10-aminomethyl-11-demethyl-12-oxocalanolide A | 1152308-67-2

• 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: 10-aminomethyl-11-demethyl-12-oxocalanolide A
• 英文别名: 6,6,10-trimethyl-4-n-propyl-10-aminomethyl-2H,6H,12H-benzo[1,2-b:3,4-b':5,6-b'']tripyranyl-2,12-dione；1'-Aminemethyl-11-demethyl-12-oxo-calanolide A；16-(aminomethyl)-10,10-dimethyl-6-propyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11-pentaene-4,18-dione
• CAS: 1152308-67-2
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: HDGSIJRYKZMEHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  10-aminomethyl-11-demethyl-12-oxocalanolide A 、 异氰酸2-甲氧苯酯 以 四氢呋喃 为溶剂， 反应 3.0h， 以55.8%的产率得到11-demethyl-10-(2-methoxyphenylthiouramido)methyl-12-oxocalanolide 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：

  10-azidomethyl-11-demethyl-12-oxocalanolide A 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以59.5%的产率得到10-aminomethyl-11-demethyl-12-oxocalanolide 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

文献信息

• TETRACYCLIC DIPYRANO-COUMARIN COMPOUNDS WITH ANTI-HIV AND ANTI-MYCOBACTERIUM TUBERCULOSIS ACTIVITIES
  申请人：Liu Gang

  公开号：US20100324067A1

  公开（公告）日：2010-12-23

  The present invention relates to tetracyclodipyrano-coumarin compounds of general formula (I), wherein the substituents are defined herein. These compounds exihibit dual biological activities of anti human immunodeficiency virus type 1 (HIV-1) infection and anti- Mycobacterium Tuberculosis (TB) infection.

  本发明涉及通式（I）的四环二吡喃香豆素类化合物，其中取代基在此定义。这些化合物表现出抗人类免疫缺陷病毒类型1（HIV-1）感染和抗结核分枝杆菌（TB）感染的双重生物活性。
• TETRACYCLODIPYRANYL COUMARINS AND THE ANTI-HIV AND ANTI-TUBERCULOSIS USES THEREOF
  申请人：Institute of Mataria Medica, Chinese Academy of Medical Sciences

  公开号：EP2216335B1

  公开（公告）日：2014-03-12
• 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.