N-acetyl-(R,S)-3,4,5-trimethoxyphenylalanine methyl ester | 82317-75-7

• 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: N-acetyl-(R,S)-3,4,5-trimethoxyphenylalanine methyl ester
• 英文别名: rac-methyl 2-acetamido-3-(3,4,5-trimethoxyphenyl)propanoate；Methyl 2-acetamido-3-(3,4,5-trimethoxyphenyl)propanoate
• CAS: 82317-75-7
• 化学式: C₁₅H₂₁NO₆
• 分子量: 311.335
• InChiKey: IQKGSVANHBSPPN-UHFFFAOYSA-N

物化性质

• 沸点：
  474.0±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-acetyl-(R,S)-3,4,5-trimethoxyphenylalanine methyl ester 在 盐酸 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis and biological activity of some very hydrophobic superagonist analogs of luteinizing hormone-releasing hormone

  摘要：

  The effect of increased hydrophobicity at position 6 of luteinizing hormone-releasing hormone (LH-RH) has been investigated by the incorporation of a series of 15 very hydrophobic, unnatural D-amino acids at this position. The unnatural amino acids studied can be considered analogues of phenylalanine with carbocyclic aromatic side chains consisting of substituted phenyl (e.g., 2,4,6-trimethylphenyl, p-biphenyl) or polycyclic aromatic (e.g., naphthalene, anthracene) units. When enzymatic resolution (subtilisin Carlsberg) of the most hydrophobic amino acids failed, the racemic amino acids were incorporated, and the diastereomeric LH-RH analogues were resolved by preparative high-performance liquid chromatography. The analogues were synthesized by the solid-phase technique. All of the synthetic compounds were very potent LH-RH superagonists, but [6-(3-(2-naphthyl)-D-alanine)]LH-RH, [6-(3-(2-naphthyl)-D-alanine), 7-(N alpha-methylleucine)]LH-RH and [6-(3-(2,4,6-trimethylphenyl)-D-alanine)]LH-RH appear to be among the most potent LH-RH agonist analogues yet reported when tested in a rat estrus cyclicity suppression assay designed to show the paradoxical antifertility effects of these compounds [ED50 approximately 7 x 10(-8) g; twice daily in saline]. These analogues are twice as potent as [D-Trp6,ProNHEt9]LH-RH in this assay system (i.e., approximately 200 times the potency of LH-RH).

  DOI：

  10.1021/jm00349a006
• 作为产物：
  描述：

  (Z)-2-methyl-4-(3,4,5-trimethoxybenzylidene)oxazol-5(4H)-one 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 17.5h， 生成 N-acetyl-(R,S)-3,4,5-trimethoxyphenylalanine methyl ester
  参考文献：
  名称：

  量身定制的肽苯基酯会通过异常分解成七聚物-六聚物组件来阻止ClpXP蛋白水解。

  摘要：

  蛋白水解复合物ClpXP是细菌稳态和发病机理的基础。由于其构象的灵活性，有效的ClpXP抑制剂的开发具有挑战性，迫切需要新的工具来解密其复杂的调控。在这里，我们提出了基于氨基酸的苯基酯作为分子探针，以研究金黄色葡萄球菌的ClpXP复合物的活性和低聚。系统地筛选（R）和（S）氨基酸导致化合物显示出有效的抑制作用，并刺激ClpXP介导的蛋白水解作用。探针的亚化学计量结合使ClpXP停滞在前所未有的七聚体-六聚体组装中，其中两个七聚体ClpP环彼此解离。同时，ClpX和ClpP之间的亲和力增加，导致两种酶的抑制作用。这种构象停滞对于ClpXP的合并关闭以及在其催化循环期间研究低聚状态是有益的。

  DOI：

  10.1002/anie.201901056

文献信息

• Methods and compositions for inducing apoptosis in cancer cells
  申请人：Nasoff Marc

  公开号：US20050079172A1

  公开（公告）日：2005-04-14

  Anti-DR4 or Anti-DR5 antibody agonists, combined with apoptosis-inducing agents, synergistically induce apoptosis in cancer cells.

  Anti-DR4或Anti-DR5抗体激动剂，与诱导细胞凋亡的药物结合使用，能够协同诱导癌细胞的凋亡。
• 2-{[N-(2-amino-3-(heteroaryl or aryl) propionyl)-aminoacyl]-amino}-alkylboronic acid derivatives
  申请人：Furet Pascal

  公开号：US20050239716A1

  公开（公告）日：2005-10-27

  The present invention relates to compounds of formula I wherein the substituents are as defined in the description, to processes for the preparation thereof, to pharmaceutical preparations comprising those compounds, and to the use thereof in the preparation of pharmaceutical compositions for the therapeutic treatment of warm-blooded animals, including humans.

  本发明涉及式I的化合物，其中取代基如描述中所定义，以及其制备方法，包括这些化合物的制药制剂，以及在制备治疗温血动物，包括人类的药物组合物时的使用。
• 2-{[n-(2-amino-3-(heteroaryl or aryl)propionyl)-aminoacyl}-amino}-alkylboronic acid derivatives
  申请人：——

  公开号：US20040167337A1

  公开（公告）日：2004-08-26

  The present invention relates to compounds of formula (I) their synthesis and pharmaceutical compositions thereof for the therapeutic treatment of a proliferative diseases in warm-blooded animals, including humans. 1

  本发明涉及式（I）化合物，它们的合成以及制备用于治疗温血动物，包括人类的增殖性疾病的制药组合物。
• Tyagi, O D; Boll, P M; Parmar, V S, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 12, p. 851 - 854
  作者：Tyagi, O D、Boll, P M、Parmar, V S、Taneja, Poonam、Singh, S K

  DOI：——

  日期：——
• 2-((N-(2-AMINO-3-(HETEROARYL OR ARYL)PROPIONYL)-AMINOACYL)-AMINO)-ALKYLBORONIC ACID DERIVATIVES
  申请人：Novartis AG

  公开号：EP1399468B1

  公开（公告）日：2006-02-15