6, 8-ditertbutyl-4-chloro-2-oxo-2H-chromene-3-carbaldehyde

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6, 8-ditertbutyl-4-chloro-2-oxo-2H-chromene-3-carbaldehyde
• 英文别名: 6,8-Ditert-butyl-4-chloro-2-oxochromene-3-carbaldehyde；6,8-ditert-butyl-4-chloro-2-oxochromene-3-carbaldehyde
• 化学式: C₁₈H₂₁ClO₃
• 分子量: 320.816
• InChiKey: HBWUXWJWYULNHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  磺胺噻唑 、 6, 8-ditertbutyl-4-chloro-2-oxo-2H-chromene-3-carbaldehyde 以 乙醇 、 溶剂黄146 为溶剂， 反应 3.0h， 以88%的产率得到4-((6,8-di-tert-butyl-4-chloro-2-oxo-2H-chromen-3-yl)methyleneamino)-N-(thiazol-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Sulfonamides containing coumarin moieties selectively and potently inhibit carbonic anhydrases II and IX: Design, synthesis, inhibitory activity and 3D-QSAR analysis

  摘要：

  A series of sulfonamides containing coumarin moieties had been prepared that showed a very interesting profile for the inhibition of two human carbonic anhydrase inhibitors. These compounds were evaluated for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA II and the tumor-associated isozyme hCA IX. The most potent inhibitor against hCA II and IX were compounds 5d (IC50 = 23 nM) and 51 (IC50 = 24 nM), respectively. These sulfonamides containing coumarin moieties may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly. Eighteen compounds were scrutinized by CoMFA and CoMSIA techniques of 3D quantitative structure activity relationship. Nine of the compounds were evaluated for cytotoxicity against human macrophage. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.035
• 作为产物：
  描述：

  2,4-二叔丁基苯酚 在 Eaton′s Reagent 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6, 8-ditertbutyl-4-chloro-2-oxo-2H-chromene-3-carbaldehyde
  参考文献：
  名称：

  Sulfonamides containing coumarin moieties selectively and potently inhibit carbonic anhydrases II and IX: Design, synthesis, inhibitory activity and 3D-QSAR analysis

  摘要：

  A series of sulfonamides containing coumarin moieties had been prepared that showed a very interesting profile for the inhibition of two human carbonic anhydrase inhibitors. These compounds were evaluated for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA II and the tumor-associated isozyme hCA IX. The most potent inhibitor against hCA II and IX were compounds 5d (IC50 = 23 nM) and 51 (IC50 = 24 nM), respectively. These sulfonamides containing coumarin moieties may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly. Eighteen compounds were scrutinized by CoMFA and CoMSIA techniques of 3D quantitative structure activity relationship. Nine of the compounds were evaluated for cytotoxicity against human macrophage. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.035

文献信息

• Sulfonamides containing coumarin moieties selectively and potently inhibit carbonic anhydrases II and IX: Design, synthesis, inhibitory activity and 3D-QSAR analysis
  作者：Zhong-Chang Wang、Ya-Juan Qin、Peng-Fei Wang、Yong-An Yang、Qing Wen、Xin Zhang、Han-Yue Qiu、Yong-Tao Duan、Yan-Ting Wang、Ya-Li Sang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2013.04.035

  日期：2013.8

  A series of sulfonamides containing coumarin moieties had been prepared that showed a very interesting profile for the inhibition of two human carbonic anhydrase inhibitors. These compounds were evaluated for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA II and the tumor-associated isozyme hCA IX. The most potent inhibitor against hCA II and IX were compounds 5d (IC50 = 23 nM) and 51 (IC50 = 24 nM), respectively. These sulfonamides containing coumarin moieties may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly. Eighteen compounds were scrutinized by CoMFA and CoMSIA techniques of 3D quantitative structure activity relationship. Nine of the compounds were evaluated for cytotoxicity against human macrophage. (C) 2013 Elsevier Masson SAS. All rights reserved.