2-acetylamino-2-(4-ethoxycarbonylbenzyl)malonic acid diethyl ester | 102321-74-4

• 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-acetylamino-2-(4-ethoxycarbonylbenzyl)malonic acid diethyl ester
• 英文别名: diethyl 2-acetamido-2-<<4-(ethoxycarbonyl)phenyl>methyl>malonate；(4-Ethoxycarbonyl-benzyl)-acetamino-malonsaeure-diethylester；Diethyl 2-acetamido-2-[(4-ethoxycarbonylphenyl)methyl]propanedioate
• CAS: 102321-74-4
• 化学式: C₁₉H₂₅NO₇
• 分子量: 379.41
• InChiKey: YAXDIGBBCSKPJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-acetylamino-2-(4-ethoxycarbonylbenzyl)malonic acid diethyl ester 在 盐酸 作用下， 以70%的产率得到4-羧基苯丙氨酸盐酸盐
  参考文献：
  名称：

  用于肽合成的生物正交和交联氨基酸的合成

  摘要：

  通过遗传或化学方法将非规范氨基酸掺入蛋白质的能力使人们可以在确定的残基处将新的化学性质引入蛋白质。然后可以使用常见的有机转化来修饰这种残基。这样，可以在不干扰肽链中任何其他相邻氨基酸的情况下改变肽的结构或功能。在这里，我们描述的合成和多种潜在的应用对-取代的苯丙氨酸衍生物，其包含异硫氰酸酯，α-二氮酮或硝酮官能团。总之，以良好的总产率合成了三种新型氨基酸。这些非规范性氨基酸允许进一步发展其他试剂无法实现的体外和体内化学选择性和区域选择性生物共轭反应。

  DOI：

  10.1007/s00726-010-0594-3
• 作为产物：
  描述：

  4-羟甲基苯甲酸乙酯 在 氢溴酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 2-acetylamino-2-(4-ethoxycarbonylbenzyl)malonic acid diethyl 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

文献信息

• Differences in Backbone Structure between Angiotensin II Agonists and Type I Antagonists
  作者：John M. Matsoukas、George Agelis、Amal Wahhab、John Hondrelis、Dimitris Panagiotopoulos、Raghav Yamdagni、Qiao Wu、Thomas Mavromoustakos、Hernani L. S. Maia

  DOI：10.1021/jm00023a005

  日期：1995.11

  ANGII type I antagonists [HSer(gamma-OMe)8]ANGII and [Sar1Nva(delta-OMe)8]ANGII in DMSO by 1D-NOE spectroscopy revealed that the Tyr-Ile-His bend, a conformational property found in ANGII and [Sar1]ANGII (J. Biol. Chem. 1994, 269, 5303) is not present in type I antagonists, providing for the first time an important conformational difference between angiotensin II agonists and type I antagonists.

  通过固相方法制备了在位置8具有O-甲基-L-高丝氨酸[HSer（γ-OMe）]和δ-甲氧基-L-正缬氨酸[Nva（delta-OMe）]的I型血管紧张素II拮抗剂，通过反相HPLC纯化，并在大鼠子宫中进行生物测定，并通过核Overhauser效应（NOE）光谱研究了它们的骨架构象性质。[Sar1，HSer-（γ-OMe）8] ANGII，[HSer（γ-OMe）8] ANGII，[Des1，HSer（γ-OMe）8] ANGII，[Sar1，Nva（delta-OMe）8]- ANGII和[Des1，Nva（delta-OMe）8] ANGII分别具有以下拮抗剂活性pA2：7.6、7.5，<6.0、7.1和6.9。[Sar1] ANGII与δ-羟基-L-正缬氨酸[Nva（delta-OH）]，δ-甲氧基-L-正缬氨酸[Nva（delta-OMe）]，4'-羧基苯丙氨酸[Phe（4'-COO
• Synthesis of bioorthogonal and crosslinking amino acids for use in peptide synthesis
  作者：G. S. M. Sundaram、Ian R. Morgan、Eric M. Tippmann

  DOI：10.1007/s00726-010-0594-3

  日期：2010.11

  syntheses and potential applications of multiple para-substituted phenylalanine derivatives comprising an isothiocyanate, α-diazoketone, or nitrone functionality. In all, three novel amino acids were synthesized in good overall yields. These non-canonical amino acids permit the further development of in vitro and in vivo chemoselective and regioselective bioconjugate reactions not possible with other

  通过遗传或化学方法将非规范氨基酸掺入蛋白质的能力使人们可以在确定的残基处将新的化学性质引入蛋白质。然后可以使用常见的有机转化来修饰这种残基。这样，可以在不干扰肽链中任何其他相邻氨基酸的情况下改变肽的结构或功能。在这里，我们描述的合成和多种潜在的应用对-取代的苯丙氨酸衍生物，其包含异硫氰酸酯，α-二氮酮或硝酮官能团。总之，以良好的总产率合成了三种新型氨基酸。这些非规范性氨基酸允许进一步发展其他试剂无法实现的体外和体内化学选择性和区域选择性生物共轭反应。
• 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.