甲基-4,6-二脱氧-2,3-O-异亚丙基-4-甲基吡喃糖苷 | 909-13-7

• 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
• 中文名称: 甲基-4,6-二脱氧-2,3-O-异亚丙基-4-甲基吡喃糖苷
• 英文名称: 7,8-dihydro-(-)-calanolide B
• 英文别名: Dihydrocostatolide；(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)-tetraen-4-one
• CAS: 909-13-7
• 化学式: C₂₂H₂₈O₅
• 分子量: 372.461
• InChiKey: YPUTYHJWWMYIGF-PZROIBLQSA-N

物化性质

• 熔点：
  159-160 °C
• 沸点：
  509.0±50.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  甲基-4,6-二脱氧-2,3-O-异亚丙基-4-甲基吡喃糖苷 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.83h， 以68%的产率得到(-)-7,8-Dihydro-12-oxocalanolide B
  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：

  (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 在 platinum(IV) oxide 、 氨 sodium tetrahydroborate 、 cerium(III) chloride 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.5h， 生成 甲基-4,6-二脱氧-2,3-O-异亚丙基-4-甲基吡喃糖苷
  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

文献信息

• Calanolide and related antiretroviral compounds, compositions, and uses
  申请人：The United States of America as represented by the Department of Health

  公开号：US05591770A1

  公开（公告）日：1997-01-07

  The present invention provides novel antiviral compounds, refered to as calanolides, related compounds, and their derivatives, which may be isolated from plants, or derived from compounds from plants, of the genus Calophyllum in accordance with the present inventive method. The compounds and their derivatives may be used alone or in combination with other antiviral agents in compositions, such as pharmaceutical compositions, to inhibit the growth or replication of a virus, such as a retrovirus, in particular a human immunodeficiency virus, specifically HIV-1 or HIV-2.

  本发明提供了一种新型抗病毒化合物，称为卡拉诺酮和相关化合物及其衍生物，可以从Calophyllum属植物中分离出来或从该属植物的化合物中衍生出来，符合本发明方法。这些化合物及其衍生物可以单独使用或与其他抗病毒药物组合使用在组成物中，例如制药组成物中，以抑制病毒的生长或复制，例如逆转录病毒，特别是人类免疫缺陷病毒，具体地是HIV-1或HIV-2。
• Calanolide and related antiviral compounds, compositions, and uses thereof
  申请人：——

  公开号：US20020086898A1

  公开（公告）日：2002-07-04

  The present invention provides novel antiviral compounds, refered to as calanolides, related compounds, and their derivatives, which may be isolated from plants, or derived from compounds from plants, of the genus Calophyllum in accordance with the present inventive method. The compounds and their derivatives may be used alone or in combination with other antiviral agents in compositions, such as pharmaceutical compositions, to inhibit the growth or replication of a virus, such as a retrovirus, in particular a human immunodeficiency virus, specifically HIV-1 or HIV-2.

  本发明提供了新型的抗病毒化合物，称为卡拉诺利德（calanolides）、相关化合物及其衍生物，可从山竹子属（Calophyllum）植物中分离或从该属植物的化合物中衍生出来，符合本发明方法。这些化合物及其衍生物可单独使用或与其他抗病毒药物组合在一起，形成组成物，如制药组成物，以抑制病毒的生长或复制，如逆转录病毒，特别是人类免疫缺陷病毒，具体是HIV-1或HIV-2。
• Calanolide and related antiviral compounds, compositions, and uses
  申请人：The United States of America as represented by the Department of Health

  公开号：US05859049A1

  公开（公告）日：1999-01-12

  The present invention provides novel antiviral compounds, refered to as calanolides, related compounds, and their derivatives, which may be isolated from plants, or derived from compounds from plants, of the genus Calophyllum in accordance with the present inventive method. The compounds and their derivatives may be used alone or in combination with other antiviral agents in compositions, such as pharmaceutical compositions, to inhibit the growth or replication of a virus, such as a retrovirus, in particular a human immunodeficiency virus, specifically HIV-1 or HIV-2.

  本发明提供了一种新的抗病毒化合物，称为卡洛利德（calanolides），相关化合物及其衍生物。这些化合物可以从喜树属（Calophyllum）植物中分离出来，或者从这些植物中的化合物衍生而来，根据本发明的方法。这些化合物及其衍生物可以单独使用或与其他抗病毒药物组合在一起，制成药物组合物，以抑制病毒的生长或复制，例如逆转录病毒，特别是人类免疫缺陷病毒，具体包括HIV-1或HIV-2。
• USE OF COMPOUNDS FOR THE TREATMENT OF PAIN
  申请人：Akron Molecules AG

  公开号：EP2846788A1

  公开（公告）日：2015-03-18
• [EN] USE OF COMPOUNDS FOR THE TREATMENT OF PAIN<br/>[FR] UTILISATION DE COMPOSÉS POUR LE TRAITEMENT DE LA DOULEUR
  申请人：AKRON MOLECULES GMBH

  公开号：WO2013167743A1

  公开（公告）日：2013-11-14

  The present invention relates to new therapies to treat pain and related diseases, as well as pharmaceutical compounds for use in said therapies.