L-γ-glutamyl-β-phenethylamine | 99633-84-8

• 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: L-γ-glutamyl-β-phenethylamine
• 英文别名: N⁵-phenethyl-L-glutamine；N⁵-Phenaethyl-L-glutamin；L-Glutaminsaeure-5-phenaethylamid；gamma-Glutamyl-phenylethylamine；(2S)-2-amino-5-oxo-5-(2-phenylethylamino)pentanoic acid
• CAS: 99633-84-8
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: MWUNDCCUMICSNT-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-苯乙胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 苯 作用下， 生成 L-γ-glutamyl-β-phenethylamine
  参考文献：
  名称：

  Edelson et al., Journal of medicinal and pharmaceutical chemistry, 1959, vol. 1, p. 165,167

  摘要：

  DOI：

文献信息

• BETA-HAIRPIN PEPTIDOMIMETICS AS SELECTIVE ELASTASE INHIBITORS
  申请人：POLYPHOR AG

  公开号：US20160333053A1

  公开（公告）日：2016-11-17

  β-Hairpin peptidomimetics of the general formula cyclo(-Xaa 1 -Xaa 2 -Thr 3 -Xaa 4 -Ser 5 -Xaa 6 -Xaa 7 -Xaa 8 -Xaa 9 -Xaa 10 -Xaa 11 -Xaa 12 -Xaa 13 -) and pharmaceutically acceptable salts thereof, with Xaa 1 , Xaa 2 , Xaa 4 , Xaa 6 , Xaa 7 , Xaa 8 , Xaa 9 , Xaa 10 , Xaa 11 , Xaa 12 and Xaa 13 being amino acid residues of certain types which are defined in the description and the claims, have elastase inhibitory properties, especially against human neutrophil elastase, and can be used for preventing infections or diseases related to such infections in healthy individuals or for slowing infections in infected patients. The compounds of the invention can further be used where cancer, or immunological diseases, or pulmonary diseases, or cardiovascular diseases, or neurodegenerative diseases, or inflammation, or diseases related to inflammation, are mediated or resulting from elastase activity. These peptidomimetics can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy.

  β-头发环肽类似物的一般公式为cyclo(-Xaa1-Xaa2-Thr3-Xaa4-Ser5-Xaa6-Xaa7-Xaa8-Xaa9-Xaa10-Xaa11-Xaa12-Xaa13-)及其药学上可接受的盐，其中Xaa1、Xaa2、Xaa4、Xaa6、Xaa7、Xaa8、Xaa9、Xaa10、Xaa11、Xaa12和Xaa13是在描述和权利要求中定义的某些类型的氨基酸残基，具有弹性酶抑制性质，特别是对人类中性粒细胞弹性蛋白酶，可用于预防健康个体中与此类感染相关的感染或疾病，或者用于减缓感染患者中的感染。该发明的化合物还可用于癌症、免疫性疾病、肺部疾病、心血管疾病、神经退行性疾病、炎症或与炎症相关的疾病由弹性酶活性介导或由此导致的情况。这些肽类似物可以通过基于混合固相和溶液相合成策略的过程制造。
• HUMAN GLUCAGON-LIKE-PEPTIDE-1 MODULATORS AND THEIR USE IN THE TREATMENT OF DIABETES RELATED CONDITIONS
  申请人：Haque Shamsul Tasir

  公开号：US20070238669A1

  公开（公告）日：2007-10-11

  The present invention provides novel human glucagon-like peptide-1 (GLP-1)-receptor modulators that have biological activity similar or superior to native GLP-1 peptide and thus are useful for the treatment or prevention of diseases or disorders associated with GLP activity. Further, the present invention provides novel, chemically modified compounds that not only stimulate insulin secretion in type II diabetics, but also produce other beneficial insulinotropic responses. These synthetic peptide GLP-1 receptor modulators exhibit increased stability to proteolytic cleavage making them ideal therapeutic candidates for oral or parenteral administration. The compounds of this invention show desirable pharmacokinetic properties and desirable potency in efficacy models of diabetes.

