N,N'-吖啶-3,6-二基二(乙酰胺) | 15724-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: N,N'-吖啶-3,6-二基二(乙酰胺)
• 中文别名: 3,6-二乙酰氨基吖啶
• 英文名称: 3,6-diacetamido-acridine
• 英文别名: 3,6-diacetamidoacridine；N,N'-acridine-3,6-diyl-bis-acetamide；N,N'-Acridin-3,6-diyl-bis-acetamid；3,6-Bis-acetylamino-acridin；N,N'-acridine-3,6-diyldi(acetamide)；3,6-Bisacetamidoacridin；N-(6-acetamidoacridin-3-yl)acetamide
• CAS: 15724-70-6
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: IPBVFYCAVIISQF-UHFFFAOYSA-N

物化性质

• 熔点：
  270 °C
• 沸点：
  673.9±25.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N,N'-吖啶-3,6-二基二(乙酰胺) 在 过氧化氢苯甲酰 、 乙醇 、 氯仿 作用下， 生成 3,6-bis-acetylamino-acridine-10-oxide
  参考文献：
  名称：

  Chalezkii et al., Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2821,2824; engl. Ausg. S. 2845, 2848

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4'-二氨基-2,2'-二硝基二苯基甲烷 在 盐酸 、 tin 作用下， 生成 N,N'-吖啶-3,6-二基二(乙酰胺)
  参考文献：
  名称：

  Benda, Chemische Berichte, 1912, vol. 45, p. 1796

  摘要：

  DOI：

文献信息

• New α,ω-diamido and α,ω-diamino mono-and bi-bridged acridine dimers
  作者：Martine Moisan、Jean-Pierre Galy、Anne-Marie Galy、Jacques Barbe

  DOI：10.1007/bf00808507

  日期：1993.1

  A novel set of dimers derived from 9-amino acridine was prepared and characterized by H-1 and C-13 NMR. These derivatives are bridged at several different positions of the heterocyclic moieties, by the way of alpha,omega-diamido or alpha,omega-diamino side-chains. Additionally the preparation of some bi-bridged compounds was achieved.
• Browning et al., Proceedings of the Royal Society of London. Series B, Biological sciences, 1917, vol. 93, p. 335,348
  作者：Browning et al.

  DOI：——

  日期：——
• Synthesis and antileishmanial activity of 6-mono-substituted and 3,6-di-substituted acridines obtained by acylation of proflavine
  作者：Carole Di Giorgio、Kamal Shimi、Gérard Boyer、Florence Delmas、Jean-Pierre Galy

  DOI：10.1016/j.ejmech.2007.02.010

  日期：2007.10

  Two new series of diaminoacridinic derivatives obtained from proflavine and N-(6-amino-3-acridinyl)acetamide were synthesised and assessed for their cytotoxic and antileishmanial activities. Two compounds, N-[6-(acetylamino)-3-acridinyl]acetamide and N-[6-(benzoylamino)-3-acridinyl] benzamide demonstrated highly specific antileishmanial properties against the intracellular amastigote form of the parasite. Structure-activity relationships established that the antiproliferative activity against human cells was greatly enhanced by the presence of a benzoylamino group in 6-mono-substituted acridines, while the presence of two acetylamino or benzoylamino groups in 3,6-di-substituted acridines strongly increased the specificity of the molecules for Leishmania parasite, suggesting that symmetric conformations could preferentially interfere with Leishmania metabolism. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Photo-inducible cytotoxic and clastogenic activities of 3,6-di-substituted acridines obtained by acylation of proflavine
  作者：Yohann Benchabane、Carole Di Giorgio、Gérard Boyer、Anne-Sophie Sabatier、Diane Allegro、Vincent Peyrot、Michel De Méo

  DOI：10.1016/j.ejmech.2009.01.010

  日期：2009.6

  The cytotoxicity and photo-enhanced cytotoxicity of a series of 18 3,6-di-substituted acridines were evaluated on both tumour CHO cells and human normal keratinocytes, and compared to their corresponding clastogenicity as assessed by the micronucleus assay.Compounds 2f tert-butyl N-[(6-tert-butoxycarbonylamino)acridin-3-yl]carbamate and 2d N-[6-(pivalamino)acridin-3-yl]pivalamide displayed a specific cytotoxicity on CHO cells. These results suggested that the two derivatives could be considered as interesting candidates for anticancer chemotherapy and hypothesized that the presence of 1,1-dimethylethyl substituents was responsible for a strong non-clastogenic cytotoxicity. Compounds 2b and 2c, on the contrary, displayed a strong clastogenicity. They indicated that the presence of nonbranched aliphatic chains on positions 3 and 6 of the acridine rings tended to induce a significant clastogenic effect. Finally, they established that most of the acridine compounds could be photo-activated by UVA-visible rays and focussed on the significant role of light irradiation on their biological properties. (C) 2009 Elsevier Masson SAS. All rights reserved.
• The Synthesis of Tritium-labeled Methyl Iodide and Acriflavine¹
  作者：N. H. Smith、K. E. Wilzbach、W. G. Brown

  DOI：10.1021/ja01609a071

  日期：1955.2