5-ethynylthiophene-2-sulfonamide | 850340-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-ethynylthiophene-2-sulfonamide
• 英文别名: 5-Ethynylthiophene-2-sulfonamide
• CAS: 850340-82-8
• 化学式: C₆H₅NO₂S₂
• 分子量: 187.243
• InChiKey: HCEALRCEDNZDIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  387.3±52.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-叠氮基萘 、 5-ethynylthiophene-2-sulfonamide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 溶剂黄146 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.83h， 以89%的产率得到5-[1-(naphthalen-1-yl)-1H-1,2,3-triazol-4-yl]thiophene-2-sulfonamide
  参考文献：
  名称：

  5-Substituted-(1,2,3-triazol-4-yl)thiophene-2-sulfonamides strongly inhibit human carbonic anhydrases I, II, IX and XII: Solution and X-ray crystallographic studies

  摘要：

  We report here a series of 2-thiophene-sulfonamides incorporating 1-substituted aryl-1,2,3-triazolyl moieties, prepared by click chemistry from 5-ethynylthiophene-2-sulfonamide and substituted aryl azides. The new sulfonamides were investigated as inhibitors of the zinc metalloenzyme CA (EC 4.2.1.1), and more specifically against the human (h) cytosolic isoforms hCA I and II and the transmembrane, tumor-associated ones hCA IX and XII: The new compounds were medium-weak hCA I inhibitors (K(I)s in the range of 224-7544 nM), but were compactly, highly effective, low nanomolar hCA II inhibitors (K(I)s of 2.2-7.7 nM). The tumor-associated hCA IX was inhibited with K(I)s ranging between 5.4 and 811 nM, whereas hCA XII with inhibition constants in the range of 3.4-239 nM. The X-ray crystal structure of the adducts of two such compounds bound to hCA II (one incorporating 1-naphthyl, the other one 3-cyanophenyl moieties) evidenced the reasons of the high affinity for hCA II. Highly favorable, predominantly hydrophobic interactions between the sulfonamide scaffold and the hCA II active site were responsible for the binding, in addition to the coordination of the sulfamoyl moiety to the zinc ion. The tails of the two inhibitors adopted very diverse orientations when bound to the active site, with the naphthyltriazolyl moiety orientated towards the hydrophobic half of the active site, and the 3-cyanophenyl one pointing towards the hydrophilic half. These data may be used for the structure-based drug design of even more effective hCA II inhibitors, with potential use as antiglaucoma agents or as diuretics. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.041
• 作为产物：
  描述：

  N-[(dimethylamino)methylidene]-5-[2-(trimethylsilyl)ethynyl]thiophene-2-sulfonamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以50%的产率得到5-ethynylthiophene-2-sulfonamide
  参考文献：
  名称：

  5-Substituted-(1,2,3-triazol-4-yl)thiophene-2-sulfonamides strongly inhibit human carbonic anhydrases I, II, IX and XII: Solution and X-ray crystallographic studies

  摘要：

  We report here a series of 2-thiophene-sulfonamides incorporating 1-substituted aryl-1,2,3-triazolyl moieties, prepared by click chemistry from 5-ethynylthiophene-2-sulfonamide and substituted aryl azides. The new sulfonamides were investigated as inhibitors of the zinc metalloenzyme CA (EC 4.2.1.1), and more specifically against the human (h) cytosolic isoforms hCA I and II and the transmembrane, tumor-associated ones hCA IX and XII: The new compounds were medium-weak hCA I inhibitors (K(I)s in the range of 224-7544 nM), but were compactly, highly effective, low nanomolar hCA II inhibitors (K(I)s of 2.2-7.7 nM). The tumor-associated hCA IX was inhibited with K(I)s ranging between 5.4 and 811 nM, whereas hCA XII with inhibition constants in the range of 3.4-239 nM. The X-ray crystal structure of the adducts of two such compounds bound to hCA II (one incorporating 1-naphthyl, the other one 3-cyanophenyl moieties) evidenced the reasons of the high affinity for hCA II. Highly favorable, predominantly hydrophobic interactions between the sulfonamide scaffold and the hCA II active site were responsible for the binding, in addition to the coordination of the sulfamoyl moiety to the zinc ion. The tails of the two inhibitors adopted very diverse orientations when bound to the active site, with the naphthyltriazolyl moiety orientated towards the hydrophobic half of the active site, and the 3-cyanophenyl one pointing towards the hydrophilic half. These data may be used for the structure-based drug design of even more effective hCA II inhibitors, with potential use as antiglaucoma agents or as diuretics. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.041

文献信息

• [EN] SUBSTITUTED ISOQUINOLINONES<br/>[FR] ISOQUINOLEINONES SUBSTITUEES
  申请人：PORTOLA PHARM INC

  公开号：WO2005035520A1

  公开（公告）日：2005-04-21

  Isoquinolinone compounds are provided that are useful for the inhibition of ADP-platelet aggregation, particularly in the treatment of thrombosis and thrombosis related conditions or disorders.

  提供了对异喹啉酮化合物，这些化合物对于抑制ADP-血小板聚集特别有用，尤其在治疗血栓形成和与血栓形成相关的疾病或疾病时。
• Acetylenyl-pyrazolo-pyrimidine derivatives
  申请人：McArthur Gatti Silvia

  公开号：US20060217387A1

  公开（公告）日：2006-09-28

  The present invention relates to compounds of formula (I): wherein R 1 to R 3 , A, M, L, E, G, and J are as defined in the description and claims. The invention also relates to a process for the manufacture of such compounds, pharmaceutical compositions containing them, and methods for treating CNS disorders.

  本发明涉及式(I)的化合物：其中R1到R3、A、M、L、E、G和J的定义如描述和索赔中所述。该发明还涉及一种制备此类化合物的方法、含有它们的药物组合物，以及治疗中枢神经系统疾病的方法。
• Substituted isoquinolinones
  申请人：Scarborough M. Robert

  公开号：US20050113399A1

  公开（公告）日：2005-05-26

  Isoquinolinone compounds are provided that are useful for the inhibition of ADP-platelet aggregation, particularly in the treatment of thrombosis and thrombosis related conditions or disorders.

  提供了一些异喹啉酮化合物，这些化合物对于抑制ADP-血小板聚集非常有用，特别是在治疗血栓形成和与血栓形成相关的疾病或疾病方面。
• ACETYLENYL-PYRAZOLO-PYRIMIDINE DERIVATIVES
  申请人：Gatti McArthur Silvia

  公开号：US20080300250A1

  公开（公告）日：2008-12-04

  The present invention relates to compounds of formula (I): wherein R 1 to R 3 , A, M, L, E, G, and J are as defined in the description and claims. The invention also relates to a process for the manufacture of such compounds, pharmaceutical compositions containing them, and methods for treating CNS disorders.

  本发明涉及式(I)的化合物： 其中R1至R3，A，M，L，E，G和J如描述和索赔中所定义。本发明还涉及制备这种化合物的方法，含有这些化合物的药物组合物以及治疗中枢神经系统疾病的方法。
• SUBSTITUTED ISOQUINOLINONES
  申请人：Portola Pharmaceuticals, Inc.

  公开号：EP1667989A1

  公开（公告）日：2006-06-14