[(2R)-2-[(4-tert-butylphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methylcarbamothioylamino]propyl] 2,2-dimethylpropanoate | 1528740-84-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: [(2R)-2-[(4-tert-butylphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methylcarbamothioylamino]propyl] 2,2-dimethylpropanoate
• CAS: 1528740-84-2
• 化学式: C₂₈H₄₀N₂O₄S
• 分子量: 500.703
• InChiKey: TVYDDDOENZEUAG-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-甲氧基-4-(甲氧基甲氧基)苯甲醛 在 sodium tetrahydroborate 、 叠氮磷酸二苯酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 [(2R)-2-[(4-tert-butylphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methylcarbamothioylamino]propyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Asymmetric synthesis and receptor activity of chiral simplified resiniferatoxin (sRTX) analogues as transient receptor potential vanilloid 1 (TRPV1) ligands

  摘要：

  The chiral isomers of the two potent simplified RTX-based vanilloids, compounds 2 and 3, were synthesized employing highly enantioselective PTC alkylation and evaluated as hTRPV1 ligands. The analysis indicated that the R-isomer was the eutomer in binding affinity and functional activity. The agonism of compound 2R was comparable to that of RTX. Docking analysis of the chiral isomers of 3 suggested the basis for its stereospecific activity and the binding mode of 3R. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.064

文献信息

• Asymmetric synthesis and receptor activity of chiral simplified resiniferatoxin (sRTX) analogues as transient receptor potential vanilloid 1 (TRPV1) ligands
  作者：Myeong Seop Kim、Yooran Ki、Song Yeon Ahn、Suyoung Yoon、Sung-Eun Kim、Hyeung-Geun Park、Wei Sun、Karam Son、Minghua Cui、Sun Choi、Larry V. Pearce、Timothy E. Esch、Ian A. DeAndrea-Lazarus、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmcl.2013.10.064

  日期：2014.1

  The chiral isomers of the two potent simplified RTX-based vanilloids, compounds 2 and 3, were synthesized employing highly enantioselective PTC alkylation and evaluated as hTRPV1 ligands. The analysis indicated that the R-isomer was the eutomer in binding affinity and functional activity. The agonism of compound 2R was comparable to that of RTX. Docking analysis of the chiral isomers of 3 suggested the basis for its stereospecific activity and the binding mode of 3R. (C) 2013 Elsevier Ltd. All rights reserved.