methyl N-cinnamoyl-(L)-leucine | 331474-57-8

• 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: methyl N-cinnamoyl-(L)-leucine
• 英文别名: N-[(2E)-1-Oxo-3-phenyl-2-propen-1-yl]-L-leucine；(2S)-4-methyl-2-[[(E)-3-phenylprop-2-enoyl]amino]pentanoic acid
• CAS: 331474-57-8
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: AQLMQEJSGNPSEX-XEHSLEBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  methyl N-cinnamoyl-(L)-leucine 在 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.01h， 生成 (S)-1-{(S)-4-Methyl-2-[(E)-(3-phenyl-acryloyl)amino]-pentanoyl}-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Reverse Turn Induced π-Facial Selectivity during Polyaniline-Supported Cobalt(II) Salen Catalyzed Aerobic Epoxidation of N-Cinnamoyl l-Proline Derived Peptides

  摘要：

  A novel chemo- and diastereoselective aerobic epoxidation of the N-cinnamoyl peptides catalyzed by polyaniline-supported cobalt(II) salen (PASCOS) is described. The N-cinnamoyl proline derived peptides 1 show a high pi-facial selectivity during these epoxidations. The origin of this diastereo-selectivity in 1 has been attributed to (i) the propensity of the N-cinnamoyl proline amide to exist predominantly as trans rotamer in CDCl3, DMSO-d(6), and CH3CN medium and (ii) existence of these peptides as organized structures (gamma- and beta-turns) due to the presence of intramolecular hydrogen bonds. An extensive solution NMR and MD simulation study on 1d and 1f indicates that the origin of the high pi-facial selectivity is due to the well-defined gamma- and beta-turns which result in the hindrance of one face of the cinnamoyl double bond in the transition state of the epoxidation reaction.

  DOI：

  10.1021/jo020352j

文献信息

• Aldehyde derivatives and their use as calpain inhibitors
  申请人：FUJIREBIO Inc.

  公开号：EP0520336A2

  公开（公告）日：1992-12-30

  Aldehyde derivatives with a specific calpain inhibiting activity and a platelet-aggregation inhibiting effect with formula (I) or formula (II): wherein R1 represents an aromatic hydrocarbon group, a heterocyclic group, or a group of -X-R3 in which X represents O, -S(O)m- (m = 0, 1, or 2), and R3 represents an aromatic hydrocarbon group, a heterocyclic group, or an alkyl group; Z represents R4-Y- or R60-CH(R5)- in which Y represents a 3- to 7-membered nitrogen-containing saturated heterocyclic group, or a single cyclic saturated hydrocarbon group, R4 represents an alkyl group, an alkenyl group, an alkynyl group, an acyl group, a sulfonyl group, an alkoxycarbonyl group, a carbamoyl group, or a thiocarbamoyl group, R5 represents hydrogen, an alkyl group, or an aromatic hydrocarbon group, and R6 represents an acyl group, a carbamoyl group, a thiocarbamoyl group, or an alkyl group; and n is an integer of 1 to 5. wherein R7, R8, R9, and R10 are defined in the specification.

  具有特异性钙蛋白酶抑制活性和血小板聚集抑制作用的式 (I) 或式 (II) 醛衍生物： 其中 R1 代表芳香烃基团、杂环基团或-X-R3 的基团，其中 X 代表 O、-S(O)m- (m = 0、1 或 2)，R3 代表芳香烃基团、杂环基团或烷基；Z 代表 R4-Y- 或 R60-CH(R5)-，其中 Y 代表 3 至 7 元含氮饱和杂环基团，或单环饱和烃基团，R4 代表烷基、烯基、炔基、酰基、磺酰基、烷基、炔基或烷基R5 代表氢、烷基或芳香烃基，R6 代表酰基、氨基甲酰基、硫代氨基甲酰基或烷基；n 是 1 至 5 的整数。 其中 R7、R8、R9 和 R10 的定义见说明书。
• COMPOSITIONS FOR PREVENTING AND TREATING DIGESTIVE DISEASES
  申请人：FUSO PHARMACEUTICAL INDUSTRIES LTD.

  公开号：EP1258251A1

  公开（公告）日：2002-11-20

  The present invention provides a composition for safely and effectively preventing and treating digestive organs diseases, particularly, gastric ulcer, duodenal ulcer, gastritis, diarrhea, enteritis and the like. There is also provided a composition having a novel mechanism of action in order to solve the problems which was difficult to be solved by the side effect previously known mechanisms of action. More particularly, there is provided a pharmaceutical composition containing an ingredient which activates PAR-2 as an essential ingredient, which is useful for inhibiting gastric acid secretion, promoting digestive tract mucus secretion, protecting digestive tract mucosa, repairing tissue of digestive organs, and preventing and treating digestive organs diseases.

  本发明提供了一种组合物，用于安全有效地预防和治疗消化器官疾病，特别是胃溃疡、十二指肠溃疡、胃炎、腹泻、肠炎等。本发明还提供了一种具有新作用机理的组合物，以解决以往已知作用机理难以解决的副作用问题。更具体地说，本发明提供了一种药物组合物，其基本成分中含有激活 PAR-2 的成分，可用于抑制胃酸分泌、促进消化道粘液分泌、保护消化道粘膜、修复消化器官组织、预防和治疗消化器官疾病。
• Compositions for preventing and treating digestive organs diseases
  申请人：——

  公开号：US20030166553A1

  公开（公告）日：2003-09-04

  The present invention provides a composition for safely and effectively preventing and treating digestive organs diseases, particularly, gastric ulcer, duodenal ulcer, gastritis, diarrhea, enteritis and the like. There is also provided a composition having a novel mechanism of action in order to solve the problems which was difficult to be solved by the side effect previously known mechanisms of action. More particularly, there is provided a pharmaceutical composition containing an ingredient which activates PAR-2 as an essential ingredient, which is useful for inhibiting gastric acid secretion, promoting digestive tract mucus secretion, protecting digestive tract mucosa, repairing tissue of digestive organs, and preventing and treating digestive organs diseases.
• US7550437B2
  申请人：——

  公开号：US7550437B2

  公开（公告）日：2009-06-23
• Reverse Turn Induced π-Facial Selectivity during Polyaniline-Supported Cobalt(II) Salen Catalyzed Aerobic Epoxidation of <i>N</i>-Cinnamoyl <scp>l</scp>-Proline Derived Peptides
  作者：Jyoti Prokosh Nandy、E. N. Prabhakaran、S. Kiran Kumar、A. C. Kunwar、Javed Iqbal

  DOI：10.1021/jo020352j

  日期：2003.3.1

  A novel chemo- and diastereoselective aerobic epoxidation of the N-cinnamoyl peptides catalyzed by polyaniline-supported cobalt(II) salen (PASCOS) is described. The N-cinnamoyl proline derived peptides 1 show a high pi-facial selectivity during these epoxidations. The origin of this diastereo-selectivity in 1 has been attributed to (i) the propensity of the N-cinnamoyl proline amide to exist predominantly as trans rotamer in CDCl3, DMSO-d(6), and CH3CN medium and (ii) existence of these peptides as organized structures (gamma- and beta-turns) due to the presence of intramolecular hydrogen bonds. An extensive solution NMR and MD simulation study on 1d and 1f indicates that the origin of the high pi-facial selectivity is due to the well-defined gamma- and beta-turns which result in the hindrance of one face of the cinnamoyl double bond in the transition state of the epoxidation reaction.