3,3'-diiodo-4,4'-dimethoxy-5,5'-bis(methoxycarbonyl)-1,1-diphenyl-1-heptene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3'-diiodo-4,4'-dimethoxy-5,5'-bis(methoxycarbonyl)-1,1-diphenyl-1-heptene
• 英文别名: 1,1 Bis(3-iodo-4-methoxy-3-methoxycarbonylphenyl) heptene；methyl 3-iodo-5-[1-(3-iodo-4-methoxy-5-methoxycarbonylphenyl)hept-1-enyl]-2-methoxybenzoate
• 化学式: C₂₅H₂₈I₂O₆
• 分子量: 678.303
• InChiKey: LNVMREVZQBIZKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,5'-亚甲基二水杨酸 在 platinum(IV) oxide chromium(VI) oxide 、 盐酸 、 氢气 、 碘 、 硝酸 、 sodium hexamethyldisilazane 、 乙酸酐 、 potassium carbonate 、 potassium iodide 、 sodium nitrite 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 20.5h， 生成 3,3'-diiodo-4,4'-dimethoxy-5,5'-bis(methoxycarbonyl)-1,1-diphenyl-1-heptene
  参考文献：
  名称：

  New Alkenyldiarylmethanes with Enhanced Potencies as Anti-HIV Agents Which Act as Non-Nucleoside Reverse Transcriptase Inhibitors

  摘要：

  Twenty-two new alkenyldiarylmethanes (ADAMs) were synthesized and evaluated for inhibition of HIV-1 replication. The most potent compound proved to be methyl 3',3 "-dichloro-4',4 "-dimethoxy-5', 5 "-bis(methoxycarbonyl)-6, (ADAM II), which displayed an EC50 of 13 nM for inhibition of the cytopathic effect of HIV-1(RF) in CEM-SS cells. ADAM II inhibited HIV-1 reverse transcriptase with an IC50 of 0.3 mu M but was inactive as an inhibitor of HIV-1 attachment/fusion to cells, protease, integrase, and the nucleocapsid protein. Molecular target-based and cell-based assays revealed that ADAM II acted biologically as a nonnucleoside reverse transcriptase inhibitor (NNRTI). ADAM II inhibited replication of a wide variety of laboratory, clinical, and clade-representative isolates of HIV-1 in T cell lines and cultures of peripheral blood mononuclear cells or monocyte/macrophages. Mutations that conferred resistance to ADAM II clustered at residues 101, 103, 108, 139, 179, 181, and 188, which line the nonnucleoside binding pocket of HIV-1 reverse transcriptase. However, HIV-1 NL4-3 strain expressing a mutation at residue 100 of reverse transcriptase, and an AZT-resistant virus, displayed increased sensitivity to ADAM II. Thus, ADAM II could serve as an adjunct therapy to AZT and NNRTIs that select for L100I resistance mutations.

  DOI：

  10.1021/jm9800595

文献信息

• Alkenyldiarylmethane non-nucleoside HIV-1 reverse transcriptase inhibitors
  申请人：——

  公开号：US20030220315A1

  公开（公告）日：2003-11-27

  Alkenyldiarylmethane (ADAM) compounds have been found effective as anti-HIV agents. Novel ADAM compounds, their pharmaceutical formulations and a method of using same to treat viral infections are described.

  Alkenyldiarylmethane (ADAM)化合物已被发现有效作为抗HIV药物。本文描述了新型ADAM化合物、它们的制药配方以及使用它们治疗病毒感染的方法。
• US6569897B1
  申请人：——

  公开号：US6569897B1

  公开（公告）日：2003-05-27