1,2,3,4-四氢-6-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-异喹啉 | 922718-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 1,2,3,4-四氢-6-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-异喹啉
• 英文名称: 6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline
• CAS: 922718-55-6
• 化学式: C₁₅H₂₂BNO₂
• 分子量: 259.156
• InChiKey: LLKNMVXSNBBOPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  380.6±42.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  7-bromo-9-cyclopropyl-6-fluoro-9H-isothiazolo[5,4-b]quinoline-3,4-dione 、 1,2,3,4-四氢-6-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-异喹啉 在 四(三苯基膦)钯 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 9-cyclopropyl-6-fluoro-7-(1,2,3,4-tetrahydro-isoquinolin-6-yl)-9H-isothiazolo[5,4-b]quinoline-3,4-dione
  参考文献：
  名称：

  Isothiazoloquinolones with Enhanced Antistaphylococcal Activities against Multidrug-Resistant Strains:  Effects of Structural Modifications at the 6-, 7-, and 8-Positions

  摘要：

  We describe the biological evaluation of isothiazoloquinolones (ITQs) having structural modifications at the 6-, 7-, and 8-positions. Addition of a methoxy substituent to C-8 effected an increase in antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and a decrease in cytotoxic activity against Hep2 cells. Removal of fluorine from C-6 or replacement of the C-8 carbon with a nitrogen compromised anti-MRSA activity. When the groups attached at C-7 were compared, the anti-MRSA activity decreased in the order 6-isoquinolinyl > 4-pyridinyl > 5-dihydroisoindolyl > 6-tetrahydroisoquinolinyl. The compound with the most desirable in vitro biological profile was 9-cyclopropyl-6-fluoro-8-methoxy-7-(2-methylpyridin-4-yl)-9H-isothiazolo[5,4-b]quinoline-3,4-dione (7g). This ITQ demonstrated (i) strong in vitro anti-MRSA activity (MIC90 = 0.5 mu g/mL), (ii) strong inhibitory activities against S. aureus DNA gyrase and topoisomerase IV, with weak activity against human topoisomerase II, (iii) weak cytotoxic activities against three cell lines, and (iv) efficacy in an in vivo murine thigh model of infection employing MRSA.

  DOI：

  10.1021/jm060844e
• 作为产物：
  描述：

  6-溴异喹啉 在 platinum(IV) oxide 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 氢气 、 potassium acetate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 1,2,3,4-四氢-6-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-异喹啉
  参考文献：
  名称：

  Isothiazoloquinolones with Enhanced Antistaphylococcal Activities against Multidrug-Resistant Strains:  Effects of Structural Modifications at the 6-, 7-, and 8-Positions

  摘要：

  We describe the biological evaluation of isothiazoloquinolones (ITQs) having structural modifications at the 6-, 7-, and 8-positions. Addition of a methoxy substituent to C-8 effected an increase in antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and a decrease in cytotoxic activity against Hep2 cells. Removal of fluorine from C-6 or replacement of the C-8 carbon with a nitrogen compromised anti-MRSA activity. When the groups attached at C-7 were compared, the anti-MRSA activity decreased in the order 6-isoquinolinyl > 4-pyridinyl > 5-dihydroisoindolyl > 6-tetrahydroisoquinolinyl. The compound with the most desirable in vitro biological profile was 9-cyclopropyl-6-fluoro-8-methoxy-7-(2-methylpyridin-4-yl)-9H-isothiazolo[5,4-b]quinoline-3,4-dione (7g). This ITQ demonstrated (i) strong in vitro anti-MRSA activity (MIC90 = 0.5 mu g/mL), (ii) strong inhibitory activities against S. aureus DNA gyrase and topoisomerase IV, with weak activity against human topoisomerase II, (iii) weak cytotoxic activities against three cell lines, and (iv) efficacy in an in vivo murine thigh model of infection employing MRSA.

  DOI：

  10.1021/jm060844e

文献信息

• [EN] TRICYCLIC HETEROCYLIC DERIVATIVES<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES TRICYCLIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2017202748A1

  公开（公告）日：2017-11-30

  Compounds of the formula (I) in which R1 and R2 have the meanings indicated in Claim 1,are inhibitors of ATR, and can be employed for the treatment of diseases such as cancer.

  式(I)中R1和R2具有权利要求书中指示的含义，是ATR的抑制剂，可用于治疗癌症等疾病。
• WO2024083111A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Isothiazoloquinolones with Enhanced Antistaphylococcal Activities against Multidrug-Resistant Strains:  Effects of Structural Modifications at the 6-, 7-, and 8-Positions
  作者：Qiuping Wang、Edlaine Lucien、Akihiro Hashimoto、Godwin C. G. Pais、David M. Nelson、Yongsheng Song、Jane A. Thanassi、Christopher W. Marlor、Christy L. Thoma、Jijun Cheng、Steven D. Podos、Yangsi Ou、Milind Deshpande、Michael J. Pucci、Douglas D. Buechter、Barton J. Bradbury、Jason A. Wiles

  DOI：10.1021/jm060844e

  日期：2007.1.1

  We describe the biological evaluation of isothiazoloquinolones (ITQs) having structural modifications at the 6-, 7-, and 8-positions. Addition of a methoxy substituent to C-8 effected an increase in antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and a decrease in cytotoxic activity against Hep2 cells. Removal of fluorine from C-6 or replacement of the C-8 carbon with a nitrogen compromised anti-MRSA activity. When the groups attached at C-7 were compared, the anti-MRSA activity decreased in the order 6-isoquinolinyl > 4-pyridinyl > 5-dihydroisoindolyl > 6-tetrahydroisoquinolinyl. The compound with the most desirable in vitro biological profile was 9-cyclopropyl-6-fluoro-8-methoxy-7-(2-methylpyridin-4-yl)-9H-isothiazolo[5,4-b]quinoline-3,4-dione (7g). This ITQ demonstrated (i) strong in vitro anti-MRSA activity (MIC90 = 0.5 mu g/mL), (ii) strong inhibitory activities against S. aureus DNA gyrase and topoisomerase IV, with weak activity against human topoisomerase II, (iii) weak cytotoxic activities against three cell lines, and (iv) efficacy in an in vivo murine thigh model of infection employing MRSA.