4-(but-2-yn-1-ylselanyl)benzenesulfonamide

• 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: 4-(but-2-yn-1-ylselanyl)benzenesulfonamide
• 英文别名: 4-[(But-2-yn-1-yl)selanyl]benzene-1-sulfonamide；4-but-2-ynylselanylbenzenesulfonamide
• 化学式: C₁₀H₁₁NO₂SSe
• 分子量: 288.229
• InChiKey: SYXVSYLKIVCGJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.11
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-selenocyanatobenzenesulfonamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 4-(but-2-yn-1-ylselanyl)benzenesulfonamide
  参考文献：
  名称：

  Design, Synthesis, and X-ray of Selenides as New Class of Agents for Prevention of Diabetic Cerebrovascular Pathology

  摘要：

  A series of novel selenides bearing benzene sulfonamide moieties was synthesized and investigated for their inhibition on six human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoforms such as the physiologically relevant hCA I, II, VA, VB, VII, and IX and the X-ray complex in adduct with hCA II for some of them investigated. These enzymes are involved in a variety of diseases including glaucoma, retinitis pigmentosa, epilepsy, arthritis, metabolic disorders, and cancer. The investigated compounds showed potent inhibitory action against hCA VA, VII, and IX, in the low nanomolar range, thus making them of interest for the development of isoform-selective inhibitors and as candidates for various biomedical applications.

  DOI：

  10.1021/acsmedchemlett.8b00076

文献信息

• Design, synthesis and X-ray crystallography of selenides bearing benzenesulfonamide moiety with neuropathic pain modulating effects
  作者：Andrea Angeli、Lorenzo di Cesare Mannelli、Elena Lucarini、Thomas S. Peat、Carla Ghelardini、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2018.05.026

  日期：2018.6

  A series of selenides bearing benzensulfonamide were investigated as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Potent inhibitory action, in the low nanomolar range, was detected against isoforms hCA II and VII, which are known to be involved in neuropathic pain modulation. These selenides showed on the other hand moderate inhibition against the cytosolic isoforms hCA I and

  研究了一系列带有苯甲磺酰胺的硒化物作为金属酶碳酸酐酶的抑制剂（CA，EC 4.2.1.1）。已检测到针对同工型hCA II和VII的低纳摩尔浓度范围的有效抑制作用，这些同型异构体已知参与神经性疼痛调节。另一方面，这些硒化物显示出对胞质同工型hCA I和跨膜hCA IX的中等抑制作用。与hCA II结合的两种衍生物的X射线晶体学数据使我们合理化了优异的抑制数据。在由奥沙利铂诱导的神经性疼痛的小鼠模型中，一些强效的CA II / VII抑制剂可诱导持久的缓解疼痛的作用。
• Selenides bearing benzenesulfonamide show potent inhibition activity against carbonic anhydrases from pathogenic bacteria Vibrio cholerae and Burkholderia pseudomallei
  作者：Andrea Angeli、Ghulam Abbas、Sonia del Prete、Clemente Capasso、Claudiu T. Supuran

  DOI：10.1016/j.bioorg.2018.05.015

  日期：2018.9

  A series of selenides bearing benzenesulfonamide moieties was evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors against the pathogenic bacteria Vibrio cholerae (VchCAa and VchCA beta) and Burkholderia pseudomallei (BpsCA beta) enzymes. The molecules represent an interesting lead for antibacterial agents with a possibly new mechanism of action showing excellent inhibitory action and selectivity for inhibiting VchCAa and BpsCA beta over the human (h) off-target isoforms hCA I and II. Identification of potent and possibly selective inhibitors of bacteria CAs over the human counterparts may lead to pharmacological tools useful for understanding the physiological role(s) of these under-investigated proteins.