rac-2-amino-3-[(1-methyl-1H-indole-2-carbonyl)amino]propionic acid | 1182348-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: rac-2-amino-3-[(1-methyl-1H-indole-2-carbonyl)amino]propionic acid
• 英文别名: 2-Amino-3-[(1-methylindole-2-carbonyl)amino]propanoic acid
• CAS: 1182348-69-1
• 化学式: C₁₃H₁₅N₃O₃
• 分子量: 261.28
• InChiKey: MBSNCWQFISASJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  97.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 5%-palladium/activated carbon 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 以72%的产率得到rac-2-amino-3-[(1-methyl-1H-indole-2-carbonyl)amino]propionic acid
  参考文献：
  名称：

  Drug Design, in Vitro Pharmacology, and Structure−Activity Relationships of 3-Acylamino-2-aminopropionic Acid Derivatives, a Novel Class of Partial Agonists at the Glycine Site on the N-Methyl-d-aspartate (NMDA) Receptor Complex

  摘要：

  Retaining agonistic activity at the glycine coagonist site of the NMDA receptor in molecules derived from glycine or D-serine has proven to be difficult because in the vicinity of the alpha-amino acid group little substitution is tolerated. We have solved this problem by replacing the hydroxy group of D-serine with an amido group, thus keeping the hydrogen donor function and allowing For further substitution and exploration of the adjacent space. Heterocyclic substitutions resulted in a series of 3-acylamino-2-aminopropionic acid derivatives, with high affinities in a binding assay for the glycine site. In a functional assay assessing the activation of the glycine site, these compounds displayed a wide range of intrinsic efficacies, from antagonism to a high degree of partial agonism. Structure-activity relationships reveal that lipophilic substituents, presumably filling an additional hydrophobic pocket, are accepted by the glycine site, provided that they are separated from the alpha-amino acid group by a short linker.

  DOI：

  10.1021/jm900363q

文献信息

• TEMPLATE-FIXED PEPTIDOMIMETICS WITH CCR10 ANTAGONISTIC ACTIVITY
  申请人：Jung Francoise

  公开号：US20120283168A1

  公开（公告）日：2012-11-08

  Novel template-fixed β-hairpin peptidomimetics of the general formula (I) wherein the single elements T or P are α-amino acid residues connected in either direction which, depending on their positions in the chain, are as defined in the description and the claims, and salts thereof, have the property to antagonize the receptor CCR10. They can be used as medicaments to treat or prevent diseases or conditions in the area of dermatological and cutaneous disorders, inflammation, allergic disorders, respiratory diseases, diseases of the gastro-intestinal tract, ophthalmic diseases, haematology and cancer. These β-hairpin peptidomimetics can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy.

  具有以下一般式(I)的小说模板固定β-发夹仿生肽，其中单个元素T或P是α-氨基酸残基，可以连接在任何方向上，具体取决于它们在链中的位置，如描述和索赔中所定义，及其盐，具有拮抗受体CCR10的特性。它们可用作药物，用于治疗或预防皮肤病和皮肤疾病、炎症、过敏性疾病、呼吸道疾病、胃肠道疾病、眼科疾病、血液学和癌症等领域。这些β-发夹仿生肽可以通过基于混合固相和溶液相合成策略的过程制备。
• TEMPLATE-FIXED PEPTIDOMIMETICS WITH CXCR7 MODULATING ACTIVITY
  申请人：Gombert Frank Otto

  公开号：US20130225506A1

  公开（公告）日：2013-08-29

  Novel template-fixed β-hairpin peptidomimetics of the general formula (I), wherein the single elements T or P are α-amino acid residues connected from the carbonyl (C═O) point of attachment to the nitrogen (N) of the next element in clockwise direction and wherein said elements, depending on their positions in the chain, are defined in the description and the claims have the property to act on the receptor CXCR7. Thus, these β-hairpin peptidomimetics can be useful in the treatment or prevention of diseases or conditions in the area of dermatological disorders, metabolic diseases, inflammatory diseases, fibrotic diseases, infectious diseases, neurological diseases, cardiovascular diseases, respiratory diseases, gastro-intestinal tract disorders, urological diseases, ophthalmic diseases, stomatological diseases, haematological diseases and cancer; or the mobilisation of stem cells.

  该模板固定的β-折叠肽类似物具有一般式（I），其中单个元素T或P是α-氨基酸残基，从羰基（C═O）连接点连接到顺时针方向下一个元素的氮（N），并且这些元素根据它们在链中的位置在说明书和权利要求中定义，具有作用于CXCR7受体的特性。因此，这些β-折叠肽类似物可用于治疗或预防皮肤疾病、代谢性疾病、炎症性疾病、纤维性疾病、感染性疾病、神经系统疾病、心血管疾病、呼吸系统疾病、胃肠道疾病、泌尿系统疾病、眼科疾病、口腔疾病、血液学疾病和癌症；或干细胞的动员。
• TEMPLATE-FIXED PEPTIDOMIMETICS WITH CCR10 ANTAGONISTIC ACTIVTY
  申请人：Polyphor Ag

  公开号：EP2501715A1

  公开（公告）日：2012-09-26
• US8754038B2
  申请人：——

  公开号：US8754038B2

  公开（公告）日：2014-06-17
• US9109009B2
  申请人：——

  公开号：US9109009B2

  公开（公告）日：2015-08-18