inophyllum A | 41135-07-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: inophyllum A
• 英文别名: (16R,17R,18S)-18-hydroxy-10,10,16,17-tetramethyl-6-phenyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11-pentaen-4-one
• CAS: 41135-07-3
• 化学式: C₂₅H₂₄O₅
• 分子量: 404.463
• InChiKey: BXENDTPSKAICGV-QTCYRWPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  inophyllum A 在 chromium trioxide-pyridine complex 作用下， 生成 inophyllum E
  参考文献：
  名称：

  来自斯里兰卡的两组化学性质不同的 calophyllum 物种

  摘要：

  摘要 对Calophyllum moonii 和C. walkeri 的叶提取物进行了研究。前者含有新黄酮类化合物，而后者含有calozeylanic酸。已经审查了七种 Calophyllum 物种的叶提取物中天然产物的分布，并且已经认识到 Calophyllum 物种中存在两个化学上不同的群体。

  DOI：

  10.1016/s0031-9422(00)85494-1
• 作为产物：
  描述：

  inophyllum E 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以7 mg的产率得到inophyllum D
  参考文献：
  名称：

  The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum inophyllum Linn

  摘要：

  As part of a search for novel inhibitors of HIV-1 reverse transcriptase, the acetone extract of the giant African snail, Achatina fulica, was shown to be active. Fractionation of the extract yielded inophyllums A, B, C, and E and calophyllolide (1a, 2a, 3a, 3b, and 6), previously isolated from Calophyllum inophyllum Linn., a known source of nutrition for A. fulica. From a methanol/ methylene chloride extract of C. inophyllum, the same natural products in considerably greater yield were isolated in addition to a novel enantiomer of soulattrolide (4), inophyllum P (2b), and two other novel compounds, inophyllums G-1 (7) and G-2 (8). The absolute stereochemistry of inophyllum, A (1a) was determined to be 10(R), 11(S), 12(S) from a single-crystal X-ray analysis of its 4-bromobenzoate derivative, and the relative stereochemistries of the other inophyllums isolated from C. inophyllum were established by a comparison of their H-1 NMR NOE values and coupling constants to those of inophyllum A (1a). Inophyllums B and P (2a and 2b) inhibited HIV reverse transcriptase with IC50 values of 38 and 130 nM, respectively, and both were active against HIV-1 in cell culture (IC50 of 1.4 and 1.6 mu M). Closely related inophyllums A, C, D, and E, including calophyllic acids, were significantly less active or totally inactive, indicating certain structural requirements in the chromanol ring. Altogether, 11 compounds of the inophyllum class were isolated from C. inophyllum and are described together with the SAR of these novel anti-HIV compounds.

  DOI：

  10.1021/jm00078a001

文献信息

• [EN] SYNTHESIS OF OPTICALLY ACTIVE CALANOLIDES A AND B AND ENANTIOMERS AND RELATED COMPOUNDS<br/>[FR] SYNTHESE DE CALANOLIDES A ET B OPTIQUEMENT ACTIFS, D'ENANTIOMERES ET DE COMPOSES CONNEXES
  申请人：THE UNIVERSITY OF TENNESSEE RESEARCH CORPORATION

  公开号：WO1996026934A1

  公开（公告）日：1996-09-06

  (EN) A method of synthesis of the four optically active stereoisomers of calanolide A and B which produces the compounds in high yields and in a high degree of purity.(FR) Procédé de synthèse des quatre stéréo-isomères optiquement actifs des calanolides A et B, permettant une production à haut rendement de composés d'une grande pureté.

  一种合成calanolide A和B的四种光学活性立体异构体的方法，该方法可以高产高纯度地合成这些化合物。
• [EN] CALANOLIDE ANTIVIRAL COMPOUNDS, COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSES ANTIVIRAUX CALANOLIDES, COMPOSITIONS ISSUES DE CES COMPOSES ET UTILISATIONS
  申请人：THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：WO1993020082A1

  公开（公告）日：1993-10-14

  (EN) The present invention provides novel antiviral compounds, refered to as calanolides, and their derivatives of formulae (I) and (II) which may be isolated from plants of the genus $i(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.(FR) Nouveaux composés antiviraux désignés par le terme de calanolides, et leurs dérivés des formules (I) et (II), pouvant être isolés à partir de végétaux du genre $i(Calophyllum). Les composés et leurs dérivés peuvent être utilisés seuls ou en combinaison avec d'autres agents antiviraux, en compositions, telles que des compositions pharmaceutiques, pour combattre la croissance ou la réplication d'un virus, tel qu'un rétrovirus en particulier le virus de l'immunodéficience humaine et, spécifiquement le HIV-1 ou le HIV-2.

  该发明提供了一种新型的抗病毒化合物，称为卡拉诺酯，以及根据本发明方法从卡洛菲勒姆属植物中分离得到的化合物和它们的衍生物的公式（I）和（II）。这些化合物和它们的衍生物可以单独使用或与其他抗病毒药物组合在一起，如药物组合物，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 ANTIVIRAL COMPOUNDS, COMPOSITIONS AND USES THEREOF
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA as represented by the SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP0633887A1

  公开（公告）日：1995-01-18
• EP0674643A4
  申请人：——

  公开号：EP0674643A4

  公开（公告）日：1995-08-08