2,3-dihydro-2-oxo-3-(4-tolylsulfonyl)-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester | 361535-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-dihydro-2-oxo-3-(4-tolylsulfonyl)-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester
• 英文别名: Tert-butyl 3-(4-methylphenyl)sulfonyl-2-oxobenzimidazole-1-carboxylate；tert-butyl 3-(4-methylphenyl)sulfonyl-2-oxobenzimidazole-1-carboxylate
• CAS: 361535-25-3
• 化学式: C₁₉H₂₀N₂O₅S
• 分子量: 388.444
• InChiKey: IRCHZQZUBLTOAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2-oxo-3-(4-tolylsulfonyl)-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester 在 盐酸 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 3.0h， 以81%的产率得到2,3-dihydro-1-(4-tolylsulfonyl)-1H-benzimidazol-2-one
  参考文献：
  名称：

  N-Arylsulfonyl-benzimidazolones as Potential Hypoglycemic Agents

  摘要：

  将标题和段落翻译成中文：

  通过在NaOH存在下将苯并咪唑酮与芳基磺酰氯反应合成了1,3-双(芳基磺酰基)-苯并咪唑酮1a-d。通过保护一个Na原子与叔丁氧羰基团化合后进行芳基磺酰化和在酸性介质中去保护，制备了单(芳基磺酰基)-苯并咪唑酮衍生物5a-c。确定了三种化合物1a、1c和5a的抗糖尿病活性。

  DOI：

  10.1515/znb-2002-0315
• 作为产物：
  描述：

  2-羟基苯并咪唑 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 2,3-dihydro-2-oxo-3-(4-tolylsulfonyl)-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  N-Arylsulfonyl-benzimidazolones as Potential Hypoglycemic Agents

  摘要：

  将标题和段落翻译成中文：

  通过在NaOH存在下将苯并咪唑酮与芳基磺酰氯反应合成了1,3-双(芳基磺酰基)-苯并咪唑酮1a-d。通过保护一个Na原子与叔丁氧羰基团化合后进行芳基磺酰化和在酸性介质中去保护，制备了单(芳基磺酰基)-苯并咪唑酮衍生物5a-c。确定了三种化合物1a、1c和5a的抗糖尿病活性。

  DOI：

  10.1515/znb-2002-0315

文献信息

• N-Arylsulfonyl-benzimidazolones as Potential Hypoglycemic Agents
  作者：Iftikhar Ahmad、Shahid Hameed、Helmut Duddeck、Sigurd Lenzen、Ingo Rustenbeck、Roshan Ahmad

  DOI：10.1515/znb-2002-0315

  日期：2002.3.1

  1,3-Bis(arylsulfonyl)-benzimidazolones 1a-d were synthesized by reacting benzimidazolones with arenesulfonyl chlorides in the presence of NaOH. Mono(arylsulfonyl)-benzimidazolone derivatives 5a-c were prepared from benzimidazolone by protecting one of the Natoms with a tert-butoxycarbonyl group followed by arylsulfonylation and deprotection in acidic medium. The antidiabetic activity of three compounds 1a, 1c and 5a has been determined.

  将标题和段落翻译成中文：

  通过在NaOH存在下将苯并咪唑酮与芳基磺酰氯反应合成了1,3-双(芳基磺酰基)-苯并咪唑酮1a-d。通过保护一个Na原子与叔丁氧羰基团化合后进行芳基磺酰化和在酸性介质中去保护，制备了单(芳基磺酰基)-苯并咪唑酮衍生物5a-c。确定了三种化合物1a、1c和5a的抗糖尿病活性。

• Conjugates of Degraded and Oxidized Hydroxyethyl Starch and Sulfonylureas: Synthesis, Characterization, and in Vivo Antidiabetic Activity
  作者：Muhammad Azhar Abbas、Shahid Hameed、Muhammad Farman、Jörg Kressler、Nasir Mahmood

  DOI：10.1021/bc500509a

  日期：2015.1.21

  Orally administered drugs usually face the problem of low water solubility, low permeability, and less retention in bloodstream leading to unsatisfactory pharmacokinetic profile of drugs. Polymer conjugation has attracted increasing interest in the pharmaceutical industry for delivering such low molecular weight (Mw) drugs as well as some complex compounds. In the present work, degraded and oxidized hydroxyethyl starch (HES), a highly biocompatible semisynthetic biopolymer, was used as a drug carrier to overcome the solubility and permeability problems. The HES was coupled with synthesized N-arylsulfonylbenzimidazolones, a class of sulfonylurea derivatives, by creating an amide linkage between the two species. The coupled products were characterized using GPC, FT-IR, 1H NMR, and 13C NMR spectroscopy. The experiments established the viability of covalent coupling between the biopolymer and N-arylsulfonylbenzimidazolones. The coupled products were screened for their in vivo antidiabetic potential on male albino rats. The coupling of sulfonylurea derivatives with HES resulted in a marked increase of the hypoglycemic activity of all the compounds. 2,3-Dihydro-3-(4-nitrobenzensulfonyl)-2-oxo-1H-benzimidazole coupled to HES10100 was found most potent with a 67% reduction in blood glucose level of the rats as compared to 41% reduction produced by tolbutamide and 38% by metformin.