(-)-calanolide B | 909-14-8

• 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: (-)-calanolide B
• 英文别名: (-)-(10S,11R,12S)-12-Hydroxy-6,6,10,11-tetramethyl-4-propyl-6,10,11,12-tetrahydro-dipyrano[2,3-f;2',3'-h]chromen-2-one；Costatolide；(16S,17R,18S)-18-hydroxy-10,10,16,17-tetramethyl-6-propyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11-pentaen-4-one
• CAS: 909-14-8
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: NIDRYBLTWYFCFV-PZROIBLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-calanolide B 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.83h， 以61%的产率得到(10S,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione
  参考文献：
  名称：

  Structure−Activity Modifications of the HIV-1 Inhibitors (+)-Calanolide A and (−)-Calanolide B

  摘要：

  The Delta(7,8) olefinic linkages within (+)-calanolide A (1) and (-)-calanolide B (2) were catalytically reduced to determine impact on the anti-HIV activity of the parent compounds. In addition, a series of structure modifications of the C-12 hydroxyl group in (-)-calanolide B was made to investigate the importance of that substituent to the HIV-1 inhibitory activity of these coumarins. A total of 14 analogs were isolated or prepared and compared to (+)-calanolide A and (-)-calanolide B in the NCI primary anti-HIV assay. While none of the compounds showed activity superior to the two unmodified leads, some structure-activity requirements were apparent from the relative anti-HIV potencies of the various analogs.

  DOI：

  10.1021/jm9602827
• 作为产物：
  描述：

  2,2-dimethyl-5-[(2S)-3-methylbut-3-en-2-yl]oxy-10-propyl-3,4-dihydropyrano[2,3-f]chromen-8-one 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 戴斯-马丁氧化剂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 生成 (-)-calanolide B
  参考文献：
  名称：

  A Catalytic Enantioselective Approach to Chromans and Chromanols. A Total Synthesis of (−)-Calanolides A and B and the Vitamin E Nucleus

  摘要：

  DOI：

  10.1021/ja981142k

文献信息

• Method and composition for treating and preventing mycobacterium infections
  申请人：Sarawak Medichem Pharmaceuticals, Inc.

  公开号：US20010027209A1

  公开（公告）日：2001-10-04

  Calanolides and analogues thereof that demonstrate potent mycobacterium activity are provided. Also provided is a method of using calanolides and analogues thereof for treating or preventing mycobacterium infections. The calanolides and analogues thereof provided are obtained via syntheses employing chromene 4 and chromanone 7 as key intermediates.

  提供了具有强效分枝杆菌活性的卡那洛利德及其类似物。还提供了一种使用卡那洛利德及其类似物治疗或预防分枝杆菌感染的方法。所提供的卡那洛利德及其类似物是通过使用色慕4和色酮7作为关键中间体合成而得到的。
• Calanolide analogues and methods of their use
  申请人：Sarawak Medichem Pharmaceuticals,Inc.

  公开号：US20020013478A1

  公开（公告）日：2002-01-31

  Calanolide analogues that demonstrate potent antiviral activity against many viruses are provided. Also provided is a method of using calanolide analogues for treating or preventing viral infections. The calanolide analogues provided are obtained via syntheses employing chromene 4 and chromanone 7 as key intermediates.

  本文提供了表现出对许多病毒具有强效抗病毒活性的Calanolide类似物。还提供了使用Calanolide类似物治疗或预防病毒感染的方法。所提供的Calanolide类似物是通过使用柿蒂素4和柿酮7作为关键中间体进行合成获得的。
• Method for treating and preventing mycobacterium infections
  申请人：Sarawak Medichem Pharmaceuticals

  公开号：US06268393B1

  公开（公告）日：2001-07-31

  Calanolides and analogues thereof that demonstrate potent mycobacterium activity are provided. Also provided is a method of using calanolides and analogues thereof for treating or preventing mycobacterium infections. The calanolides and analogues thereof provided are obtained via syntheses employing chromene 4 and chromanone 7 as key intermediates.

  提供了表现出强效分枝杆菌活性的卡拉诺里德及其类似物。还提供了使用卡拉诺里德及其类似物治疗或预防分枝杆菌感染的方法。所提供的卡拉诺里德及其类似物是通过使用4-色基香豆素和7-色基香酮作为关键中间体进行合成获得的。
• Method for the preparation of (+)-calanolide A and analogues thereof
  申请人：Sarawak MediChem Pharmaceuticals, Inc.

  公开号：US05859050A1

  公开（公告）日：1999-01-12

  A method of preparing (+)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. According to the disclosed method, chromene 4 intermediate was subjected to a chlorotitanium-mediated aldol reaction with acetaldehyde to selectively produce (.+-.)-8a. Separation and enzyme-mediated resolution of (.+-.)-8a produced (+)-8a. Cyclization of (+)-8a under neutral Mitsunobu conditions followed by Luche reduction of (+)-7 produced (+)-calanolide A in high yield and enantiomeric purity. The method of the invention has been extended to produce potent antiviral calanolide A analogues.

  提供了一种从香豆素4制备(+)-卡拉诺利德A，一种有效的HIV反转录酶抑制剂的方法。根据公开的方法，香豆素4中间体经过氯钛介导的醛缩反应与乙醛反应，选择性地产生(.+-.)-8a。分离和酶介导的分辨(.+-.)-8a产生(+)-8a。在中性Mitsunobu条件下，(+)-8a的环化反应，随后是(+)-7的Luche还原反应，产生高收率和对映纯度的(+)-卡拉诺利德A。该发明的方法已扩展到生产有效的抗病毒卡拉诺利德A类似物。
• (+)-calanolide A and analogues thereof
  申请人：Sarawak MediChem Pharmaceuticals, Inc.

  公开号：US05872264A1

  公开（公告）日：1999-02-16

  A method of preparing (+)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. According to the disclosed method, chromene 4 intermediate was subjected to a chlorotitanium-mediated aldol reaction with acetaldehyde to selectively produce (.+-.)-8a. Separation and enzyme-mediated resolution of (.+-.)-8a produced (+)-8a. Cyclization of (+)-8a under neutral Mitsunobu conditions followed by Luche reduction of (.+-.)-7 produced (+)-calanolide A in high yield and enantiomeric purity. The method of the invention has been extended to produce potent antiviral calanolide A analogues.

  本发明提供了一种从4-色基香豆素制备高效的HIV反转录酶抑制剂(+)-Calanolide A, 1的方法。根据揭示的方法，将4-色基香豆素中间体经过氯化钛介导的醛缩反应与乙醛反应，选择性地产生(.+-.)-8a。通过分离和酶介导的分辨，得到(+)-8a。在中性Mitsunobu条件下对(+)-8a进行环化，随后对(.+-.)-7进行Luche还原，高产率和对映纯度地产生了(+)-Calanolide A。该发明的方法已扩展到生产高效的抗病毒Calanolide A类似物。