(2S,5S,8S,16S)-16-Amino-5-benzyl-2-isobutyl-3,6,10,17-tetraoxo-1,4,7,11-tetraaza-cycloheptadecane-8-carboxylic acid amide | 221301-41-3

• 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: (2S,5S,8S,16S)-16-Amino-5-benzyl-2-isobutyl-3,6,10,17-tetraoxo-1,4,7,11-tetraaza-cycloheptadecane-8-carboxylic acid amide
• CAS: 221301-41-3
• 化学式: C₂₅H₃₈N₆O₅
• 分子量: 502.614
• InChiKey: XMZNLOSFDGPWDM-MUGJNUQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.77
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  185.51
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  H-Ser-OAllyl 、 、 (2S,5S,8S,16S)-16-Amino-5-benzyl-2-isobutyl-3,6,10,17-tetraoxo-1,4,7,11-tetraaza-cycloheptadecane-8-carboxylic acid amide 生成 (2S,5S,8S,16S)-16-[(S)-2-((S)-2-Amino-3-hydroxy-propionylamino)-3-(3-fluoro-phenyl)-propionylamino]-5-benzyl-2-isobutyl-3,6,10,17-tetraoxo-1,4,7,11-tetraaza-cycloheptadecane-8-carboxylic acid amide
  参考文献：
  名称：

  Macrocyclic hexapeptide analogues of the thrombin receptor (PAR-1) activation motif SFLLRN

  摘要：

  The thrombin receptor (PAR-1) is activated by alpha-thrombin to stimulate various cell types, including platelets, through the tethered-ligand sequence SFLLRN. Macrocyclic peptide analogues of SFLLRN were synthesized and evaluated in vitro. In general, the compounds were much less potent in inducing platelet aggregation relative to SFLLRN-NH2 and did not act as antagonists of alpha-thrombin. Derivative 3c was the most potent macrocycle in activating PAR-1, with an EC50 of 24 mu M. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00731-8
• 作为产物：
  描述：

  (S)-3-((S)-2-{(S)-2-[(S)-6-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoylamino]-4-methyl-pentanoylamino}-3-phenyl-propionylamino)-N-benzhydryl-succinamic acid 在 4-二甲氨基吡啶 、 氢氟酸 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 苯甲醚 、 二乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成 (2S,5S,8S,16S)-16-Amino-5-benzyl-2-isobutyl-3,6,10,17-tetraoxo-1,4,7,11-tetraaza-cycloheptadecane-8-carboxylic acid amide
  参考文献：
  名称：

  Macrocyclic hexapeptide analogues of the thrombin receptor (PAR-1) activation motif SFLLRN

  摘要：

  The thrombin receptor (PAR-1) is activated by alpha-thrombin to stimulate various cell types, including platelets, through the tethered-ligand sequence SFLLRN. Macrocyclic peptide analogues of SFLLRN were synthesized and evaluated in vitro. In general, the compounds were much less potent in inducing platelet aggregation relative to SFLLRN-NH2 and did not act as antagonists of alpha-thrombin. Derivative 3c was the most potent macrocycle in activating PAR-1, with an EC50 of 24 mu M. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00731-8