4-[(2-chlorophenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one | 6690-48-8

• 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: 4-[(2-chlorophenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one
• 英文别名: (E)-4-((2-chlorophenyl)diazenyl)phenol；4-[(E)-(Chlorophenyl)diazenyl]phenol；2'-Chlor-4-hydroxyazobenzol
• CAS: 6690-48-8
• 化学式: C₁₂H₉ClN₂O
• 分子量: 232.669
• InChiKey: UROTXSKVENIXIY-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.95
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 4-[(2-chlorophenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one 、 二甲胺 以 乙醇 、 水 为溶剂， 反应 24.0h， 以88%的产率得到4-(2-Chloro-phenylazo)-2,6-bis-dimethylaminomethyl-phenol
  参考文献：
  名称：

  Mannich bases of phenolic azobenzenes possessing cytotoxic activity

  摘要：

  A number of arylazophenols 1 were converted into the corresponding mono Mannich bases 2 from which two quaternary salts 3a,b and an ester 3c were prepared, A series of bis Mannich bases 4 were also synthesized. The angles (theta) made between one of the aryl rings and the adjacent ate linkage were determined by electronic absorption spectroscopy. X-ray crystallographic data were obtained for some of the Mannich bases. The compounds were evaluated against murine P388 D1 and L1210 cells and two human T-lymphocyte (Molt 4, GEM) lines, and most of the derivatives were also screened against a panel of human tumour cell lines. A number of correlations were noted between cytotoxicity and various physicochemical constants as well as some structural features determined by X-ray crystallography. Several of the Mannich bases were shown to have mutagenic properties using the lambda RK mutatest; the compounds in series 2 and 4 have the ability to penetrate the central nervous system, as revealed by their anticonvulsant properties. While series 2-4 have the potential to deaminate forming ortho quinone methides which would be capable of alkylating cellular thiols, the results of stability studies suggest that the bioactivities noted were due to the molecules per se.

  DOI：

  10.1016/s0223-5234(97)83284-9
• 作为产物：
  描述：

  邻氯苯胺 、 苯酚 在 盐酸 、 sodium hydroxide 、 sodium nitrite 作用下， 生成 4-[(2-chlorophenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Mannich bases of phenolic azobenzenes possessing cytotoxic activity

  摘要：

  A number of arylazophenols 1 were converted into the corresponding mono Mannich bases 2 from which two quaternary salts 3a,b and an ester 3c were prepared, A series of bis Mannich bases 4 were also synthesized. The angles (theta) made between one of the aryl rings and the adjacent ate linkage were determined by electronic absorption spectroscopy. X-ray crystallographic data were obtained for some of the Mannich bases. The compounds were evaluated against murine P388 D1 and L1210 cells and two human T-lymphocyte (Molt 4, GEM) lines, and most of the derivatives were also screened against a panel of human tumour cell lines. A number of correlations were noted between cytotoxicity and various physicochemical constants as well as some structural features determined by X-ray crystallography. Several of the Mannich bases were shown to have mutagenic properties using the lambda RK mutatest; the compounds in series 2 and 4 have the ability to penetrate the central nervous system, as revealed by their anticonvulsant properties. While series 2-4 have the potential to deaminate forming ortho quinone methides which would be capable of alkylating cellular thiols, the results of stability studies suggest that the bioactivities noted were due to the molecules per se.

  DOI：

  10.1016/s0223-5234(97)83284-9

文献信息

• SHUKUROV, A.;MAXSUMOV, A. G., UZB. XIM. ZH.,(1988) N 3, 31-34
  作者：SHUKUROV, A.、MAXSUMOV, A. G.

  DOI：——

  日期：——