methyl 6-oxo-5,6-dihydrophenanthridine-2-carboxylate | 37046-44-9

• 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: methyl 6-oxo-5,6-dihydrophenanthridine-2-carboxylate
• 英文别名: methyl 6-oxo-5H-phenanthridine-2-carboxylate
• CAS: 37046-44-9
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: LALNRHJOXQSKCW-UHFFFAOYSA-N

物化性质

• 沸点：
  353.5±21.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 6-oxo-5,6-dihydrophenanthridine-2-carboxylate 在 水 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 C₁₇H₁₃NO₃
  参考文献：
  名称：

  Phenanthridin-6-one derivatives as the first class of non-steroidal pharmacological chaperones for Niemann-Pick disease type C1 protein

  摘要：

  Niemann-Pick disease type C is a fatal, progressive neurodegenerative disease mostly caused by mutations in Nieamnn-Pick type C1 (NPC1), a late endosomal membrane protein that is essential for intracellular cholesterol transport. The most prevalent mutation, I1061T (Ile to Thr), interferes with the protein folding process. Consequently, mutated but intrinsically functional NPC1 proteins are prematurely degraded via proteasome, leading to loss of NPC1 function. Previously, we reported sterol derivatives as pharmacological chaperones for NPC1, and showed that these derivatives can normalize folding-defective phenotypes of I1061T NPC1 mutant by directly binding to, and stabilizing, the protein. Here, we report a series of compounds containing a phenanthridin-6-one scaffold as the first class of non-steroidal pharmacological chaperones for NPC1. We also examined their structure-activity relationships. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.04.062
• 作为产物：
  描述：

  methyl 4-(3,3-diethyltriaz-1-enyl)-3-iodobenzoate 在 potassium phosphate 、 3,3,3-膦三基三丙酸 、 三苯胂 、 叠氮基三甲基硅烷 、 palladium diacetate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 methyl 6-oxo-5,6-dihydrophenanthridine-2-carboxylate
  参考文献：
  名称：

  Long-Lived Luminogenic Probe for Detection of RNA in a Crude Solution of Living Bacterial Cells

  摘要：

  A pre-type sensitizer for a lanthanide complex on an oligonucleotide was successfully converted to a perfect final structure in a target DNA/RNA-templated reaction, without any chemical reagent or enzyme, under neutral conditions. The final form of the lanthanide oligonucleotide provided a long-lived luminescence signal, appropriate for time-gated luminescence analysis and signal amplification. Target DNA/RNA-assisted time-gated luminescence analysis is a powerful tool for elimination of autofluorescence and detection of target RNA in living bacterial cells.

  DOI：

  10.1021/ja406724k

文献信息

• Metal-Oxidant-Free Cobalt-Catalyzed C(sp²)–H Carbonylation of <i>ortho</i>-Arylanilines: An Approach toward Free (<i>NH</i>)-Phenanthridinones
  作者：Fei Ling、Chaowei Zhang、Chongren Ai、Yaping Lv、Weihui Zhong

  DOI：10.1021/acs.joc.8b00730

  日期：2018.5.18

  A traceless directing group assisted Co-catalyzed C(sp2)–H carbonylation of ortho-arylanilines for the synthesis of free (NH)-phenanthridinones in metal-based-oxidant-free fashion was accomplished. This protocol employs diisopropyl azodicarboxylate as the CO source and oxygen as the sole oxidant, and provides good yields with various functional tolerance. The methodology has been applied for the total

  一个无痕的指导小组以金属基无氧化剂的方式辅助了邻芳基苯胺的共催化C（sp 2）–H羰基化合成了游离的（NH）-菲啶酮。该方案采用偶氮二羧酸二异丙酯作为一氧化碳源，氧气作为唯一的氧化剂，并具有良好的收率和各种功能耐受性。该方法已应用于PARP抑制剂PJ-34的全合成。此外，动力学同位素效应实验表明，CH键断裂可能发生在速率确定步骤中。
• Synthesis of phenanthridinones viapalladium-catalyzed C(sp²)–H aminocarbonylation of unprotected o-arylanilines
  作者：Dongdong Liang、Ziwei Hu、Jiangling Peng、Jinbo Huang、Qiang Zhu

  DOI：10.1039/c2cc36817j

  日期：——

  An efficient synthesis of free (NH)-phenanthridinones through Pd-catalyzed C(sp(2))-H aminocarbonylation of unprotected o-arylanilines under an atmospheric pressure of CO has been developed. Some ortho heteroarene substituted anilines as well as N-alkyl protected o-arylanilines are also suitable substrates for this C-H aminocarbonylation reaction.

