4-{[(4-氯苯基)亚肼基]甲基}吡啶 | 66784-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-{[(4-氯苯基)亚肼基]甲基}吡啶
• 英文名称: 4-{[(4-chlorophenyl)hydrazono]methyl}pyridine
• 英文别名: pyridine-4-aldehyde (4-chloro-phenyl)hydrazone；4-chloro-N-(pyridin-4-ylmethylideneamino)aniline
• CAS: 66784-47-2
• 化学式: C₁₂H₁₀ClN₃
• 分子量: 231.685
• InChiKey: IONVYBCQSMGHKM-UHFFFAOYSA-N

物化性质

• 沸点：
  378.6±38.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-{[(4-氯苯基)亚肼基]甲基}吡啶 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以31%的产率得到N-(4-chlorophenyl)pyridine-4-carbohydrazonoyl chloride
  参考文献：
  名称：

  Tri- and Tetrasubstituted Pyrazole Derivates: Regioisomerism Switches Activity from p38MAP Kinase to Important Cancer Kinases

  摘要：

  In the course of searching for new p38 alpha MAP kinase inhibitors, we found that the regioisomeric switch from 3-(4-fluorophenyl)-4-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine to 4-(4-fluorophenyl)-3-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine led to an almost complete loss of p38a inhibition, but they showed activity against important cancer kinases. Among the tested derivatives, 4-(4-fluorophenyl)-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-1H-pyrazol-S-amine (6a) exhibited the best activity, with IC50 in the nanomolar range against Src, B-Raf wt, B-Raf V600E, EGFRs, and VEGFR-2, making it a good lead for novel anticancer programs.

  DOI：

  10.1021/jm201391u
• 作为产物：
  描述：

  4-吡啶甲醛 、 4-氯苯肼 以 乙醇 为溶剂， 生成 4-{[(4-氯苯基)亚肼基]甲基}吡啶
  参考文献：
  名称：

  Tri- and Tetrasubstituted Pyrazole Derivates: Regioisomerism Switches Activity from p38MAP Kinase to Important Cancer Kinases

  摘要：

  In the course of searching for new p38 alpha MAP kinase inhibitors, we found that the regioisomeric switch from 3-(4-fluorophenyl)-4-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine to 4-(4-fluorophenyl)-3-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine led to an almost complete loss of p38a inhibition, but they showed activity against important cancer kinases. Among the tested derivatives, 4-(4-fluorophenyl)-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-1H-pyrazol-S-amine (6a) exhibited the best activity, with IC50 in the nanomolar range against Src, B-Raf wt, B-Raf V600E, EGFRs, and VEGFR-2, making it a good lead for novel anticancer programs.

  DOI：

  10.1021/jm201391u

文献信息

• Process for the preparation of cationic dyestuffs
  申请人：Bayer Aktiengesellschaft

  公开号：US04349670A1

  公开（公告）日：1982-09-14

  To prepare dyestuffs of the general formula ##STR1## in which R.sup.1 and R.sup.2 represent methyl or ethyl, n represents 0 or 1, B represents the divalent radical of a 5-membered or 6-membered heterocyclic ring system and X.sup.- represents an anion, and wherein the ring a can be substituted by C.sub.1 - to C.sub.4 -alkyl radicals, C.sub.1 - to C.sub.4 -alkoxy radicals or halogen, compounds of the formula ##STR2## wherein R.sup.1, B and n have the meaning indicated above, m represents 0 or 1 and the ring a can be substituted by C.sub.1 - to C.sub.4 -alkyl, C.sub.1 - to C.sub.4 -alkoxy or halogen, or of the formula ##STR3## in which B and R.sup.1 have the abovementioned meaning and the ring a can be substituted by C.sub.1 - to C.sub.4 -alkyl, C.sub.1 - to C.sub.4 -alkoxy or halogen, are reacted with arylsulphonic acid esters of the formula ##STR4## wherein R represents hydrogen, C.sub.1 - to C.sub.4 -alkyl or halogen and R.sup.2 represents methyl or ethyl, in the presence of water and acid-binding agents at temperatures of 20.degree.-70.degree. C., and, if appropriate, the arylsulphonate anion is replaced by another anion customary in dyestuff chemistry.

  为了制备一般公式为##STR1##的染料，其中R.sup.1和R.sup.2代表甲基或乙基，n代表0或1，B代表5-或6-成员杂环环系统的二价基团，X.sup.-代表阴离子，且环a可以被C.sub.1-到C.sub.4-烷基基团，C.sub.1-到C.sub.4-烷氧基团或卤素取代，化合物的公式为##STR2##其中R.sup.1，B和n具有上述所示含义，m代表0或1，环a可以被C.sub.1-到C.sub.4-烷基，C.sub.1-到C.sub.4-烷氧基或卤素取代，或者公式为##STR3##其中B和R.sup.1具有上述所述含义，环a可以被C.sub.1-到C.sub.4-烷基，C.sub.1-到C.sub.4-烷氧基或卤素取代，与染料化学中常见的芳基磺酸酯反应，其公式为##STR4##其中R代表氢，C.sub.1-到C.sub.4-烷基或卤素，R.sup.2代表甲基或乙基，在水和酸性结合剂存在下，在20度至70度的温度下反应，如有必要，芳基磺酸盐阴离子被其他染料化学中常见的阴离子替代。
• Tri- and Tetrasubstituted Pyrazole Derivates: Regioisomerism Switches Activity from p38MAP Kinase to Important Cancer Kinases
  作者：Bassam Abu Thaher、Martina Arnsmann、Frank Totzke、Jan E. Ehlert、Michael H. G. Kubbutat、Christoph Schächtele、Markus O. Zimmermann、Pierre Koch、Frank M. Boeckler、Stefan A. Laufer

  DOI：10.1021/jm201391u

  日期：2012.1.26

  In the course of searching for new p38 alpha MAP kinase inhibitors, we found that the regioisomeric switch from 3-(4-fluorophenyl)-4-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine to 4-(4-fluorophenyl)-3-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine led to an almost complete loss of p38a inhibition, but they showed activity against important cancer kinases. Among the tested derivatives, 4-(4-fluorophenyl)-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-1H-pyrazol-S-amine (6a) exhibited the best activity, with IC50 in the nanomolar range against Src, B-Raf wt, B-Raf V600E, EGFRs, and VEGFR-2, making it a good lead for novel anticancer programs.