cinnamoyl-L-phenylalanine

• 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: cinnamoyl-L-phenylalanine
• 英文别名: (N)-2-phenylacrylamido-3-phenylpropionic acid；N-cinnamoyl-L-phenylalanine；Cinnamoylphenylalanin；(2S)-3-phenyl-2-(3-phenylprop-2-enoylamino)propanoic acid
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: YFHVCODMDZNZEA-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 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：

  cinnamoyl-L-phenylalanine 在 甲醇 、 sodium tetrahydroborate 、 戴斯-马丁氧化剂 、 sodium hydrogensulfite 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  抗肠病毒71(EV71)4-亚氨基恶唑烷-2-酮类 化合物及其制备方法和用途

  摘要：

  一种4‑亚氨基恶唑烷‑2‑酮类肠病毒71(EV71)3C蛋白酶抑制剂，其结构通式为化合物(M)所示，结构中的各变量在说明书中定义，这些化合物有效地抑制或阻断了肠病毒71的复制。本发明涉及含有式(M)结构的化合物、其各种光学异构体、药物活性的代谢物、可药用盐、溶剂化物以及前药在制备治疗手足口病毒感染疾病抗病毒药物的发现和应用。本发明还涉及制备式(M)结构化合物的中间体和合成方法。

  公开号：

  CN107459511B
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 在 水 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 cinnamoyl-L-phenylalanine
  参考文献：
  名称：

  α-Ketoamides as Broad-Spectrum Inhibitors of Coronavirus and Enterovirus Replication: Structure-Based Design, Synthesis, and Activity Assessment

  摘要：

  The main protease of coronaviruses and the 3C protease of enteroviruses share a similar active-site architecture and a unique requirement for glutamine in the P1 position of the substrate. Because of their unique specificity and essential role in viral polyprotein processing, these proteases are suitable targets for the development of antiviral drugs. In order to obtain near-equipotent, broad-spectrum antivirals against alphacoronaviruses, betacoronaviruses, and enteroviruses, we pursued a structure-based design of peptidomimetic alpha-ketoamides as inhibitors of main and 3C proteases. Six crystal structures of protease-inhibitor complexes were determined as part of this study. Compounds synthesized were tested against the recombinant proteases as well as in viral replicons and virus-infected cell cultures; most of them were not cell-toxic. Optimization of the P2 substituent of the alpha-ketoamides proved crucial for achieving near-equipotency against the three virus genera. The best near-equipotent inhibitors, 11u (P2 = cyclopentylmethyl) and 11r (P2 = cyclo-hexylmethyl), display low-micromolar EC50 values against enteroviruses, alphacoronaviruses, and betacoronaviruses in cell cultures. In Huh7 cells, 11r exhibits three-digit picomolar activity against the Middle East Respiratory Syndrome coronavirus.

  DOI：

  10.1021/acs.jmedchem.9b01828

文献信息

• N-acylated amino acids containing a??-chloroethylthio grouping
  作者：V. I. Vidugirene、T. A. Pranskene、L. P. Rasteikene、M. G. Lin'kova、I. L. Knunyants

  DOI：10.1007/bf00851222

  日期：1972.8
• Shalaby; El-Sawy; El-Salam, O. I. Abd, Egyptian Journal of Chemistry, 2008, vol. 51, # 6, p. 807 - 821
  作者：Shalaby、El-Sawy、El-Salam, O. I. Abd、Abdullah、Elshihaby, Soha A.

  DOI：——

  日期：——
• Synthesis of N-Cinnamoyl dipeptide esters and investigation of their self-assembly leading to Nanorods formation
  作者：Shete, Saurabh、Gavali, Manoj、Ramana、Maduskar, Mandar、Karanjule, Nanabhau、Yadav, Dilip Kumar

  DOI：10.56042/ijc.v62i11.1580

  日期：——
• α-Ketoamides as Broad-Spectrum Inhibitors of Coronavirus and Enterovirus Replication: Structure-Based Design, Synthesis, and Activity Assessment
  作者：Linlin Zhang、Daizong Lin、Yuri Kusov、Yong Nian、Qingjun Ma、Jiang Wang、Albrecht von Brunn、Pieter Leyssen、Kristina Lanko、Johan Neyts、Adriaan de Wilde、Eric J. Snijder、Hong Liu、Rolf Hilgenfeld

  DOI：10.1021/acs.jmedchem.9b01828

  日期：2020.5.14

  The main protease of coronaviruses and the 3C protease of enteroviruses share a similar active-site architecture and a unique requirement for glutamine in the P1 position of the substrate. Because of their unique specificity and essential role in viral polyprotein processing, these proteases are suitable targets for the development of antiviral drugs. In order to obtain near-equipotent, broad-spectrum antivirals against alphacoronaviruses, betacoronaviruses, and enteroviruses, we pursued a structure-based design of peptidomimetic alpha-ketoamides as inhibitors of main and 3C proteases. Six crystal structures of protease-inhibitor complexes were determined as part of this study. Compounds synthesized were tested against the recombinant proteases as well as in viral replicons and virus-infected cell cultures; most of them were not cell-toxic. Optimization of the P2 substituent of the alpha-ketoamides proved crucial for achieving near-equipotency against the three virus genera. The best near-equipotent inhibitors, 11u (P2 = cyclopentylmethyl) and 11r (P2 = cyclo-hexylmethyl), display low-micromolar EC50 values against enteroviruses, alphacoronaviruses, and betacoronaviruses in cell cultures. In Huh7 cells, 11r exhibits three-digit picomolar activity against the Middle East Respiratory Syndrome coronavirus.
• 抗肠病毒71(EV71)4-亚氨基恶唑烷-2-酮类 化合物及其制备方法和用途
  申请人：南开大学

  公开号：CN107459511B

  公开（公告）日：2020-05-29

  一种4‑亚氨基恶唑烷‑2‑酮类肠病毒71(EV71)3C蛋白酶抑制剂，其结构通式为化合物(M)所示，结构中的各变量在说明书中定义，这些化合物有效地抑制或阻断了肠病毒71的复制。本发明涉及含有式(M)结构的化合物、其各种光学异构体、药物活性的代谢物、可药用盐、溶剂化物以及前药在制备治疗手足口病毒感染疾病抗病毒药物的发现和应用。本发明还涉及制备式(M)结构化合物的中间体和合成方法。