1-[4-(methylsulfonyl)phenyl]pyrazole-5-carbaldehyde | 572912-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[4-(methylsulfonyl)phenyl]pyrazole-5-carbaldehyde
• 英文别名: 2-(4-methanesulfonyl-phenyl)-2H-pyrazole-3-carbaldehyde；2-(4-methylsulfonylphenyl)pyrazole-3-carbaldehyde
• CAS: 572912-95-9
• 化学式: C₁₁H₁₀N₂O₃S
• 分子量: 250.278
• InChiKey: QMPLQTZHKQTZIK-UHFFFAOYSA-N

物化性质

• 熔点：
  142-144 °C(Solv: isopropanol (67-63-0))
• 沸点：
  471.0±41.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-苯基羟胺 盐酸盐 、 1-[4-(methylsulfonyl)phenyl]pyrazole-5-carbaldehyde 以 乙醇 为溶剂， 反应 2.0h， 以21%的产率得到(E)-1-[2-(4-methylsulfonylphenyl)pyrazol-3-yl]-N-phenoxymethanimine
  参考文献：
  名称：

  Synthesis of heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors: effects on the inhibitory activity of the replacement of the cyclopentene central core with pyrazole, thiophene or isoxazole ring

  摘要：

  Several heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors, in which the cyclopentene moiety was replaced by pyrazole, thiophene or isoxazole ring, were synthesized, in order to verify the influence of the different nature of the central core on the COX inhibitory properties of these kinds of molecules. Among the compounds tested, only the 3-(p-methylsulfonylphenyl) substituted thiophene derivatives 17 and 22, showed a certain COX-2 inhibitory activity, accompanied by an appreciable COX-2 versus COX-1 selectivity. Only one of the 1-(p-methylsulfonylphenyl)pyrazole compounds (16) displayed a modest inhibitory activity towards both type of isoenzymes. while the pyrazole 1-(p-aminosulfonylphenyl) substituted 12 proved to be significantly active only towards COX-1. All the isoxazole derivatives were inactive on both COX isoforms. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01448-4
• 作为产物：
  描述：

  4-甲硫基苯肼盐酸盐 在 Oxone 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 水 为溶剂， 反应 11.0h， 生成 1-[4-(methylsulfonyl)phenyl]pyrazole-5-carbaldehyde
  参考文献：
  名称：

  Synthesis of heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors: effects on the inhibitory activity of the replacement of the cyclopentene central core with pyrazole, thiophene or isoxazole ring

  摘要：

  Several heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors, in which the cyclopentene moiety was replaced by pyrazole, thiophene or isoxazole ring, were synthesized, in order to verify the influence of the different nature of the central core on the COX inhibitory properties of these kinds of molecules. Among the compounds tested, only the 3-(p-methylsulfonylphenyl) substituted thiophene derivatives 17 and 22, showed a certain COX-2 inhibitory activity, accompanied by an appreciable COX-2 versus COX-1 selectivity. Only one of the 1-(p-methylsulfonylphenyl)pyrazole compounds (16) displayed a modest inhibitory activity towards both type of isoenzymes. while the pyrazole 1-(p-aminosulfonylphenyl) substituted 12 proved to be significantly active only towards COX-1. All the isoxazole derivatives were inactive on both COX isoforms. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01448-4

文献信息

• Substituted pyridines that are JNK inhibitors
  申请人：Merck Sharp & Dohme

  公开号：US08278337B2

  公开（公告）日：2012-10-02

  Disclosed are compounds of the formula (I) wherein X is N or CH, and Y is N or CR5. Also disclosed are methods of treating JNK and ERK mediated diseases using the compounds of formula 1.0.

  本发明涉及式(I)的化合物，其中X为N或CH，Y为N或CR5。本发明还涉及使用式1.0的化合物治疗JNK和ERK介导的疾病的方法。
• NOVEL JNK INHIBITORS
  申请人：Belanger David B.

  公开号：US20100179141A1

  公开（公告）日：2010-07-15

  Disclosed are compounds of the formula (I) wherein X is N or CH, and Y is N or CR 5 . Also disclosed are methods of treating JNK and ERK mediated diseases using the compounds of formula 1.0.

  本文披露了式(I)化合物，其中X为N或CH，Y为N或CR5。同时，本文还披露了使用式1.0化合物治疗JNK和ERK介导的疾病的方法。
• WO2008/82487
  申请人：——

  公开号：——

  公开（公告）日：——
• JNK INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2132178B1

  公开（公告）日：2015-08-19
• US8278337B2
  申请人：——

  公开号：US8278337B2

  公开（公告）日：2012-10-02