DDE271 | 247095-15-4

• 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: DDE271
• 英文别名: 5,7-Dihydroxy-8-acetyl-4-propyl-coumarin；8-acetyl-5,7-dihydroxy-4-propylchromen-2-one
• CAS: 247095-15-4
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: LFPFTYXAPKVMAR-UHFFFAOYSA-N

物化性质

• 沸点：
  519.2±39.0 °C(predicted)
• 密度：
  1.327±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  DDE271 在 吡啶 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 生成 5-hydroxy-6-(1-(hydroxyimino)ethyl)-2,2-dimethyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one
  参考文献：
  名称：

  N-Oxide heterocycles and imidazoles replacing ring D of calanolides against Mycobacterium tuberculosis

  摘要：

  We have explored the chemistry of N-oxide heterocycles and imidazoles replacing ring D of the natural product (+)-calanolide A, and have synthesized 12 new analogues, two of which were active against both R Mtb and NR Mtb with MIC values of 12.5 mu g/mL, which would lead to further optimization for more potent anti-TB candidates. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.11.001
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 aluminum (III) chloride 、 三氟化硼乙醚 作用下， 反应 6.0h， 生成 DDE271
  参考文献：
  名称：

  N-Oxide heterocycles and imidazoles replacing ring D of calanolides against Mycobacterium tuberculosis

  摘要：

  We have explored the chemistry of N-oxide heterocycles and imidazoles replacing ring D of the natural product (+)-calanolide A, and have synthesized 12 new analogues, two of which were active against both R Mtb and NR Mtb with MIC values of 12.5 mu g/mL, which would lead to further optimization for more potent anti-TB candidates. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.11.001

文献信息

• Scaffold-hopping strategy toward calanolides with nitrogen-containing heterocycles
  作者：Xiao-Yong Guo、Gang Liu

  DOI：10.1016/j.cclet.2013.03.007

  日期：2013.4

  (+)-Calanolide A was the first natural product identified as an active agent against HIV-1 and Mycobacterium tuberculosis (Mtb). In devising a scaffold-hopping strategy of structure modification of (+)-calanolide A, we focused on the synthesis of calanolides by replacing ring D with various five or six membered nitrogen-containing heterocycles, hoping to get further understanding of the structure-activity relationship. (C) 2013 Gang Liu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  （+)-Calanolide A是首个被确认为对HIV-1和结核杆菌（Mtb）有效的天然产物。在设计针对(+)-calanolide A的结构改进方案时，我们采用了“结构跳板”策略，专注于通过替代环D来合成各种新型的含氮杂环（五元或六元），这有助于进一步揭示其构效关系。 (C) 2013 Gang Liu. 本文由Elsevier B.V.代表中国化学会出版。保留所有权利。
• BTK inhibitors
  申请人：Uckun M. Fatih

  公开号：US20060167090A1

  公开（公告）日：2006-07-27

  The invention provides BTK inhibitors, methods for their identification and use, and pharmaceutical compositions comprising BTK inhibitors, including allergy treatments.

  本发明提供了BTK抑制剂，其识别和使用方法，以及包括过敏治疗在内的BTK抑制剂的药物组合物。
• BTK inhibitors and methods for their identification and use
  申请人：Parker Hughes Institute

  公开号：US20030144351A1

  公开（公告）日：2003-07-31

  The invention provides BTK inhibitors, methods for their identification and use, and pharmaceutical compositions comprising BTK inhibitors, including allergy treatments.

  本发明提供了BTK抑制剂，其鉴定和使用方法，以及包含BTK抑制剂的药物组合物，包括过敏治疗。
• 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.
• BTK INHIBITORS AND METHODS FOR THEIR IDENTIFICATION AND USE
  申请人：Parker Hughes Institute

  公开号：EP1071658A2

  公开（公告）日：2001-01-31