ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isobutyl-1-thio-α-D-mannopyranoside | 400835-47-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isobutyl-1-thio-α-D-mannopyranoside
• CAS: 400835-47-4
• 化学式: C₂₇H₄₂O₇S
• 分子量: 510.692
• InChiKey: UYCOJKKRCXYEFH-PUQCGMQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isobutyl-1-thio-α-D-mannopyranoside 在 溴 、 silver carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  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：

  ethyl 1-thio-α-D-mannopyranoside 在 咪唑 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl-2-O-benzyl-3,4-O-[1',2'-dimethoxycyclohexan-1',2'-diyl]-6-O-isobutyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation ofα4β1 Integrin Antagonists Based onβ-D-Mannose as Rigid Scaffold

  摘要：

  A cyclic peptide role model was used for the design and synthesis of a new class of biologically active and α4 -selective integrin antagonists (e.g. 1) based on β-D-mannose. These carbohydrate-based peptidomimetics were synthesized to include the functional groups of their cyclic peptide precursors without the redundant amide backbone.

  DOI：

  10.1002/1521-3773(20011015)40:20<3870::aid-anie3870>3.0.co;2-x