(10R,11R)-6,6,10,11-Tetramethyl-4-propyl-7,8,10,11-tetrahydro-6H-dipyrano[2,3-f;2',3'-h]chromene-2,12-dione

• 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: (10R,11R)-6,6,10,11-Tetramethyl-4-propyl-7,8,10,11-tetrahydro-6H-dipyrano[2,3-f;2',3'-h]chromene-2,12-dione
• 英文别名: (+)-trans-7,8-Dihydroketone；(16R,17R)-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)-tetraene-4,18-dione
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: DOQZDHYXBAJGFY-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (10R,11R)-6,6,10,11-Tetramethyl-4-propyl-7,8,10,11-tetrahydro-6H-dipyrano[2,3-f;2',3'-h]chromene-2,12-dione 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 偶氮二异丁腈 、 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 反应 9.75h， 生成 (10S,11R,12R)-12-羟基-6,6,10,11-四甲基-4-丙基-11,12-二氢-2H,6H,10H-二吡喃并[2,3-f:2',3'-h]色烯-2-酮
  参考文献：
  名称：

  Total Synthesis of (±)-Calanolide A

  摘要：

  The total synthesis of (+/-)-Calanolide A, incorporating a ring-forming sequence different from previous procedures, is described.

  DOI：

  10.1080/00397919608003823
• 作为产物：
  描述：

  (10R,11R)-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 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、202.65 kPa 条件下， 反应 2.0h， 以82%的产率得到(10R,11R)-6,6,10,11-Tetramethyl-4-propyl-7,8,10,11-tetrahydro-6H-dipyrano[2,3-f;2',3'-h]chromene-2,12-dione
  参考文献：
  名称：

  Anti-HIV natural product (+)-calanolide A is active against both drug-susceptible and drug-resistant strains of Mycobacterium tuberculosis

  摘要：

  Naturally occurring anti-HIV-1 agent (+)-calanolide A was found to be active against all of the strains of Mycobacterium tuberculosis tested, including those resistant to the standard antitubercular drugs. Efficacy evaluations in macrophages revealed that (+)-calanolide A significantly inhibited intracellular replication of M. tuberculosis H37Rv at concentrations below the MIC observed in vitro. Preliminary mechanistic studies indicated that (+)-calanolide A rapidly inhibits RNA and DNA synthesis followed by an inhibition of protein synthesis. Compared with known inhibitors, this scenario is more similar to effects observed with rifampin, an inhibitor of RNA synthesis. Since (+)-calanolide A was active against a rifampin-resistant strain, it is believed that these two agents may involve different targets. (+)-Calanolide A and its related pyranocoumarins are the first class of compounds identified to possess antimycobacterial and antiretroviral activities, representing a new pharmacophore for anti-TB activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.012

文献信息

• Total Synthesis of (±)-Calanolide A
  作者：Ken S. Rehder、John A. Kepler

  DOI：10.1080/00397919608003823

  日期：1996.11

  The total synthesis of (+/-)-Calanolide A, incorporating a ring-forming sequence different from previous procedures, is described.
• Anti-HIV natural product (+)-calanolide A is active against both drug-susceptible and drug-resistant strains of Mycobacterium tuberculosis
  作者：Ze-Qi Xu、William W Barrow、William J Suling、Louise Westbrook、Esther Barrow、Yuh-Meei Lin、Michael T Flavin

  DOI：10.1016/j.bmc.2003.11.012

  日期：2004.3

  Naturally occurring anti-HIV-1 agent (+)-calanolide A was found to be active against all of the strains of Mycobacterium tuberculosis tested, including those resistant to the standard antitubercular drugs. Efficacy evaluations in macrophages revealed that (+)-calanolide A significantly inhibited intracellular replication of M. tuberculosis H37Rv at concentrations below the MIC observed in vitro. Preliminary mechanistic studies indicated that (+)-calanolide A rapidly inhibits RNA and DNA synthesis followed by an inhibition of protein synthesis. Compared with known inhibitors, this scenario is more similar to effects observed with rifampin, an inhibitor of RNA synthesis. Since (+)-calanolide A was active against a rifampin-resistant strain, it is believed that these two agents may involve different targets. (+)-Calanolide A and its related pyranocoumarins are the first class of compounds identified to possess antimycobacterial and antiretroviral activities, representing a new pharmacophore for anti-TB activity. (C) 2003 Elsevier Ltd. All rights reserved.