3-Amino-4-{[(diphenyl-p-tolyl-methyl)-amino]-methyl}-benzoic acid | 470461-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-Amino-4-{[(diphenyl-p-tolyl-methyl)-amino]-methyl}-benzoic acid
• 英文别名: 3-Amino-4-({[(4-methylphenyl)diphenylmethyl] amino}methyl)benzoic Acid
• CAS: 470461-87-1
• 化学式: C₂₈H₂₆N₂O₂
• 分子量: 422.527
• InChiKey: RZCKUAXGCUKXPP-UHFFFAOYSA-N

物化性质

• 沸点：
  618.8±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  75.35
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-氟-5-硝基苯甲酰氯 、 Fmoc-O-叔丁基-L-谷氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 3-Amino-4-{[(diphenyl-p-tolyl-methyl)-amino]-methyl}-benzoic acid 以55%的产率得到3-[(12S,15S)-20-amino-12-(4-aminobutyl)-7-carbamoyl-11,14,17-trioxo-2,10,13,16-tetrazatricyclo[16.4.0.04,9]docosa-1(18),4(9),5,7,19,21-hexaen-15-yl]propanoic acid
  参考文献：
  名称：

  Syntheses and Activities of New C¹⁰ β-Turn Peptidomimetics

  摘要：

  A program to identify small molecules that mimic or disrupt protein-protein interactions led us to design the peptidomimetics 1-3. Solid-phase syntheses of 1-3 were developed. The purities of the crude materials isolated from the resin tend to be highest for the S- and N-compounds 2 and 3 and better than in the corresponding syntheses of peptidomimetics A. The particular dipeptide units incorporated were chosen to correspond with the turn regions of the neurotrophins (e.g., nerve growth factor {NGF} and the neurotrophin factor-3 {NT-3}). Preliminary studies were performed to access the binding of these analogues to Trk receptors and their ability to induce cell survival (just as NGF and NT-3 do). Several active compounds were identified. However, poor water solubilities of some of the other compounds preclude reliable testing. Consequently, solid-phase modifications to the synthetic procedures were investigated to provide access to the derivatives 12-14 in which the aromatic nitro group is replaced by amine, guanidine, or sulfonamide functionalities. The latter are more acceptable pharmacophores than nitro groups and also tend to increase the water solubilities of the peptidomimetics.

  DOI：

  10.1021/jo034167x
• 作为产物：
  描述：

  4-{[(Diphenyl-p-tolyl-methyl)-amino]-methyl}-3-nitro-benzoic acid 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 以90%的产率得到3-Amino-4-{[(diphenyl-p-tolyl-methyl)-amino]-methyl}-benzoic acid
  参考文献：
  名称：

  Syntheses and Activities of New C¹⁰ β-Turn Peptidomimetics

  摘要：

  A program to identify small molecules that mimic or disrupt protein-protein interactions led us to design the peptidomimetics 1-3. Solid-phase syntheses of 1-3 were developed. The purities of the crude materials isolated from the resin tend to be highest for the S- and N-compounds 2 and 3 and better than in the corresponding syntheses of peptidomimetics A. The particular dipeptide units incorporated were chosen to correspond with the turn regions of the neurotrophins (e.g., nerve growth factor {NGF} and the neurotrophin factor-3 {NT-3}). Preliminary studies were performed to access the binding of these analogues to Trk receptors and their ability to induce cell survival (just as NGF and NT-3 do). Several active compounds were identified. However, poor water solubilities of some of the other compounds preclude reliable testing. Consequently, solid-phase modifications to the synthetic procedures were investigated to provide access to the derivatives 12-14 in which the aromatic nitro group is replaced by amine, guanidine, or sulfonamide functionalities. The latter are more acceptable pharmacophores than nitro groups and also tend to increase the water solubilities of the peptidomimetics.

  DOI：

  10.1021/jo034167x

文献信息

• New Templates for Syntheses of Ring-Fused, C¹⁰ β-Turn Peptidomimetics Leading to the First Reported Small-Molecule Mimic of Neurotrophin-3
  作者：Mookda Pattarawarapan、Maria Clara Zaccaro、Uri H. Saragovi、Kevin Burgess

  DOI：10.1021/jm0255421

  日期：2002.9.1

  beta-Turn peptidomimetics 1 were designed to mimic hot spots of neurotrophin-3 (NT-3) and others. Solid-phase syntheses of these were developed, though limitations were encountered with scale-up. Consequently, an alternative design with 2 was investigated. 1 and 2 favored distorted type I beta-turn conformations in solution. It was found that peptidomimetic 2b has NT-3-like neurotrophic activity in cell survival assays, selectively binds the NT-3 receptor TrkC, and induces the tyrosine phosphorylation of the TrkC receptor.
• Lee, Hong Boon; Pattarawarapan, Mookda; Roy, Sudipta, Chemical Communications, 2003, # 14, p. 1674 - 1675
  作者：Lee, Hong Boon、Pattarawarapan, Mookda、Roy, Sudipta、Burgess, Kevin

  DOI：——

  日期：——