N-BOC-(3S,4R)-4-(4-氯苯基)吡咯烷-3-羧酸 | 851484-56-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: N-BOC-(3S,4R)-4-(4-氯苯基)吡咯烷-3-羧酸
• 英文名称: trans-1-tert-butoxycarbonyl-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid
• 英文别名: (3S,4R)-N-Boc-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid；(3S,4R)-1-(tert-butoxycarbonyl)-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid；(3S,4R)-1-Boc-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid；trans-1-(Tert-butoxycarbonyl)-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid；(3S,4R)-4-(4-chlorophenyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylic acid
• CAS: 851484-56-5
• 化学式: C₁₆H₂₀ClNO₄
• 分子量: 325.792
• InChiKey: NSBYJYHHDUOADW-QWHCGFSZSA-N

物化性质

• 沸点：
  465.1±45.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-BOC-(3S,4R)-4-(4-氯苯基)吡咯烷-3-羧酸 在 盐酸 、 三乙酰氧基硼氢化钠 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Pyrrolidines as potent functional agonists of the human melanocortin-4 receptor

  摘要：

  A series of pyrrolidine derivatives were synthesized and characterized as potent agonists of the human melanocortin-4 receptor. For example, 28c had a K-i of 13 nM in binding affinity and EC50 of 6.9 nM in agonist potency with an intrinsic activity of 100% of the endogenous ligand alpha-MSH. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.088
• 作为产物：
  描述：

  tert-butyl (3S,4R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-4-(4-chlorophenyl)pyrrolidine-1-carboxylate 在 lithium hydroxide 、 双氧水 作用下， 反应 2.0h， 以96%的产率得到N-BOC-(3S,4R)-4-(4-氯苯基)吡咯烷-3-羧酸
  参考文献：
  名称：

  Synthesis and characterization of pyrrolidine derivatives as potent agonists of the human melanocortin-4 receptor

  摘要：

  A series of trans-4-phenylpyrrolidine-3-carboxamides were synthesized and characterized as potent ligands of the human melanocortin-4 receptor. Interestingly, a pair of diastereoisomers 20f-1 and 20f-2 displayed potent functional agonist and antagonist activity, respectively. Thus, the 3S, 4R-compound 20f-1 possessed a K-i of 11 nM and an EC50 of 24 nM, while its 3R, 4S-isomer 20f-2 exhibited a K-i of 8.6 and an IC50 of 65 nM. Both compounds were highly selective over other melanocortin receptor subtypes. The MC4R agonist 20f-1 also demonstrated efficacy in diet-induced obese rats. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.079

文献信息

• MELANOCORTIN RECEPTOR AGONISTS
  申请人：Lee Koo

  公开号：US20100120783A1

  公开（公告）日：2010-05-13

  The present invention relates to a compound having a good agonistic activity to melanocortin receptor, or pharmaceutically acceptable salt or isomer thereof, and an agonistic composition for melanocortin receptor comprising the same as an active ingredient.

  本发明涉及一种对黑皮质素受体具有良好激动活性的化合物，或其药学上可接受的盐或异构体，以及包含该化合物作为活性成分的黑皮质素受体激动剂组合物。
• 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。
• Ligands of melanocortin receptors and compositions and methods related thereto
  申请人：Tran Anh Joe

  公开号：US20050192286A1

  公开（公告）日：2005-09-01

  Compounds which function as melanocortin receptor ligands and having utility in the treatment of melanocortin receptor-based disorders. The compounds have the following structure (I): including stereoisomers, prodrugs, and pharmaceutically acceptable salts thereof, wherein m, n, q, s, R 1 , R 1 a, R 1b , R 2 , R 3 , R 4 , X 1 , X 2 and X 3 are as defined herein. Pharmaceutical compositions containing a compound of structure (I), as well as methods relating to the use thereof, are also disclosed.

  具有在治疗基于黑色素细胞激素受体的疾病中有用的功能的化合物。该化合物具有以下结构（I）：包括立体异构体，前药和药物可接受的盐，其中m，n，q，s，R1，R1a，R1b，R2，R3，R4，X1，X2和X3如本文所定义。还公开了含有结构（I）的化合物的制药组合物，以及与其使用相关的方法。
• Organic Compounds and Their Uses
  申请人：Brandl Trixi

  公开号：US20080045530A1

  公开（公告）日：2008-02-21

  The present application describes organic compounds that are useful for the treatment, prevention and/or amelioration of human diseases.

  本申请描述了有机化合物，可用于治疗、预防和/或改善人类疾病。
• Melanocortin receptor agonists
  申请人：LG Life Sciences Ltd.

  公开号：US07879852B2

  公开（公告）日：2011-02-01

  The present invention relates to a compound of the following formula 1, pharmaceutically acceptable salt and isomer thereof effective as agonist of melanocortin receptor, and an agonistic composition of melanocortin receptor comprising the same as active ingredient.

  本发明涉及以下公式1的化合物，药学上可接受的盐和异构体，作为黑色素细胞素受体激动剂，以及含有其作为活性成分的黑色素细胞素受体激动剂组合物。