((3-(4-(((2-(3-(((tert-butoxy)carbonyl)amino)propoxy)benzoyl)(6-phenoxy-2-benzothiazolyl)amino)methyl)phenoxy)propyl)carbonimidoyl)-bis-carbamic acid bis(tert-butyl) ester | 754992-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3-(4-(((2-(3-(((tert-butoxy)carbonyl)amino)propoxy)benzoyl)(6-phenoxy-2-benzothiazolyl)amino)methyl)phenoxy)propyl)carbonimidoyl)-bis-carbamic acid bis(tert-butyl) ester
• CAS: 754992-79-5
• 化学式: C₄₉H₆₀N₆O₁₀S
• 分子量: 925.116
• InChiKey: FQOKTXZRJJTCLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  66.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  188.24
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  ((3-(4-(((2-(3-(((tert-butoxy)carbonyl)amino)propoxy)benzoyl)(6-phenoxy-2-benzothiazolyl)amino)methyl)phenoxy)propyl)carbonimidoyl)-bis-carbamic acid bis(tert-butyl) ester 在 茴香硫醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以79%的产率得到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：

  N-Boc-3-氨基丙基溴 在 sodium hydroxide 、 二乙胺基三氟化硫 、 potassium carbonate 、 一水合肼 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 ((3-(4-(((2-(3-(((tert-butoxy)carbonyl)amino)propoxy)benzoyl)(6-phenoxy-2-benzothiazolyl)amino)methyl)phenoxy)propyl)carbonimidoyl)-bis-carbamic acid bis(tert-butyl) ester
  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