N-(3-(2-(N-(6-(4-benzyloxyphenoxy)benzothiazol-2-yl)-N-(4-(3-(1,3-dihydro-1,3-dioxoisoindol-2-yl)propoxy)benzyl)carbamoyl)phenoxy)propyl)carbamic acid tert-butyl ester | 496064-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-(2-(N-(6-(4-benzyloxyphenoxy)benzothiazol-2-yl)-N-(4-(3-(1,3-dihydro-1,3-dioxoisoindol-2-yl)propoxy)benzyl)carbamoyl)phenoxy)propyl)carbamic acid tert-butyl ester
• CAS: 496064-24-5
• 化学式: C₅₃H₅₀N₄O₉S
• 分子量: 919.067
• InChiKey: YMHWDRIBGTURSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.87
• 重原子数：
  67.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  145.83
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-(3-(2-(N-(6-(4-benzyloxyphenoxy)benzothiazol-2-yl)-N-(4-(3-(1,3-dihydro-1,3-dioxoisoindol-2-yl)propoxy)benzyl)carbamoyl)phenoxy)propyl)carbamic acid tert-butyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 [3-(2-{[4-(3-amino-propoxy)-benzyl]-[6-(4-benzyloxy-phenoxy)-benzothiazol-2-yl]-carbamoyl}-phenoxy)-propyl]-carbamic acid 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
• 作为产物：
  描述：

  2-(3-(tert-butoxycarbonylamino)propoxy)benzoyl fluoride 、 2-(3-(4-((6-(4-benzyloxyphenoxy)benzothiazol-2-ylamino)methyl)phenoxy)propyl)isoindole-1,3-dione 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以70%的产率得到N-(3-(2-(N-(6-(4-benzyloxyphenoxy)benzothiazol-2-yl)-N-(4-(3-(1,3-dihydro-1,3-dioxoisoindol-2-yl)propoxy)benzyl)carbamoyl)phenoxy)propyl)carbamic acid 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