N-(2-苯并噻唑基)邻苯二甲酰亚胺 | 60945-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: N-(2-苯并噻唑基)邻苯二甲酰亚胺
• 英文名称: 2-(2-benzothiazole)-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-(benzo[d]thiazol-2-yl)isoindoline-1,3-dione；2-(benzo[d]thiazol-2-yl)isoindolin-1,3-dione；N-benzothiazol-2-yl-phthalimide；2-Phthalimino-benzthiazol；N-(2-Benzothiazolyl)phthalimide；2-(1,3-benzothiazol-2-yl)isoindole-1,3-dione
• CAS: 60945-03-1
• 化学式: C₁₅H₈N₂O₂S
• 分子量: 280.307
• InChiKey: LSXOUPJSDGCGMO-UHFFFAOYSA-N

物化性质

• 熔点：
  143-147 °C(Solv: ethanol (64-17-5))
• 沸点：
  522.8±33.0 °C(Predicted)
• 密度：
  1.526±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  N-(2-Carboxybenzoyl)-2-aminobenzothiazole 在 吡啶 、 乙酸酐 作用下， 反应 16.0h， 生成 N-(2-苯并噻唑基)邻苯二甲酰亚胺
  参考文献：
  名称：

  某些邻苯二甲酰亚胺基衍生物的合成及光谱

  摘要：

  DOI：

  10.1021/je00056a031

文献信息

• Thalidomide analogues: Tumor necrosis factor-alpha inhibitors and their evaluation as anti-inflammatory agents
  作者：Juan José Casal、Mariela Bollini、María Elisa Lombardo、Ana María Bruno

  DOI：10.1016/j.ejps.2015.12.017

  日期：2016.2

  A series of related thalidomide derivatives (2-9) were synthesized by microwave irradiation and evaluated for anti-inflammatory activity. Such activity was assessed in vivo and ex vivo. Compounds 2, 8 and 9 showed the highest levels of inhibition of TNF-alpha production. On rat paw edema and hyperalgesia assays, compound 9, (1,4-phthalazinedione) demonstrated the highest in vivo anti-inflammatory activity

  通过微波辐射合成了一系列相关的沙利度胺衍生物（2-9），并评估了其抗炎活性。在体内和离体评估了这种活性。化合物2、8和9表现出最高的TNF-α抑制水平。在大鼠爪水肿和痛觉过敏试验中，化合物9（1,4-酞嗪二酮）表现出最高的体内抗炎活性。因此，化合物9可以被认为是有希望的化合物，可以对其进行进一步修饰以获得用于治疗炎性疾病的新药剂。
• Copper or Silver-Mediated Oxidative C(sp²)–H/N–H Cross-Coupling of Phthalimide and Heterocyclic Arenes: Access to <i>N</i>-Arylphthalimides
  作者：Tatyana V. Gryaznova、Kirill V. Kholin、Elizaveta O. Nikanshina、Vera V. Khrizanforova、Sofia O. Strekalova、Robert R. Fayzullin、Yulia H. Budnikova

  DOI：10.1021/acs.organomet.9b00443

  日期：2019.10.14

  Copper or silver-catalyzed direct C(sp2)–H/N–H electrochemical cross-coupling of phthalimide and heterocyclic arenes (2-phenylpyridine, benzo[h]quinoline, benzoxazole, and benzothiazole, etc.) for the efficient synthesis of phthalimide derivatives is described. This reaction features good yield, mild conditions, and broad substrate scope, which provides an efficient and straightforward protocol to

  铜或银催化的直接C（SP 2）-H / N-H电化学交叉耦合邻苯二甲酰亚胺和杂环芳烃的（2-苯基吡啶，苯并[ ħ描述了用于有效合成邻苯二甲酰亚胺衍生物的[喹啉，苯并恶唑和苯并噻唑等]。该反应具有良好的收率，温和的条件和广泛的底物范围，从而提供了一种有效而直接的方案来获得这类叔胺。所提出的方案第一次不仅基于铜催化剂而且基于银，而以前从未用于此目的，并且两者均给出了可比的结果。机械研究（伏安法，ESR研究）表明，在此过程中，通过Cu（I）/ Cu（II）/ Cu（III）或Ag（I）/ Ag（III）循环完成的自由基途径可能被排除在外。
• An efficient green synthesis of new benzothiazoles containing sulfonamide or cyclic imide moieties
  作者：Chafika Bougheloum、Sabrina Alioua、Robila Belghiche、Nesma Benali、Abdelrani Messalhi

  DOI：10.1002/jhet.3753

  日期：2020.1

  An efficient and convenient protocol for the one‐pot synthesis of new benzothiazoles bearing sulfonamide or cyclic imide moieties using Cesium salt of Wells‐Dawson heteropolyacid (Cs5HP2W18O62) as solid catalyst and water as solvent under ultrasound irradiation was reported. The reaction speed was remarkably catalyzed with the aid of ultrasound irradiation. Moreover, this approach prepares multiple

  报道了在Wells-Dawson杂多酸铯盐（Cs 5 HP 2 W 18 O 62）作为固体催化剂和水作为溶剂在超声辐射下单锅合成带有磺酰胺或环状酰亚胺部分的新型苯并噻唑的有效简便方法。。借助超声辐照显着地催化了反应速度。此外，这种方法还带来了许多其他好处，例如操作简便，更高的产量和能源性能。
• Ushenko,I.K.; Chovnik,L.I., Journal of general chemistry of the USSR, 1960, vol. 30, p. 2640 - 2646
  作者：Ushenko,I.K.、Chovnik,L.I.

  DOI：——

  日期：——
• Synthesis and anti-angiogenic activity of benzothiazole, benzimidazole containing phthalimide derivatives
  作者：Shunmugam Nagarajan、Syamantak Majumder、Upendra Sharma、Saranya Rajendran、Neeraj Kumar、Suvro Chatterjee、Bikram Singh

  DOI：10.1016/j.bmcl.2012.10.106

  日期：2013.1

  Benzothiazole and benzimidazole containing phthalimide derivatives (NK037, NK041, NK042, NK0139A and NK0148) have been synthesized and their anti-angiogenic activity was evaluated using ex vivo egg yolk angiogenesis model. A comparative study with pure thalidomide (NKTA) has also been performed to describe the efficacy of these derivatives in blocking angiogenesis. NK037, NK041 and NK042 were equally potent in blocking egg yolk angiogenesis and the anti-angiogenesis effect was higher than NKTA suggesting the efficacy of these three derivatives in blocking angiogenesis when compare to control. Other two derivatives NK0139A and NK0148 showed effect less than NKTA and stronger than control in ex vivo angiogenesis. (c) 2012 Published by Elsevier Ltd.