N-(2-phenylethyl)-4-chlorobenzenesulfonamide | 133276-82-1

• 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: N-(2-phenylethyl)-4-chlorobenzenesulfonamide
• 英文别名: 4-chloro-N-phenethyl-benzenesulfonamide；2-(p-Chlorobenzenesulphonylamino)ethyl-benzene；4-chloro-N-phenethylbenzenesulfonamide；4-chloro-N-(2-phenylethyl)benzenesulfonamide
• CAS: 133276-82-1
• 化学式: C₁₄H₁₄ClNO₂S
• mdl: MFCD00708546
• 分子量: 295.79
• InChiKey: ILLHJXGCNCFSMF-UHFFFAOYSA-N

物化性质

• 沸点：
  445.1±55.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-phenylethyl)-4-chlorobenzenesulfonamide 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-(2-phenylethyl)-N-[(4-chlorophenyl)sulfonyl]glycine
  参考文献：
  名称：

  Progresses in the pursuit of aldose reductase inhibitors: The structure-based lead optimization step

  摘要：

  Aldose reductase (ALR2) is a crucial enzyme in the development of the major complications of diabetes mellitus. Very recently it has been demonstrated that the ARL2 inhibitor, fidarestat, significantly prevents inflammatory signals (TNF-alpha, LPS) that cause cancer (colon, breast, prostate and lung), metastasis, asthma, and other inflammatory diseases. Currently, fidarestat is in phase Ill clinical trial for diabetic neuropathy and was found to be safe. Thus the finding of novel, potent ARL2 inhibitors is today more than in the past in great demand as they can pave the way for a novel therapeutic approach for a number of diseases besides the diabetes. Herein, starting from the virtual screening-derived ALR2 inhibitor S12728 (1), a rational receptor-based lead optimization has been undertaken. The design and synthetic efforts here reported led to the discovery of several new compounds endowed with low micromolar/submicromolar activities. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.045
• 作为产物：
  描述：

  4-氯苯磺酰氯 以91%的产率得到N-(2-phenylethyl)-4-chlorobenzenesulfonamide
  参考文献：
  名称：

  LIBRARIES OF N-SUBSTITUTED-N-PHENYLETHYLSULFONAMIDES FOR DRUG DISCOVERY

  摘要：

  不断寻找治疗和预防疾病的新化合物。该发明涉及N-取代-N-苯乙基磺酰胺库，可用于寻找和鉴定能够调节生物靶点功能活性的新领先化合物。

  公开号：

  US20120122920A1

文献信息

• N-SUBSTITUTED-N-PHENYLETHYLSULFONAMIDES FOR THE IDENTIFICATION OF BIOLOGICAL AND PHARMACOLOGICAL ACTIVITY
  申请人：Castells Boliart Josep

  公开号：US20120149909A1

  公开（公告）日：2012-06-14

  Novel compounds are continually sought after to treat and prevent diseases and disorders. The invention relates to N-substituted-N-phenylethylsulfonamides useful for being biologically and pharmacologically screened, and to contribute to the exploration and identification of new lead molecules that are capable of modulating the functional activity of a biological target.

  小说化合物不断被寻找用于治疗和预防疾病和疾病。该发明涉及对N-取代-N-苯基乙磺酰胺的研究，该研究有助于进行生物和药理筛选，并有助于探索和识别能够调节生物靶点功能活性的新引物分子。
• Arylsulphonamides pharmaceutical compositions containing these compounds
  申请人：Dr. Karl Thomas GmbH

  公开号：US05294626A1

  公开（公告）日：1994-03-15

  The invention relates to new arylsulphonamides of the formula ##STR1## (wherein A, B and R.sub.1 to R.sub.6 are as defined in claim 1, the enantiomers, the cis- and trans-isomers thereof where R.sub.4 and R.sub.5 together represent a carbon-carbon bond, and the addition salts thereof, more particularly for pharmaceutical use the physiologically acceptable addition salts thereof with inorganic or organic bases, if R.sub.6 represents a hydroxy group) which have useful pharmacological properties, particularly antithrombotic activities and thromboxane-mediating activities. Furthermore, the new compounds are also thromboxane antagonists (TRA) and thromboxane synthesis inhibitors (TSH) They also have an effect on PGE.sub.2 production.

