(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid | 156109-64-7

• 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-phenylpentanoic acid
• 英文别名: (R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid；(2R)-5-phenyl-2-t-butoxycarbonylmethyl-pentanoic acid；(2R)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-5-phenylpentanoic acid
• CAS: 156109-64-7
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: BLLMQOGLBBYQOS-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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-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
• 作为产物：
  描述：

  5-苯基戊酰氯 在 lithium hydroxide 、 正丁基锂 、 双氧水 、 lithium diisopropyl amide 、 sodium nitrite 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.42h， 生成 (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid
  参考文献：
  名称：

  Inhibition of Membrane-Type 1 Matrix Metalloproteinase by Hydroxamate Inhibitors:  An Examination of the Subsite Pocket

  摘要：

  The membrane-type 1 matrix metalloproteinase (MT1-MMP) has been reported to mediate the activation of pro-gelatinase A (proMMP-2), which is associated with tumor proliferation and metastasis. MT1-MMP can also digest extracellular matrix (ECM) such as interstitial collagens, gelatin, and proteoglycan and thus may play an important role in pathophysiological digestion of ECM. We studied the inhibitory effect of various hydroxamate MMP inhibitors, including known inhibitors such as BB-94, BB-2516, GM6001, and Ro31-9790, on a deletion mutant of MT1-MMP lacking the transmembrane domain (Delta MT1) to further characterize the enzyme and develop a selective inhibitor for MT1-MMP. The evaluation of the inhibitory activities of various hydroxamates reveals general structural profiles affecting selectivities toward MMPs. In particular, a longer side chain at the P1' position is preferable for the binding to MMP-2, -3, and -9 and MT1-MMP. For the P2' position, an a-branched alkyl group is critical for the binding toward Delta MT1, while the introduction of a bulky group at the a-position of hydroxamic acid seems to diminish the activity against Delta MT1. Summation of the data on the sensitivity of Delta MT1 to various hydroxamate inhibitors indicates that (1) the volume of the S1' subsite of Delta MT1 is similar to that of MMP-2, -3, and -9, which is bigger than that of MMP-1, and (2) the S1 and S2' subsites are narrower than those in other MMPs. On the basis of these results, the hydroxamates with a P1' phenylpropyl and P2' alpha-branched alkyl group were synthesized and evaluated for inhibitory activity. These inhibitors (1h,i) showed strong activity against Delta MT1 over MMP-1, but no selectivity between Delta MT1 and MMP-9. These results are explained using molecular modeling studies conducted on MT1-MMP.

  DOI：

  10.1021/jm970404a

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。
• Rapid Synthesis of Matrix Metalloproteinase Inhibitors via Ugi Four-Component Condensation
  作者：Christopher D. Floyd、Laura A. Harnett、Andrew Miller、Sanjay Patel、Lydia Saroglou、Mark Whittaker

  DOI：10.1055/s-1998-1729

  日期：1998.6

  By employing ammonia, together with a mono succinate ester, an aldehyde and an isonitrile in the Ugi four-component condensation the basic structure of pseudopeptide succinyl matrix metalloproteinase inhibitors is constructed in a single step. Deprotection of the ester provides the carboxylic acid zinc(II) binding group required for biological activity.

  通过在 Ugi 四组份缩合过程中使用氨、琥珀酸单酯、醛和异腈，只需一个步骤就能构建出琥珀酰基基质金属蛋白酶抑制剂的基本结构。酯的去保护作用提供了生物活性所需的羧酸锌（II）结合基团。