4,4'-Dimethoxy-3,3'-bis(methoxycarbonyl)benzophenone | 207743-20-2

• 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: 4,4'-Dimethoxy-3,3'-bis(methoxycarbonyl)benzophenone
• 英文别名: methyl 2-methoxy-5-(4-methoxy-3-methoxycarbonylbenzoyl)benzoate
• CAS: 207743-20-2
• 化学式: C₁₉H₁₈O₇
• 分子量: 358.348
• InChiKey: FWCHSXJYUJWDAU-UHFFFAOYSA-N

物化性质

• 熔点：
  142-144 °C
• 沸点：
  514.4±50.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,4'-Dimethoxy-3,3'-bis(methoxycarbonyl)benzophenone 在 platinum(IV) oxide 氢气 、 硝酸 、 乙酸酐 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 3,3'-diamino-5,5'-bis(methoxycarbonyl)-4,4'-dimethoxybenzophenone
  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
• 作为产物：
  描述：

  5,5'-亚甲基二水杨酸 在 chromium(VI) oxide 、 乙酸酐 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 19.0h， 生成 4,4'-Dimethoxy-3,3'-bis(methoxycarbonyl)benzophenone
  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：Purdue Research Foundation

  公开号：US06569897B1

  公开（公告）日：2003-05-27

  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的抗HIV剂。本文介绍了新型ADAM化合物、它们的制药配方以及使用方法，用于治疗病毒感染。
• [EN] ALKENYLDIARYLMETHANE NON-NUCLEOSIDE HIV-1 REVERSE TRANSCRIPTASE INHIBITORS<br/>[FR] INHIBITEURS DE TRANSCRIPTASE INVERSE DU VIH-1 NON NUCLEOSIDIQUES PRESENTANT UNE STRUCTURE ALCENYLDIARYLMETHANE COMMUNE
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO1999036384A1

  公开（公告）日：1999-07-22

  (EN) 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.(FR) On a découvert que des composés d'alcényldiarylméthane (ADAM) sont efficaces en tant qu'agents anti-VIH. On décrit dans cette invention de nouveaux composés ADAM, des compositions pharmaceutiques contenant ces derniers ainsi qu'un procédé d'utilisation de ces mêmes composés pour traiter des infections virales.

  (中)发现Alkenyldiarylmethane (ADAM)化合物作为抗HIV剂非常有效。本发明描述了新的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。
• ALKENYLDIARYLMETHANE NON-NUCLEOSIDE HIV-1 REVERSE TRANSCRIPTASE INHIBITORS
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：EP1047656A1

  公开（公告）日：2000-11-02
• EP1047656A4
  申请人：——

  公开号：EP1047656A4

  公开（公告）日：2003-07-30
• US6569897B1
  申请人：——

  公开号：US6569897B1

  公开（公告）日：2003-05-27