2-acetamido-2,3-dihydro-1H-indene-5-sulfonyl chloride | 74124-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-acetamido-2,3-dihydro-1H-indene-5-sulfonyl chloride
• 英文别名: 2-acetylamino-indan-5-sulfonyl chloride；N-acetyl-5-chlorosulfonyl-2-indanamine
• CAS: 74124-92-8
• 化学式: C₁₁H₁₂ClNO₃S
• mdl: MFCD27500981
• 分子量: 273.74
• InChiKey: XNVZUBLWWSTORI-UHFFFAOYSA-N

物化性质

• 沸点：
  488.3±45.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险类别：
  8,6.1
• 危险性防范说明：
  P260,P264,P270,P271,P280,P301+P330+P331,P302+P352,P303+P361+P353,P304+P340,P305+P351+P338,P310,P405,P501
• 危险品运输编号：
  2923
• 危险性描述：
  H301,H311,H314,H331
• 包装等级：
  III

反应信息

• 作为反应物：
  描述：

  2-acetamido-2,3-dihydro-1H-indene-5-sulfonyl chloride 在 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 N-(5-sulfamoyl-2,3-dihydro-1H-inden-2-yl)acetamide
  参考文献：
  名称：

  Indanesulfonamides as Carbonic Anhydrase Inhibitors. Toward Structure-Based Design of Selective Inhibitors of the Tumor-Associated Isozyme CA IX

  摘要：

  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.

  DOI：

  10.1021/jm0600287
• 作为产物：
  描述：

  2-氨基茚满盐酸盐 在 氯磺酸 、 sodium acetate 作用下， 反应 4.0h， 生成 2-acetamido-2,3-dihydro-1H-indene-5-sulfonyl chloride
  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
• 作为试剂：
  描述：

  N-(2,3-二氢-1H-茚-2-基)乙酰胺 、 氯磺酸 、 N-(5-sulfamoyl-2,3-dihydro-1H-inden-2-yl)acetamide 、 氨 在 乙酸乙酯 、 2-acetamido-2,3-dihydro-1H-indene-5-sulfonyl chloride 、 N-acetyl sulfonamide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以to give 5-sulfamyl-2-indanamine which的产率得到2-amino-2,3-dihydro-1H-indene-5-sulfonamide
  参考文献：
  名称：

  Pharmaceutical compositions and method of inhibiting phenylethanolamine

  摘要：

  药物组合物和使用具有4和/或5取代基的2-茚胺化合物抑制苯乙醇胺N-甲基转移酶的方法。

  公开号：

  US04192888A1

文献信息

• Process for the preparation of substituted tetralin and substituted indane derivatives
  申请人：Zhang-Plasket Fan

  公开号：US20050240049A1

  公开（公告）日：2005-10-27

  The present invention relates to novel processes for the preparation of substituted tetralin. and substituted indane derivatives. The present invention is further directed to novel processes for the preparation of intermediates in the preparation of the substituted tetralin and substituted indane derivatives.

  本发明涉及一种制备取代四氢萘和取代茚衍生物的新工艺。本发明还涉及一种用于制备取代四氢萘和取代茚衍生物中间体的新工艺。
• PROCESS FOR THE PREPARATION OF SUBSTITUTED TETRALIN AND SUBSTITUTED INDANE DERIVATIVES
  申请人：Zhan-Plasket Fan

  公开号：US20090326258A1

  公开（公告）日：2009-12-31

  The present invention relates to novel processes for the preparation of substituted tetralin and substituted indane derivatives. The present invention is further directed to novel processes for the preparation of intermediates in the preparation of the substituted tetralin and substituted indane derivatives.

  本发明涉及制备取代四氢萘和取代茚烷衍生物的新型工艺。本发明还涉及制备取代四氢萘和取代茚烷衍生物的中间体的新型工艺。
• Process for the Preparation of Substituted Tetralin and Substituted Indane Derivatives
  申请人：Zhang-Plasket Fan

  公开号：US20080096962A1

  公开（公告）日：2008-04-24

  The present invention relates to novel processes for the preparation of substituted tetralin and substituted indane derivatives. The present invention is further directed to novel processes for the preparation of intermediates in the preparation of the substituted tetralin and substituted indane derivatives.

  本发明涉及一种制备取代四氢萘和取代茚烷衍生物的新工艺。本发明进一步涉及一种制备取代四氢萘和取代茚烷衍生物的中间体的新工艺。
• BICYCLIC ARYL-SULFONIC ACID [1,3,4]-THIADIAZOL-2-YL-AMIDES, PROCESSES FOR THEIR PREPARATION, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR THEIR USE
  申请人：SCHOENAFINGER Karl

  公开号：US20100022603A1

  公开（公告）日：2010-01-28

  The present invention comprises bicyclic aryl-sulfonic acid [1,3,4]-thiadiazol-2-yl-amides, their functional derivatives thereof as well as their physiologically acceptable salts and pharmaceutical compositions thereof that exhibit peroxisome proliferator activated receptor (PPAR) PPARdelta and PPARgamma agonist activity. The structure of the compounds of the invention are defined by Formula I below, wherein the various substituents are defined herein, including their physiologically acceptable salts. Processes for the preparation of compounds are also disclosed. The compounds are suitable for the treatment of fatty acid metabolism and glucose utilization disorders, disorders relating to insulin resistance are involved as well as demyelinating and other neurodegenerative disorders of the central and peripheral nervous system.

  本发明涉及双环芳基磺酸[1,3,4]-噻二唑-2-基酰胺及其功能衍生物，以及其生理上可接受的盐和药物组合物，具有过氧化物酶体增殖激活受体（PPAR）PPARδ和PPARγ激动剂活性。本发明化合物的结构由以下式I定义，其中各种取代基在此定义，包括其生理上可接受的盐。本发明还公开了制备该化合物的方法。该化合物适用于治疗与脂肪酸代谢和葡萄糖利用障碍有关的疾病，涉及胰岛素抵抗以及中枢和外周神经系统的脱髓鞘和其他神经退行性疾病。
• Bicyclic aryl-sulfonic acid [1,3,4]-thiadiazol-2-yl-amides, processes for their preparation, pharmaceutical compositions and methods for their use
  申请人：Sanofi-Aventis

  公开号：US07612104B2

  公开（公告）日：2009-11-03

  The present invention comprises bicyclic aryl-sulfonic acid [1,3,4]-thiadiazol-2-yl-amides, their functional derivatives thereof as well as their physiologically acceptable salts and pharmaceutical compositions thereof that exhibit peroxisome proliferator activated receptor (PPAR) PPARdelta and PPARgamma agonist activity. The structure of the compounds of the invention are defined by Formula I below, wherein the various substituents are defined herein, including their physiologically acceptable salts. Processes for the compounds preparation are also disclosed. The compounds are suitable for the treatment of fatty acid metabolism and glucose utilization disorders, disorders relating to insulin resistance are involved as well as demyelinating and other neurodegenerative disorders of the central and peripheral nervous system.

  本发明涵盖双环芳基磺酸[1,3,4]-噻二唑-2-基酰胺及其功能衍生物，以及其生理上可接受的盐和制药组合物，具有过氧化物酶体增殖物激活受体（PPAR）PPARδ和PPARγ激动剂活性。本发明化合物的结构由下式I定义，其中各种取代基在此处定义，包括其生理上可接受的盐。本发明还公开了制备该化合物的方法。该化合物适用于治疗与脂肪酸代谢和葡萄糖利用障碍有关的疾病，与胰岛素抵抗有关的疾病，以及中枢和周围神经系统的脱髓鞘和其他神经退行性疾病。