N,N-二(2-氯乙基)-3-甲氧基苯胺 | 6636-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: N,N-二(2-氯乙基)-3-甲氧基苯胺
• 英文名称: N,N-bis(2-chloroethyl)-3-methoxylaniline
• 英文别名: N,N-bis-(2-chloro-ethyl)-m-anisidine；N,N-Bis-(2-chlor-aethyl)-m-anisidin；N,N-Bis-<2-chlor-aethyl>-3-methoxy-anilin；n,n-Bis(2-chloroethyl)-3-methoxyaniline
• CAS: 6636-74-4
• 化学式: C₁₁H₁₅Cl₂NO
• 分子量: 248.152
• InChiKey: YEUHPMAALSITIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二(2-氯乙基)-3-甲氧基苯胺 生成 N,N-bis-(2-chloro-ethyl)-3-methoxy-4-nitroso-aniline
  参考文献：
  名称：

  Ross et al., Journal of the Chemical Society, 1955, p. 3110,3115

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-bis(2-(methylsulfonyloxy)ethyl)-3-methoxylaniline 在 sodium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以40%的产率得到N,N-二(2-氯乙基)-3-甲氧基苯胺
  参考文献：
  名称：

  Synthesis and structure–analgesic activity relationships of a novel series of monospirocyclopiperazinium salts (MSPZ)

  摘要：

  A series of monospirocyclopiperazinium salts were designed and synthesized to search for a peripherally-acting analgesic drug with low side effects. Extensive SAR studies revealed that a suitable (NRR3)-R-2 was critical for the analgesic activity, which might be beneficial to expose the cationic nitrogen to bind to the receptor, and possibly interact with the receptor via pi-pi interaction. Introduction of substituting group on the N-4-phenyl ring could improve the activity, and the best position was the 4-position. Compound 14n showed more potent analgesic activity (63%, 20 mu M/kg, sc) and holds promise for development as a mechanically new analgesic drug. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.052

文献信息

• Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines
  作者：Brian D. Palmer、William R. Wilson、Susan M. Pullen、William A. Denny

  DOI：10.1021/jm00163a019

  日期：1990.1

  A series of aniline mustards with a wide range of electron-donating and -withdrawing substituents in the 3- and 4-positions has been synthesized and evaluated for cytotoxicity in cell culture to examine the potential of using nitro group deactivated nitrogen mustards for the design of novel hypoxia-selective anticancer drugs (Denny, W. A.; Wilson, W. R. J. Med. Chem. 1986, 29, 879). Hydrolytic half-lives in tissue culture media, determined by bioassay against a cell line (UV4) defective in the repair of DNA interstrand cross-links showed the expected dependence on the Hammett electronic parameter, sigma, varying from 0.13 h for the 4-amino analogue to greater than 100 h for analogues with strongly electron-withdrawing substituents. Cytotoxic potencies in aerobic UV4 cultures showed a similar dependence on sigma. This dependence predicted that the 4-nitroaniline mustard would be 7200-fold less potent than its potential six-electron reduction product, the 4-amino compound, in growth inhibition assays using a 1-h drug exposure. The measured differential was much lower (225-fold) because of the instability of the latter compound, but a differential of 17,500-fold was observed in the initial rate of killing by using a clonogenic assay. The potential for formation of reactive mustards by reduction to the amine or hydroxylamine was demonstrated by the 4-nitroso compound, which had an aerobic toxicity similar to that of the amine. Although these features confirmed the original rationale, the 3-nitro- and 4-nitroaniline mustards had only minimal hypoxic selectivity against UV cells. Toxicity to hypoxic cells appears to be limited by the low reduction potentials of these compounds and consequent lack of enzymatic nitroreduction. However, this study has demonstrated that nitro groups can be used to latentiate aromatic nitrogen mustards and indicates that examples with higher reduction potentials could provide useful hypoxia-selective therapeutic agents.
• 276. Aryl-2-halogenoalkylamines. Part XVI. The preparation of derivatives of 4-[di-(2-chloroalkyl)amino]azobenzenes
  作者：W. C. J. Ross、G. P. Warwick

  DOI：10.1039/jr9560001364

  日期：——
• Synthesis and structure–analgesic activity relationships of a novel series of monospirocyclopiperazinium salts (MSPZ)
  作者：Song-Wen Lin、Qi Sun、Ze-Mei Ge、Xin Wang、Jia Ye、Run-Tao Li

  DOI：10.1016/j.bmcl.2010.12.052

  日期：2011.2

  A series of monospirocyclopiperazinium salts were designed and synthesized to search for a peripherally-acting analgesic drug with low side effects. Extensive SAR studies revealed that a suitable (NRR3)-R-2 was critical for the analgesic activity, which might be beneficial to expose the cationic nitrogen to bind to the receptor, and possibly interact with the receptor via pi-pi interaction. Introduction of substituting group on the N-4-phenyl ring could improve the activity, and the best position was the 4-position. Compound 14n showed more potent analgesic activity (63%, 20 mu M/kg, sc) and holds promise for development as a mechanically new analgesic drug. (C) 2010 Elsevier Ltd. All rights reserved.
• Ross et al., Journal of the Chemical Society, 1955, p. 3110,3115
  作者：Ross et al.

  DOI：——

  日期：——