integric acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: integric acid
• 英文别名: (1S,4R,7S,8aR)-4-[(E)-2,4-dimethyloct-2-enoyl]oxy-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid
• 化学式: C₂₅H₃₄O₆
• 分子量: 430.541
• InChiKey: UIXJDFDDMXCJCT-KIBVBBMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  97.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  integric acid 在 Wilkinson's catalyst 氢气 作用下， 以 甲苯 为溶剂， 以64%的产率得到(1S,4R,7S,8aR)-4-((E)-2,4-Dimethyl-oct-2-enoyloxy)-8a-methyl-7-(1-methyl-2-oxo-ethyl)-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid
  参考文献：
  名称：

  Chemical and enzymatic modifications of integric acid and HIV-1 integrase inhibitory activity

  摘要：

  Integric acid (1), an acyl eremophilane sesquiterpenoid, was identified as an inhibitor of HIV-1 integrase, the enzyme responsible for provirus entry into the host cell nucleus and integration in to the host genome. Chemical and enzymatic modification of integric acid led to the preparation of several selective chemical derivatives of integric acid. Preparation, HIV-1 inhibitory activity, and the structure-activity relationship against coupled and strand transfer assays are described. It appears that most of the groups present in the natural product are required for inhibition of HIV-1 integrase strand transfer activity. In contrast, inhibition of 3' processing activity is less stringent suggesting distinct SAR for the two integrase reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00666-6

文献信息

• Structure and absolute stereochemistry of HIV-1 integrase inhibitor integric acid. A novel eremophilane sesquiterpenoid produced by a Xylaria sp.
  作者：Sheo B. Singh、Deborah Zink、Jon Polishook、Delia Valentino、Ali Shafiee、Keith Silverman、Peter Felock、Ana Teran、Dolores Vilella、Daria J. Hazuda、Russell B. Lingham

  DOI：10.1016/s0040-4039(99)01878-x

  日期：1999.12

  natural product libraries we have discovered integric acid, a novel eremophilane sesquiterpenoid, from a Xylaria sp. It inhibited 3′ -end processing, strand transfer and disintegration reactions catalyzed by HIV-1 integrase with IC50 values of 3–10 μM. The isolation, structure elucidation, relative, and absolute stereochemistry of integric acid are described.

  HIV-1整合酶对于病毒复制至关重要，在宿主中不存在，因此是开发无毒抗病毒治疗的潜在目标。从天然产物文库的筛选中，我们从Xylaria sp。中发现了整联酸，一种新的全草双倍体倍半萜。它抑制了HIV-1整合酶催化的3'末端加工，链转移和分解反应，IC 50值为3–10μM。描述了完整酸的分离，结构阐明，相对和绝对立体化学。