bicolorine | 65367-81-9

• 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: bicolorine
• 英文别名: 5-Methyl-9H-[1,3]dioxolo[4,5-j]phenanthridin-5-ium chloride；5-methyl-[1,3]dioxolo[4,5-j]phenanthridin-5-ium;chloride
• CAS: 65367-81-9
• 化学式: C₁₅H₁₂NO₂*Cl
• 分子量: 273.719
• InChiKey: OOPDPMYYWQANBR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.45
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  22.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bicolorine 在 potassium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 13.0h， 以80%的产率得到N-methylcrinasiadine
  参考文献：
  名称：

  菲啶骨架石蒜科生物碱的合成

  摘要：

  报道了合成金缕梅科生物碱的策略，包括克林达西定，三叶啶，双色氨酸，N-甲基肉桂酸，5,6-二氢双色氨酸，加兰地吲哚，赖氨酸A和赖氨酸B。还证明了对接近双色氨酸，5，6-二氢双色氨酸，三叶啶和N-甲基肉桂酸的任选合成途径的研究。此外，以铃木偶合反应为关键步骤，简明地制备了三种结构相关的生物碱加兰索尔，溶血素A和溶血素B。

  DOI：

  10.1016/j.tet.2016.07.065
• 作为产物：
  描述：

  6-溴-3,4-亚甲基二氧苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium azide 、 tripotassium phosphate "n" hydrate 、 三氟甲磺酸 、 potassium acetate 、 silver(I) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 甲苯 、 乙腈 为溶剂， 反应 138.08h， 生成 bicolorine
  参考文献：
  名称：

  菲啶骨架石蒜科生物碱的合成

  摘要：

  报道了合成金缕梅科生物碱的策略，包括克林达西定，三叶啶，双色氨酸，N-甲基肉桂酸，5,6-二氢双色氨酸，加兰地吲哚，赖氨酸A和赖氨酸B。还证明了对接近双色氨酸，5，6-二氢双色氨酸，三叶啶和N-甲基肉桂酸的任选合成途径的研究。此外，以铃木偶合反应为关键步骤，简明地制备了三种结构相关的生物碱加兰索尔，溶血素A和溶血素B。

  DOI：

  10.1016/j.tet.2016.07.065

文献信息

• A ruthenium-catalyzed free amine directed (5+1) annulation of anilines with olefins: diverse synthesis of phenanthridine derivatives
  作者：Deepan Chowdhury、Suman Dana、Anup Mandal、Mahiuddin Baidya

  DOI：10.1039/c9cc05717j

  日期：——

  annulation between 2-aminobiphenyls and activated olefins is disclosed for succinct synthesis of valuable phenanthridine scaffolds. The protocol avails a common organic functional group, free amine, as a directing group and represents a unique combination of C–H activation/annulation/C–C bond cleavage cascade that bodes well in the production of bioactive alkaloids including trisphaeridine and bicolorine

  公开了2-氨基联苯和活化的烯烃之间的钌（II）催化的交叉环（5 + 1）环化，用于简洁地合成有价值的菲啶骨架。该方案利用一个常见的有机官能团，即游离胺作为指导基团，代表了C–H活化/环化/ C–C键裂解级联的独特组合，预示着生物活性生物碱（包括三叶啶和双色氨酸）的产生。
• Antileukemic activity of ungeremine and related compounds. Preparation of analogs of ungeremine by a practical photochemical reaction
  作者：Robert K. Y. Zee-Cheng、Shou-Jen Yan、C. C. Cheng

  DOI：10.1021/jm00200a011

  日期：1978.2

  A number of alkoxypyrrolophenanthridinium salts and their analogues related to the antileukemic alkaloid ungeremine were prepared by a practical photochemical cyclization. The importance of the quaternary nitrogen atom and of alkoxy groups, the planarity of a molecule, and steric considerations relative to antileukemic activity are discussed.

  通过实际的光化学环化反应制备了许多与抗生物碱生物碱松香胺有关的烷氧基吡咯并菲基吡啶鎓盐及其类似物。讨论了季氮原子和烷氧基的重要性，分子的平面性以及相对于抗白血病活性的空间考虑因素。
• Metal-free tandem carbene N–H insertions and C–C bond cleavages
  作者：Pu Chen、Jiang Nan、Yan Hu、Yifan Kang、Bo Wang、Yangmin Ma、Michal Szostak

  DOI：10.1039/d0sc05763k

  日期：——

  with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C–C cleavage. Compared to the simple N–H insertion manipulation of diazo, this method elegantly accomplishes a tandem N–H insertion/SEAr/C–C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and

  已经实现了 2-芳基苯胺与重氮化合物的无金属 C-H [5 + 1] 环化反应，通过高度选择性的 C-C 裂解产生两种普遍的菲啶。与重氮的简单 N-H 插入操作相比，该方法优雅地完成了串联 N-H 插入/S E Ar/C-C 裂解/芳构化反应，这种新转化的合成效用通过简洁的合成trisphaeridine 和 bicolorine 生物碱。
• Hydride-Induced Anionic Cyclization: An Efficient Method for the Synthesis of 6-<i>H</i>-Phenanthridines via a Transition-Metal-Free Process
  作者：Wei-Lin Chen、Chun-Yuan Chen、Yan-Fu Chen、Jen-Chieh Hsieh

  DOI：10.1021/acs.orglett.5b00544

  日期：2015.3.20

  A novel procedure for hydride-induced anionic cyclization has been developed. It includes the reduction of a biaryl bromo-nitrile with a nucleophilic aromatic substitution (SNAr). A range of polysubstituted 6-H-phenanthridines were so obtained in moderate to good yield with good substrate tolerance. This method involves a concise transition-metal-free process and was applied to synthesize natural alkaloids.
• Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs
  作者：Simone A. Baechler、Markus Fehr、Michael Habermeyer、Andreas Hofmann、Karl-Heinz Merz、Heinz-Herbert Fiebig、Doris Marko、Gerhard Eisenbrand

  DOI：10.1016/j.bmc.2012.11.011

  日期：2013.2

  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.