seq-trans-1-Nitro-2-dimethylamino-1-benzoyl-aethylen | 20408-12-2

• 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: seq-trans-1-Nitro-2-dimethylamino-1-benzoyl-aethylen
• 英文别名: (E)-3-(dimethylamino)-2-nitro-1-phenylprop-2-en-1-one
• CAS: 20408-12-2
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: DDZTXIJOLLRJKP-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  seq-trans-1-Nitro-2-dimethylamino-1-benzoyl-aethylen 在 palladium on activated charcoal 一水合肼 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 4-(4-amino-5-phenyl-1H-pyrazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors:  Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)

  摘要：

  A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of ii (4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.

  DOI：

  10.1021/jm960803q
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 苯甲酰硝基甲烷 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 seq-trans-1-Nitro-2-dimethylamino-1-benzoyl-aethylen
  参考文献：
  名称：

  Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors:  Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)

  摘要：

  A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of ii (4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.

  DOI：

  10.1021/jm960803q

文献信息

• Severin,T.; Boehme,H.-J., Chemische Berichte, 1968, vol. 101, # 8, p. 2925 - 2930
  作者：Severin,T.、Boehme,H.-J.

  DOI：——

  日期：——
• TRKA KINASE INHIBITORS, COMPOSITIONS AND METHODS THEREOF
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20170114071A1

  公开（公告）日：2017-04-27

  The present invention is directed to six membered heteroaryl benzamide compounds of formula (I), which are tropomyosin-related kinase (Trk) family protein pain, inflammation, cancer, restenosis, atherosclerosis, psoriasis, thrombosis, a disease, disorder, injury, or malfunction relating to dysmyelination or demyelination or a disease or disorder associated with abnormal activities of nerve growth factor (NGF) receptor TrkA.
• US9815846B2
  申请人：——

  公开号：US9815846B2

  公开（公告）日：2017-11-14
• [EN] TRKA KINASE INHIBITORS, COMPOSITIONS AND METHODS THEREOF<br/>[FR] INHIBITEURS DE LA KINASE TRKA, COMPOSITIONS EN CONTENANT ET MÉTHODES ASSOCIÉES
  申请人：MERCK SHARP & DOHME

  公开号：WO2015148344A2

  公开（公告）日：2015-10-01

  The present invention is directed to six membered heteroaryl benzamide compounds of formula (I), which are tropomyosin-related kinase (Trk) family protein kinase inhibitors, and hence are useful in the treatment of pain, inflammation, cancer, restenosis, atherosclerosis, psoriasis, thrombosis, a disease, disorder, injury, or malfunction relating to dysmyelination or demyelination or a disease or disorder associated with abnormal activities of nerve growth factor (NGF) receptor TrkA.
• [EN] TrkA KINASE INHIBITORS,COMPOSITIONS AND METHODS THEREOF<br/>[FR] INHIBITEURS DE LA KINASE TRKA, COMPOSITIONS ET MÉTHODES ASSOCIÉES
  申请人：MERCK SHARP & DOHME

  公开号：WO2015143654A1

  公开（公告）日：2015-10-01

  The present invention is directed to six membered heteroaryl benzamide compounds of formula (I) which are tropomyosin-related kinase (Trk) family protein kinase inhibitors, and hence are useful in the treatment of pain, inflammation, cancer, restenosis, atherosclerosis, psoriasis, thrombosis, a disease, disorder, injury, or malfunction relating to dysmyelination or demyelination or a disease or disorder associated with abnormal activities of nerve growth factor (NGF) receptor TrkA.