Trimethylsilyl 8-[(2-methoxybenzoyl)amino]octanoate | 1026344-83-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Trimethylsilyl 8-[(2-methoxybenzoyl)amino]octanoate
• CAS: 1026344-83-1
• 化学式: C₁₉H₃₁NO₄Si
• 分子量: 365.545
• InChiKey: QCZFFGFSHPFBOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Trimethylsilyl 8-[(2-methoxybenzoyl)amino]octanoate 在 sodium hydroxide 作用下， 反应 2.0h， 生成 8-N(2-methoxybenzoyl)aminocaprylic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Compounds That Facilitate the Gastrointestinal Absorption of Heparin

  摘要：

  A family of novel compounds (delivery agents) that promote the gastrointestinal absorption of USP heparin in rats and primates has been discovered. The delivery agents in combination with heparin were administered either orally or intracolonically in an aqueous propylene glycol solution and caused dramatic increases in both plasma heparin concentrations (anti-Factor Xa) and clotting times (APTT). Using one of the most effective delivery agents in this series, an estimated relative bioavailability of 8% can be achieved following oral administration to cynomolgus monkeys. To establish a correlation between the in vivo data and an in vitro parameter, immobilized artificial membrane (IAM) chromatography was performed. Log relative k' values were correlated to the efficiency of oral heparin delivery.

  DOI：

  10.1021/jm970811m
• 作为产物：
  描述：

  8-氨基辛酸 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 Trimethylsilyl 8-[(2-methoxybenzoyl)amino]octanoate
  参考文献：
  名称：

  Synthesis and Evaluation of Compounds That Facilitate the Gastrointestinal Absorption of Heparin

  摘要：

  A family of novel compounds (delivery agents) that promote the gastrointestinal absorption of USP heparin in rats and primates has been discovered. The delivery agents in combination with heparin were administered either orally or intracolonically in an aqueous propylene glycol solution and caused dramatic increases in both plasma heparin concentrations (anti-Factor Xa) and clotting times (APTT). Using one of the most effective delivery agents in this series, an estimated relative bioavailability of 8% can be achieved following oral administration to cynomolgus monkeys. To establish a correlation between the in vivo data and an in vitro parameter, immobilized artificial membrane (IAM) chromatography was performed. Log relative k' values were correlated to the efficiency of oral heparin delivery.

  DOI：

  10.1021/jm970811m

文献信息

• Studies Directed at the Use of a Parallel Synthesis Matrix to Increase Throughput in an in Vivo Assay
  作者：Andrea Leone-Bay、John Freeman、Doris O'Toole、Connie Rosado-Gray、Sirpa Salo-Kostmayer、Monica Tai、Frank Mercogliano、Robert A. Baughman

  DOI：10.1021/jm990416r

  日期：2000.9.1

  Heparin is the anticoagulant of choice for hospitalized patients, but it is dosed only by injection because it is not absorbed following oral administration. We have discovered and prepared compounds (delivery agents) that facilitate the gastrointestinal absorption of heparin in rats, monkeys, and humans when given orally. We are currently developing a parallel synthesis approach to increase our delivery agent screening throughput in vivo. This approach has been used to produce micromolar quantities of compounds for testing in rats in a 5 x 5 parallel synthesis array. Using an amine benzoylation reaction sequence, 10 mixtures were prepared. These mixtures contained equal weight quantities of five N-substituted, non-alpha, amino acid delivery agents. Each of these mixtures was orally administered to rats in combination with heparin, and plasma clotting times (APTT) were measured to determine activity. Deconvolution of the data accurately identified the most active individual components. Independent synthesis of these compounds verified their activity. This parallel synthesis approach is an effective tool for the screening of oral heparin delivery agents and has increased screening throughput significantly.
• Synthesis and Evaluation of Compounds That Facilitate the Gastrointestinal Absorption of Heparin
  作者：Andrea Leone-Bay、Duncan R. Paton、John Freeman、Christine Lercara、Doris O'Toole、David Gschneidner、Eric Wang、Elizabeth Harris、Connie Rosado、Theresa Rivera、Aldonna DeVincent、Monica Tai、Frank Mercogliano、Rajesh Agarwal、Harry Leipold、Robert A. Baughman

  DOI：10.1021/jm970811m

  日期：1998.3.1

  A family of novel compounds (delivery agents) that promote the gastrointestinal absorption of USP heparin in rats and primates has been discovered. The delivery agents in combination with heparin were administered either orally or intracolonically in an aqueous propylene glycol solution and caused dramatic increases in both plasma heparin concentrations (anti-Factor Xa) and clotting times (APTT). Using one of the most effective delivery agents in this series, an estimated relative bioavailability of 8% can be achieved following oral administration to cynomolgus monkeys. To establish a correlation between the in vivo data and an in vitro parameter, immobilized artificial membrane (IAM) chromatography was performed. Log relative k' values were correlated to the efficiency of oral heparin delivery.