methyl 2,3-methylendioxy-4-methoxy-5-bromobenzoate | 93399-24-7

• 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: methyl 2,3-methylendioxy-4-methoxy-5-bromobenzoate
• 英文别名: Methyl 2,3-methylenedioxy-4-methoxy-5-bromobenzoate；methyl 6-bromo-7-methoxy-1,3-benzodioxole-4-carboxylate
• CAS: 93399-24-7
• 化学式: C₁₀H₉BrO₅
• 分子量: 289.082
• InChiKey: UDWCKXMUUUOZIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3-methylendioxy-4-methoxy-5-bromobenzoate 在 硝酸 作用下， 反应 0.08h， 以67%的产率得到6-Brom-7-methoxy-5-nitro-1,3-benzdioxol-4-carbonsaeuremethylester
  参考文献：
  名称：

  Derivate des 1.3-BenzdioxoIs, 52 Darstellung und Reaktionen von 1.3-Dioxolo[4.5-b]phenazinen / Derivatives of 1,3-Benzdioxoles, 52 Preparation and Reactions of 1,3-Dioxolo[4,5-b]phenazines

  摘要：

  我们描述了通过对应的2,2'-二氨基二苯胺进行氯化铁氧化制备1,3-二氧杂环[4,5-b]苝啉4 a -p的过程。它们是通过将o-硝基卤代苯1 a -g与o-硝基苯胺2 a-i缩合得到相应的2,2'-二硝基二苯胺3 a -p，然后用H₂/Pd还原而得到的。

  DOI：

  10.1515/znb-1984-0717
• 作为产物：
  描述：

  methyl 2,3,4-trihydroxybenzoate 在 Sodium tetraborate decahydrate 、 sodium hydroxide 、 溴 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 methyl 2,3-methylendioxy-4-methoxy-5-bromobenzoate
  参考文献：
  名称：

  Anti-aids agents—XXVI. Structure-activity correlations of Gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues

  摘要：

  Bioactivity-directed fractionation of an ethanolic extract of the stems of Kadsura interior led to the isolation and identification of 12 known lignans (1-12). Seven of these compounds (1, 6, 8-12) were active as anti-HIV agents. Gomisin-G (11) exhibited the most potent anti-HIV activity with EC50 and therapeutic index (TI) Values of 0.006 mu g/mL and 300, respectively. Schisantherin-D (6), kadsuranin (8), and schisandrin-C (10) showed good activity with EC50 values of 0.5, 0.8, and 1.2 mu g/mL, and TI values of 110, 56, and 33.3, respectively. Ten related synthetic biphenyl compounds, five variously substituted bismethylenedioxy, dimethoxy, and dimethoxycarbonyl isomers (18-22) and five brominated derivatives (23-27) also were evaluated for inhibitory activity against HIV-1 replication in acutely infected H9 cells. The total syntheses of two new isomers (21 and 22) are reported for the first time. The anti-HIV data indicated that the relative position and types of substituents on the phenolic hydroxy groups of either the natural lignans or the synthetic biphenyl compounds rather than the numbers of bromine(s) on the aromatic rings art of primary importance. In the cyclooctane ring of the natural lignans, the position and substitution of hydroxy groups are also important to enhanced anti-HIV activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00118-1

文献信息

• Brominated hexahydroxybiphenyl derivatives
  申请人：Biotech Research Laboratories

  公开号：US05612341A1

  公开（公告）日：1997-03-18

  Disclosed herein are derivatives of 4,4'-dimethoxy-5,6,5'6'-bimethylenedioxy 2,2'-dimethoxycarbonyl biphenyl (DDB) which were synthesized and found to have anti-HIV activity. Of the compounds studied, 3,3'-dibromo DDB and 3-bromo-DDB initially exhibited the greatest anti-HIV activity.

  本文披露了4,4'-二甲氧基-5,6,5'6'-双甲亚甲基二氧基2,2'-二甲氧羰基联苯（DDB）的衍生物，这些衍生物经过合成后发现具有抗HIV活性。在研究的化合物中，3,3'-二溴DDB和3-溴-DDB最初表现出最强的抗HIV活性。
• DALLACKER, F.;WAGNER, A., Z. NATURFORSCH., 1984, 39, N 7, 936-949
  作者：DALLACKER, F.、WAGNER, A.

  DOI：——

  日期：——
• EP0837677A4
  申请人：——

  公开号：EP0837677A4

  公开（公告）日：1999-12-15
• BROMINATED HEXAHYDROXYBIPHENYL DERIVATIVES
  申请人：THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP0837677A1

  公开（公告）日：1998-04-29
• US5612341A
  申请人：——

  公开号：US5612341A

  公开（公告）日：1997-03-18