1H-异吲哚-1,3(2H)-二酮,2-[2-(二苯基甲氧基)乙基]- | 101620-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1H-异吲哚-1,3(2H)-二酮,2-[2-(二苯基甲氧基)乙基]-
• 英文名称: 2-(2-(benzhydryloxy)ethyl)isoindoline-1,3-dione
• 英文别名: 2-(2-Benzhydryloxyethyl)isoindole-1,3-dione
• CAS: 101620-15-9
• 化学式: C₂₃H₁₉NO₃
• 分子量: 357.409
• InChiKey: ISNSEWWWXWKMCH-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C(Solv: ethanol (64-17-5))
• 沸点：
  502.0±38.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-异吲哚-1,3(2H)-二酮,2-[2-(二苯基甲氧基)乙基]- 在 肼 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以15%的产率得到2-{[(diphenyl)methyl]oxy}ethylamine
  参考文献：
  名称：

  Design, synthesis and pharmacological characterization of analogs of 2-aminoethyl diphenylborinate (2-APB), a known store-operated calcium channel blocker, for inhibition of TRPV6-mediated calcium transport

  摘要：

  2-Aminoethyl diphenylborinate (2-APB) is a known modulator of the IP3 receptor, the calcium ATPase SERCA, the calcium release-activated calcium channel Orai and TRP channels. More recently, it was shown that 2-APB is an efficient inhibitor of the epithelial calcium channel TRPV6 which is overexpressed in prostate cancer. We have conducted a structure-activity relationship study of 2-APB congeners to understand their inhibitory mode of action on TRPV6. Whereas modifying the aminoethyl moiety did not significantly change TRPV6 inhibition, substitution of the phenyl rings of 2-APB did. Our data show that the diaryl borinate moiety is required for biological activity and that the substitution pattern of the aryl rings can influence TRPV6 versus SOCE inhibition. We have also discovered that 2-APB is hydrolyzed and transesterified within minutes in solution. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.037
• 作为产物：
  描述：

  二苯甲醇 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 19.0h， 生成 1H-异吲哚-1,3(2H)-二酮,2-[2-(二苯基甲氧基)乙基]-
  参考文献：
  名称：

  Design, synthesis and pharmacological characterization of analogs of 2-aminoethyl diphenylborinate (2-APB), a known store-operated calcium channel blocker, for inhibition of TRPV6-mediated calcium transport

  摘要：

  2-Aminoethyl diphenylborinate (2-APB) is a known modulator of the IP3 receptor, the calcium ATPase SERCA, the calcium release-activated calcium channel Orai and TRP channels. More recently, it was shown that 2-APB is an efficient inhibitor of the epithelial calcium channel TRPV6 which is overexpressed in prostate cancer. We have conducted a structure-activity relationship study of 2-APB congeners to understand their inhibitory mode of action on TRPV6. Whereas modifying the aminoethyl moiety did not significantly change TRPV6 inhibition, substitution of the phenyl rings of 2-APB did. Our data show that the diaryl borinate moiety is required for biological activity and that the substitution pattern of the aryl rings can influence TRPV6 versus SOCE inhibition. We have also discovered that 2-APB is hydrolyzed and transesterified within minutes in solution. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.037

文献信息

• New prenylamine analogues: synthesis and Ca2+-entry blocking activity
  作者：PM Caldirola、H van der Goot、H Timmerman

  DOI：10.1016/0223-5234(92)90136-o

  日期：1992.9

  The synthesis of a series of diphenylalkylamine derivatives related to prenylamine is reported. The amphetamine group in the prenylamine structure was replaced by other moieties. In addition to substitutions in the aromatic rings, heteroatoms such as sulphur and oxygen were introduced in the chain. The calcium-entry blocking activity was assayed in binding experiments on a guinea-pig brain membrane preparation by displacing [H-3]-nitrendipine.