(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid | 343251-07-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid
• 英文别名: (2R)-2-(2-tert-butoxy-2-oxoethyl)-5-cyclohexylpentanoic acid；(R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid；(2R)-5-cyclohexyl-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]pentanoic acid
• CAS: 343251-07-0
• 化学式: C₁₇H₃₀O₄
• 分子量: 298.423
• InChiKey: VVYVFZRWUJASEV-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid 在 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 、 xylene 为溶剂， 反应 59.5h， 生成 (3R)-6-cyclohexyl-3-(3-{[(methylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoic acid
  参考文献：
  名称：

  Potent and Selective Nonpeptidic Inhibitors of Procollagen C-Proteinase

  摘要：

  6-Cyclohexyl-N-hydroxy-3-(1,2,4-oxadiazol-5-yl)hexanamides were previously disclosed as inhibitors of procollagen C-proteinase (PCP) culminating in the identification of amide 1. Our objective was to discover a second inhibitor that would have improved affinity for PCP and to optimize properties for transepidermal delivery (TED) to intact skin. Further investigation of this template identified a number of potent PCP inhibitors (IC50 values of 2-6 nM) with improved TED flux. Sulfonamide 56 had excellent PCP enzyme activity when measured with a peptide substrate (K-i 8.7 nM) or with the endogenous substrate procollagen (IC50 3.4 nM) and demonstrates excellent selectivity over MMPs involved in wound healing (> 10 000-fold). In the fibroplasia model, 56 inhibited deposition of insoluble collagen by 76 +/- 2% at 10 mu M and was very effective at penetrating human skin in vitro with a TED flux of 1.5 mu g/cm(2)/h, which compares favorably with values for agents that are known to penetrate skin well in vivo. Based on this profile, 56 (UK-421,045) was selected as a candidate for further preclinical evaluation as a topically applied, dermal anti-scarring agent.

  DOI：

  10.1021/jm061010z
• 作为产物：
  描述：

  (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid 在 铑 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以to leave the title compound as an oil (2.0 g)的产率得到(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid
  参考文献：
  名称：

  3-heterocyclypropanohydroxamic acid PCP inhibitors

  摘要：

  化合物的公式（1）及其盐，溶剂合物，前药等，其中取代基具有此处提到的值，是前胶原C-蛋白酶（PCP）抑制剂，并在由PCP介导的疾病中具有效用。

  公开号：

  US06831088B2

文献信息

• 3-heterocyclylpropanohydroxamic acid PCP inhibitors
  申请人：——

  公开号：US20030069291A1

  公开（公告）日：2003-04-10

  Compounds of formula (I): 1 and their salts, solvates, hydrates and prodrugs are useful PCP inhibitors, processes for making the same, compositions comprising the same, and methods of treating a PCP-mediated condition or disease using the same.

  式(I)的化合物及其盐、溶剂合物、水合物和前药是有用的PCP抑制剂，制备这些化合物的方法，包含这些化合物的组合物，以及使用这些化合物治疗PCP介导的疾病或病症的方法。
• 3-ox(adi) azolylpropanohydroxamic acids useful as procollagen C- Proteinase inhibitors
  申请人：——

  公开号：US20020151535A1

  公开（公告）日：2002-10-17

  Compounds of formula (I): 1 wherein the substituents are as defined herein, and their salt, solvates, and prodrugs are procollagen C-proteinase (PCP) inhibitors useful in treating conditions mediated by PCP.

  式（I）的化合物： 其中取代基如本文所定义，并且它们的盐、溶剂合物和前药是用于治疗由PCP介导的疾病的前胶原C蛋白酶（PCP）抑制剂。
• Novel olefination process to itaconate and succinate derivatives
  申请人：——

  公开号：US20020058832A1

  公开（公告）日：2002-05-16

  An efficient and selective process, capable of scale-up, to make itaconate derivatives of formula (IV), and/or succinate derivatives of formula (V) and/or (VI) by asymmetric hydrogenation of the itaconate derivatives. 1

  一种高效且选择性的工艺，可扩大规模，通过对顺丁烯二酸衍生物进行不对称加氢，制备化学式（IV）的顺丁烯二酸衍生物，以及/或化学式（V）和/或（VI）的琥珀酸衍生物。
• Procollagen C-proteinase inhibitors
  申请人：——

  公开号：US20010021718A1

  公开（公告）日：2001-09-13

  1 and their salts, solvates, prodrugs, etc., wherein the substituents have the values mentioned herein, are Procollagen C-Proteinase (PCP) inhibitors and have utility in conditions mediated by PCP.

  它们及其盐、溶剂合物、前药等，其中取代基具有此处提及的值，是Procollagen C-蛋白酶（PCP）抑制剂，并在由PCP介导的疾病中具有用途。
• [EN] OX(ADI)AZOLYL-HYDROXAMIC ACIDS USEFUL AS PROCOLLAGEN C-PROTEINASE INHIBITORS<br/>[FR] ACIDES OX(ADI)AZOLYL-HYDROXAMIQUES UTILISES COMME INHIBITEURS DE LA PROCOLLAGENE C-PROTEINASE
  申请人：PFIZER LTD

  公开号：WO2001047901A1

  公开（公告）日：2001-07-05

  Compounds of formula (I) and their salts, solvates, prodrugs, etc., wherein the substituents have the values mentioned herein, are Procollagen C-Proteinase (PCP) inhibitors and have utility in conditions mediated by PCP.

  式(I)化合物及其盐、溶剂化物、前药等，其中取代基具有此处提及的值，是前胶原C-蛋白酶（PCP）抑制剂，在由PCP介导的疾病中具有应用价值。