(S)-1-(2,3,6,7-tetramethoxyphenanthrene-9-carbonyl)pyrrolidine-2-carboxylic acid methyl ester | 84471-44-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (S)-1-(2,3,6,7-tetramethoxyphenanthrene-9-carbonyl)pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: (S)-methyl 1-(2,3,6,7-tetramethoxyphenanthrene-9-carbonyl)pyrrolidine-2-carboxylate；(S)-methyl N-(2,3,6,7-tetramethoxyphenanthr-9-ylcarbonyl)-pyrrolidine-2-carboxylate；methyl (2S)-1-(2,3,6,7-tetramethoxyphenanthrene-9-carbonyl)pyrrolidine-2-carboxylate
• CAS: 84471-44-3
• 化学式: C₂₅H₂₇NO₇
• 分子量: 453.492
• InChiKey: CEQLIBULRFOAFZ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-1-(2,3,6,7-tetramethoxyphenanthrene-9-carbonyl)pyrrolidine-2-carboxylic acid methyl ester 在 水 、 氯甲酸乙酯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.5h， 生成 (S)-1-(2,3,6,7-tetramethoxyphenanthrene-9-carbonyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Antiviral Activity Evaluation of Phenanthrene-Based Antofine Derivatives

  摘要：

  On the basis of our previous structure activity relationship (SAR) and antiviral mechanism studies, a series of phenanthrene-based antofine derivatives (1-12 and 18-50) were designed targeting tobacco mosaic virus (TMV) RNA and synthesized and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds exhibited good to excellent in vivo anti-TMV activity, of which compounds 19 and 27 displayed higher activity than commercial Ribavirin, thus emerging as potential inhibitors of plant virus. The novel concise structure provides another new template for antiviral studies.

  DOI：

  10.1021/jf302746m
• 作为产物：
  描述：

  2,3,6,7-四甲氧基-9-羧基菲 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (S)-1-(2,3,6,7-tetramethoxyphenanthrene-9-carbonyl)pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  基于菲的酪氨酸衍生物作为潜在抗病毒剂的设计，合成和抗病毒评价

  摘要：

  设计，合成了一系列C9取代的菲基酪氨酸衍生物（PBT），并首先评估了它们对烟草花叶病毒（TMV）的抗病毒活性。这些化合物具有菲核结构，并且与酪氨酸碱生物碱相比，可以高效地合成，收率很高。生物测定结果表明，这些化合物中的一些在体内对TMV的抗病毒活性高于酪氨酸和商业宁南霉素。特别是，化合物3，4，9，13，和16成为潜在的植物病毒抑制剂。这些新发现表明，这些基于菲的酪氨酸衍生物（PBT）代表了抗病毒研究的另一个新模板，可以被认为是针对植物病毒感染的新疗法。

  DOI：

  10.1021/jf103440s

文献信息

• Intramolecular Dehydrogenative Coupling of 2,3-Diaryl Acrylic Compounds: Access to Substituted Phenanthrenes
  作者：Vijay Gupta、V. U. Bhaskara Rao、Tamal Das、Kumar Vanka、Ravi P. Singh

  DOI：10.1021/acs.joc.6b00507

  日期：2016.7.1

  environmentally benign intramolecular dehydrogenative coupling of various 1,2-diarylethylenes for the synthesis of phenanthrenes in excellent yield has been described. This new methodology uses ceric ammonium nitrate (CAN) as a promoter at room temperature and has been extended to intermolecular synthesis of biaryl compounds. The electron transfer from methoxyarene to cerium leads to cationic radical formation

  已经描述了用于以优异的产率合成菲的各种1,2-二芳基乙烯的简单，容易且对环境无害的分子内脱氢偶联。这种新的方法在室温下使用硝酸铈铵（CAN）作为促进剂，并已扩展到联芳基化合物的分子间合成。电子从甲氧基芳烃转移到铈导致阳离子自由基的形成，其进一步进行分子内偶联。通过EPR光谱进行的初步机理研究和密度泛函理论计算得出了相似的观点。
• Synthesis and Antitumor Activities of Phenanthrene-Based Alkaloids
  作者：Songtao Li、Li Han、Liang Sun、Dan Zheng、Jiang Liu、Yingbo Fu、Xueshi Huang、Zhanyou Wang

  DOI：10.3390/molecules14125042

  日期：——

  A series of phenanthrene-based tylophorine derivatives (PBTs) were synthesized and their cytotoxic activities against the H460 human large-cell lung carcinoma cell line were evaluated. Among these compounds, N-(3-hydroxy-2,6,7-tri-methoxyphenanthr-9-ylmethyl)-L-prolinol (5a), and N-(3-hydroxy-2,6,7-trimethoxy-phenanthr-9-ylmethyl)-L-valinol (9) exhibited good activities, with IC50 values of 11.6 and 6.1 mM, respectively.

  研究人员合成了一系列菲基泰洛泊林衍生物（PBTs），并评估了它们对 H460 人大细胞肺癌细胞系的细胞毒活性。在这些化合物中，N-（3-羟基-2,6,7-三甲氧基菲-9-基甲基）-L-脯氨醇（5a）和 N-（3-羟基-2,6,7-三甲氧基菲-9-基甲基）-L-缬氨醇（9）表现出良好的活性，其 IC50 值分别为 11.6 和 6.1 mM。
• Design, Synthesis, and Antiviral Evaluation of Phenanthrene-Based Tylophorine Derivatives as Potential Antiviral Agents
  作者：Kailiang Wang、Yanna Hu、Yuxiu Liu、Na Mi、Zhijin Fan、Yu Liu、Qingmin Wang

  DOI：10.1021/jf103440s

  日期：2010.12.8

  A series of C9-substituted phenanthrene-based tylophorine derivatives (PBTs) were designed, synthesized, and first evaluated for their antiviral activities against tobacco mosaic virus (TMV). These compounds contain a phenanthrene core structure and can be synthesized some efficiently with excellent yields compared with tylophorine alkaloid. The bioassay results show that some of these compounds exhibited

  设计，合成了一系列C9取代的菲基酪氨酸衍生物（PBT），并首先评估了它们对烟草花叶病毒（TMV）的抗病毒活性。这些化合物具有菲核结构，并且与酪氨酸碱生物碱相比，可以高效地合成，收率很高。生物测定结果表明，这些化合物中的一些在体内对TMV的抗病毒活性高于酪氨酸和商业宁南霉素。特别是，化合物3，4，9，13，和16成为潜在的植物病毒抑制剂。这些新发现表明，这些基于菲的酪氨酸衍生物（PBT）代表了抗病毒研究的另一个新模板，可以被认为是针对植物病毒感染的新疗法。
• Design, Synthesis, and Antiviral Activity Evaluation of Phenanthrene-Based Antofine Derivatives
  作者：Ziwen Wang、Peng Wei、Xu Xizhi、Yuxiu Liu、Lizhong Wang、Qingmin Wang

  DOI：10.1021/jf302746m

  日期：2012.9.5

  On the basis of our previous structure activity relationship (SAR) and antiviral mechanism studies, a series of phenanthrene-based antofine derivatives (1-12 and 18-50) were designed targeting tobacco mosaic virus (TMV) RNA and synthesized and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds exhibited good to excellent in vivo anti-TMV activity, of which compounds 19 and 27 displayed higher activity than commercial Ribavirin, thus emerging as potential inhibitors of plant virus. The novel concise structure provides another new template for antiviral studies.