LN5VY52Mrq | 1392223-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: LN5VY52Mrq
• 英文别名: 8-bromo-6-pyridin-3-yl-3,4-dihydro-1H-quinolin-2-one
• CAS: 1392223-79-8
• 化学式: C₁₄H₁₁BrN₂O
• 分子量: 303.158
• InChiKey: HYNLMTDSFSQFFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-噻吩硼酸 、 LN5VY52Mrq 在 四丁基溴化铵 、 palladium diacetate 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 6.0h， 以83%的产率得到6-pyridin-3-yl-8-thiophen-3-yl-3,4-dihydro-1H-quinolin-2-one
  参考文献：
  名称：

  Selective Dual Inhibitors of CYP19 and CYP11B2: Targeting Cardiovascular Diseases Hiding in the Shadow of Breast Cancer

  摘要：

  Postmenopausal women are at high risk for cardiovascular diseases because of the estrogen deficiency. As for postmenopausal breast cancer patients, this risk is even higher due to inhibition of estrogens biosyntheses in peripheral tissue by the aromatase (CYP19) inhibitors applied. Because estrogen deficiency results in significantly elevated aldosterone levels, which are a major cause of cardiovascular diseases, dual inhibition of CYP19 and CYP11B2 (aldosterone synthase) is a promising treatment for breast cancer and the coinstantaneous cardiovascular diseases. By combination of important structural features of known CYP19 and CYP11B2 inhibitors, we succeeded in obtaining compounds 3 and 5 as selective dual inhibitors with IC50 values around 50 and 20 nM toward CYP19 and CYP11B2, respectively. These compounds showed also good selectivity toward CYP11B1 (selectivity factors (IC50 (CYP11B1)/IC50 (CYP11B2)) around 50) and CYP17 (no inhibition).

  DOI：

  10.1021/jm3004637
• 作为产物：
  描述：

  6-(吡啶-3-基)-3,4-二氢喹啉-2(1H)-酮 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以90%的产率得到LN5VY52Mrq
  参考文献：
  名称：

  Selective Dual Inhibitors of CYP19 and CYP11B2: Targeting Cardiovascular Diseases Hiding in the Shadow of Breast Cancer

  摘要：

  Postmenopausal women are at high risk for cardiovascular diseases because of the estrogen deficiency. As for postmenopausal breast cancer patients, this risk is even higher due to inhibition of estrogens biosyntheses in peripheral tissue by the aromatase (CYP19) inhibitors applied. Because estrogen deficiency results in significantly elevated aldosterone levels, which are a major cause of cardiovascular diseases, dual inhibition of CYP19 and CYP11B2 (aldosterone synthase) is a promising treatment for breast cancer and the coinstantaneous cardiovascular diseases. By combination of important structural features of known CYP19 and CYP11B2 inhibitors, we succeeded in obtaining compounds 3 and 5 as selective dual inhibitors with IC50 values around 50 and 20 nM toward CYP19 and CYP11B2, respectively. These compounds showed also good selectivity toward CYP11B1 (selectivity factors (IC50 (CYP11B1)/IC50 (CYP11B2)) around 50) and CYP17 (no inhibition).

  DOI：

  10.1021/jm3004637

文献信息

• Selective Dual Inhibitors of CYP19 and CYP11B2: Targeting Cardiovascular Diseases Hiding in the Shadow of Breast Cancer
  作者：Qingzhong Hu、Lina Yin、Rolf W. Hartmann

  DOI：10.1021/jm3004637

  日期：2012.8.23

  Postmenopausal women are at high risk for cardiovascular diseases because of the estrogen deficiency. As for postmenopausal breast cancer patients, this risk is even higher due to inhibition of estrogens biosyntheses in peripheral tissue by the aromatase (CYP19) inhibitors applied. Because estrogen deficiency results in significantly elevated aldosterone levels, which are a major cause of cardiovascular diseases, dual inhibition of CYP19 and CYP11B2 (aldosterone synthase) is a promising treatment for breast cancer and the coinstantaneous cardiovascular diseases. By combination of important structural features of known CYP19 and CYP11B2 inhibitors, we succeeded in obtaining compounds 3 and 5 as selective dual inhibitors with IC50 values around 50 and 20 nM toward CYP19 and CYP11B2, respectively. These compounds showed also good selectivity toward CYP11B1 (selectivity factors (IC50 (CYP11B1)/IC50 (CYP11B2)) around 50) and CYP17 (no inhibition).