N-cyclopentanoylphenylalanine | 75691-91-7

• 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
• 英文名称: N-cyclopentanoylphenylalanine
• 英文别名: cyco-C5H9CO-Phe-OH；N-(Cyclopentylcarbonyl)-L-phenylalanine；Nalpha-cyclopentanecarbonylphenylalanine；(2S)-2-(cyclopentanecarbonylamino)-3-phenylpropanoic acid
• CAS: 75691-91-7
• 化学式: C₁₅H₁₉NO₃
• mdl: MFCD16377811
• 分子量: 261.321
• InChiKey: ODNCESTYJYAFQZ-ZDUSSCGKSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  508.1±39.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.466
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cyclopentanoylphenylalanine 在 盐酸 、 异丁基硼酸 、 1-羟基苯并三唑 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 6.42h， 生成 ((R)-1-((S)-2-(cyclopentanecarboxamido)-3-phenylpropanamido)-3-methylbutyl)boronic acid
  参考文献：
  名称：

  由αα-和αβ-氨基酸构建的新型二肽基硼酸蛋白酶体抑制剂的设计，合成和对接研究

  摘要：

  设计并合成了一系列由αα-和αβ-氨基酸构建的新型二肽基硼酸蛋白酶体抑制剂。通过1 H NMR，13 C NMR，LC-MS和HRMS阐明了它们的结构。评价这些化合物对人蛋白酶体的β5亚基抑制活性。结果表明，由αα-氨基酸组成的二肽基硼酸抑制剂的活性与硼替佐米相同。有趣的是，那些衍生自αβ-氨基酸的酶的活性完全丧失了。在所有抑制剂中，化合物22（IC 50  = 4.82 nM）对蛋白酶体活性的抑制作用最强。化合物22还是对三种具有IC 50的MM细胞系最有活性的在抑制细胞生长试验中，其值小于5 nM。分子对接研究表明，22个蛋白非常适合蛋白酶体的β5亚基活性口袋。

  DOI：

  10.1016/j.bmcl.2016.03.007
• 作为产物：
  描述：

  环戊基甲酰氯 在 lithium hydroxide monohydrate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 N-cyclopentanoylphenylalanine
  参考文献：
  名称：

  由αα-和αβ-氨基酸构建的新型二肽基硼酸蛋白酶体抑制剂的设计，合成和对接研究

  摘要：

  设计并合成了一系列由αα-和αβ-氨基酸构建的新型二肽基硼酸蛋白酶体抑制剂。通过1 H NMR，13 C NMR，LC-MS和HRMS阐明了它们的结构。评价这些化合物对人蛋白酶体的β5亚基抑制活性。结果表明，由αα-氨基酸组成的二肽基硼酸抑制剂的活性与硼替佐米相同。有趣的是，那些衍生自αβ-氨基酸的酶的活性完全丧失了。在所有抑制剂中，化合物22（IC 50  = 4.82 nM）对蛋白酶体活性的抑制作用最强。化合物22还是对三种具有IC 50的MM细胞系最有活性的在抑制细胞生长试验中，其值小于5 nM。分子对接研究表明，22个蛋白非常适合蛋白酶体的β5亚基活性口袋。

  DOI：

  10.1016/j.bmcl.2016.03.007

文献信息

• N-Acylphenylalanines and related compounds. A new class of oral hypoglycemic agents
  作者：Hisashi Shinkai、Koji Toi、Izumi Kumashiro、Yoshiko Seto、Mariko Fukuma、Katsuaki Dan、Shigeshi Toyoshima

  DOI：10.1021/jm00119a007

  日期：1988.11

  N-Benzoyl-DL-phenylalanine (1) was found to possess hypoglycemic activity. A series of the analogues of compound 1 were prepared and evaluated for their blood glucose lowering activity. Both the steric effects of the phenylalanine moiety and the effects of variations in the acyl moiety were investigated. This study elucidated some of the structure-activity relationships and led to the development of

  N-苯甲酰基-DL-苯丙氨酸（1）被发现具有降血糖活性。制备了一系列化合物1的类似物，并评估了它们的降血糖活性。研究了苯丙氨酸部分的空间影响和酰基部分变化的影响。这项研究阐明了一些构效关系，并导致了N-（4-乙基苯甲酰基）-D-苯丙氨酸（34）的开发，其效力是初始化合物1的50倍。
• Anti-hypertensive agents
  申请人：University of Miami

  公开号：US04692458A1

  公开（公告）日：1987-09-08

  Novel inhibitors of angiotensin converting enzyme having the general formula R--A--S--Z are disclosed as potent inhibitors of angiotensin converting enzyme and are useful anti-hypertensive agents.

