5-oxo-2,2-diphenyl-1,3,2-oxazaborolidin-3-ium-2-uide | 26546-27-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-oxo-2,2-diphenyl-1,3,2-oxazaborolidin-3-ium-2-uide
• 英文别名: 2,2-Diphenyl-1-oxa-3-azonia-2-boranuidacyclopentan-5-one
• CAS: 26546-27-0
• 化学式: C₁₄H₁₄BNO₂
• 分子量: 239.082
• InChiKey: DNSLODXLJMGOJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二苯基硼酸酐 、 聚甘氨酸 以 乙腈 为溶剂， 反应 2.5h， 以75%的产率得到5-oxo-2,2-diphenyl-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

• Palladium-catalyzed cross-coupling of aryl chlorides with O, N-chelate stabilized diarylborinates
  作者：Nan Zhang、Chen Wang、Gang Zou、Jie Tang

  DOI：10.1016/j.jorganchem.2017.05.013

  日期：2017.8

  diarylborinic acids in palladium catalyzed Suzuki coupling of aryl chlorides. 3-Dimethylaminopropyl diarylborinates (B-5a), featuring a six-membered O, N-chelated boron ring that was confirmed by single crystal X-ray diffraction, displayed a delicately balanced stability and reactivity. Their cross-coupling with structurally various aryl chlorides could be effected as efficiently as that of the parent diarylborinic

  已经制备了一系列O，N-螯合的二芳基硼酸酯，并且在钯催化的芳基氯化物的Suzuki偶联中作为氧不稳定的二芳基硼酸的芳基硼替代物进行了测试。3-二甲基氨基丙基二芳基硼酸酯（B-5a）具有六元O，N螯合的硼环，该环经单晶X射线衍射确认，显示出微妙的平衡稳定性和反应性。通过使用0.1〜1mol％的Pd（OAc）2 / IPr / P（OPh）3作为催化剂体系，它们可以与母体二芳基硼酸的交联效率达到与母体二芳基硼酸的交联效率一样高，从而在其中提供相应的联芳基。好到极好的产量。
• 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.