  本发明提供了新型人类胰高血糖素样肽-1（GLP-1）受体调节剂，其生物活性类似或优于天然GLP-1肽，因此可用于治疗或预防与GLP活性相关的疾病或障碍。此外，本发明提供了新的化学修饰化合物，不仅可以刺激2型糖尿病患者的胰岛素分泌，还可以产生其他有益的胰岛素促进反应。这些合成肽GLP-1受体调节剂表现出对蛋白酶水解的稳定性增加，使它们成为口服或静脉注射理想的治疗候选药物。本发明的化合物在糖尿病疗效模型中表现出理想的药代动力学特性和理想的效力。
• Cyclic peptides and use thereof
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：EP0528312A2

  公开（公告）日：1993-02-24

  Disclosed are (1) a cyclic hexapeptide represented by formula [I] or a salt thereof: wherein X and Y each represent a-amino acid residues, A represents a D-acidic-a-amino acid residue, B represents a neutral-a-amino acid residue, C represents an L-a-amino acid residue and D represents a D-a-amino acid residue having an aromatic ring group; and (2) a pharmaceutical composition comprising the peptide represented by formula [I] or a pharmaceutically acceptable salt thereof as an active ingredient.

  公开了 (1) 由式 [I] 表示的环六肽或其盐： 其中 X 和 Y 分别代表 a-氨基酸残基，A 代表 D-酸性-a-氨基酸残基，B 代表中性-a-氨基酸残基，C 代表 L-a-氨基酸残基，D 代表具有芳香环基的 D-a-氨基酸残基；以及 (2) 一种药物组合物，其活性成分包含式 [I] 所代表的肽或其药学上可接受的盐。
• Methods and compositions for the prophylactic and/or therapeutic treatment of organ hypofunction
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：EP0626174A2

  公开（公告）日：1994-11-30

  Compounds having antagonistic activity on endothelin receptors can be effectively used for prophylaxis and/or treatment of hypofunction of organs which occurs in their surgery or transplant.

  对内皮素受体具有拮抗活性的化合物可有效用于预防和/或治疗器官移植手术中出现的器官功能减退。
• Cyclic hexapeptides having endothelin antagonistic activity
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：EP0655463A1

  公开（公告）日：1995-05-31

  A cyclic hexapeptide represented by the formula:         cyclo[A-Asp(R¹)-Y-NH-CHR²-CO-C-D-Trp(Nin-R³)-]   (I) wherein A is a D-acidic-α-amino acid residue; Y is an acidic-α-amino acid residue; C is an L-α-amino acid residue; R¹ is a group represented by the formula: wherein X¹ and X² are independently H, C₁₋₆ alkyl, C₁₋₆ alkoxy, halogen or nitro, and may bind together to form a ring in cooperation with the adjacent carbon atom; R² is C₁₋₆ alkyl, C₃₋₇ cycloalkyl, C₃₋₇ cycloalkyl-C₁₋₃ alkyl, C₁₋₆ alkylthio-C₁₋₃ alkyl, C₃₋₇ cycloalkylthio-C₁₋₃ alkyl, C₁₋₅ alkoxy-C₁₋₃ alkyl, C₃₋₇ cycloalkoxy-C₁₋₃ alkyl, C₁₋₆ alkylthio, C₃₋₇ cycloalkylthio, C₁₋₅ alkoxy or C₃₋₇ cycloalkoxy; R³ is H, C₁₋₆ alkyl, C₃₋₇ cycloalkyl, -COR⁴, - COOR⁵ or -CONHR⁶; when X¹, X² and R³ are all hydrogen atoms, R² is not an isobutyl group, or a saalt thereof, which exhibits excellent antagonistic action against endothelin receptors, particularly endothelin B receptors.

  一种由式表示的环状六肽： 环[A-Asp(R¹)-Y-NH-CHR²-CO-C-D-Trp(Nin-R³)-] (I) 其中 A 是 D-酸性-α-氨基酸残基；Y 是酸性-α-氨基酸残基；C 是 L-α-氨基酸残基；R¹ 是由式表示的基团： 其中X¹和X²独立地为H、C₁₋₆烷基、C₁₋₆烷氧基、卤素或硝基，并可与相邻碳原子结合在一起形成环；R² 是 C₁₋₆烷基、C₃₋₇ 环烷基、C₃₋₇ 环烷基-C₁₋₃ 烷基、C₁₋₆烷硫基-C₁₋₃ 烷基、C₃₋₇ 环烷基硫基-C₁₋₃ 烷基、C₁₋₅烷氧基-₁₋₃ 烷基、C₃₋₇ 环烷氧基-₁₋₃ 烷基、C₁₋₆烷硫基、C₃₋₇ 环烷基硫基、C₁₋₅烷氧基或 C₃₋₇ 环烷氧基；R³ 是 H、C₁₋₆ 烷基、C₃₋₇ 环烷基、-COR⁴、- COOR⁵ 或 -CONHR⁶；当 X¹、X² 和 R³ 均为氢原子时，R² 不是异丁基，也不是其对内皮素受体，特别是对内皮素 B 受体有极好的拮抗作用的异丁基。