菲啶-4-羧酸 | 104728-15-6

• 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: 菲啶-4-羧酸
• 英文名称: phenanthridine-4-carboxylic acid
• CAS: 104728-15-6
• 化学式: C₁₄H₉NO₂
• 分子量: 223.231
• InChiKey: ZMVAZMYLGJVVTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基亚硝基脲 、 菲啶-4-羧酸 在 potassium hydroxide 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 12.0h， 以45%的产率得到methyl phenanthridine-4-carboxylate
  参考文献：
  名称：

  在C ？之间进行替换引导的切换。2-氨基苯甲酸酯与2-卤代芳基醛在钯/铜催化级联反应中的H活化和脱羧交叉偶联

  摘要：

  级联转换：由2-氨基苯甲酸钾和2-卤代芳基醛之间的Pd / Cu催化反应一步制得菲啶，吡唑[4,3- c ]喹啉和异隐油菜碱（参见方案）。虽然经由级联亚胺化/ C进行2-氨基苯甲酸酯反应 ħ官能化，6-硝基-2-氨基苯甲酸酯的反应中通过串联亚胺化/脱羧交叉偶联接踵而至。

  DOI：

  10.1002/chem.201301705
• 作为产物：
  描述：

  3-甲基-2-硝基苯胺 在 chromium(VI) oxide 、 盐酸 、 PPA 、 硫酸 、 potassium acetate 、 氢气 、 铁粉 、 sodium nitrite 作用下， 反应 48.5h， 生成 菲啶-4-羧酸
  参考文献：
  名称：

  Potential antitumor agents. 55. 6-Phenylphenanthridine-4-carboxamides: a new class of DNA-intercalating antitumor agents

  摘要：

  Derivatives of the DNA-intercalating agent N-[2-(dimethylamino)ethyl]phenanthridine-4-carboxamide have been prepared and shown to have moderate in vivo antitumor activity against both the P388 leukemia and Lewis lung carcinoma. This demonstrates that the effective pharmacophore in the broad class of tricyclic carboxamides is not limited to linear tricyclic chromophores. Both 7 and the 6-phenyl derivative 10 have identical DNA binding properties, suggesting that the phenyl ring of 10 is not involved in the DNA intercalation site. A series of phenyl-substituted derivatives of 10 was evaluated. Aza substituents led to compounds with the highest in vivo cytotoxicity and in vivo P388 activity, but the in vivo solid tumor activity of the substituted 6-phenylphenanthridine-4-carboxamides was in general low.

  DOI：

  10.1021/jm00399a015

文献信息

• Synthesis of Phenanthridine Derivatives via Photolysis
  作者：Anna M. Linsenmeier、Craig M. Williams、Stefan Bräse

  DOI：10.1021/jo201542x

  日期：2011.11.4

  An improved photochemical method for producing the prolifically bioactive phenanthridine system is reported. A wide variety of derivatives were obtained in two steps in yields ranging from 31 to 95%.
• Synthesis of the Isoxazolo[4,3,2-<i>de</i>]phenanthridinone Moiety of the Parnafungins
  作者：Quan Zhou、Barry B. Snider

  DOI：10.1021/ol901054r

  日期：2009.7.2

  A practical route to the labile tetracyclic isoxazolo[4,3,2-de]phenanthridinone moiety of the antifungal parnafungins has been developed. Zinc reduction of a methyl 2'-hydroxymethyl-2-nitro-3-biphenylcarboxylate, which was prepared by a Suzuki coupling, afforded a benzisoxazolone that was treated with MsCl and base to generate the labile tetracyclic ring system in 37-47% yield. This compound decomposes to the phenanthridine in CDCl3 and the phenanthridine N-oxide in aqueous base.
• Synthesis of Hexacyclic Parnafungin A and C Models
  作者：Quan Zhou、Barry B. Snider

  DOI：10.1021/jo101826p

  日期：2010.12.3

  A convergent, practical route to unstable hexacyclic parnafungin A and C models has been developed. Two iodoxanthones were prepared in four or five steps (33-50% overall yield). Suzuki-Miyaura coupling of the iodoxanthones with excess readily available 3-carbomethoxy-2-nitrophenyl pinacol boronate afforded the hindered highly functionalized 2-arylxanthones (53-58%) in the first key step. In the second key step, zinc reduction gave benzisoxazolinones that were treated with MsCl and then base to generate the unstable hexacyclic parnafungin A (13% overall yield for 8 steps) and C (8% overall yield for 9 steps) models. Analogously to the parnafungins, hexacyclic parnafungin C model decomposes to a phenanthridine with a half-life of 2 d in CDCI3.
• Sengupta, Dibyendu; Anand, Nitya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 923 - 927
  作者：Sengupta, Dibyendu、Anand, Nitya

  DOI：——

  日期：——
• ATWELL, GRAHAM J.;BAGULEY, BRUCE C.;DENNY, WILLIAM A., J. MED. CHEM., 31,(1988) N 4, 774-779
  作者：ATWELL, GRAHAM J.、BAGULEY, BRUCE C.、DENNY, WILLIAM A.

  DOI：——

  日期：——