  该发明涉及新的芳基磺酰胺，其化学式为##STR1##（其中A、B和R.sub.1到R.sub.6如权利要求1中所定义，其对映体，顺式和反式异构体，其中R.sub.4和R.sub.5一起代表碳-碳键，以及其加合盐，更具体地用于药物的生理上可接受的与无机或有机碱形成的加合盐，如果R.sub.6代表一个羟基），这些化合物具有有用的药理特性，特别是抗血栓活性和血栓素介导活性。此外，这些新化合物也是血栓素拮抗剂（TRA）和血栓素合成抑制剂（TSH），它们还对PGE.sub.2的产生有影响。
• Arylsulphonamides, pharmaceutical compositions containing these compounds
  申请人：Dr. Karl Thomae GmbH

  公开号：US05426119A1

  公开（公告）日：1995-06-20

  The invention relates to new arylsulphonamides of the formula ##STR1## (wherein A, B and R.sub.1 to R.sub.6 are as defined in claim 1, the enantiomers, the cis- and trans-isomers thereof where R.sub.4 and R.sub.5 together represent a carbon-carbon bond, and the addition salts thereof, more particularly for pharmaceutical use the physiologically acceptable addition salts thereof with inorganic or organic bases, if R.sub.6 represents a hydroxy group) which have useful pharmacological properties, particularly antithrombotic activities and thromboxane-mediating activities. Furthermore, the new compounds are also thromboxane antagonists (TRA) and thromboxane synthesis inhibitors (TSH). They also have an effect on PGE.sub.2 production.

  本发明涉及新的芳基磺酰胺，其化学式为##STR1##（其中A，B和R.sub.1至R.sub.6如权利要求1所定义，其对映异构体，其中R.sub.4和R.sub.5共同表示碳-碳键的顺式和反式异构体，以及其加合物盐，更特别地，用于药物的生理学上可接受的无机或有机碱的加合物盐，如果R.sub.6表示羟基）。这些化合物具有有用的药理学特性，特别是抗血栓活性和血栓素介导的活性。此外，这些新化合物也是血栓素拮抗剂（TRA）和血栓素合成抑制剂（TSH）。它们还具有对PGE.sub.2产生的影响。
• Arylsulphonamides, pharmaceutical compositions containing these
  申请人：Dr. Karl Thomae GmbH

  公开号：US05681961A1

  公开（公告）日：1997-10-28

  The invention relates to new arylsulphonamides of the formula ##STR1## (wherein A, B and R.sub.1 to R.sub.6 are as defined in claim 1, the enantiomers, the cis- and trans-isomers thereof where R.sub.4 and R.sub.5 together represent a carbon-carbon bond, and the addition salts thereof, more particularly for pharmaceutical use the physiologically acceptable addition salts thereof with inorganic or organic bases, if R.sub.6 represents a hydroxy group) which have useful pharmacological properties, particularly antithrombotic activities and thromboxane-mediating activities. Furthermore, the new compounds are also thromboxane antagonists (TRA) and thromboxane synthesis inhibitors (TSH). They also have an effect on PGE.sub.2 production.

  该发明涉及一种新的芳基磺酰胺，其化学式为##STR1##（其中A、B和R.sub.1到R.sub.6如权利要求1所定义，其对映异构体，顺式和反式异构体，其中R.sub.4和R.sub.5共同表示碳-碳键，以及其加合盐，特别是用无机或有机碱的生理上可接受的加合盐，如果R.sub.6表示羟基）。这些化合物具有有用的药理学性质，特别是抗血栓活性和血栓素介导活性。此外，新的化合物也是血栓素拮抗剂（TRA）和血栓素合成抑制剂（TSH）。它们还对PGE.sub.2的产生有影响。
• LIBRARIES OF N-SUBSTITUTED-N-PHENYLETHYLSULFONAMIDES FOR THE IDENTIFICATION OF BIOLOGICAL AND PHARMACOLOGICAL ACTIVITY
  申请人：Castells Boliart Josep

  公开号：US20120122710A1

  公开（公告）日：2012-05-17

  New compounds are continually sought after for the treatment and prevention of disorders. The invention relates to N-substituted-N-phenylethylsulfonamides which can be biologically and pharmacologically traced, in order to be used in the search for, and identification of, new lead compounds that can modulate the functional activity of a biological target.

  不断寻找治疗和预防疾病的新化合物。本发明涉及N-取代-N-苯乙基磺酰胺，可在生物学和药理学上追踪，以便用于寻找和识别可以调节生物靶点的功能活性的新先导化合物。