2-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-1-(3-methoxyphenyl)ethan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-1-(3-methoxyphenyl)ethan-1-one
• 英文别名: 2-(4-Methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-1-(3-methoxyphenyl)ethanone；2-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-1-(3-methoxyphenyl)ethanone
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: FWUSDXQBNFRZIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  那可汀 在 硝酸 作用下， 以 甲醇 为溶剂， 反应 2.08h， 生成 2-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-1-(3-methoxyphenyl)ethan-1-one
  参考文献：
  名称：

  C(SP3)-H 键的无金属活化，特权 1-取代-1,2,3,4-四氢异喹啉的实用快速合成

  摘要：

  Cotarnine 和酰基/芳基酮在绿色溶剂中的反应提供了一种有效的方法，通过 C(SP3)-H 键的无金属激活，以优异的收率获得一系列特权 1,2,3,4-四氢异喹啉。这种一锅程序在室温下无碱条件下进行，并具有广泛的功能。该反应具有高度化学选择性，可在多克规模上进行扩展，并且通过简单过滤分离出纯产物，无需后处理。有趣的是，从可塔宁卤化物盐的补充两步程序以良好的收率提供了曼尼希产品。范围详细说明了 9-溴可豆碱盐，以获取 9-溴香豆素启发的多种类似物。

  DOI：

  10.1002/ejoc.201700471

文献信息

• Methods of preventing or treating flavivirus virus infections and methods of inhibiting the entry of flvivirus, enterovirus or lentivirus into host cells
  申请人：City University of Hong Kong

  公开号：US11357771B2

  公开（公告）日：2022-06-14

  A method of preventing or treating a subject suffering from a flavivirus infection by administering an effective amount of berbamine or its analogue to the subject, berbamine has a structure of Formula (I), wherein the flavivirus infection is caused by Japanese encephalitis virus, Zika virus or Dengue virus. A method of inhibiting the entry of a flavivirus, an enterovirus and/or a lentivirus into host cells includes contacting the host cells with an effective amount of berbamine of its analogue, berbamine has a structure of Formula (I), wherein the flavivirus is Japanese encephalitis virus, Zika virus or Dengue virus.

  一种通过向受试者施用有效量的小檗胺或其类似物来预防或治疗黄病毒感染的方法，小檗胺具有式(I)的结构，其中黄病毒感染是由日本脑炎病毒、寨卡病毒或登革病毒引起的。一种抑制黄病毒、肠道病毒和/或慢病毒进入宿主细胞的方法，包括使宿主细胞与有效量的伯胺或其类似物接触，伯胺具有式（I）的结构，其中黄病毒是日本脑炎病毒、寨卡病毒或登革病毒。
• METHODS OF PREVENTING OR TREATING FLAVIVIRUS VIRUS INFECTIONS AND METHODS OF INHIBITING THE ENTRY OF FLVIVIRUS, ENTEROVIRUS OR LENTIVIRUS INTO HOST CELLS
  申请人：City University of Hong Kong

  公开号：US20210060002A1

  公开（公告）日：2021-03-04

  A method of preventing or treating a subject suffering from a flavivirus infection by administering an effective amount of berbamine or its analogue to the subject, berbamine has a structure of Formula (I), wherein the flavivirus infection is caused by Japanese encephalitis virus, Zika virus or Dengue virus. A method of inhibiting the entry of a flavivirus, an enterovirus and/or a lentivirus into host cells includes contacting the host cells with an effective amount of berbamine of its analogue, berbamine has a structure of Formula (I), wherein the flavivirus is Japanese encephalitis virus, Zika virus or Dengue virus.
• [EN] USE OF BERBAMINE OR ITS ANALOGUE FOR PREVENTING OR TREATING RNA VIRUS INFECTION<br/>[FR] UTILISATION DE BERBAMINE OU DE SON ANALOGUE POUR LA PRÉVENTION OU LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'ARN
  申请人：UNIV CITY HONG KONG

  公开号：WO2021043234A1

  公开（公告）日：2021-03-11

  Provided herein is a method of preventing or treating a subject suffering from a flavivirus infection by administering an effective amount of berbamine or its analogue to the subject, berbamine has a structure of Formula (I), wherein the flavivirus infection is caused by Japanese encephalitis virus, Zika virus or Dengue virus, and a method of inhibiting the entry of a flavivirus, an enterovirus and/or a lentivirus into host cells, comprising contacting the host cells with an effective amount of berbamine of its analogue, berbamine has a structure of Formula (I), wherein the flavivirus is Japanese encephalitis virus, Zika virus or Dengue virus. Also provided is a method of preventing or treating a subject suffering from a coronavirus, particularly the coronavirus is SARS-CoV-2 or MERS-CoV, a method of inhibiting the entry of a coronavirus into host cells, as well as use of berbamine or its analogue in the preparation of a medicament for preventing or treating a flavivirus infection, enterovirus infection, lentivirus infection or coronavirus infection.
• Metal-Free Activation of C(sp³ )-H Bond, and a Practical and Rapid Synthesis of Privileged 1-Substituted 1,2,3,4-Tetrahydroisoquinolines
  作者：Santosh Kumar Choudhury、Pragati Rout、Bibhuti Bhusan Parida、Jean-Claude Florent、Ludger Johannes、Ganngam Phaomei、Emmanuel Bertounesque、Laxmidhar Rout

  DOI：10.1002/ejoc.201700471

  日期：2017.9.25

  reaction of cotarnine and acyl/aryl ketones in green solvents provides an efficient approach to an array of privileged 1,2,3,4-tetrahydroisoquinolines in excellent yields by metal free Activaion of C(SP3)-H bonds. This one-pot procedure takes place under base-free conditions at room temperature, and tolerates a wide range of functionalities. The reaction is highly chemo-selective, scalable in multi-gram

  Cotarnine 和酰基/芳基酮在绿色溶剂中的反应提供了一种有效的方法，通过 C(SP3)-H 键的无金属激活，以优异的收率获得一系列特权 1,2,3,4-四氢异喹啉。这种一锅程序在室温下无碱条件下进行，并具有广泛的功能。该反应具有高度化学选择性，可在多克规模上进行扩展，并且通过简单过滤分离出纯产物，无需后处理。有趣的是，从可塔宁卤化物盐的补充两步程序以良好的收率提供了曼尼希产品。范围详细说明了 9-溴可豆碱盐，以获取 9-溴香豆素启发的多种类似物。