4,5,6,7-tetrabromo-7a-(6'-hydroxy-2',4',5',7'-tetraiodo-3'-oxo-3H-xanthen-9'-yl)benzoic acid | 951288-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4,5,6,7-tetrabromo-7a-(6'-hydroxy-2',4',5',7'-tetraiodo-3'-oxo-3H-xanthen-9'-yl)benzoic acid
• 英文别名: 2,3,4,5-Tetrabromo-6-(3-hydroxy-2,4,5,7-tetraiodo-6-oxoxanthen-9-yl)benzoic acid
• CAS: 951288-27-0
• 化学式: C₂₀H₄Br₄I₄O₅
• 分子量: 1151.48
• InChiKey: PTCUBBBOXTXZAR-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：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1',2',3',4'-tetrabromofluorescein 在 碘 、 碘酸 作用下， 以 乙醇 、 水 为溶剂， 以37%的产率得到4,5,6,7-tetrabromo-7a-(6'-hydroxy-2',4',5',7'-tetraiodo-3'-oxo-3H-xanthen-9'-yl)benzoic acid
  参考文献：
  名称：

  Rose Bengal analogs and vesicular glutamate transporters (VGLUTs)

  摘要：

  Vesicular glutamate transporters (VGLUTs) allow the loading of presynaptic glutamate vesicles and thus play a critical role in glutamatergic synaptic transmission. Rose Bengal (RB) is the most potent known VGLUT inhibitor (K-i 25 nM); therefore we designed, synthesized and tested in brain preparations, a series of analogs based on this scaffold. We showed that among the two tautomers of RB, the carboxylic and not the lactonic form is active against VGLUTs and generated a pharmacophore model to determine the minimal structure requirements. We also tested RB specificity in other neurotransmitter uptake systems. RB proved to potently inhibit VMAT (K-i 64 nM) but weakly VACHT (K-i > 9.7 mu M) and may be a useful tool in glutamate/acetylcholine co-transmission studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.069

文献信息

• Process for the Synthesis of 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one (Rose Bengal) and Related Xanthenes
  申请人：Singer Jamie

  公开号：US20110071217A1

  公开（公告）日：2011-03-24

  A new process for the manufacture of iodinated xanthenes in high purity includes a cyclization step followed by an iodination step. No extraction, chromatographic or solvent concentration steps are required, and the intermediate as well as final compounds are isolated via filtration or similar means. The process requires a single organic solvent, and the steps are completed at temperatures below 100° C. The exclusion of chloride ions, of chloride free-radicals, hypochlorite ions, or hypochlorous acid as reagents or from reagents that may generate these species in situ in the presence of oxidants, prevents undesirable impurity formation. Several new compounds have been conceived and isolated using these methods. These new compounds are also formed into new medicaments.

  一种用于高纯度碘化黄色素制造的新工艺包括一个环化步骤，然后是一个碘化步骤。不需要提取、色谱或溶剂浓缩步骤，中间体和最终化合物均通过过滤或类似手段分离。该工艺需要一种有机溶剂，并且步骤在100°C以下的温度下完成。通过排除氯化物离子、氯自由基、次氯酸根离子或次氯酸作为试剂或从可能在氧化剂存在的情况下生成这些物种的试剂中排除，防止不良杂质形成。使用这些方法已经构思并分离出了几种新化合物。这些新化合物也被制成了新药物。
• [EN] PROCESS FOR THE SYNTHESIS OF 4,5,6,7-TETRACHLORO-3',6'-DIHYDROXY-2',4',5'7'-TETRAIODO-3H-SPIRO[ISOBENZOFURAN-1,9'-XANTHEN]-3-ONE (ROSE BENGAL) AND RELATED XANTHENES<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE 4,5,6,7-TÉTRACHLORO-3',6'-DIHYDROXY-2',4',5'7'-TÉTRAÏODO-3H-SPIRO[ISOBENZOFURAN-1,9'-XANTHEN]-3-ONE (ROSE BENGALE) ET DE XANTHÈNES APPARENTÉS
  申请人：PROVECTUS PHARMACEUTICALS INC

  公开号：WO2011035161A1

  公开（公告）日：2011-03-24

  A new process for the manufacture of iodinated xanthenes in high purity includes a cyclization step followed by an iodination step. No extraction, chromatographic or solvent concentration steps are required, and the intermediate as well as final compounds are isolated via filtration or similar means. The process requires a single organic solvent, and the steps are completed at temperatures below 100°C. The exclusion of chloride ions, of chloride free-radicals, hypochlorite ions, or hypochlorous acid as reagents or from reagents that may generate these species in situ in the presence of oxidants, prevents undesirable impurity formation. Several new compounds have been conceived and isolated using these methods. These new compounds are also formed into new medicaments.

  一种制备高纯度碘代黄色素的新工艺包括环化步骤和碘化步骤。不需要萃取、色谱或溶剂浓缩步骤，中间体和最终化合物均通过过滤或类似手段分离。该工艺需要单一有机溶剂，并且步骤在100℃以下完成。排除氯离子、自由氯自由基、次氯酸盐离子或次氯酸作为试剂或从可能在氧化剂存在下生成这些物种的试剂中排除，可以防止不良杂质形成。使用这些方法已经构思并分离出几种新化合物。这些新化合物也被制成了新药物。
• Process for the Synthesis of 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one(Rose Bengal) and Related Xanthenes
  申请人：Provectus Pharmaceuticals, Inc.

  公开号：US20130274322A1

  公开（公告）日：2013-10-17

  A new process for the manufacture of iodinated xanthenes in high purity includes a cyclization step followed by an iodination step. No extraction, chromatographic or solvent concentration steps are required, and the intermediate as well as final compounds are isolated via filtration or similar means. The process requires a single organic solvent, and the steps are completed at temperatures below 100° C. The exclusion of chloride ions, of chloride free-radicals, hypochlorite ions, or hypochlorous acid as reagents or from reagents that may generate these species in situ in the presence of oxidants, prevents undesirable impurity formation. Several new compounds have been conceived and isolated using these methods. These new compounds are also formed into new medicaments.

  一种制备高纯度碘代黄色素的新工艺，包括环化步骤和碘化步骤。不需要提取、色谱或溶剂浓缩步骤，中间体和最终化合物均通过过滤或类似方法分离。该工艺需要单一有机溶剂，并且步骤在100℃以下完成。排除氯离子、氯自由基、次氯酸根离子或次氯酸作为试剂或从可能在氧化剂存在下生成这些物种的试剂中生成，防止不良杂质的形成。使用这些方法已经构思和分离了几种新化合物。这些新化合物也被制成新药物。
• PROCESS FOR THE SYNTHESIS OF 4,5,6,7-TETRACHLORO-3',6'-DIHYDROXY-2',4',5'7'-TETRAIODO-3H-SPIRO[ISOBENZOFURAN-1,9'-XANTHEN]-3-ONE (ROSE BENGAL) AND RELATED XANTHENES
  申请人：Provectus Pharmatech, Inc.

  公开号：EP2464225A1

  公开（公告）日：2012-06-20
• US20140343296A1
  申请人：——

  公开号：US20140343296A1

  公开（公告）日：2014-11-20