(E)-2-Naphthalen-2-ylmethyl-3-phenylamino-acrylonitrile | 89445-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2-Naphthalen-2-ylmethyl-3-phenylamino-acrylonitrile
• 英文别名: 2-(2-Naphthylmethyl)-3-anilinoacrylonitrile；3-anilino-2-(naphthalen-2-ylmethyl)prop-2-enenitrile
• CAS: 89445-76-1
• 化学式: C₂₀H₁₆N₂
• 分子量: 284.36
• InChiKey: RBKJGDHNKKFLFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  盐酸胍 、 (E)-2-Naphthalen-2-ylmethyl-3-phenylamino-acrylonitrile 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 36.0h， 以1.3 g的产率得到2,4-Diamino-5-(2-naphthylmethyl)pyrimidine
  参考文献：
  名称：

  Folate-Synthesizing Enzyme System as Target for Development of Inhibitors and Inhibitor Combinations against Candida albicansSynthesis and Biological Activity of New 2,4-Diaminopyrimidines and 4‘-Substituted 4-Aminodiphenyl Sulfones

  摘要：

  The paper describes the design, synthesis, and testing of inhibitors of folate-synthesizing enzymes and of whole cell cultures of Candida albicans. The target enzymes used were dihydropteroic acid synthase (SYN) and dihydrofolate reductase (DHFR). Several series of new 2,4-diaminopyrimidines were synthesized and tested as inhibitors of DHFR and compared with their activity against DHFR derived from mycobacteria and Escherichia coli. To test for selectivity, also rat DHFR was used. A series of substituted 4-aminodiphenyl sulfones was tested for inhibitory activity against SYN and the I-50 values compared to those obtained previously against Plasmodium berghei- and E. coli-derived SYN. Surprisingly, QSAR equations show very similar structural dependencies. To find an explanation for the large difference in the I-50 values observed for enzyme inhibition (SYN, DHFR) and for inhibition of cell cultures of Candida, mutant strains with overexpressed efflux pumps and strains in which such pumps are deleted were included in the study and the MICs compared. Efflux pumps were responsible for the low activity of some of the tested derivatives, others showed no increase in activity after pumps were knocked out. In this case it may be speculated that these derivatives are not able to enter the cells.

  DOI：

  10.1021/jm030931w
• 作为产物：
  描述：

  苯胺 、 在 盐酸 作用下， 以 异丙醇 为溶剂， 生成 (E)-2-Naphthalen-2-ylmethyl-3-phenylamino-acrylonitrile
  参考文献：
  名称：

  Folate-Synthesizing Enzyme System as Target for Development of Inhibitors and Inhibitor Combinations against Candida albicansSynthesis and Biological Activity of New 2,4-Diaminopyrimidines and 4‘-Substituted 4-Aminodiphenyl Sulfones

  摘要：

  The paper describes the design, synthesis, and testing of inhibitors of folate-synthesizing enzymes and of whole cell cultures of Candida albicans. The target enzymes used were dihydropteroic acid synthase (SYN) and dihydrofolate reductase (DHFR). Several series of new 2,4-diaminopyrimidines were synthesized and tested as inhibitors of DHFR and compared with their activity against DHFR derived from mycobacteria and Escherichia coli. To test for selectivity, also rat DHFR was used. A series of substituted 4-aminodiphenyl sulfones was tested for inhibitory activity against SYN and the I-50 values compared to those obtained previously against Plasmodium berghei- and E. coli-derived SYN. Surprisingly, QSAR equations show very similar structural dependencies. To find an explanation for the large difference in the I-50 values observed for enzyme inhibition (SYN, DHFR) and for inhibition of cell cultures of Candida, mutant strains with overexpressed efflux pumps and strains in which such pumps are deleted were included in the study and the MICs compared. Efflux pumps were responsible for the low activity of some of the tested derivatives, others showed no increase in activity after pumps were knocked out. In this case it may be speculated that these derivatives are not able to enter the cells.

  DOI：

  10.1021/jm030931w
• 作为试剂：
  描述：

  (E)-2-Naphthalen-2-ylmethyl-3-phenylamino-acrylonitrile 、 sodium methylate 、 盐酸胍 在 (E)-2-Naphthalen-2-ylmethyl-3-phenylamino-acrylonitrile 、 乙醇 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以which was isolated (2.66 g)的产率得到2,4-Diamino-5-(2-naphthylmethyl)pyrimidine
  参考文献：
  名称：

  2,4-diamino-5-(1,2,3,4-tetrahydro-(substituted or

  摘要：

  式子(II)的化合物 ##STR1## 或其盐、N-氧化物或酰基衍生物，其中Y是一个 ##STR2## 的基团，该基团是可选取代的，且在A、B、C、D或E位置之一可选包含一个氮原子，其中虚线代表芳香环，除非其中一个环包含氮原子，在这种情况下，该环要么是芳香的，要么是部分饱和的，具有抗微生物特性。还公开了制备这些化合物的方法、含有它们的药物组合物以及化合物的医药用途。

  公开号：

  US04587341A1