1H-吡咯-3-羰基氯化,1-(苯磺酰)- | 147716-06-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1H-吡咯-3-羰基氯化,1-(苯磺酰)-
• 英文名称: 1-benzenesulfonyl-1H-pyrrole-3-carbonyl chloride
• 英文别名: 1-phenylsulfonylpyrrole-3-carbonyl chloride；1-(benzenesulfonyl)pyrrole-3-carbonyl chloride
• CAS: 147716-06-1
• 化学式: C₁₁H₈ClNO₃S
• 分子量: 269.708
• InChiKey: WTBQGYFOUUEOKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  440.8±37.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-吡咯-3-羰基氯化,1-(苯磺酰)- 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 tris[2-(methoxyethoxy)ethyl]amine 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 、 甲苯 为溶剂， 反应 27.0h， 生成 [3-(benzofuran-5-carbonyl)pyrrol-1-yl]acetic acid ethyl ester
  参考文献：
  名称：

  Substituted Pyrrol-1-ylacetic Acids That Combine Aldose Reductase Enzyme Inhibitory Activity and Ability To Prevent the Nonenzymatic Irreversible Modification of Proteins from Monosaccharides

  摘要：

  Starting from the known inhibitory activity of (3-benzoylpyrrol-1-yl)acetic acid (1) and (2-benzoylpyrrol-1-yl)acetic acid (II), a series of 3-aroyl and 2,4-bis-aroyl derivatives (54-75) were synthesized and tested for inhibition of aldose reductase, an enzyme involved in the appearance of diabetic complications. It was found that a number of the tested compounds exhibited considerable activity in the micromolar range. Important structural features for the potent compounds is the presence of substituents with relatively low Hammett sigma values and/ or moieties which increase their overall aromatic area. The most active derivative was the [2,4-bis(4-methoxybenzoyl)pyrrol-1-yl] acetic acid (75), with potency favorably compared to known ARIs such as tolrestat, epalrestat, zopolrestat, and fidarestat. Four selected derivatives were also evaluated for their ability to interfere with the oxidative modification of serum albumin in an in vitro experimental glycation model of diabetes mellitus. All of them showed considerable activity, comparable to the known inhibitor trolox. Our results, taken together, indicate that compound 75 combines favorably two biological activities directly connected to a number of pathological conditions related to the chronic diabetes mellitus.

  DOI：

  10.1021/jm0209477
• 作为产物：
  描述：

  1-苯磺酰基-1H-吡咯-3-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 生成 1H-吡咯-3-羰基氯化,1-(苯磺酰)-
  参考文献：
  名称：

  N-取代吡咯衍生物吲唑甲酰胺作为大豆脂氧合酶抑制剂的设计、合成和药理评价

  摘要：

  在本文中，我们试图开发一类针对脂氧合酶的新型化合物，脂氧合酶是白三烯生物合成中的关键酶，与一系列炎症性疾病有关。鉴于缺乏合适的人类 5-脂氧合酶晶体学数据，使用解析的大豆脂氧合酶-1 和 -3 结构作为模板生成准确的药效团模型，该模型进一步用于虚拟筛选目的。八种化合物 （1–8） 来自内部库，由通过羧酰胺接头与 5-或 6-吲唑部分偶联的 N-取代吡咯组成。根据大豆脂氧合酶体外测定，本研究发现带有萘基的 hit 分子 8，IC 50 值为 22 μM。用喹啉部分等位取代萘基环和还原羰基羧酰胺基团分别导致化合物 9-12 和 13。化合物 12 显示出最有前途的酶抑制作用。此外，发现化合物 8 和 12 在体内分别使角叉菜胶诱导的爪水肿降低 52.6% 和 49.8%。鉴于其显着的体外和体内抗炎活性取得了令人鼓舞的结果，化合物 8 和 12 可以进一步优化，以便将来发现新的 5-脂氧合酶抑制剂。

  DOI：

  10.1007/s11030-023-10775-8
• 作为试剂：
  描述：

  2 - (甲硫基)-5 - (三正丁基锡)嘧啶 在 bis-triphenylphosphine-palladium(II) chloride 、 1H-吡咯-3-羰基氯化,1-(苯磺酰)- 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以61%的产率得到2-methylthio-5-(1-phenylsulfonylpyrrol-3-ylcarbonyl)pyrimidine
  参考文献：
  名称：

  Gaare, Kristin; Repstad, Terje; Benneche, Tore, Acta Chemica Scandinavica, 1993, vol. 47, # 1, p. 57 - 62

  摘要：

  DOI：

文献信息

• Gaare, Kristin; Repstad, Terje; Benneche, Tore, Acta Chemica Scandinavica, 1993, vol. 47, # 1, p. 57 - 62
  作者：Gaare, Kristin、Repstad, Terje、Benneche, Tore、Undheim, Kjell

  DOI：——

  日期：——
• Substituted Pyrrol-1-ylacetic Acids That Combine Aldose Reductase Enzyme Inhibitory Activity and Ability To Prevent the Nonenzymatic Irreversible Modification of Proteins from Monosaccharides
  作者：Ioannis Nicolaou、Vassilis J. Demopoulos

  DOI：10.1021/jm0209477

  日期：2003.1.1

  Starting from the known inhibitory activity of (3-benzoylpyrrol-1-yl)acetic acid (1) and (2-benzoylpyrrol-1-yl)acetic acid (II), a series of 3-aroyl and 2,4-bis-aroyl derivatives (54-75) were synthesized and tested for inhibition of aldose reductase, an enzyme involved in the appearance of diabetic complications. It was found that a number of the tested compounds exhibited considerable activity in the micromolar range. Important structural features for the potent compounds is the presence of substituents with relatively low Hammett sigma values and/ or moieties which increase their overall aromatic area. The most active derivative was the [2,4-bis(4-methoxybenzoyl)pyrrol-1-yl] acetic acid (75), with potency favorably compared to known ARIs such as tolrestat, epalrestat, zopolrestat, and fidarestat. Four selected derivatives were also evaluated for their ability to interfere with the oxidative modification of serum albumin in an in vitro experimental glycation model of diabetes mellitus. All of them showed considerable activity, comparable to the known inhibitor trolox. Our results, taken together, indicate that compound 75 combines favorably two biological activities directly connected to a number of pathological conditions related to the chronic diabetes mellitus.