4-bromo-7-methoxy-2,3-dihydro-1H-inden-1-ol | 928169-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4-bromo-7-methoxy-2,3-dihydro-1H-inden-1-ol
• CAS: 928169-32-8
• 化学式: C₁₀H₁₁BrO₂
• 分子量: 243.1
• InChiKey: VRGOTVKWGTZDDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-7-methoxy-2,3-dihydro-1H-inden-1-ol 在 氯仿 、 palladium on activated charcoal 、 二苯基膦叠氮化物 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 37.0h， 生成 1-amino-7-methoxyindane
  参考文献：
  名称：

  1-氨基茚满和苯胺衍生的新型磺酰胺的合成及碳酸酐酶抑制作用

  摘要：

  三个 1-氨基茚满、四个苯胺和 BnOH 或 t-BuOH 与氯磺酰基异氰酸酯反应得到氨磺酰基氨基甲酸酯。Pd-C 催化氨基甲酸酯的氢解反应或用 CF3CO2H 对氨基甲酸酯的 Boc 基团进行脱保护，得到了七种新型磺酰胺。人碳酸酐酶 (hCA) 同工酶 I 和 II（hCA I 和 hCA II）是在琼脂糖凝胶 4B-酪氨酸-磺胺上通过一步亲和层析从新鲜人血红细胞中纯化的。使用酯酶活性以 4-硝基苯乙酸酯 (NPA) 作为底物，确定了新型磺酰胺对两种同工酶的抑制特性。经测试的源自 1-氨基茚满和苯胺的新型磺酰胺在纳摩尔范围内有效地抑制了 hCA I 和 II。在这些化合物中，

  DOI：

  10.1002/ardp.201400257
• 作为产物：
  描述：

  4-溴-7-甲氧基-1-茚酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到4-bromo-7-methoxy-2,3-dihydro-1H-inden-1-ol
  参考文献：
  名称：

  Illudalic acid as a potential LAR inhibitor: Synthesis, SAR, and preliminary studies on the mechanism of action

  摘要：

  A novel synthesis of the human leukocyte common antigen-related (LAR) phosphatase inhibitor, illudalic acid, has been achieved by a route more amenable to structure modi. cations. A series of simpler analogues of illudalic acid was synthesized and evaluated for potency in inhibiting LAR. The structure -activity relationship (SAR) study has shown that the 5-formyl group and the hemi-acetal lactone are crucial for effective inhibition of LAR activity, and are the key pharmacophores of illudalic acid. The fused dimethylcyclopentene ring moiety evidently helps to enhance the potency of illudalic acid against LAR. A preliminary study of the mechanism of action of illudalic acid against LAR was conducted using electrospray ionization mass spectrometry (ESI-MS) and molecular docking techniques. The results are in full agreement with the described mechanism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.014

文献信息

• Synthesis and Carbonic Anhydrase Inhibitory Effects of Novel Sulfamides Derived from 1-Aminoindanes and Anilines
  作者：Yusuf Akbaba、Enes Bastem、Fevzi Topal、İlhami Gülçin、Ahmet Maraş、Süleyman Göksu

  DOI：10.1002/ardp.201400257

  日期：2014.12

  seven novel sulfamides. Human carbonic anhydrase (hCA) isoenzymes I and II (hCA I and hCA II) were purified from fresh human blood erythrocytes with one‐step affinity chromatography on Sepharose 4B‐tyrosine‐sulfanilamide. The inhibitory properties of the novel sulfamides on both isoenzymes were determined using the esterase activity with 4‐nitrophenyl acetate (NPA) as substrate. The tested novel sulfamides

  三个 1-氨基茚满、四个苯胺和 BnOH 或 t-BuOH 与氯磺酰基异氰酸酯反应得到氨磺酰基氨基甲酸酯。Pd-C 催化氨基甲酸酯的氢解反应或用 CF3CO2H 对氨基甲酸酯的 Boc 基团进行脱保护，得到了七种新型磺酰胺。人碳酸酐酶 (hCA) 同工酶 I 和 II（hCA I 和 hCA II）是在琼脂糖凝胶 4B-酪氨酸-磺胺上通过一步亲和层析从新鲜人血红细胞中纯化的。使用酯酶活性以 4-硝基苯乙酸酯 (NPA) 作为底物，确定了新型磺酰胺对两种同工酶的抑制特性。经测试的源自 1-氨基茚满和苯胺的新型磺酰胺在纳摩尔范围内有效地抑制了 hCA I 和 II。在这些化合物中，
• Illudalic acid as a potential LAR inhibitor: Synthesis, SAR, and preliminary studies on the mechanism of action
  作者：Qing Ling、Yue Huang、Yueyang Zhou、Zhengliang Cai、Bing Xiong、Yahui Zhang、Lanping Ma、Xin Wang、Xin Li、Jia Li、Jingkang Shen

  DOI：10.1016/j.bmc.2008.06.014

  日期：2008.8

  A novel synthesis of the human leukocyte common antigen-related (LAR) phosphatase inhibitor, illudalic acid, has been achieved by a route more amenable to structure modi. cations. A series of simpler analogues of illudalic acid was synthesized and evaluated for potency in inhibiting LAR. The structure -activity relationship (SAR) study has shown that the 5-formyl group and the hemi-acetal lactone are crucial for effective inhibition of LAR activity, and are the key pharmacophores of illudalic acid. The fused dimethylcyclopentene ring moiety evidently helps to enhance the potency of illudalic acid against LAR. A preliminary study of the mechanism of action of illudalic acid against LAR was conducted using electrospray ionization mass spectrometry (ESI-MS) and molecular docking techniques. The results are in full agreement with the described mechanism. (C) 2008 Elsevier Ltd. All rights reserved.