  有效的合成游离（NH）-菲啶酮通过CO的大气压下未保护的邻芳基苯胺的Pd催化C（sp（2））-H氨基羰基化反应。一些邻杂芳基取代的苯胺以及N-烷基保护的邻芳基苯胺也是该CH氨基羰基化反应的合适底物。
• Nickel-Catalyzed Lactamization Reaction of 2-Arylanilines with CO₂
  作者：Lu Wang、Hanxuan Wu、Yucheng Zhao、Bin Li、Baiquan Wang

  DOI：10.1021/acs.orglett.4c01156

  日期：——

  Transition-metal-catalyzed lactamization and lactonization of C–H bonds with CO2 assisted by the chelation of amino or hydroxyl groups have been developed but limited to the use of precious metal catalysts such as palladium and rhodium. In this work, we report the nonprecious metal nickel-catalyzed lactamization reaction of 2-arylanilines with CO2 under redox-neutral conditions via C–H bond activation

  过渡金属催化的内酰胺化以及C-H键与CO 2在氨基或羟基螯合辅助下的内酯化已经得到发展，但仅限于使用贵金属催化剂，例如钯和铑。在这项工作中，我们报道了在氧化还原中性条件下通过C-H键活化发生的非贵金属镍催化的2-芳基苯胺与CO 2的内酰胺化反应。该反应表现出优异的官能团耐受性，以中等到高产率提供各种菲啶酮。
• Phenanthridin-6-one derivatives as the first class of non-steroidal pharmacological chaperones for Niemann-Pick disease type C1 protein
  作者：Hiromitsu Fukuda、Fumika Karaki、Kosuke Dodo、Tomomi Noguchi-Yachide、Minoru Ishikawa、Yuichi Hashimoto、Kenji Ohgane

  DOI：10.1016/j.bmcl.2017.04.062

  日期：2017.6

  Niemann-Pick disease type C is a fatal, progressive neurodegenerative disease mostly caused by mutations in Nieamnn-Pick type C1 (NPC1), a late endosomal membrane protein that is essential for intracellular cholesterol transport. The most prevalent mutation, I1061T (Ile to Thr), interferes with the protein folding process. Consequently, mutated but intrinsically functional NPC1 proteins are prematurely degraded via proteasome, leading to loss of NPC1 function. Previously, we reported sterol derivatives as pharmacological chaperones for NPC1, and showed that these derivatives can normalize folding-defective phenotypes of I1061T NPC1 mutant by directly binding to, and stabilizing, the protein. Here, we report a series of compounds containing a phenanthridin-6-one scaffold as the first class of non-steroidal pharmacological chaperones for NPC1. We also examined their structure-activity relationships. (C) 2017 Elsevier Ltd. All rights reserved.
• Long-Lived Luminogenic Probe for Detection of RNA in a Crude Solution of Living Bacterial Cells
  作者：Hisao Saneyoshi、Yoshihiro Ito、Hiroshi Abe

  DOI：10.1021/ja406724k

  日期：2013.9.18

  A pre-type sensitizer for a lanthanide complex on an oligonucleotide was successfully converted to a perfect final structure in a target DNA/RNA-templated reaction, without any chemical reagent or enzyme, under neutral conditions. The final form of the lanthanide oligonucleotide provided a long-lived luminescence signal, appropriate for time-gated luminescence analysis and signal amplification. Target DNA/RNA-assisted time-gated luminescence analysis is a powerful tool for elimination of autofluorescence and detection of target RNA in living bacterial cells.