  本发明公开了一种具有一般式R--A--S--Z的血管紧张素转换酶新型抑制剂，其为强效的血管紧张素转换酶抑制剂，可用作抗高血压药物。
• Microsphere Formation in a Series of Derivatized .alpha.-Amino Acids: Properties, Molecular Modeling, and Oral Delivery of Salmon Calcitonin
  作者：Andrea Leone-Bay、Campbell McInnes、NaiFang Wang、Frenel DeMorin、Doug Achan、Christine Lercara、Donald Sarubbi、Susan Haas、Jeffery Press

  DOI：10.1021/jm00021a014

  日期：1995.10

  A series of benzoylated and phenylsulfonylated amino acids are novel, low molecular weight, self-assembling molecules. At low pH, these compounds form microspheres that dissolve readily under neutral conditions. In a given synthetic series, those molecules with low aqueous solubility formed microspheres more readily than did the molecules possessing high water solubility, suggesting that the hydrophobicity of these compounds contributes to the ability to form microspheres. In addition, molecular modeling studies on selected compounds have shown that microsphere formation may depend also on various aromatic ring and dipole-dipole interactions, which could effect the extent and types of favorable stacking conformations between molecules. The microspheres prepared from these compounds have been used to effect the oral delivery of salmon calcitonin, a model protein drug, in both rodents and primates.
• .alpha.-Hydroxy Phosphinyl-Based Inhibitors of Human Renin
  作者：Dinesh V. Patel、Katherine Rielly-Gauvin、Denis E. Ryono、Charles A. Free、W. Lynn Rogers、Sandra A. Smith、Jack M. DeForrest、Robert S. Oehl、Edward W. Petrillo

  DOI：10.1021/jm00022a022

  日期：1995.10

  The design and application of alpha-hydroxy phosphonates, a new class of transition state analogs, toward the discovery of novel and potent inhibitors of the aspartyl protease renin is described. Tripeptidic alpha-hydroxy diethyl phosphonate 3, the first example in this series, was found to be a good inhibitor of human renin (IC50 = 29 nM), and preliminary studies led to the choice of alpha-hydroxy dimethyl phosphonate 15 (IC50 = 16 nM) as a base-line compound for further structure-activity relationship study. Corresponding phosphinate (28-30) and phosphine oxide (23 and 24) analogs of 15 were prepared to assess the steric and electronic requirements around the phosphorus center. Evaluation of these analogs suggested that the presence of at least one alkoxy group on phosphorus was a critical requirement for good activity. Inhibitors with leucine at P-2 possessed better in vitro activity than the corresponding P-2 histidine analogs (15, IC50 = 16 nM vs 37, IC50 = 220 nM; 33, IC50 = 8.5 nM vs 40, IC50 = 41 nM). Compound 34 (IC50 = 31 nM), the P-3 aminocaproic analog of 15, showed complete and long-lasting inhibition of plasma renin activity while eliciting a 10-15 mmHg drop in mean arterial pressure when administered intravenously at 1 mu mol/kg in conscious, sodium-depleted, cynomolgus monkeys. In summary, the alpha-hydroxy phosphonates represent a promising and structurally novel class of transition state analog inhibitors of human renin.
• TOESIMA, SIGEHRU;SEHDO, TOSIKO;NIIMI, XISASI;TOI, KODZI;KUMASIRO, IDZUMI
  作者：TOESIMA, SIGEHRU、SEHDO, TOSIKO、NIIMI, XISASI、TOI, KODZI、KUMASIRO, IDZUMI

  DOI：——

  日期：——