(2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropyl pivalate | 1003002-86-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropyl pivalate
• 英文别名: [(2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropyl] 2,2-dimethylpropanoate
• CAS: 1003002-86-5
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: LJNUUDXXLKBONR-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropyl pivalate 在 sodium tetrahydroborate 、 叠氮磷酸二苯酯 、 高碘酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 生成 (2R)-3-azido-2-benzylpropyl pivalate
  参考文献：
  名称：

  α-Methylated simplified resiniferatoxin (sRTX) thiourea analogues as potent and stereospecific TRPV1 antagonists

  摘要：

  A series of alpha-methylated analogues of the potent sRTX thiourea antagonists were investigated as rTRPV1 ligands in order to examine the effect of alpha-methylation on receptor activity. The SAR analysis indicated that activity was stereospecific with the (R)-configuration of the newly formed chiral center providing high binding affinity and potent antagonism while the configuration of the C-region was not significant. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.054
• 作为产物：
  描述：

  溴甲苯 在 吡啶 、 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropyl pivalate
  参考文献：
  名称：

  α-Methylated simplified resiniferatoxin (sRTX) thiourea analogues as potent and stereospecific TRPV1 antagonists

  摘要：

  A series of alpha-methylated analogues of the potent sRTX thiourea antagonists were investigated as rTRPV1 ligands in order to examine the effect of alpha-methylation on receptor activity. The SAR analysis indicated that activity was stereospecific with the (R)-configuration of the newly formed chiral center providing high binding affinity and potent antagonism while the configuration of the C-region was not significant. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.054

文献信息

• Stereospecific High-affinity TRPV1 Antagonists: Chiral <i>N</i>-(2-Benzyl-3-pivaloyloxypropyl) 2-[4-(methylsulfonylamino)phenyl]propionamide Analogues
  作者：HyungChul Ryu、Mi-Kyoung Jin、Su Yeon Kim、Hyun-Kyung Choi、Sang-Uk Kang、Dong Wook Kang、Jeewoo Lee、Larry V. Pearce、Vladimir A. Pavlyukovets、Matthew A. Morgan、Richard Tran、Attila Toth、Daniel J. Lundberg、Peter M. Blumberg

  DOI：10.1021/jm701049p

  日期：2008.1.1

  Previously, we reported the thiourea antagonists 2a and 2b as potent and high affinity TRPV1 antagonists. For further optimization of the lead compounds, a series of their amide and alpha-substituted amide surrogates were investigated and novel chiral N-(2-benzyl-3-pivaloyloxypropyl) 2-[4-(methylsulfonylamino)phenyl]propionamide analogues were characterized as potent and stereospecific rTRPV1 antagonists. In particular, compounds 72 and 73 displayed high binding affinities, with K-i values of 4.12 and 1.83 nM and potent antagonism with Ki values of 0.58 and 5.2 nM, respectively, in rTRPV1/CHO cells. These values are comparable or more potent than those of 5-iodoRTX under the same assay conditions. A distinctive binding model that includes two hydrophobic pockets is proposed for this series of compounds based on docking studies of 57 and 72 with a homology model of the TM3/4 region of TRPV1.
• α-Methylated simplified resiniferatoxin (sRTX) thiourea analogues as potent and stereospecific TRPV1 antagonists
  作者：Ho Shin Kim、Mi-Kyoung Jin、Sang-Uk Kang、Ju-Ok Lim、Phuong-Thao Tran、Van-Hai Hoang、Jihyae Ann、Tae-Hwan Ha、Larry V. Pearce、Vladimir A. Pavlyukovets、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmcl.2014.04.054

  日期：2014.6

  A series of alpha-methylated analogues of the potent sRTX thiourea antagonists were investigated as rTRPV1 ligands in order to examine the effect of alpha-methylation on receptor activity. The SAR analysis indicated that activity was stereospecific with the (R)-configuration of the newly formed chiral center providing high binding affinity and potent antagonism while the configuration of the C-region was not significant. (C) 2014 Elsevier Ltd. All rights reserved.