(4S)-3-<(2E)-3-(4-chlorophenyl)propenoyl>-4-phenylmethyl-1,3-oxazolidin-2-one | 133729-81-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4S)-3-<(2E)-3-(4-chlorophenyl)propenoyl>-4-phenylmethyl-1,3-oxazolidin-2-one
• 英文别名: (S,E)-4-benzyl-3-(3-(4-chlorophenyl)acryloyl)oxazolidin-2-one；(4S)-4-benzyl-3-[(2E)-3-(4-chlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one；(S)-4-benzyl-3-[(2E)-3-(4-chlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one；(4S)-4-benzyl-3-[(E)-3-(4-chlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 133729-81-4
• 化学式: C₁₉H₁₆ClNO₃
• 分子量: 341.794
• InChiKey: DRRQORJNXFYQBQ-YRYLYKBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  (4S)-3-<(2E)-3-(4-chlorophenyl)propenoyl>-4-phenylmethyl-1,3-oxazolidin-2-one 在 sodium methylate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 rac-methyl (3S,4R)-1-benzyl-4-(4-chlorophenyl)pyrrolidine-3-carboxylate
  参考文献：
  名称：

  Structure-Based Design of Potent and Selective Leishmania N-Myristoyltransferase Inhibitors

  摘要：

  Inhibitors of Leishmania N-myristoyltransferase (NMT), a potential target for the treatment of leishmaniasis, obtained from a high-throughput screen, were resynthesized to validate activity. Crystal structures bound to Leishmania major NMT were obtained, and the active diastereoisomer of one of the inhibitors was identified. On the basis of structural insights, enzyme inhibition was increased 40-fold through hybridization of two distinct binding modes, resulting in novel, highly potent Leishmania donovani NMT inhibitors with good selectivity over the human enzyme.

  DOI：

  10.1021/jm5011397
• 作为产物：
  描述：

  对氯肉桂酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 24.25h， 生成 (4S)-3-<(2E)-3-(4-chlorophenyl)propenoyl>-4-phenylmethyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Structure-Based Design of Potent and Selective Leishmania N-Myristoyltransferase Inhibitors

  摘要：

  Inhibitors of Leishmania N-myristoyltransferase (NMT), a potential target for the treatment of leishmaniasis, obtained from a high-throughput screen, were resynthesized to validate activity. Crystal structures bound to Leishmania major NMT were obtained, and the active diastereoisomer of one of the inhibitors was identified. On the basis of structural insights, enzyme inhibition was increased 40-fold through hybridization of two distinct binding modes, resulting in novel, highly potent Leishmania donovani NMT inhibitors with good selectivity over the human enzyme.

  DOI：

  10.1021/jm5011397

文献信息

• Pharmaceutically active compounds
  申请人：Calabrese Antony Andrew

  公开号：US20050176772A1

  公开（公告）日：2005-08-11

  The present invention relates to a class of melanocortin MCR4 agonists of general formula (I) wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein and especially to selective MCR4 agonist compounds, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes.

  本发明涉及一类通式（I）所示的黑素皮质素MCR4激动剂，其中R1、R2、R3、R4和R5如本文所定义，特别涉及选择性MCR4激动剂化合物，它们在医学上的应用，含有它们的组合物，用于它们制备的工艺以及用于这些工艺的中间体。
• Acylated piperidine derivatives as melanocortin-4 receptor agonists
  申请人：——

  公开号：US20040092501A1

  公开（公告）日：2004-05-13

  Certain novel 4-substituted N-acylated piperidine derivatives are agonists of the human melanocortin receptor(s) and, in particular, are selective agonists of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the activation of MC-4R, such as obesity, diabetes, sexual dysfunction, including erectile dysfunction and female sexual dysfunction.

  某些新型4-取代N-酰化哌啶衍生物是人类黑色素细胞激素受体的激动剂，特别是人类黑色素细胞激素-4受体（MC-4R）的选择性激动剂。因此，它们对于治疗、控制或预防对MC-4R的激活敏感的疾病和失调，如肥胖症、糖尿病、性功能障碍，包括勃起功能障碍和女性性功能障碍，是有用的。
• (3,5-dimethylpiperidin-1yl)(4-phenylpyrrolidin-3-yl)methanone derivatives as MCR4 agonists
  申请人：Pfizer Inc

  公开号：US07649002B2

  公开（公告）日：2010-01-19

  The present invention relates to a class of melanocortin MCR4 agonists of general formula (I) wherein R1, R2, R3, R4 and R5 are as defined herein and especially to selective MCR4 agonist compounds, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes.

  本发明涉及一类黑素细胞激素MCR4激动剂，其一般式为（I），其中R1、R2、R3、R4和R5如本文所定义，特别是选择性MCR4激动剂化合物，它们在医学上的使用，包含它们的组合物，制备它们的过程以及用于这种过程的中间体。
• Piperazine derivative
  申请人：Astellas Pharma Inc.

  公开号：US10301286B2

  公开（公告）日：2019-05-28

  To provide a compound which can be used as an MC4 receptor agonist. The present inventors have investigated MC4 receptor agonists, and have found that a piperazine derivative has an action related to the agonists, thereby completing the present invention. That is, the piperazine derivative of the present invention has an MC4 receptor agonistic action, and can be used as an agent for preventing or treating bladder and/or urinary tract diseases, in particular, underactive bladder, hypotonic bladder, acontractile bladder, detrusor underactivity, neurogenic bladder, urethral relaxation failure, detrusor-external urethral sphincter dyssynergia, and voiding dysfunctions in benign prostatic hyperplasia.

  提供一种可用作 MC4 受体激动剂的化合物。 本发明者对 MC4 受体激动剂进行了研究，发现一种哌嗪衍生物具有与激动剂相关的作用，从而完成了本发明。也就是说，本发明的哌嗪衍生物具有 MC4 受体激动剂的作用，可用作预防或治疗膀胱和/或尿路疾病的药物，特别是膀胱功能减退症、本发明的哌嗪衍生物具有 MC4 受体激动作用，可用作预防或治疗膀胱和/或尿路疾病的药物，特别是低张性膀胱、收缩性膀胱、逼尿肌活动不足、神经源性膀胱、尿道松弛衰竭、逼尿肌-外尿道括约肌功能障碍以及良性前列腺增生症的排尿功能障碍。
• Rueck, Karola; Kunz, Horst, Synthesis, 1993, # 10, p. 1018 - 1028
  作者：Rueck, Karola、Kunz, Horst

  DOI：——

  日期：——