2-methoxy-8,9-methylenedioxy-phenanthridine | 53937-22-7

• 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: 2-methoxy-8,9-methylenedioxy-phenanthridine
• 英文别名: 2-methoxy-[1,3]dioxolo[4,5-j]phenanthridine；2-Methoxy-[1,3]dioxolo[4,5-j]phenanthridine
• CAS: 53937-22-7
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: UPYHVBBCFJUKCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-8,9-methylenedioxy-phenanthridine 在 sodium chloride 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 水 、 硝基苯 为溶剂， 反应 1.0h， 生成 2-Methoxy-5-methyl-[1,3]dioxolo[4,5-j]phenanthridin-5-ium;chloride
  参考文献：
  名称：

  Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs

  摘要：

  The plant alkaloid lycobetaine has potent topoisomerase-targeting properties and shows anticancer activity. Based on these findings, several lycobetaine analogs were synthesized mainly differing in their substituents at 2, 8 and 9 position and their biological activities were evaluated. The topoisomerase-targeting properties and cytotoxicity of these structural analogs were assessed in the human gastric carcinoma cell line GXF251L. Performing a plasmid relaxation assay, an increased inhibition of topoisomerase I was found with N-methylphenanthridinium chlorides bearing a 8,9-methylenedioxy moiety or a methoxy group in 2-position. Furthermore, quaternized phenanthridinium derivatives bearing either a 2-methoxy or a 8,9-methylenedioxy moiety in conjunction with a 2-hydroxy or 2-methoxy group display potent topoisomerase II inhibition as shown by decatenation of kinetoplast DNA. In general, the N-methylphenanthridinium chlorides possess more potency in inhibiting topoisomerase I than topoisomerase II. All quaternized derivatives also exhibited potent inhibition of tumor cell growth in the low micromolar concentration range. Hence, N-methylphenanthridinium compounds were found to represent a promising class of compounds, potently inhibiting both, topoisomerases I and II, and may be further developed into clinically useful topoisomerase inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.011
• 作为产物：
  描述：

  6-溴-3,4-亚甲基二氧苯甲醛 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 28.0h， 生成 2-methoxy-8,9-methylenedioxy-phenanthridine
  参考文献：
  名称：

  Gupta, Y. P.; Chawla, Ravinder; Sawal, K. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 7, p. 652 - 654

  摘要：

  DOI：

文献信息

• Aryl-aryl coupling induced by n-tributylstannyl hydride an efficient phenanthridine synthesis
  作者：A.M. Rosa、S. Prabhakar、A.M. Lobo

  DOI：10.1016/s0040-4039(00)98810-5

  日期：1990.1

  N-(o-Bromobenzyl) anilines undergo smooth cyclisation,via dihydrophenanthridines, to phenanthridines by intramolecular addition of aryl radicals to theoposition of the aryl ring bearing the nitrogen atom.

  N-（邻溴苄基）苯胺通过分子内加成芳基到带有氮原子的芳基环上，通过二氢菲啶进行平滑环化，形成菲啶。
• The directed metalation connection to aryl-aryl cross coupling.Regiospecific synthesis of phenanthridines, phenanthridinones and the biphenyl alkaloid ismine
  作者：M.A. Siddiqui、V. Snieckus

  DOI：10.1016/s0040-4039(00)80787-x

  日期：1988.1
• An application of the photocyclization reaction of schiff bases to the synthesis of a phenanthridine alkaloid
  作者：Tadamasa Onaka、Yoshihiro Kanda、Mitsutaka Natsume

  DOI：10.1016/s0040-4039(01)82438-2

  日期：1974.1
• GUPTA, Y. P.;CHAWLA, RAVINDER;SAWAL, K. K., INDIAN J. CHEM., 1982, 21, N 7, 652-654
  作者：GUPTA, Y. P.、CHAWLA, RAVINDER、SAWAL, K. K.

  DOI：——

  日期：——
• SIDDIOUI, M. A.;SNIECKUS, V., TETRAHEDRON LETT., 29,(1988) N 43, C. 5463-5466
  作者：SIDDIOUI, M. A.、SNIECKUS, V.

  DOI：——

  日期：——