2-(6-苯基己酰氨基)乙酸 | 741694-69-9

• 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
• 中文名称: 2-(6-苯基己酰氨基)乙酸
• 英文名称: N-(6-phenylhexanoyl)glycine
• 英文别名: 6-phenylhexanoylglycine；2-(6-phenylhexanoylamino)acetic acid
• CAS: 741694-69-9
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: BWKKSNHRJBCIMD-UHFFFAOYSA-N

物化性质

• 熔点：
  88-90 °C
• 沸点：
  503.7±43.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  2-(6-苯基己酰氨基)乙酸 、 L-色氨酸乙酯盐酸盐 在 N-乙基吗啉 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以74%的产率得到Ph(CH2)5C(O)-Gly-L-Trp-OEt
  参考文献：
  名称：

  Design and synthesis of cholecystokinin-4 dipeptide analogues with anxiolytic and anxiogenic activities

  摘要：

  A new series of dipeptide analogues of the general formula Ph(CH2) (n) CO-NH(CH2) (m) CO-Trp-NH2 (n = 1, 3-5; m = 1-3) was designed based on the structure of the endogenous tetrapeptide cholescystokinin-4 (CCK-4) and the topochemical Shemyakin-Ovchinnikov-Ivanov principle. The L-tryptophan derivatives exhibited anxiolytic properties and the D-tryptophan derivatives, anxiogenic properties. The dipeptide Ph(CH2)(5)CO-Gly-L-Trp-NH2 (GB-115) with the activity in rats of 0.05-0.2 mg/kg after oral and intraperitoneal administration was chosen for further studies as a promising anxiolytic agent.

  DOI：

  10.1134/s1068162007040036

文献信息

• A study of the biologically active conformation of the cholecystokinin-4 dipeptide analogue GB-115
  作者：T. A. Gudasheva、V. P. Lezina、E. P. Kir’yanova、O. A. Deeva、L. G. Kolik、S. B. Seredenin

  DOI：10.1134/s1068162013030060

  日期：2013.5

  spectroscopy method in solution and the structure-activity relationship study of a series sterically restricted analogs allowed to detect the possible biologically active conformation of N-(6-phenylhexanoyl)glycyl-tryptophan amide (GB-115), a highly active dipeptide cholecystokinin-4 analog with anxiolytic activity. The structure-activity relationship study of GB-115 and the series of its' glycine-

  溶液中1H NMR光谱法进行的构象分析以及一系列空间受限类似物的构效关系研究，可检测N-（6-苯基己酰基）甘氨酰色氨酸酰胺（GB-115）的可能的生物活性构象。具有抗焦虑活性的高活性二肽胆囊收缩素-4类似物。GB-115及其一系列具有不同C端取代基的含甘氨酸和脯氨酸的类似物的结构活性关系研究检测到具有β-turn构象的化合物的抗焦虑活性和具有gamma-turn构象的化合物的无活性构象。因此，GB-115的生物活性构象是beta-turn。核Overhauser效应研究的结果使betaII-turn构象符合GB-115生物活性构象。
• [EN] DOUBLE-ACYLATED GLP-1 DERIVATIVES<br/>[FR] DÉRIVÉS DE GLP-1 DOUBLEMENT ACYLÉS
  申请人：NOVO NORDISK AS

  公开号：WO2012062803A1

  公开（公告）日：2012-05-18

  The invention relates to a derivative of a GLP-1 analogue, which analogue comprises a first K residue at a position corresponding to position 18 of GLP-1 (7-37) (SEQ ID NO: 1 ), a second K residue at another position, and a maximum of twelve amino acid changes as compared to GLP-1 (7-37); which derivative comprises two protracting moieties attached to said first and second K residue, respectively, via a linker, wherein the protracting moiety is selected from Chem. 1, Chem. 2, and Chem. 3: Chem. : HOOC-(CH2)x-CO-* Chem. 2: HOOC-C6H4-0-(CH2)y-CO-* Chem. 3: R2-C6H4-(CH2)z-CO-*, in which x is an integer in the range of 6-18, y is an integer in the range of 3-17, z is an integer in the range of 1 -5, and R2 is a group having a molar mass not higher than 150 Da; and the linker comprises Chem. 4: *-NH-(CH2)2-(0-(CH2)2)k-0-(CH2)n-CO-*. wherein k is an integer in the range of 1 -5, and n is an integer in the range of 1 -5; or a pharmaceutically acceptable salt, amide, or ester thereof. The invention also relates to the pharmaceutical use thereof, for example in the treatment and/or prevention of all forms of diabetes and related diseases, as well as to corresponding novel peptides and side chain intermediates. The derivatives are suitable for oral administration.
• Design and synthesis of cholecystokinin-4 dipeptide analogues with anxiolytic and anxiogenic activities
  作者：T. A. Gudasheva、E. P. Kir’yanova、L. G. Kolik、M. A. Konstantinopol’skii、S. B. Seredenin

  DOI：10.1134/s1068162007040036

  日期：2007.7

  A new series of dipeptide analogues of the general formula Ph(CH2) (n) CO-NH(CH2) (m) CO-Trp-NH2 (n = 1, 3-5; m = 1-3) was designed based on the structure of the endogenous tetrapeptide cholescystokinin-4 (CCK-4) and the topochemical Shemyakin-Ovchinnikov-Ivanov principle. The L-tryptophan derivatives exhibited anxiolytic properties and the D-tryptophan derivatives, anxiogenic properties. The dipeptide Ph(CH2)(5)CO-Gly-L-Trp-NH2 (GB-115) with the activity in rats of 0.05-0.2 mg/kg after oral and intraperitoneal administration was chosen for further studies as a promising anxiolytic agent.