1H-Isoindole-1,3(2H)-dione,2-[3-[4-[[(6-phenoxy-2-benzothiazolyl)amino]methyl]phenoxy]propyl]- | 754992-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1H-Isoindole-1,3(2H)-dione,2-[3-[4-[[(6-phenoxy-2-benzothiazolyl)amino]methyl]phenoxy]propyl]-
• 英文别名: 2-(3-(4-((6-phenoxybenzothiazol-2-ylamino)methyl)phenoxy)propyl)isoindole-1,3-dione
• CAS: 754992-74-0
• 化学式: C₃₁H₂₅N₃O₄S
• 分子量: 535.623
• InChiKey: IASNKJVSHQUQIE-UHFFFAOYSA-N

物化性质

• 熔点：
  189-190 °C
• 沸点：
  727.6±70.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.77
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.76
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1H-Isoindole-1,3(2H)-dione,2-[3-[4-[[(6-phenoxy-2-benzothiazolyl)amino]methyl]phenoxy]propyl]- 在 茴香硫醚 、 一水合肼 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-(3-Amino-propoxy)-N-[4-(3-guanidino-propoxy)-benzyl]-N-(6-phenoxy-benzothiazol-2-yl)-benzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of nonpeptide mimetics of ω-conotoxin GVIA

  摘要：

  A benzothiazole-derived compound (4a) designed to mimic the C-alpha-C-beta bond vectors and terminal functionalities of Lys2, TyrI3 and Arg17 in omega-conotoxin GVIA was synthesised, together with analogues (4b-d), which had each side-chain mimic systematically truncated or eliminated. The affinity of these compounds for rat brain N-type and P/Q-type voltage gated calcium channels (VGCCs) was determined. In terms of N-type channel affinity and selectivity, two of these compounds (4a and 4d) were found to be highly promising, first generation mimetics of omega-conotoxin. The fully functionalised mimetic (4a) showed low PM binding affinity to N-type VGCCs (IC50 = 1.9 muM) and greater than 20-fold selectivity for this channel sub-type over P/Q-type VGCCs, whereas the mimetic in which the guanidine-type side chain was truncated back to an amine (4d, IC50 = 4.1 muM) showed a greater than 25-fold selectivity for the N-type channel. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.040
• 作为产物：
  描述：

  2-[3-(4-{[(E)-6-Phenoxy-benzothiazol-2-ylimino]-methyl}-phenoxy)-propyl]-isoindole-1,3-dione 在 sodium tetrahydroborate 作用下， 以 乙醇 、 甲苯 为溶剂， 以0.77 g的产率得到1H-Isoindole-1,3(2H)-dione,2-[3-[4-[[(6-phenoxy-2-benzothiazolyl)amino]methyl]phenoxy]propyl]-
  参考文献：
  名称：

  Synthesis and biological evaluation of nonpeptide mimetics of ω-conotoxin GVIA

  摘要：

  A benzothiazole-derived compound (4a) designed to mimic the C-alpha-C-beta bond vectors and terminal functionalities of Lys2, TyrI3 and Arg17 in omega-conotoxin GVIA was synthesised, together with analogues (4b-d), which had each side-chain mimic systematically truncated or eliminated. The affinity of these compounds for rat brain N-type and P/Q-type voltage gated calcium channels (VGCCs) was determined. In terms of N-type channel affinity and selectivity, two of these compounds (4a and 4d) were found to be highly promising, first generation mimetics of omega-conotoxin. The fully functionalised mimetic (4a) showed low PM binding affinity to N-type VGCCs (IC50 = 1.9 muM) and greater than 20-fold selectivity for this channel sub-type over P/Q-type VGCCs, whereas the mimetic in which the guanidine-type side chain was truncated back to an amine (4d, IC50 = 4.1 muM) showed a greater than 25-fold selectivity for the N-type channel. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.040