2-[(4-phenylazophenyl)hydrazono]malononitrile | 66706-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 2-[(4-phenylazophenyl)hydrazono]malononitrile
• 英文别名: Propanedinitrile, [[4-(phenylazo)phenyl]hydrazono]-；2-[(4-phenyldiazenylphenyl)hydrazinylidene]propanedinitrile
• CAS: 66706-98-7
• 化学式: C₁₅H₁₀N₆
• 分子量: 274.285
• InChiKey: LDBWPTYGGBUCTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  449.5±47.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(4-phenylazophenyl)hydrazono]malononitrile 在 一水合肼 作用下， 反应 1.0h， 以90%的产率得到3,5-diamino-4-(4-phenylazophenylazo)-1H-pyrazole
  参考文献：
  名称：

  Synthesis, antitumor evaluation, molecular modeling and quantitative structure–activity relationship (QSAR) of some novel arylazopyrazolodiazine and triazine analogs

  摘要：

  The synthesis, in vivo and in vitro antitumor evaluation, and QSAR studies of some novel pyrazole analogs against Ehrlich Ascites Carcinoma (EAC) cells were described. In vitro results revealed that compounds 10, 6 and 4 were the most potent analogs against EAC, respectively. Moreover, in vivo evaluation of compounds 6 and 10 proved their capability to normalize the blood picture in comparison to 5-FU, a well known anticancer drug. These novel pyrazole analogs were molecularly designed with the goal of having significant potent cytotoxic effect against EAC cells. To develop a QSAR model capable of identifying the key molecular descriptors associated with the biological activity of the novel pyrazole analogs and predicting the cytotoxic effect for other novel pyrazole analogs against EAC cells, different QSAR models, using different physicochemical and topological molecular descriptors, were developed. Different molecular descriptors were predicted solely from the chemical structures of 16 pyrazolo-diazine and triazine analogs following the prediction of the equilibrium molecular geometry of each analog at the DFT level using B88-LYP functional energy and double zeta valence polarized (DZVP) basis set. It was found that dipole moment, excitation energy, the energy value of LUMO, solvent accessible surface area, and heat of formation were the key molecular descriptors in descriping the cytotoxic effect of those compounds against EAC. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.05.053
• 作为产物：
  描述：

  对氮蒽蓝 、 丙二腈 在 溶剂黄146 、 sodium nitrite 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以80%的产率得到2-[(4-phenylazophenyl)hydrazono]malononitrile
  参考文献：
  名称：

  Synthesis, antitumor evaluation, molecular modeling and quantitative structure–activity relationship (QSAR) of some novel arylazopyrazolodiazine and triazine analogs

  摘要：

  The synthesis, in vivo and in vitro antitumor evaluation, and QSAR studies of some novel pyrazole analogs against Ehrlich Ascites Carcinoma (EAC) cells were described. In vitro results revealed that compounds 10, 6 and 4 were the most potent analogs against EAC, respectively. Moreover, in vivo evaluation of compounds 6 and 10 proved their capability to normalize the blood picture in comparison to 5-FU, a well known anticancer drug. These novel pyrazole analogs were molecularly designed with the goal of having significant potent cytotoxic effect against EAC cells. To develop a QSAR model capable of identifying the key molecular descriptors associated with the biological activity of the novel pyrazole analogs and predicting the cytotoxic effect for other novel pyrazole analogs against EAC cells, different QSAR models, using different physicochemical and topological molecular descriptors, were developed. Different molecular descriptors were predicted solely from the chemical structures of 16 pyrazolo-diazine and triazine analogs following the prediction of the equilibrium molecular geometry of each analog at the DFT level using B88-LYP functional energy and double zeta valence polarized (DZVP) basis set. It was found that dipole moment, excitation energy, the energy value of LUMO, solvent accessible surface area, and heat of formation were the key molecular descriptors in descriping the cytotoxic effect of those compounds against EAC. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.05.053

文献信息

• Sturdik, Ernest; Durcova, Edita; Mikes, Vladimir, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 11, p. 2819 - 2825
  作者：Sturdik, Ernest、Durcova, Edita、Mikes, Vladimir、Dadak, Vladimir、Balaz, Stefan、et al.

  DOI：——

  日期：——
• Synthesis, antitumor evaluation, molecular modeling and quantitative structure–activity relationship (QSAR) of some novel arylazopyrazolodiazine and triazine analogs
  作者：Ahmed El-Shafei、A.A. Fadda、A.M. Khalil、T.A.E. Ameen、Farid A. Badria

  DOI：10.1016/j.bmc.2009.05.053

  日期：2009.7

  The synthesis, in vivo and in vitro antitumor evaluation, and QSAR studies of some novel pyrazole analogs against Ehrlich Ascites Carcinoma (EAC) cells were described. In vitro results revealed that compounds 10, 6 and 4 were the most potent analogs against EAC, respectively. Moreover, in vivo evaluation of compounds 6 and 10 proved their capability to normalize the blood picture in comparison to 5-FU, a well known anticancer drug. These novel pyrazole analogs were molecularly designed with the goal of having significant potent cytotoxic effect against EAC cells. To develop a QSAR model capable of identifying the key molecular descriptors associated with the biological activity of the novel pyrazole analogs and predicting the cytotoxic effect for other novel pyrazole analogs against EAC cells, different QSAR models, using different physicochemical and topological molecular descriptors, were developed. Different molecular descriptors were predicted solely from the chemical structures of 16 pyrazolo-diazine and triazine analogs following the prediction of the equilibrium molecular geometry of each analog at the DFT level using B88-LYP functional energy and double zeta valence polarized (DZVP) basis set. It was found that dipole moment, excitation energy, the energy value of LUMO, solvent accessible surface area, and heat of formation were the key molecular descriptors in descriping the cytotoxic effect of those compounds against EAC. Published by Elsevier Ltd.