2-methoxy-5-methylbenzenesulfonic acid 3-[2-(3-allyloxy-4-cyanophenyl)ethoxy]phenyl ester | 372523-05-2

• 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: 2-methoxy-5-methylbenzenesulfonic acid 3-[2-(3-allyloxy-4-cyanophenyl)ethoxy]phenyl ester
• 英文别名: [3-[2-(4-Cyano-3-prop-2-enoxyphenyl)ethoxy]phenyl] 2-methoxy-5-methylbenzenesulfonate
• CAS: 372523-05-2
• 化学式: C₂₆H₂₅NO₆S
• 分子量: 479.554
• InChiKey: CKQMOWIXCULHIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-methylbenzenesulfonic acid 3-[2-(3-allyloxy-4-cyanophenyl)ethoxy]phenyl ester 在 sodium tetrahydroborate 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以71%的产率得到2-methoxy-5-methylbenzenesulfonic acid 3-[2-(4-cyano-3-hydroxyphenyl)ethoxy]phenyl ester
  参考文献：
  名称：

  Statistical Molecular Design, Parallel Synthesis, and Biological Evaluation of a Library of Thrombin Inhibitors

  摘要：

  A library of thrombin inhibitors has been designed using statistical molecular design. An aromatic scaffold was used, with three varied positions corresponding to three pockets at the active site of thrombin (the S-, P-, and D-pockets). The selection was performed in the building block space, and previously acquired data were included in the design procedure. The design resulted in six, four, and six building blocks for the first (S), second (P), and third (D) pockets, respectively. A second round of selection applied to the combined selected building blocks resulted in a subset of 18 compounds. The selected library was synthesized in parallel and biologically evaluated. The compounds were analyzed with respect to their inhibition (pIC(50)) of thrombin; membrane permeability, estimated by migration behavior in micellar media (CE log k') and pK(a); and specificity with respect to inhibition (K-i) of trypsin. Multivariate QSAR studies of the responses yielded valuable results and information that could only be found using statistical molecular design in combination with multivariate analysis.

  DOI：

  10.1021/jm010833f
• 作为产物：
  描述：

  acetic acid 2-(3-hydroxyphenyl)ethyl ester 在 甲醇 、 硝基乙烷 、 乙基溴化镁 、 sodium acetate 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 21.5h， 生成 2-methoxy-5-methylbenzenesulfonic acid 3-[2-(3-allyloxy-4-cyanophenyl)ethoxy]phenyl ester
  参考文献：
  名称：

  Statistical Molecular Design, Parallel Synthesis, and Biological Evaluation of a Library of Thrombin Inhibitors

  摘要：

  A library of thrombin inhibitors has been designed using statistical molecular design. An aromatic scaffold was used, with three varied positions corresponding to three pockets at the active site of thrombin (the S-, P-, and D-pockets). The selection was performed in the building block space, and previously acquired data were included in the design procedure. The design resulted in six, four, and six building blocks for the first (S), second (P), and third (D) pockets, respectively. A second round of selection applied to the combined selected building blocks resulted in a subset of 18 compounds. The selected library was synthesized in parallel and biologically evaluated. The compounds were analyzed with respect to their inhibition (pIC(50)) of thrombin; membrane permeability, estimated by migration behavior in micellar media (CE log k') and pK(a); and specificity with respect to inhibition (K-i) of trypsin. Multivariate QSAR studies of the responses yielded valuable results and information that could only be found using statistical molecular design in combination with multivariate analysis.

  DOI：

  10.1021/jm010833f