2,3-Dihydropyrrolo[1,2-b][1,2]benzisothiazole-1-carboxylic acid 5,5-dioxide | 361521-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2,3-Dihydropyrrolo[1,2-b][1,2]benzisothiazole-1-carboxylic acid 5,5-dioxide
• 英文别名: 2,3-dihydropyrrolo[1,2-b][1,2]benzisothiazole-5,5-dioxo-1-carboxylic acid；5,5-dioxo-2,3-dihydropyrrolo[1,2-b][1,2]benzothiazole-1-carboxylic acid
• CAS: 361521-67-7
• 化学式: C₁₁H₉NO₄S
• 分子量: 251.263
• InChiKey: HXAREYFFIHRZGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.68
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,3-Dihydropyrrolo[1,2-b][1,2]benzisothiazole-1-carboxylic acid 5,5-dioxide 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 2,3-Dihydropyrrolo[1,2-b][1,2]benzisothiazole-1-[N-(4-methylphenyl)]carboxamide 5,5-dioxide
  参考文献：
  名称：

  糖精衍生的 Sultams 的光异构化；第 3 部分：来自 Dihydropyrrolo[1,2-b][1,2]benzisothiazole 5,5-Dioxides 的 Dihydro[1]benzothieno[3,2-b]pyrrole 4,4-Dioxides

  摘要：

  1-取代的2,3-二氢吡咯并[1,2-b][1,2]苯异噻唑 5,5-二氧化物 7a-c,e 在254 nm波长的紫外照射下，在乙腈中顺利高效地转化为2,3-二氢[1]苯噻吩[3,2-b]吡咯 4,4-二氧化物 8a-c,e。产品的结构通过光谱方法和8b的单晶X射线结构测定得到了阐明。

  DOI：

  10.1055/s-2001-15073
• 作为产物：
  描述：

  Methyl 4-(1,1,3-trioxo-1,2-benzothiazol-2-yl)butanoate 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以89%的产率得到2,3-Dihydropyrrolo[1,2-b][1,2]benzisothiazole-1-carboxylic acid 5,5-dioxide
  参考文献：
  名称：

  糖精衍生的 Sultams 的光异构化；第 3 部分：来自 Dihydropyrrolo[1,2-b][1,2]benzisothiazole 5,5-Dioxides 的 Dihydro[1]benzothieno[3,2-b]pyrrole 4,4-Dioxides

  摘要：

  1-取代的2,3-二氢吡咯并[1,2-b][1,2]苯异噻唑 5,5-二氧化物 7a-c,e 在254 nm波长的紫外照射下，在乙腈中顺利高效地转化为2,3-二氢[1]苯噻吩[3,2-b]吡咯 4,4-二氧化物 8a-c,e。产品的结构通过光谱方法和8b的单晶X射线结构测定得到了阐明。

  DOI：

  10.1055/s-2001-15073

文献信息

• Synthesis, antimicrobial, DNA cleavage and antioxidant activities of tricyclic sultams derived from saccharin
  作者：Ibrahim Elghamry、Magdy M. Youssef、Mohammed A. Al-Omair、Hany Elsawy

  DOI：10.1016/j.ejmech.2017.07.079

  日期：2017.10

  were synthesized from saccharin and their chemical structures were confirmed by spectroscopic tools. Then, their antibacterial activities and MIC were evaluated against two strains of gram positive and gram-negative bacteria. The MIC values of the tested compounds are in the of range 8–33 μg/ml. In addition, their DNA cleavage ability, binding affinity and their anticancer activities against hepatic

  由糖精合成了两个系列的三环稠合缩合产物（羧酸盐，3a，b和5a，f，g和苯胺5b-e），并通过光谱学工具确认了其化学结构。然后，针对两种革兰氏阳性和革兰氏阴性细菌菌株评估了它们的抗菌活性和MIC。被测化合物的MIC值在8-33μg/ ml的范围内。另外，测试了它们的DNA切割能力，结合亲和力和对肝癌细胞的抗癌活性。并且还测量了它们的抗氧化活性。四种羧酸衍生物（3a，5a，5f和5g）和一种苯胺（5d）的测试化合物在整个研究过程中被证明是最高的活性。
• A New Asymmetric Photoisomerization of 2,3-Dihydropyrrolo[1,2-b]benzisothiazole 5,5-Dioxides
  作者：Ibrahim Elghamry、Dietrich Dopp

  DOI：10.5012/jkcs.2010.54.6.727

  日期：2010.12.20

  A tricyclic ring system bearing new stereogenic center namely 2,3-dihydro[1]benzothieno[3,2-b]pyrrole 4,4-dioxide was synthesized by asymmetric photoisomerization of 2,3-dihydropyrrolo[1,2-b]benzisothiazole 5,5-dioxide by irradiation with 245 nm emission of the low-pressure mercury lamp. The chemical structure and the purity of the photoproduct were delineated preliminarily by IR, NMR, and MS and finally

  通过2,3-二氢吡咯并[1,2-b]苯并噻唑的不对称光异构化反应，合成了一个具有新立体中心的2,3-二氢[1]苯并噻吩并[3,2-b]吡咯4,4-二氧化物的三环体系。通过以245 nm发射的低压汞灯照射5,5-二氧化物。初步通过IR，NMR和MS描述了光产物的化学结构和纯度，最后通过单晶X射线晶体学确认。
• Design, synthesis and biological evaluation of novel desmuramyldipeptide analogs
  作者：Žiga Jakopin、Emanuela Corsini、Martina Gobec、Irena Mlinarič-Raščan、Marija Sollner Dolenc

  DOI：10.1016/j.ejmech.2011.05.042

  日期：2011.9

  A series of novel desmuramyldipeptides have been designed and synthesized as part of our search for therapeutically useful muramyldipeptide (MOP) analogs. Their immunomodulatory properties were initially assessed in vitro, evaluating their effect on lipopolysaccharide (LPS)-induced cytokine release in THP-1 cells. Following the initial screening, selected compounds were further investigated for immunomodulatory properties using LPS and phorbol 12-myristate 13-acetate (PMA)/ionomycin-stimulated human peripheral blood mononuclear cells. The results confirmed the immunomodulatory properties of some of the synthesized desmuramyldipeptide analogs. Taken together, presented data confirmed the immunostimulatory effect of compound 44, MDP derivative incorporating a pyrido-fused [1,2]-benzisothiazole moiety, while for compounds 32 and 39, indole scaffold-based derivatives of MOP, an immunosuppressive effect was observed. Further studies will be necessary to address their potential therapeutic use as immunomodulatory drugs, both as immunostimulants or anti-inflammatory agents. (C) 2011 Elsevier Masson SAS. All rights reserved.