苯胺,4-硝基-N,N-二戊基- | 154884-56-7

• 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: 苯胺,4-硝基-N,N-二戊基-
• 英文名称: N,N-dipentyl-4-nitroaniline
• 英文别名: N,N-dipentyl-p-nitroaniline；4-nitro-N,N-dipentylaniline
• CAS: 154884-56-7
• 化学式: C₁₆H₂₆N₂O₂
• 分子量: 278.395
• InChiKey: GHBLLAYLVNGBCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯胺,4-硝基-N,N-二戊基- 在 platinum on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 N,N-二戊基苯-1,4-二胺
  参考文献：
  名称：

  Structure−Activity Relationships for the Antileishmanial and Antitrypanosomal Activities of 1‘-Substituted 9-Anilinoacridines

  摘要：

  Members of the class of 9-anilinoacridine topoisomerase II inhibitors bearing lipophilic electron-donating 1'-anilino substituents are active against both the promastigote and amastigote forms of the parasite Leishmania major. A series of analogues of the known 1'-NHhexyl lead compound were prepared and evaluated against L. major in macrophage culture to further develop structure-activity relationships (SAR). Toxicity toward mammalian cells was measured in a human leukemia cell line, and the ratio of the two IC50 values (IC50(J)/IC50(L)) was used as a measure of the in vitro therapeutic index (IVTI). A 3,6-diNMe(2) substitution pattern on the acridine greatly increased toxicity to L. major without altering mammalian toxicity, increasing IVTIs over that of the lead compound. The 2-OMe, 6-Cl acridine substitution pattern used in the antimalarial drug mepacrine also resulted in potent antileishmanial activity and high IVTIs. Earlier suggestions of the utility of 2'-OR groups in lowering mammalian cytotoxicity were not borne out in this wider study. A series of very lipophilic 1'-NRR (symmetric dialkylamino)-substituted analogues showed relatively high antileishmanial potency, but no clear trend was apparent across the series, and none were superior to the 1'-NH(CH2)(5)Me subclass. Subsets of the most active 1'-N(R)(CH2)(5)Me- and 1'-N(alkyl)(2)-substituted compounds against L. major were also evaluated against Leishmania donovani, Trypanosoma cruzi, and Trypanosoma brucei, but no consistent SAR could be discerned in these physiologically diverse test systems. The present study has confirmed earlier conclusions that lipophilic electron-donating groups at the 1'-position of 9-anilinoacridines provide high activity against L. major, but the SAR patterns observed do not carry over to the other parasites studied.

  DOI：

  10.1021/jm970232h
• 作为产物：
  描述：

  对氟硝基苯 、 二戊胺 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以62%的产率得到苯胺,4-硝基-N,N-二戊基-
  参考文献：
  名称：

  超声促进卤代苯胺芳香亲核取代的研究

  摘要：

   研究了用不同的胺对卤代芳烃进行声化学亲核取代。发现反应过程强烈地依赖于胺的碱性，膨松度和沸点以及取代基的吸电子性能。

  DOI：

  10.1007/s00706-002-0505-8

文献信息

• New Experiments in the Reductive N-Alkylation and N-Peralkylation of Aromatic Amines
  作者：G. Verardo、A. G. Giumanini、P. Strazzolini

  DOI：10.1080/00397919408012638

  日期：1994.3

  Some secondary and primary aromatic amines were variously N-alkylated and N-peralkylated by the aldehyde-sodium borohydride procedure in acidic aqueous solution. The procedure lends itself to the alpha-mono and alpha,alpha'-dideuterium labelling of the new N-substituent(s).
• Synthesis and Physical Characterization of Some New Hydrophobic Forms of the Solvatochromic <i>N</i>,<i>N</i>-Dialkyl-<i>p</i>-nitroanilines
  作者：G. Mansour、W. Creedon、P. C. Dorrestein、J. Maxka、J. C. MacDonald、R. Helburn

  DOI：10.1021/jo0014764

  日期：2001.6.1