜 、 lipase AY₃₀ from Candida rugosa 作用下， 生成 (2S,4R)-1-苯甲基2-甲基4-羟基哌啶-1,2-二甲酸基酯
  参考文献：
  名称：

  水解酶在合成环状氨基酸中的用途

  摘要：

  描述了具有所有必要结构特征以使其成为用于药物化学的理想支架的几种环状氨基酸的合成。每个合成过程中的关键步骤是使用水解酶来定义手性中心。为了将这些结构单元详细化为更复杂的分子，使用了结晶和不对称氢化来定义进一步的立体中心。

  DOI：

  10.1016/j.tet.2003.10.116

文献信息

• MACROCYCLIC SERINE PROTEASE INHIBITORS
  申请人：Parsy Christophe Claude

  公开号：US20100260710A1

  公开（公告）日：2010-10-14

  Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula Ia or Ib, pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

  本文提供了大环丝氨酸蛋白酶抑制剂化合物，例如，Ia或Ib式的化合物，包括这些化合物的药物组合物，以及其制备方法。还提供了它们用于治疗宿主HCV感染的方法。
• SUBSTITUTED THIAZOLIDINEDIONE INDAZOLES, INDOLES AND BENZOTRIAZOLES AS ESTROGEN-RELATED RECEPTOR-a MODULATORS
  申请人：Bignan Gilles

  公开号：US20110294780A1

  公开（公告）日：2011-12-01

  The present invention relates to compounds of Formula (I), methods for preparing these compounds, compositions, intermediates and derivatives thereof and for treating a condition including but not limited to ankylosing spondylitis, artherosclerosis, arthritis (such as rheumatoid arthritis, infectious arthritis, childhood arthritis, psoriatic arthritis, reactive arthritis), bone-related diseases (including those related to bone formation), breast cancer (including those unresponsive to anti-estrogen therapy), cardiovascular disorders, cartilage-related disease (such as cartilage injury/loss, cartilage degeneration, and those related to cartilage formation), chondrodysplasia, chondrosarcoma, chronic back injury, chronic bronchitis, chronic inflammatory airway disease, chronic obstructive pulmonary disease, diabetes, disorders of energy homeostasis, gout, pseudogout, lipid disorders, metabolic syndrome, multiple myeloma, obesity, osteoarthritis, osteogenesis imperfecta, osteolytic bone metastasis, osteomalacia, osteoporosis, Paget's disease, periodontal disease, polymyalgia rheumatica, Reiter's syndrome, repetitive stress injury, hyperglycemia, elevated blood glucose level, and insulin resistance.

  本发明涉及式(I)的化合物，制备这些化合物的方法，组合物，中间体及其衍生物，并用于治疗包括但不限于强直性脊柱炎，动脉粥样硬化，关节炎（如类风湿关节炎，感染性关节炎，儿童关节炎，银屑病性关节炎，反应性关节炎），与骨相关的疾病（包括与骨形成有关的疾病），乳腺癌（包括对抗雌激素治疗无效的癌症），心血管疾病，软骨相关疾病（如软骨损伤/丧失，软骨退化以及与软骨形成有关的疾病），软骨发育不良，软骨肉瘤，慢性腰部损伤，慢性支气管炎，慢性炎症性气道疾病，慢性阻塞性肺疾病，糖尿病，能量稳态紊乱，痛风，假性痛风，脂质紊乱，代谢综合征，多发性骨髓瘤，肥胖，骨关节炎，遗传性骨发育不全，骨溶解性骨转移，软骨软化症，骨质疏松症，帕金森病，牙周病，多肌痛风，Reiter综合征，重复性应激损伤，高血糖，血糖水平升高和胰岛素抵抗等病症的方法。
• Macrocyclic serine protease inhibitors
  申请人：Parsy Christophe Claude

  公开号：US08377962B2

  公开（公告）日：2013-02-19

  Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula Ia or Ib, pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

  本文提供了大环丝氨酸蛋白酶抑制剂化合物，例如Ia或Ib式的化合物，包括含有该化合物的制药组合物以及其制备方法。还提供了它们用于治疗宿主中需要治疗HCV感染的方法。
• Discovery and structural diversity of the hepatitis C virus NS3/4A serine protease inhibitor series leading to clinical candidate IDX320
  作者：Christophe C. Parsy、François-René Alexandre、Valérie Bidau、Florence Bonnaterre、Guillaume Brandt、Catherine Caillet、Sylvie Cappelle、Dominique Chaves、Thierry Convard、Michel Derock、Damien Gloux、Yann Griffon、Lisa B. Lallos、Frederic Leroy、Michel Liuzzi、Anna-Giulia Loi、Laure Moulat、Musiu Chiara、Houcine Rahali、Virginie Roques、Elodie Rosinovsky、Simon Savin、Maria Seifer、David Standring、Dominique Surleraux

  DOI：10.1016/j.bmcl.2015.09.009

  日期：2015.11

  Exploration of the P2 region by mimicking the proline motif found in BILN2061 resulted in the discovery of two series of potent HCV NS3/4A protease inhibitors. X-ray crystal structure of the ligand in contact with the NS3/4A protein and modulation of the quinoline heterocyclic region by structure based design and modeling allowed for the optimization of enzyme potency and cellular activity. This research led to the selection of clinical candidate IDX320 having good genotype coverage and pharmacokinetic properties in various species. (C) 2015 Elsevier Ltd. All rights reserved.
• Novel constrained CCK-B dipeptoid antagonists derived from pipecolic acid
  作者：Bruno Bellier、Sophie Da Nascimento、Hervé Meudal、Edith Gincel、Bernard P. Roques、Christiane Garbay

  DOI：10.1016/s0960-894x(98)00231-5

  日期：1998.6

  A new series of 4-substituted pipecolic acid derivatives was prepared and incorporated into dipeptoids. The resulting products behave as moderately potent CCK-B antagonists but their constrained structure and its comparison with structurally related compounds yield valuable information about the conformational requirements for optimal recognition of the CCK-B receptor by antagonists. (C) 1998 Elsevier Science Ltd. All rights reserved.