5-[(E)-2-[[(E)-2-(3,4,5-trihydroxyphenyl)ethenyl]sulfonylmethylsulfonyl]ethenyl]benzene-1,2,3-triol | 862097-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-[(E)-2-[[(E)-2-(3,4,5-trihydroxyphenyl)ethenyl]sulfonylmethylsulfonyl]ethenyl]benzene-1,2,3-triol
• 英文别名: 1,2,3-Benzenetriol, 5,5'-(methylenebis(sulfonyl-(1E)-2,1-ethenediyl))bis-
• CAS: 862097-17-4
• 化学式: C₁₇H₁₆O₁₀S₂
• 分子量: 444.44
• InChiKey: XNXJTMYPDIHLNJ-ZPUQHVIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  206
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以142 mg的产率得到5-[(E)-2-[[(E)-2-(3,4,5-trihydroxyphenyl)ethenyl]sulfonylmethylsulfonyl]ethenyl]benzene-1,2,3-triol
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Geminal Disulfones as HIV-1 Integrase Inhibitors

  摘要：

  Integration of HIV-1 viral DNA into the host genome is carried out by HIV-integrase (IN) and is a critical step in viral replication. Although several classes of compounds have been reported to inhibit IN in enzymatic assays, inhibition is not always correlated with antiviral activity. Moreover, potent antiviral IN inhibitors such as the chicoric acids do not act upon the intended enzymatic target but behave as entry inhibitors instead. The charged nature of the chicoric acids contributes to poor cellular uptake, and these compounds are further plagued by rapid ester hydrolysis in vivo. To address these critical deficiencies, we designed neutral, nonhydrolyzable analogues of the chicoric acids. Herein, we report the synthesis, enzyme inhibition studies, and cellular antiviral data for a series of geminal disulfones. Of the 10 compounds evaluated, 8 showed moderate to high inhibition of IN in purified enzyme assays. The purified enzyme data correlated with antiviral assays for all but two compounds, suggesting alternative modes of inhibition. Time-of-addition studies were performed on these analogues, and the results indicate that they inhibit an early stage in the replication process, perhaps entry. In contrast, the most potent member of the correlative group shows behavior consistent with IN being the cellular target.

  DOI：

  10.1021/jm049171v

文献信息

• [EN] COMPOUNDS AND METHODS FOR INHIBITING VIRAL ENTRY<br/>[FR] COMPOSES ET METHODES PERMETTANT D'INHIBER UNE ENTREE VIRALE
  申请人：UNIV CALIFORNIA

  公开号：WO2007065032A2

  公开（公告）日：2007-06-07

  [EN] A series of geminal disulfone-containing compounds are described with utility in the treatment of HIV. An early stage inhibitor acts as a small molecule coreceptor-independent inhibitor of viral entry and can be used in combination therapy with other antiviral agents, including those described herein.
  [FR] Cette invention concerne une série de composés contenant des disulfones géminaux qui conviennent pour le traitement du VIH. Un inhibiteur de stade précoce agit comme co-récépteur de petites molécules/inhibiteur indépendant d'entrée virale et peut s'utiliser dans le cadre d'une thérapie combinatoire avec d'autres anti-viraux, dont ceux décrits ici.
• [EN] C-X-C MOTIF CHEMOKINE RECEPTOR 4 ANTAGONIST<br/>[FR] ANTAGONISTE DU RÉCEPTEUR 4 DE CHIMIOKINE À MOTIF C-X-C
  申请人：INST NAT SANTE RECH MED

  公开号：WO2021156451A1

  公开（公告）日：2021-08-12

  The present inventors have discovered a protease-resistant peptide fragment (termed pepRF1) of the Dengue virus capsid protein that is a potent antagonist of C-X-C motif chemokine receptor 4 (CXCR4). This peptide fragment may be useful, for example, in the treatment of CXCR4 mediated conditions, such as HIV and cancer. Thus, the present invention relates to a pepRF1 peptide consisting of the amino acid 10 sequence of SEQ ID NO: 3. The pepRF1 peptide may consist of residues 66 to 82 of the capsid protein of Dengue virus 2, 1 or 3; or residues 65 to 81 of the Dengue virus 2 capsid protein; or the corresponding residues in another Dengue virus capsid protein. For example, the pepRF1 peptide may consist of any one of SEQ ID NOs: 10 to 14.