N-(4-chlorobenzyl)-D,L-alanine | 68319-26-6

• 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-(4-chlorobenzyl)-D,L-alanine
• 英文别名: N-(4-Chlorbenzyl)-DL-alanin；2-[(4-chlorophenyl)methylazaniumyl]propanoate
• CAS: 68319-26-6
• 化学式: C₁₀H₁₂ClNO₂
• 分子量: 213.664
• InChiKey: FBMVXXOKUYWDEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯甲酸-9-芴基甲酯 、 N-(4-chlorobenzyl)-D,L-alanine 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 2-{4-chlorobenzyl-[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propionic acid
  参考文献：
  名称：

  [DE] NICHT-PEPTIDISCHE BRS-3-AGONISTEN
  [EN] NON-PEPTIDIC BRS-3 AGONISTS
  [FR] AGONISTES DU RECEPTEUR BRS-3 NON PEPTIDIQUES

  摘要：

  新的、选择性的BRS-3激动剂有效化合物已被描述，其具有通用式(I)，其中A<1>、A<2>、A<3>、R<1>、R<2>、R<3>、Ar<1>、Ar<2>、Ar<3>、m和n具有描述中指定的含义，以及包含这些化合物的药物和制备式(I)化合物的方法。

  公开号：

  WO2003104196A1
• 作为产物：
  描述：

  对氯苄胺 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 N-(4-chlorobenzyl)-D,L-alanine
  参考文献：
  名称：

  Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3

  摘要：

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.

  DOI：

  10.1021/jm0210921

文献信息

• [DE] NICHT-PEPTIDISCHE BRS-3-AGONISTEN<br/>[EN] NON-PEPTIDIC BRS-3 AGONISTS<br/>[FR] AGONISTES DU RECEPTEUR BRS-3 NON PEPTIDIQUES
  申请人：SOLVAY PHARM GMBH

  公开号：WO2003104196A1

  公开（公告）日：2003-12-18

  Es werden neue, selektiv BRS-3 agonistisch wirksame Verbindungen der allgemeinen Formel (I), worin A<1>, A<2 >, A<3 >, R<1>, R<2> , R<3 >, Ar<1> , Ar<2> , Ar<3> , m und n die in der Beschreibung angegebenen Bedeutungen besitzen, sowie diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung von Verbindungen der Formel (I) beschrieben.

  新的、选择性的BRS-3激动剂有效化合物已被描述，其具有通用式(I)，其中A<1>、A<2>、A<3>、R<1>、R<2>、R<3>、Ar<1>、Ar<2>、Ar<3>、m和n具有描述中指定的含义，以及包含这些化合物的药物和制备式(I)化合物的方法。
• Synthesis, crystal structures, and antibacterial studies of silver(I) complexes with reduced Schiff base amino acid ligands
  作者：Hai-Yan Liu、Qing-Hua Guan、Jun Tian、Peng Du、Hong Chen

  DOI：10.1007/s11243-016-0060-5

  日期：2016.9

  Three Ag(I) complexes of reduced Schiff base amino acid ligands, [Ag2(Hshis)2]·3H2O (1), Ag(Hcgly) (2), and Ag(cala) (3) (H2shis = N-(2-hydroxybenzyl)-l-histidine, H2cgly = N-(2-hydroxy-5-chlorobenzyl)-glycine, Hcala = N-(4-chlorobenzyl)-d,l-alanine), have been synthesized and characterized by X-ray crystallography. Complex 1 shows a dimeric structure, while complex 2 shows one-dimensional zigzag chains

  三种还原席夫碱氨基酸配体的 Ag(I) 复合物 [Ag2(Hshis)2]·3H2O (1)、Ag(Hcgly) (2) 和 Ag(cala) (3) (H2shis = N-(2) -羟基苄基)-l-组氨酸，H2cgly = N-(2-羟基-5-氯苄基)-甘氨酸，Hcala = N-(4-氯苄基)-d,l-丙氨酸)，已合成并通过 X 射线表征晶体学。配合物 1 显示二聚体结构，而配合物 2 显示一维锯齿形链，通过氢键延伸成二维超分子片。复合体 3 展示了一个带有悬臂的 2D 片状结构。已经研究了复合物的抗微生物活性。
• Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3
  作者：Dirk Weber、Claudia Berger、Peter Eickelmann、Jochen Antel、Horst Kessler

  DOI：10.1021/jm0210921

  日期：2003.5.1

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.