3-[1,1-bis(methylethyl)-2-methyl-1-silapropylthio]phenyl acetate | 474658-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-[1,1-bis(methylethyl)-2-methyl-1-silapropylthio]phenyl acetate
• 英文别名: 3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenyl acetate；[3-tri(propan-2-yl)silylsulfanylphenyl] acetate
• CAS: 474658-40-7
• 化学式: C₁₇H₂₈O₂SSi
• 分子量: 324.56
• InChiKey: UIPZDKVCCVFAFK-UHFFFAOYSA-N

物化性质

• 沸点：
  384.5±34.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-bromo-4-oxopentanoate 、 3-[1,1-bis(methylethyl)-2-methyl-1-silapropylthio]phenyl acetate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以920 mg (73%)的产率得到ethyl 5-(3-acetyloxyphenylthio)-4-oxopentanoate
  参考文献：
  名称：

  Substituted benzofurans and benzothiophenes, methods of making and methods of use as integrin antagonists

  摘要：

  本发明涉及一种新的取代苯并呋喃和苯并噻吩化合物，它们是αV（αv）整合素的拮抗剂，例如αvβ3和αvβ5整合素，其药学上可接受的盐以及其药物组合物。这些化合物可用于治疗由αvβ3和αvβ5整合素介导的病理条件，包括肿瘤生长、转移、再狭窄、骨质疏松、炎症、黄斑变性、糖尿病性视网膜病变和类风湿性关节炎等疾病。这些化合物具有通用的化学式I：1，其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、m、n、i、j和k在此处被定义。

  公开号：

  US20030018064A1
• 作为产物：
  描述：

  3-碘苯酚 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 3-[1,1-bis(methylethyl)-2-methyl-1-silapropylthio]phenyl acetate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Novel Potent and Selective α_vβ₃/α_vβ₅ Integrin Dual Inhibitors with Improved Bioavailability. Selection of the Molecular Core

  摘要：

  A novel series of potent and selective alpha(v)beta(3)/alpha(v)beta(5) dual inhibitors was designed, synthesized, and evaluated against several integrins. These compounds were synthesized through a Mitsunobu reaction between the guanidinium mimetics and the corresponding central templates. Guanidinium mimetics with enhaced rigidity (i.e., (2-pyridylamino)propoxy versus the 2-(6-methylamino-2-pyridyl)ethoxy) led to improved activity toward alpha(v)beta(3). Exemplary oral bioavailability in mice was achieved using the indole central scaffold. Although, oral bioavailability was maintained when the indole molecular core was replace with the bioisosteric benzofuran or benzothiophene ring systems, it was found to not significantly impact the integrin activity or selectivity. However, the indole series displayed the best in vivo pharmacokinetic properties. Thus, the indole series was selected for further structure-activity relationships to obtain more potent alpha(v)beta(3)/alpha(v)beta(5) dual antagonist with improved oral bioavailability.

  DOI：

  10.1021/jm049725u