6-demethoxyacronycine | 92599-96-7

• 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
• 英文名称: 6-demethoxyacronycine
• 英文别名: 3,3,12-Trimethyl-3,12-dihydro-7H-pyrano[2,3-c]acridin-7-one；3,3,12-trimethylpyrano[2,3-c]acridin-7-one
• CAS: 92599-96-7
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: OQHMSKQIPWZJKT-UHFFFAOYSA-N

物化性质

• 沸点：
  471.1±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-demethoxyacronycine 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 丁酮 、 叔丁醇 为溶剂， 反应 5.0h， 生成 (+/-)-cis-1,2-di-O-carbonyl-1,2-dihydroxy-1,2-dihydro-6-demethoxyacronycine
  参考文献：
  名称：

  Synthesis and Cytotoxic and Antitumor Activity of Esters in the 1,2-Dihydroxy-1,2-dihydroacronycine Series

  摘要：

  Seven 1,2-dihydroxy-1,2-dihydroacronycine and 1,2-dihydroxy-1,2-dihydro-6-demethoxyacronycine esters and diesters were synthesized via osmic oxidation of acronycine or 6-demethoxyacronycine followed by acylation. The 6-demethoxyacronycine derivatives were found to be inactive, whereas in contrast, all of the acronycine derivatives were more potent than acronycine itself when tested against L1210 cells in vitro. Four selected acronycine derivatives (17, 19, 21, and 22) were evaluated in vivo against murine P388 leukemia and colon 38 adenocarcinoma implanted in mice. All compounds were markedly active against P388 at doses 4-16-fold lower than acronycine itself. Against the colon 38 adenocarcinoma, the three compounds 17, 21, and 22 were highly efficient. 1,2-Diacetoxy-1,2-dihydroacronycine (17) was the most active, all the treated mice being tumor-free on day 23.

  DOI：

  10.1021/jm9602975
• 作为产物：
  描述：

  2-methylbut-3-yn-2-yl 3-nitrophenyl ether 在 盐酸 、 sodium hydroxide 、 苄基三乙基氯化铵 、 potassium acetate 、 copper diacetate 、 铁粉 、 三乙胺 、 三氟乙酸酐 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 109.5h， 生成 6-demethoxyacronycine
  参考文献：
  名称：

  Elomri, Abdelhakim; Michel, Sylvie; Tillequin, Francois, Heterocycles, 1992, vol. 34, # 4, p. 799 - 806

  摘要：

  DOI：

文献信息

• Synthesis and Cytotoxic Activity of Acronycine Derivatives Modified at the Pyran Ring.
  作者：Abdelhakim ELOMRI、Alexios-Leandros SKALTSOUNIS、Sylvie MICHEL、Francois TILLEQUIN、Michel KOCH、Yves ROLLAND、Alain PIERRE、Ghanem ATASSI

  DOI：10.1248/cpb.44.2165

  日期：——

  Nitration of acronycine (1) and 6-demethoxyacronycine (3) afforded 2-nitroacronycine (2) and 2-nitro-6-demethoxyacronycine (4), respectively. Reduction of 2-nitroacronycine yielded, depending on the conditions, 2-nitro-1,2-dihydroacronycine (5), 2-oxo-1,2-dihydroacronycine oxime (7) or 2-amino-1,2-dihydroacronycine (6). This latter was readily converted into 2-dimethylamino-1,2-dihydroacronycine (8)

  硝化丙烯醛（1）和6-去甲氧基精氨酸（3）分别得到2-硝基丙氨酸（2）和2-硝基-6-脱甲氧基丙氨酸（4）。根据条件的不同，还原2-硝基阿卡西霉素产生2-硝基-1,2-二氢阿卡霉素（5），2-氧-1,2-二氢阿卡霉素肟（7）或2-氨基1,2-二氢阿卡霉素（6） ）。后者很容易转化为2-二甲基氨基-1，2-二氢加速胺（8），2-乙酰氨基-1，2-二氢加速胺（9）和2-苯甲酰基氨基-1，2-二氢加速胺（10）。评估了这些化合物对L1210白血病细胞的细胞毒性。化合物2和7在抑制L1210细胞增殖方面分别比丙烯醛高300倍和10倍。化合物2没有针对P388白血病和C38结肠腺癌的抗肿瘤活性。
• Coppola, Gary M., Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 913 - 914
  作者：Coppola, Gary M.

  DOI：——

  日期：——
• Elomri, Abdelhakim; Michel, Sylvie; Tillequin, Francois, Heterocycles, 1992, vol. 34, # 4, p. 799 - 806
  作者：Elomri, Abdelhakim、Michel, Sylvie、Tillequin, Francois、Koch, Michel

  DOI：——

  日期：——
• Synthesis and Cytotoxic and Antitumor Activity of Esters in the 1,2-Dihydroxy-1,2-dihydroacronycine Series
  作者：Abdelhakim Elomri、Sofia Mitaku、Sylvie Michel、Alexios-Léandros Skaltsounis、François Tillequin、Michel Koch、Alain Pierré、Nicolas Guilbaud、Stéphane Léonce、Laurence Kraus-Berthier、Yves Rolland、Ghanem Atassi

  DOI：10.1021/jm9602975

  日期：1996.1.1

  Seven 1,2-dihydroxy-1,2-dihydroacronycine and 1,2-dihydroxy-1,2-dihydro-6-demethoxyacronycine esters and diesters were synthesized via osmic oxidation of acronycine or 6-demethoxyacronycine followed by acylation. The 6-demethoxyacronycine derivatives were found to be inactive, whereas in contrast, all of the acronycine derivatives were more potent than acronycine itself when tested against L1210 cells in vitro. Four selected acronycine derivatives (17, 19, 21, and 22) were evaluated in vivo against murine P388 leukemia and colon 38 adenocarcinoma implanted in mice. All compounds were markedly active against P388 at doses 4-16-fold lower than acronycine itself. Against the colon 38 adenocarcinoma, the three compounds 17, 21, and 22 were highly efficient. 1,2-Diacetoxy-1,2-dihydroacronycine (17) was the most active, all the treated mice being tumor-free on day 23.