1,2-demethylnuciferine | 69424-55-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 1,2-demethylnuciferine
• 英文别名: dl-1,2-Dihydroxyaporphin；6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,2-diol；1,2-Dihydroxyaporphine；6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,2-diol
• CAS: 69424-55-1
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: SYKWSIUDXOQIDR-UHFFFAOYSA-N

物化性质

• 沸点：
  472.1±45.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-demethylnuciferine 在 cesium fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以76%的产率得到(+/-)-roemerine
  参考文献：
  名称：

  3,4-Dihydroxy- and 3,4-methylenedioxy- phenanthrene-type alkaloids with high selectivity for D2 dopamine receptor

  摘要：

  Dopamine-mediated neurotransmission plays an important role in relevant psychiatric and neurological disorders. Nowadays, there is an enormous interest in the development of new drugs acting at the dopamine receptors (DR) as potential new targets for the treatment of schizophrenia or Parkinson's disease. Previous studies have revealed that isoquinoline compounds such as tetrahydroisoquinolines (THIQs) can behave as selective D-2 dopaminergic alkaloids. In the present study we have synthesized five aporphine compounds and five phenanthrene alkaloids and evaluated their potential dopaminergic activity. Binding studies on rat striatal membranes were used to evaluate their affinity and selectivity towards D-1 and D-2 DR. Phenanthrene type alkaloids, in particular the 3,4-dihydroxy- and 3,4-methylenedioxy derivatives, displayed high selectivity towards D-2 DR. Therefore, they are potential candidates to be used in the treatment of schizophrenia (antagonists) or Parkinson's disease (agonists) due to their scarce D-1 DR-associated side effects. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.078
• 作为产物：
  描述：

  2-(2-bromophenyl)-N-(3,4-dimethoxyphenethyl)acetamide 在 sodium tetrahydroborate 、 palladium diacetate 、 三溴化硼 、 potassium carbonate 、 三氯氧磷 、 2-二苯基磷-2'-(N,N-二甲氨基)联苯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 11.0h， 生成 1,2-demethylnuciferine
  参考文献：
  名称：

  3,4-Dihydroxy- and 3,4-methylenedioxy- phenanthrene-type alkaloids with high selectivity for D2 dopamine receptor

  摘要：

  Dopamine-mediated neurotransmission plays an important role in relevant psychiatric and neurological disorders. Nowadays, there is an enormous interest in the development of new drugs acting at the dopamine receptors (DR) as potential new targets for the treatment of schizophrenia or Parkinson's disease. Previous studies have revealed that isoquinoline compounds such as tetrahydroisoquinolines (THIQs) can behave as selective D-2 dopaminergic alkaloids. In the present study we have synthesized five aporphine compounds and five phenanthrene alkaloids and evaluated their potential dopaminergic activity. Binding studies on rat striatal membranes were used to evaluate their affinity and selectivity towards D-1 and D-2 DR. Phenanthrene type alkaloids, in particular the 3,4-dihydroxy- and 3,4-methylenedioxy derivatives, displayed high selectivity towards D-2 DR. Therefore, they are potential candidates to be used in the treatment of schizophrenia (antagonists) or Parkinson's disease (agonists) due to their scarce D-1 DR-associated side effects. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.078

文献信息

• [EN] PHARMACEUTICAL COMPOSITION FOR USE IN THE TREATMENT OF NEUROLOGICAL DISEASES<br/>[FR] COMPOSITION PHARMACEUTIQUE DESTINÉE À ÊTRE UTILISÉE DANS LE TRAITEMENT DE MALADIES NEUROLOGIQUES
  申请人：ACLIPSE ONE INC

  公开号：WO2021026413A1

  公开（公告）日：2021-02-11

  The present invention relates to pharmaceutical compositions for administration to mammals that include (6aS)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient that provides pharmacokinetic profiles useful for the treatment of neurodegenerative diseases.

  本发明涉及用于给哺乳动物的药物组合物，包括（6aS）-6-甲基-5,6,6a,7-四氢-4H-二苯并[de,g]喹啉-10,11-二酚或其药用可接受的盐，以及至少一种提供药代动力学特性的药用可接受的赋形剂，用于治疗神经退行性疾病。
• Aporphines. 9. Synthesis and Pharmacological Evaluation of (±) 9, 10-Dihydroxyaporphine [(±)-Isoapomorphine], (±)-,(-)-, and (±)-1,2-Dihydroxyaporphine, and (+)-1, 2, 9, 10 - Tetrahydroxyaporphine.
  作者：John Neumeyer、Monica McCarthy、Sam Battista、Franklin Rosenberg、David Teiger

  DOI：10.1021/jm00269a602

  日期：1973.11
• CRYSTALLINE FORM OF S-APOMORPHINE
  申请人：Aclipse One, Inc.

  公开号：EP3793980A1

  公开（公告）日：2021-03-24
• Anti-Inflammatory and Anti-Allergy Extracts from Nettle
  申请人：Alberte Randall S.

  公开号：US20100009927A1

  公开（公告）日：2010-01-14

  The present invention relates in part to nettle extracts that are useful for treating or preventing seasonal allergies, allergic rhinitis, and other inflammatory conditions.
• METHODS OF SCREENING USING AMPHIBIANS
  申请人：Brändli André W.

  公开号：US20120010103A1

  公开（公告）日：2012-01-12

  High-throughput methods of screening agents for activities affecting renal, cardiac, blood or lymphatic vascular development and functions in amphibians in multiwell plates are provided. Also provided are novel compounds that modulate blood and lymphatic vascular development.