2-(5-methylthiophen-2-yl)-2-phenyl-1,3,2-oxazaborolidin-3-ium-2-uide | 1435463-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-(5-methylthiophen-2-yl)-2-phenyl-1,3,2-oxazaborolidin-3-ium-2-uide
• 英文别名: 2-(5-Methylthiophen-2-yl)-2-phenyl-1-oxa-3-azonia-2-boranuidacyclopentane；2-(5-methylthiophen-2-yl)-2-phenyl-1-oxa-3-azonia-2-boranuidacyclopentane
• CAS: 1435463-76-5
• 化学式: C₁₃H₁₆BNOS
• 分子量: 245.153
• InChiKey: GHYBLWLPZXHEBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5-Methylthiophen-2-yl)-phenylborinic acid 、 C.I.酸性橙108 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 2-(5-methylthiophen-2-yl)-2-phenyl-1,3,2-oxazaborolidin-3-ium-2-uide
  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

• 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
  作者：Alexandre Hofer、Gergely Kovacs、Anna Zappatini、Michele Leuenberger、Matthias A. Hediger、Martin Lochner

  DOI：10.1016/j.bmc.2013.03.037

  日期：2013.6

  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.