2-<3-<2-<(2,3,:4,6-di-O-isopropylidene-α-D-mannopyranosyl)oxy>phenyl>phenyl>ethanethiol S-acetate | 171905-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<3-<2-<(2,3,:4,6-di-O-isopropylidene-α-D-mannopyranosyl)oxy>phenyl>phenyl>ethanethiol S-acetate
• 英文别名: S-[2-[3-[2-[[(1R,2S,6S,7R,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl]oxy]phenyl]phenyl]ethyl] ethanethioate
• CAS: 171905-82-1
• 化学式: C₂₈H₃₄O₇S
• 分子量: 514.64
• InChiKey: CKDOWQWTCCQGGN-JMTTVTNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  97.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-<3-<2-<(2,3,:4,6-di-O-isopropylidene-α-D-mannopyranosyl)oxy>phenyl>phenyl>ethanethiol S-acetate 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 反应 240.0h， 以38%的产率得到2-<3-<2-(α-D-mannopyranosyloxy)phenyl>phenyl>ethanesulfonic acid
  参考文献：
  名称：

  Rational Design and Synthesis of Small Molecule, Non-oligosaccharide Selectin Inhibitors: (.alpha.-D-Mannopyranosyloxy)biphenyl-Substituted Carboxylic Acids

  摘要：

  The calcium dependent E-selectin/sialyl Lewis(x) (sLe(x)) interaction plays a key role in inflammation where it mediates the rolling of leukocytes prior to firm adhesion and extravasation from the vasculature. A model of E-selectin/sLe(x) binding, along with previously reported structure-activity relationships of sLe(x)-related oligosaccharide, was used in the rational design of non-oligosaccharide inhibitors of this pivotal interaction. A palladium-mediated biaryl-coupling (Suzuki) reaction was used as the key step to prepare a number of substituted biphenyls which were assayed for their ability to inhibit the binding of E-, P-, and L-selectin-IgG fusion proteins to sLe(x) expressed on the surface of HL60 cells. Some of the compounds developed had greater in vitro potency than the parent sLe(x) tetrasaccharide and are currently being evaluated in in vivo models of inflammation to select a candidate for clinical development.

  DOI：

  10.1021/jm00026a004
• 作为产物：
  描述：

  methyl 3-<2-<(2,3,:4,6-di-O-isopropylidene-α-D-mannopyranosyl)oxy>phenyl>phenylacetate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 2-<3-<2-<(2,3,:4,6-di-O-isopropylidene-α-D-mannopyranosyl)oxy>phenyl>phenyl>ethanethiol S-acetate
  参考文献：
  名称：

  Rational Design and Synthesis of Small Molecule, Non-oligosaccharide Selectin Inhibitors: (.alpha.-D-Mannopyranosyloxy)biphenyl-Substituted Carboxylic Acids

  摘要：

  The calcium dependent E-selectin/sialyl Lewis(x) (sLe(x)) interaction plays a key role in inflammation where it mediates the rolling of leukocytes prior to firm adhesion and extravasation from the vasculature. A model of E-selectin/sLe(x) binding, along with previously reported structure-activity relationships of sLe(x)-related oligosaccharide, was used in the rational design of non-oligosaccharide inhibitors of this pivotal interaction. A palladium-mediated biaryl-coupling (Suzuki) reaction was used as the key step to prepare a number of substituted biphenyls which were assayed for their ability to inhibit the binding of E-, P-, and L-selectin-IgG fusion proteins to sLe(x) expressed on the surface of HL60 cells. Some of the compounds developed had greater in vitro potency than the parent sLe(x) tetrasaccharide and are currently being evaluated in in vivo models of inflammation to select a candidate for clinical development.

  DOI：

  10.1021/jm00026a004

文献信息

• Rational Design and Synthesis of Small Molecule, Non-oligosaccharide Selectin Inhibitors: (.alpha.-D-Mannopyranosyloxy)biphenyl-Substituted Carboxylic Acids
  作者：Timothy P. Kogan、Brian Dupre、Karin M. Keller、Ian L. Scott、Huong Bui、Robert V. Market、Pamela J. Beck、Jennifer A. Voytus、B. Mitch Revelle、Delores Scott

  DOI：10.1021/jm00026a004

  日期：1995.12

  The calcium dependent E-selectin/sialyl Lewis(x) (sLe(x)) interaction plays a key role in inflammation where it mediates the rolling of leukocytes prior to firm adhesion and extravasation from the vasculature. A model of E-selectin/sLe(x) binding, along with previously reported structure-activity relationships of sLe(x)-related oligosaccharide, was used in the rational design of non-oligosaccharide inhibitors of this pivotal interaction. A palladium-mediated biaryl-coupling (Suzuki) reaction was used as the key step to prepare a number of substituted biphenyls which were assayed for their ability to inhibit the binding of E-, P-, and L-selectin-IgG fusion proteins to sLe(x) expressed on the surface of HL60 cells. Some of the compounds developed had greater in vitro potency than the parent sLe(x) tetrasaccharide and are currently being evaluated in in vivo models of inflammation to select a candidate for clinical development.