8-Hydroxy-6-propyl-3,11-dioxatetracyclo[8.5.0.02,7.012,14]pentadeca-1(10),2(7),5,8-tetraene-4,15-dione | 1152308-86-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-Hydroxy-6-propyl-3,11-dioxatetracyclo[8.5.0.02,7.012,14]pentadeca-1(10),2(7),5,8-tetraene-4,15-dione
• 英文别名: 8-hydroxy-6-propyl-3,11-dioxatetracyclo[8.5.0.02,7.012,14]pentadeca-1(10),2(7),5,8-tetraene-4,15-dione
• CAS: 1152308-86-5
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: HZQFOWJRESIBHK-UHFFFAOYSA-N

物化性质

• 熔点：
  201.3-203.2 °C
• 沸点：
  549.4±50.0 °C(predicted)
• 密度：
  1.426±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1-二乙氧基-3-甲基-2-丁烯 、 8-Hydroxy-6-propyl-3,11-dioxatetracyclo[8.5.0.02,7.012,14]pentadeca-1(10),2(7),5,8-tetraene-4,15-dione 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以48%的产率得到10,11-cyclopropyl-12-oxo-calanolide A
  参考文献：
  名称：

  Highly Suppressing Wild-Type HIV-1 and Y181C Mutant HIV-1 Strains by 10-Chloromethyl-11-demethyl-12-oxo-calanolide A with Druggable Profile

  摘要：

  We herein report a new compound: 10-chloromethyl-11-demethyl-12-oxo-calanolide A (20, EC50 = 7.4 nM, St = 1417), which demonstrates a druggable profile with 32.7% oral bioavailability in rat, tolerated oral single dose toxicity in mice, and especially the feature of highly efficient suppression of the wild-type HIV-1 and Y181C mutant HIV-1 at an EC50 = 7.4 nM and EC50 = 0.46 nM, respectively.

  DOI：

  10.1021/jm901653e
• 作为产物：
  描述：

  8-(bromomethyl)-5-hydroxy-4-propyl-8,9-dihydro-2H,10H-pyrano[2,3-f]chromene-2,10-dione 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以79.3%的产率得到8-Hydroxy-6-propyl-3,11-dioxatetracyclo[8.5.0.02,7.012,14]pentadeca-1(10),2(7),5,8-tetraene-4,15-dione
  参考文献：
  名称：

  Highly Suppressing Wild-Type HIV-1 and Y181C Mutant HIV-1 Strains by 10-Chloromethyl-11-demethyl-12-oxo-calanolide A with Druggable Profile

  摘要：

  We herein report a new compound: 10-chloromethyl-11-demethyl-12-oxo-calanolide A (20, EC50 = 7.4 nM, St = 1417), which demonstrates a druggable profile with 32.7% oral bioavailability in rat, tolerated oral single dose toxicity in mice, and especially the feature of highly efficient suppression of the wild-type HIV-1 and Y181C mutant HIV-1 at an EC50 = 7.4 nM and EC50 = 0.46 nM, respectively.

  DOI：

  10.1021/jm901653e

文献信息

• Highly Suppressing Wild-Type HIV-1 and Y181C Mutant HIV-1 Strains by 10-Chloromethyl-11-demethyl-12-oxo-calanolide A with Druggable Profile
  作者：Hai Xue、Xiaofan Lu、Purong Zheng、Li Liu、Chunyan Han、Jinping Hu、Zijie Liu、Tao Ma、Yan Li、Lin Wang、Zhiwei Chen、Gang Liu

  DOI：10.1021/jm901653e

  日期：2010.2.11

  We herein report a new compound: 10-chloromethyl-11-demethyl-12-oxo-calanolide A (20, EC50 = 7.4 nM, St = 1417), which demonstrates a druggable profile with 32.7% oral bioavailability in rat, tolerated oral single dose toxicity in mice, and especially the feature of highly efficient suppression of the wild-type HIV-1 and Y181C mutant HIV-1 at an EC50 = 7.4 nM and EC50 = 0.46 nM, respectively.