2-amino-3-(4-ethylphenyl)propionic acid hydrochloride | 856570-89-3

• 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: 2-amino-3-(4-ethylphenyl)propionic acid hydrochloride
• 英文别名: D,L-p-ethylphenylalanine hydrochloride；4-Ethyl-L-phenylalanin-hydrochlorid；4-Ethyl-D-phenylalanin-hydrochlorid；4-ethyl-phenylalanine ; hydrochloride；4-Aethyl-phenylalanin; Hydrochlorid；2-amino-3-(4-ethylphenyl)propanoic acid;hydrochloride
• CAS: 856570-89-3
• 化学式: C₁₁H₁₅NO₂*ClH
• 分子量: 229.707
• InChiKey: VFRJAOUCZSPKAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-3-(4-ethylphenyl)propionic acid hydrochloride 在 盐酸 、 五氯化磷 、 三乙胺 、 乙酰氯 作用下， 以 乙酸乙酯 为溶剂， 反应 7.0h， 生成 3-(4-ethylphenyl)-2-{2-[(1H-indole-2-carbonyl)amino]benzoylamino}propionic acid ethyl ester
  参考文献：
  名称：

  Anthranilic acid based CCK1 receptor antagonists: preliminary investigation on their second “touch point”

  摘要：

  In this phase of structure-affinity relationship study of VL-0395, a new anthranilic acid based CCK1 selective antagonist, we propose a series Of Unnatural aminoacidic derivatives. The result of this work is the identification of a new CCK ligand, which possesses an affinity (IC50 = 35 nm) one order of magnitude greater than the lead and, as a general rule, it points out how the hypothesized receptorial pocket which accommodates the Phe residue allows much more structural modification than that interacting with the N-terminal group. Hence, the modification of the C-terminal pharmacophoric group of our lead VL-0395 can not only enhance the affinity of anthranific acid derivatives but can modulate the selectivity for one CCK receptor subtype or afford mixed antagonists. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.01.002
• 作为产物：
  描述：

  1-(溴甲基)-4-乙基苯 在 盐酸 、 sodium ethanolate 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 0.5h， 生成 2-amino-3-(4-ethylphenyl)propionic acid hydrochloride
  参考文献：
  名称：

  Anthranilic acid based CCK1 receptor antagonists: preliminary investigation on their second “touch point”

  摘要：

  In this phase of structure-affinity relationship study of VL-0395, a new anthranilic acid based CCK1 selective antagonist, we propose a series Of Unnatural aminoacidic derivatives. The result of this work is the identification of a new CCK ligand, which possesses an affinity (IC50 = 35 nm) one order of magnitude greater than the lead and, as a general rule, it points out how the hypothesized receptorial pocket which accommodates the Phe residue allows much more structural modification than that interacting with the N-terminal group. Hence, the modification of the C-terminal pharmacophoric group of our lead VL-0395 can not only enhance the affinity of anthranific acid derivatives but can modulate the selectivity for one CCK receptor subtype or afford mixed antagonists. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.01.002

文献信息

• The Analogs of 8-D-Homoarginin-vasopressin with O-Substituted Phenylalanine in Position 2: Synthesis and Some Biological Properties
  作者：Miroslava Žertová、Zdenko Procházka、Jiřina Slaninová、Tomislav Barth、Pavel Majer、Michal Lebl

  DOI：10.1135/cccc19921103

  日期：——

  Solid phase methodology on p-methylbenzhydrylamine resin was used for the synthesis of four analogs of vasopressin with the non coded amino acids, D-homoarginine (in position 8) and o-substituted L- or D-phenylalanine (in position 2). [L-Phe(o-Me)²,D-Har⁸]vasopressin (I), [D-Phe(o-Me)²,D-Har⁸]vasopressin (II), [L-Phe(o-Et)²,D-Har⁸]vasopressin (III) and [D-Phe(o-Et)²,D-Har⁸]vasopressin (IV) were synthesized. All analogs had very low antidiuretic activity. Analogs I and IV were low pressor inhibitors. All analogs were found to be the uterotonic inhibitors, the most potent on in vitro being [D-Phe(o-Et)²,D-Har⁸]vasopressin with a pA₂ = 8.4.

  在p-甲基苄基胺树脂上使用固相方法合成了四个非编码氨基酸类似加压素的类似物，其中包括D-同型精氨酸（位于第8位）和o-取代的L-或D-苯丙氨酸（位于第2位）。[L-Phe(o-Me)2,D-Har8]加压素（I），[D-Phe(o-Me)2,D-Har8]加压素（II），[L-Phe(o-Et)2,D-Har8]加压素（III）和[D-Phe(o-Et)2,D-Har8]加压素（IV）已经合成。所有类似物的抗利尿活性非常低。类似物I和IV是低血压抑制剂。所有类似物都被发现是子宫张力素抑制剂，其中体外抑制作用最强的是[D-Phe(o-Et)2,D-Har8]加压素，其pA2 = 8.4。
• MIYAKE, AKIO;ITOH, KATSUMI;AONO, TETSUYA;KISHIMOTO, SHOJI;MATSUSHITA, YOS+, J. TAKEDA RES. LAB., 1984, 43, N 3-4, 53-76
  作者：MIYAKE, AKIO、ITOH, KATSUMI、AONO, TETSUYA、KISHIMOTO, SHOJI、MATSUSHITA, YOS+

  DOI：——

  日期：——
• Anthranilic acid based CCK1 receptor antagonists: preliminary investigation on their second “touch point”
  作者：Antonio Varnavas、Lucia Lassiani、Valentina Valenta、Laura Mennuni、Francesco Makovec、Dimitra Hadjipavlou-Litina

  DOI：10.1016/j.ejmech.2005.01.002

  日期：2005.6

  In this phase of structure-affinity relationship study of VL-0395, a new anthranilic acid based CCK1 selective antagonist, we propose a series Of Unnatural aminoacidic derivatives. The result of this work is the identification of a new CCK ligand, which possesses an affinity (IC50 = 35 nm) one order of magnitude greater than the lead and, as a general rule, it points out how the hypothesized receptorial pocket which accommodates the Phe residue allows much more structural modification than that interacting with the N-terminal group. Hence, the modification of the C-terminal pharmacophoric group of our lead VL-0395 can not only enhance the affinity of anthranific acid derivatives but can modulate the selectivity for one CCK receptor subtype or afford mixed antagonists. (c) 2005 Elsevier SAS. All rights reserved.