2-(valproylcarboxamido)-5-sulfonamidoindane

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(valproylcarboxamido)-5-sulfonamidoindane
• 英文别名: 2-propyl-N-(5-sulfamoyl-2,3-dihydro-1H-inden-2-yl)pentanamide
• 化学式: C₁₇H₂₆N₂O₃S
• 分子量: 338.471
• InChiKey: XBYJCVDSFWJBSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基茚满盐酸盐 在 吡啶 、 盐酸 、 氯磺酸 、 ammonium hydroxide 、 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 52.0h， 生成 2-(valproylcarboxamido)-5-sulfonamidoindane
  参考文献：
  名称：

  碳酸酐酶抑制剂。结合茚满部分的抗惊厥磺酰胺的设计。

  摘要：

  从市售的1-和2-茚满胺开始制备了一系列带有茚满基部分的芳族磺酰胺，并研究了它们作为两种碳酸酐酶（CA，EC 4.2.1.1）同工酶hCA I和II的抑制剂的活性。结合了乙酰胺基，4-氯-苯甲酰基，丙戊酰基，四氟和五氟苯甲酰基的新磺酰胺可作为慢红细胞同工酶hCA I（K（i）在1.6-8.5 nM范围内）的非常有效的抑制剂，与同功酶II相比，其对此类抑制剂的亲和力通常较低。一些衍生物还表现出优异的hCA II抑制特性（K（i）s在2.3-12 nM范围内），但是与其他磺酰胺/氨基磺酸CA抑制剂（如甲唑酰胺）相比，这些磺酰胺的抗惊厥活性相当低。 。此外，

  DOI：

  10.1016/j.bmcl.2004.09.061

文献信息

• Indanesulfonamides as Carbonic Anhydrase Inhibitors. Toward Structure-Based Design of Selective Inhibitors of the Tumor-Associated Isozyme CA IX
  作者：Anne Thiry、Marie Ledecq、Alessandro Cecchi、Jean-Michel Dogné、Johan Wouters、Claudiu T. Supuran、Bernard Masereel

  DOI：10.1021/jm0600287

  日期：2006.5.1

  Carbonic anhydrases are ubiquitous metalloenzymes which are involved in fundamental processes (i.e., acid-base regulation, respiration, calcification, etc.). The carbonic anhydrase isozyme IX becomes an interesting pharmacological target due to its overexpression in cancer and its absence in normal tissue. Therefore, several indanesulfonamides were synthesized and tested for their inhibition both against the human CA IX and against two other biologically relevant isozymes (CA I and II). Structure-activity relationships are discussed and point out different compounds for its selectivity and activity against CA IX. To establish preliminary hypothesis for the design of new isozyme-selective CA IX inhibitors, we conducted molecular modeling. We describe here the first human CA IX model built by homology with another CA isozyme already crystallized. Docking studies were performed to explore the binding mode of our indanesulfonamide derivatives.
• Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties
  作者：Celine Chazalette、Bernard Masereel、Stéphanie Rolin、Anne Thiry、Andrea Scozzafava、Alessio Innocenti、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2004.09.061

  日期：2004.12

  red blood cell isozyme hCA I (K(i)s in the range of 1.6-8.5 nM), which usually has a lower affinity for such inhibitors, as compared to isozyme II. Some derivatives also showed excellent hCA II inhibitory properties (K(i)s in the range of 2.3-12 nM), but the anticonvulsant activity of these sulfonamides was rather low as compared to that of other sulfonamide/sulfamate CA inhibitors, such as methazolamide

  从市售的1-和2-茚满胺开始制备了一系列带有茚满基部分的芳族磺酰胺，并研究了它们作为两种碳酸酐酶（CA，EC 4.2.1.1）同工酶hCA I和II的抑制剂的活性。结合了乙酰胺基，4-氯-苯甲酰基，丙戊酰基，四氟和五氟苯甲酰基的新磺酰胺可作为慢红细胞同工酶hCA I（K（i）在1.6-8.5 nM范围内）的非常有效的抑制剂，与同功酶II相比，其对此类抑制剂的亲和力通常较低。一些衍生物还表现出优异的hCA II抑制特性（K（i）s在2.3-12 nM范围内），但是与其他磺酰胺/氨基磺酸CA抑制剂（如甲唑酰胺）相比，这些磺酰胺的抗惊厥活性相当低。 。此外，