trifluoroacetaldehyde N-(2,4,6-trichlorophenyl)-hydrazone | 118236-82-1

• 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: trifluoroacetaldehyde N-(2,4,6-trichlorophenyl)-hydrazone
• 英文别名: 2,4,6-trichloro-N-(2,2,2-trifluoroethylideneamino)aniline
• CAS: 118236-82-1
• 化学式: C₈H₄Cl₃F₃N₂
• 分子量: 291.487
• InChiKey: WOXUHGYFYRXSHC-UHFFFAOYSA-N

物化性质

• 熔点：
  43-45 °C
• 沸点：
  267.6±40.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trifluoroacetaldehyde N-(2,4,6-trichlorophenyl)-hydrazone 在 N-溴代丁二酰亚胺(NBS) 、 sodium ethanolate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 5-amino-4-carboxamido-1-(2,4,6-trichlorophenyl)-3-trifluoromethylpyrazole
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1-Aryl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one Inhibitors of Cyclin-Dependent Kinases

  摘要：

  Using a high-throughput screening strategy, a series of 1-aryl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-ones was identified that inhibit the cyclin-dependent kinase (CDK) 4/cyclin D1 complex-mediated phosphorylation of a protein substrate with IC(50)s in the low micromolar range. On the basis of preliminary structure-activity relationships (SAR), a model was proposed in which these inhibitors occupy the ATP-binding site of the enzyme, forming critical hydrogen bonds to the same residue (Val96) to which the amino group in ATP is presumed to bind. X-ray diffraction studies on a later derivative bound to CDK2 support this binding mode. Iterative cycles of synthesis and screening lead to a novel series of potent, CDK2-selective 6-(arylmethyl)pyrazolopyrimidinones. Placement of a hydrogen-bond donor in the meta-position on the 6-arylmethyl group resulted in approximately 100-fold increases in CDK4 affinity, giving ligands that were equipotent inhibitors of CDK4 and CDK2. These compounds exhibit antiproliferative effects in the NCI HCT116 and other cell lines. The potency of these antiproliferative effects is enhanced in anilide derivatives and translates into tumor growth inhibition in a mouse xenograft model.

  DOI：

  10.1021/jm020455u
• 作为产物：
  描述：

  2,4,6-三氯苯肼 、 1-乙氧基-2,2,2-三氟乙醇 以 乙醇 为溶剂， 反应 16.0h， 生成 trifluoroacetaldehyde N-(2,4,6-trichlorophenyl)-hydrazone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1-Aryl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one Inhibitors of Cyclin-Dependent Kinases

  摘要：

  Using a high-throughput screening strategy, a series of 1-aryl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-ones was identified that inhibit the cyclin-dependent kinase (CDK) 4/cyclin D1 complex-mediated phosphorylation of a protein substrate with IC(50)s in the low micromolar range. On the basis of preliminary structure-activity relationships (SAR), a model was proposed in which these inhibitors occupy the ATP-binding site of the enzyme, forming critical hydrogen bonds to the same residue (Val96) to which the amino group in ATP is presumed to bind. X-ray diffraction studies on a later derivative bound to CDK2 support this binding mode. Iterative cycles of synthesis and screening lead to a novel series of potent, CDK2-selective 6-(arylmethyl)pyrazolopyrimidinones. Placement of a hydrogen-bond donor in the meta-position on the 6-arylmethyl group resulted in approximately 100-fold increases in CDK4 affinity, giving ligands that were equipotent inhibitors of CDK4 and CDK2. These compounds exhibit antiproliferative effects in the NCI HCT116 and other cell lines. The potency of these antiproliferative effects is enhanced in anilide derivatives and translates into tumor growth inhibition in a mouse xenograft model.

  DOI：

  10.1021/jm020455u

文献信息

• 5-amino-3-halogenoalkyl-1-aryl-pyrazoles, composition containing them,
  申请人：Bayer Aktiengesellschaft

  公开号：US04808623A1

  公开（公告）日：1989-02-28

  Novel insecticidally active compounds of the formula ##STR1## in which R.sup.1 represents halogenoalkyl, R.sup.2 represents cyano, hydroxycarbonyl, carbamoyl, thiocarbamoyl, alkoxycarbonyl, N-alkylcarbamoyl or N,N-dialkylcarbamoyl, or represents alkenyloxycarbonyl, N-alkenylcarbamoyl, N,N-dialkenylcarbamoyl, alkinyloxycarbonyl, N-alkinylcarbamoyl, N,N-dialkinylcarbamoyl or N-arylcarbamoyl and Ar represents substituted phenyl, with the exception of the 4-nitrophenyl radical.

  该公式表示的新型杀虫活性化合物为##STR1##其中R.sup.1代表卤代烷基，R.sup.2代表氰基、羟基羰基、氨基羰基、硫氨基羰基、烷氧羰基、N-烷基氨基羰基或N,N-二烷基氨基羰基，或代表烯氧羰基、N-烯基氨基羰基、N,N-二烯基氨基羰基、炔氧羰基、N-炔基氨基羰基、N,N-二炔基氨基羰基或N-芳基氨基羰基，Ar代表取代苯基，但不包括4-硝基苯基基团。
• 3-halogenoalkyl-1-aryl-pyrazole pesticides, compositions and use
  申请人：Bayer Aktiengesellschaft

  公开号：US04868198A1

  公开（公告）日：1989-09-19

  Arthropodically active 3-halogenoalkyl-1-arylpyrzoles of the formula ##STR1## in which R.sup.1 represents halogenoalkyl, R.sup.2 represents cyano, or represents hydroxycarbonyl, or represents carbamoyl or thiocarbamoyl, or represents alkoxycarbonyl, N-alkylcarbamoyl or N,N-dialkylcarbamoyl, or represents alkenyloxycarbonyl, N-alkenylcarbamoyl or N,N-dialkenylcarbamoyl, or represents alkinyloxycarbonyl, N-alkinylcarbamoyl, N,N-dialkinylcarbamoyl or N-arylcarbamoyl, or represents alkylcarbonyl, halogenoalkycarbonyl or cycloalkylcarbonyl, R.sup.3 represents hydrogen, alkyl, halogenoalkyl or cycloalkyl and Ar represents substituted phenyl, with the exception of the 2,4-dinitrophenyl radical.

  公式为##STR1##的具有节肢动物活性的3-卤代烷基-1-芳基吡唑化合物，其中R.sup.1代表卤代烷基，R.sup.2代表氰基，或代表羟基羰基，或代表氨基甲酰基或硫氨基甲酰基，或代表烷氧羰基，N-烷基氨基甲酰基或N,N-二烷基氨基甲酰基，或代表烯氧羰基，N-烯基氨基甲酰基或N,N-二烯基氨基甲酰基，或代表炔氧羰基，N-炔基氨基甲酰基，N,N-二炔基氨基甲酰基或N-芳基氨基甲酰基，或代表烷基羰基，卤代烷基羰基或环烷基羰基，R.sup.3代表氢、烷基、卤代烷基或环烷基，Ar代表取代苯基，但不包括2,4-二硝基苯基基团。