[2-((8bS,9aS,10S,13R,13aR,14aS)-10-Benzyloxy-13-isobutoxymethyl-8b,14a-dimethoxy-8b,10,11,13,13a,14a-hexahydro-9aH-9,12,14-trioxa-benzo[b]triphenylen-11-yloxy)-ethoxy]-tert-butyl-diphenyl-silane | 647029-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: [2-((8bS,9aS,10S,13R,13aR,14aS)-10-Benzyloxy-13-isobutoxymethyl-8b,14a-dimethoxy-8b,10,11,13,13a,14a-hexahydro-9aH-9,12,14-trioxa-benzo[b]triphenylen-11-yloxy)-ethoxy]-tert-butyl-diphenyl-silane
• CAS: 647029-90-1
• 化学式: C₅₁H₆₀O₉Si
• 分子量: 845.117
• InChiKey: SAJIHNPFWSVGJM-URNYROEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.33
• 重原子数：
  61.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  83.07
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  [2-((8bS,9aS,10S,13R,13aR,14aS)-10-Benzyloxy-13-isobutoxymethyl-8b,14a-dimethoxy-8b,10,11,13,13a,14a-hexahydro-9aH-9,12,14-trioxa-benzo[b]triphenylen-11-yloxy)-ethoxy]-tert-butyl-diphenyl-silane 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 {2-[(8bS,9aS,10S,13R,13aR,14aS)-10-(2-Benzyloxy-ethoxy)-13-isobutoxymethyl-8b,14a-dimethoxy-8b,10,11,13,13a,14a-hexahydro-9aH-9,12,14-trioxa-benzo[b]triphenylen-11-yloxy]-ethoxy}-tert-butyl-diphenyl-silane
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of Mannose-Based Peptidomimetics Selectively Blocking Integrin α4β7 Binding to Mucosal Addressin Cell Adhesion Molecule-1

  摘要：

  As part of our ongoing research in the development of alpha4beta7 integrin antagonists, we are interested in peptidomimetics based on a rigid scaffold to allow the display of essential side chains in a suitable binding conformation while eliminating backbone amide bonds and therefore improving pharmacokinetic parameters of the drug. Except for a few examples, peptidomimetics scaffolds have only been moderately successful and often yield molecules that lack the potency of their peptide counterparts. However, we present herein a successful application of using a rigid scaffold. Starting from a mannopyranoside analogue previously discovered in our laboratory as an inhibitor of the alpha4beta1/vascular cell adhesion molecule interaction, a biased library of functionalized carbohydrates was developed. One compound emerged from this library as an active and selective antagonist toward the alpha4beta7/mucosal addressin cell adhesion molecule interaction. Conformational. implications and the relevance of different pharmacophoric patterns will be discussed in order to explain the reverse selectivity and enhanced affinity.

  DOI：

  10.1021/jm020487h
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 [2'-hydroxyethyl]-2-O-benzyl-3,4-O-[9',10'-dimethoxyphenanthrene-9',10'-diyl]-6-O-isobutyl-α,β-D-mannopyranoside 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以85%的产率得到[2-((8bS,9aS,10S,13R,13aR,14aS)-10-Benzyloxy-13-isobutoxymethyl-8b,14a-dimethoxy-8b,10,11,13,13a,14a-hexahydro-9aH-9,12,14-trioxa-benzo[b]triphenylen-11-yloxy)-ethoxy]-tert-butyl-diphenyl-silane
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of Mannose-Based Peptidomimetics Selectively Blocking Integrin α4β7 Binding to Mucosal Addressin Cell Adhesion Molecule-1

  摘要：

  As part of our ongoing research in the development of alpha4beta7 integrin antagonists, we are interested in peptidomimetics based on a rigid scaffold to allow the display of essential side chains in a suitable binding conformation while eliminating backbone amide bonds and therefore improving pharmacokinetic parameters of the drug. Except for a few examples, peptidomimetics scaffolds have only been moderately successful and often yield molecules that lack the potency of their peptide counterparts. However, we present herein a successful application of using a rigid scaffold. Starting from a mannopyranoside analogue previously discovered in our laboratory as an inhibitor of the alpha4beta1/vascular cell adhesion molecule interaction, a biased library of functionalized carbohydrates was developed. One compound emerged from this library as an active and selective antagonist toward the alpha4beta7/mucosal addressin cell adhesion molecule interaction. Conformational. implications and the relevance of different pharmacophoric patterns will be discussed in order to explain the reverse selectivity and enhanced affinity.

  DOI：

  10.1021/jm020487h