N-methyl-5,6-dihydrobenzo[c]phenanthridine | 51066-30-9

• 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: N-methyl-5,6-dihydrobenzo[c]phenanthridine
• 英文别名: dihydrosanguinarine；DHB；5,6-Dihydro-5-methylbenzophenanthridin；5-methyl-5,6-dihydro-benzo[c]phenanthridine；5-methyl-6H-benzo[c]phenanthridine
• CAS: 51066-30-9
• 化学式: C₁₈H₁₅N
• 分子量: 245.324
• InChiKey: JBYOMDIDAUKPAE-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  449.8±24.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  亚磷酸二丁酯 、 N-methyl-5,6-dihydrobenzo[c]phenanthridine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 copper(I) bromide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 24.0h， 以41%的产率得到dibutyl (5-methyl-5,6-dihydrobenzo[c]phenanthridin-6-yl)phosphonate
  参考文献：
  名称：

  Synthesis of N -methyl-5,6-dihydrobenzo[ c ]phenanthridine and its sp 3 C(6)–H bond functionalization via oxidative cross-dehydrogenative coupling reactions

  摘要：

  An expeditious route involving a Pd-catalyzed intramolecular biaryl-coupling for the synthesis of the N-methyl-5,6-dihydrobenzo[c]phenanthridine scaffold has been developed. For the first time, we herein report the sp(3) C(6)-H functionalization of this heterocyclic scaffold through DDQ-mediated cross-dehydrogenative coupling reactions with nitroalkanes, dialkyl malonates, alkynes, dialkyl phosphites, carbonyl compounds, pyrrole, and indoles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.018
• 作为产物：
  描述：

  2-bromo-N-(α-naphthyl)benzylamine 在 C₁₈H₃₃P*BF₃*FH 、 palladium diacetate 、 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 mineral oil 为溶剂， 反应 22.5h， 生成 N-methyl-5,6-dihydrobenzo[c]phenanthridine
  参考文献：
  名称：

  Synthesis of N -methyl-5,6-dihydrobenzo[ c ]phenanthridine and its sp 3 C(6)–H bond functionalization via oxidative cross-dehydrogenative coupling reactions

  摘要：

  An expeditious route involving a Pd-catalyzed intramolecular biaryl-coupling for the synthesis of the N-methyl-5,6-dihydrobenzo[c]phenanthridine scaffold has been developed. For the first time, we herein report the sp(3) C(6)-H functionalization of this heterocyclic scaffold through DDQ-mediated cross-dehydrogenative coupling reactions with nitroalkanes, dialkyl malonates, alkynes, dialkyl phosphites, carbonyl compounds, pyrrole, and indoles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.018

文献信息

• Sanguinarine as a new chemical entity of thioredoxin reductase inhibitor to elicit oxidative stress and promote tumor cell apoptosis
  作者：Juan Yao、Dongzhu Duan、Zi-Long Song、Junmin Zhang、Jianguo Fang

  DOI：10.1016/j.freeradbiomed.2020.01.008

  日期：2020.5

  The alteration of redox homeostasis is a hallmark of cancer cells. As a critical player in regulating cellular redox signaling, thioredoxin reductase (TrxR) enzymes are increasingly recognized as attractive targets for anticancer drug development. We reported herein the natural product sanguinarine (SAN) as a potent inhibitor of TrxR with a new chemical sca ffold. Inhibition of TrxR leads to accumulation of the oxidized thioredoxin, elicits oxidative stress, and finally promotes apoptosis of cancer cells. Further synthesis of di fferent model compounds of SAN demonstrated that the phenanthridinium unit is responsible for the TrxR inhibition. The core structure of SAN, e.g., the phenanthridinium moiety, is di fferent from those of known TrxR inhibitors, and thus SAN is a new chemical entity of TrxR inhibitors and may serve a lead for further development. In addition, as the phenan- thridinium sca ffold is widely present in natural products, the disclosure of TrxR inhibition by such unit sheds light in understanding the pharmacological actions of these molecules.
• Synthesis of N -methyl-5,6-dihydrobenzo[ c ]phenanthridine and its sp 3 C(6)–H bond functionalization via oxidative cross-dehydrogenative coupling reactions
  作者：Adriana Romo-Pérez、Luis D. Miranda、Abraham García

  DOI：10.1016/j.tetlet.2015.10.018

  日期：2015.12

  An expeditious route involving a Pd-catalyzed intramolecular biaryl-coupling for the synthesis of the N-methyl-5,6-dihydrobenzo[c]phenanthridine scaffold has been developed. For the first time, we herein report the sp(3) C(6)-H functionalization of this heterocyclic scaffold through DDQ-mediated cross-dehydrogenative coupling reactions with nitroalkanes, dialkyl malonates, alkynes, dialkyl phosphites, carbonyl compounds, pyrrole, and indoles. (C) 2015 Elsevier Ltd. All rights reserved.