3-(1-chloro-7-methoxynaphthalen-2-yl)-5-fluoropyridine | 1447449-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1-chloro-7-methoxynaphthalen-2-yl)-5-fluoropyridine
• 英文别名: 3-(1-Chloro-7-methoxynaphthalen-2-yl)-5-fluoropyridine
• CAS: 1447449-89-9
• 化学式: C₁₆H₁₁ClFNO
• 分子量: 287.721
• InChiKey: RPIYHUIWRDPDMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1-chloro-7-methoxynaphthalen-2-yl)-5-fluoropyridine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以66%的产率得到8-chloro-7-(5-fluoropyridin-3-yl)naphthalen-2-ol
  参考文献：
  名称：

  Highly Potent and Selective Nonsteroidal Dual Inhibitors of CYP17/CYP11B2 for the Treatment of Prostate Cancer To Reduce Risks of Cardiovascular Diseases

  摘要：

  Dual CYP17/CYP11B2 inhibitors are proposed as a novel strategy for the treatment of prostate cancer to reduce risks of cardiovascular diseases. Via a combination of ligand- and structure-based approaches, a series of dual inhibitors were designed leading to the 2-(3-pyridyl)naphthalenes 10 and 11 with strong inhibition of both enzymes (IC50 values around 20 nM) and excellent selectivities over CYP11B1, CYP19, and CYP3A4. These compounds are considered as promising candidates for further in vivo evaluation.

  DOI：

  10.1021/jm400484p
• 作为产物：
  描述：

  7-甲氧基-2-萘 在 吡啶 、 N-氯代丁二酰亚胺 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 14.25h， 生成 3-(1-chloro-7-methoxynaphthalen-2-yl)-5-fluoropyridine
  参考文献：
  名称：

  Highly Potent and Selective Nonsteroidal Dual Inhibitors of CYP17/CYP11B2 for the Treatment of Prostate Cancer To Reduce Risks of Cardiovascular Diseases

  摘要：

  Dual CYP17/CYP11B2 inhibitors are proposed as a novel strategy for the treatment of prostate cancer to reduce risks of cardiovascular diseases. Via a combination of ligand- and structure-based approaches, a series of dual inhibitors were designed leading to the 2-(3-pyridyl)naphthalenes 10 and 11 with strong inhibition of both enzymes (IC50 values around 20 nM) and excellent selectivities over CYP11B1, CYP19, and CYP3A4. These compounds are considered as promising candidates for further in vivo evaluation.

  DOI：

  10.1021/jm400484p

文献信息

• Highly Potent and Selective Nonsteroidal Dual Inhibitors of CYP17/CYP11B2 for the Treatment of Prostate Cancer To Reduce Risks of Cardiovascular Diseases
  作者：Mariano A. E. Pinto-Bazurco Mendieta、Qingzhong Hu、Matthias Engel、Rolf W. Hartmann

  DOI：10.1021/jm400484p

  日期：2013.8.8

  Dual CYP17/CYP11B2 inhibitors are proposed as a novel strategy for the treatment of prostate cancer to reduce risks of cardiovascular diseases. Via a combination of ligand- and structure-based approaches, a series of dual inhibitors were designed leading to the 2-(3-pyridyl)naphthalenes 10 and 11 with strong inhibition of both enzymes (IC50 values around 20 nM) and excellent selectivities over CYP11B1, CYP19, and CYP3A4. These compounds are considered as promising candidates for further in vivo evaluation.