4-(N',N'-dimethylaminomethyleneaminosulfonyl)benzoyl chloride | 798572-79-9

• 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-(N',N'-dimethylaminomethyleneaminosulfonyl)benzoyl chloride
• 英文别名: 4-[(E)-dimethylaminomethylideneamino]sulfonylbenzoyl chloride
• CAS: 798572-79-9
• 化学式: C₁₀H₁₁ClN₂O₃S
• 分子量: 274.728
• InChiKey: BKIRVPGCSLYXCF-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(N',N'-dimethylaminomethyleneaminosulfonyl)benzoyl chloride 在 potassium carbonate 、 一水合肼 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.83h， 生成 5-(4-aminosulfonylphenyl)-(4-fluorophenyl)-3-pivaloylmethoxy-pyrazole
  参考文献：
  名称：

  Synthesis of 4,5-Diaryl-1H-pyrazole-3-ol Derivatives as Potential COX-2 Inhibitors

  摘要：

  4,5-Diaryl-1H-pyrazole-3-ol was utilized as a versatile template to synthesize several classes of compounds such as pyrazolo-oxazines 7, pyrazolo-benzooxazines 9, pyrazolo-oxazoles 10, and its analogues 11a-c as potential COX-2 inhibitors. Compounds 11b,c were successfully synthesized with use of pyridinium p-toluenesulfonate mediated cyclization of the ketal intermediate. Diaryl-pyrazolo-benzooxazepine analogues were synthesized by using Cu-mediated cyclization of the O-alkylated arylbromide intermediate. Arylsulfonamides were synthesized efficiently on a large scale with 4-[4-(4-fluorophenyl)-5-hydroxy-2H-pyrazol-3-yl]benzenesulfonamide 31 template readily synthesized from commercially available 4-sulfamoyl benzoic acid 29. The structure of a representative compound from each class was confirmed by X-ray crystallography. Selected compounds tested for inhibitory activity against COX-1 and COX-2 enzymes showed good selectivity for COX-2 versus COX-1 enzyme.

  DOI：

  10.1021/jo049264k
• 作为产物：
  描述：

  对羧基苯磺酰胺 、 N,N-二甲基甲酰胺 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-(N',N'-dimethylaminomethyleneaminosulfonyl)benzoyl chloride
  参考文献：
  名称：

  Synthesis of 4,5-Diaryl-1H-pyrazole-3-ol Derivatives as Potential COX-2 Inhibitors

  摘要：

  4,5-Diaryl-1H-pyrazole-3-ol was utilized as a versatile template to synthesize several classes of compounds such as pyrazolo-oxazines 7, pyrazolo-benzooxazines 9, pyrazolo-oxazoles 10, and its analogues 11a-c as potential COX-2 inhibitors. Compounds 11b,c were successfully synthesized with use of pyridinium p-toluenesulfonate mediated cyclization of the ketal intermediate. Diaryl-pyrazolo-benzooxazepine analogues were synthesized by using Cu-mediated cyclization of the O-alkylated arylbromide intermediate. Arylsulfonamides were synthesized efficiently on a large scale with 4-[4-(4-fluorophenyl)-5-hydroxy-2H-pyrazol-3-yl]benzenesulfonamide 31 template readily synthesized from commercially available 4-sulfamoyl benzoic acid 29. The structure of a representative compound from each class was confirmed by X-ray crystallography. Selected compounds tested for inhibitory activity against COX-1 and COX-2 enzymes showed good selectivity for COX-2 versus COX-1 enzyme.

  DOI：

  10.1021/jo049264k

文献信息

• 2-Imino-benzimidazoles
  申请人：Roth P. Gregory

  公开号：US20070232673A1

  公开（公告）日：2007-10-04

  Novel compounds of Formula (I) or pharmaceutically acceptable salts, prodrugs and biologically active metabolites thereof of Formula (I) wherein the substituents are as defined herein, which are useful as therapeutic agents.

  本发明涉及式（I）的新化合物或其药学上可接受的盐、前药和生物活性代谢物，其中取代基如本文所定义，其作为治疗剂具有用处。
• Synthesis of 4,5-Diaryl-1<i>H</i>-pyrazole-3-ol Derivatives as Potential COX-2 Inhibitors
  作者：Meena V. Patel、Randy Bell、Sandra Majest、Rodger Henry、Teodozyj Kolasa

  DOI：10.1021/jo049264k

  日期：2004.10.1

  4,5-Diaryl-1H-pyrazole-3-ol was utilized as a versatile template to synthesize several classes of compounds such as pyrazolo-oxazines 7, pyrazolo-benzooxazines 9, pyrazolo-oxazoles 10, and its analogues 11a-c as potential COX-2 inhibitors. Compounds 11b,c were successfully synthesized with use of pyridinium p-toluenesulfonate mediated cyclization of the ketal intermediate. Diaryl-pyrazolo-benzooxazepine analogues were synthesized by using Cu-mediated cyclization of the O-alkylated arylbromide intermediate. Arylsulfonamides were synthesized efficiently on a large scale with 4-[4-(4-fluorophenyl)-5-hydroxy-2H-pyrazol-3-yl]benzenesulfonamide 31 template readily synthesized from commercially available 4-sulfamoyl benzoic acid 29. The structure of a representative compound from each class was confirmed by X-ray crystallography. Selected compounds tested for inhibitory activity against COX-1 and COX-2 enzymes showed good selectivity for COX-2 versus COX-1 enzyme.