(+/-)-roemerine | 2030-53-7

• 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: (+/-)-roemerine
• 英文别名: (±)-roemerine；(-)-roemerine；L-nuceferine；Aporheine；roemerine；remerine；11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene
• CAS: 2030-53-7；15548-23-9
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: JCTYWRARKVGOBK-UHFFFAOYSA-N

物化性质

• 沸点：
  424.0±34.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  102-103°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-roemerine 在 L-酒石酸 作用下， 生成 莲碱
  参考文献：
  名称：

  The Synthesis of l-Roemerine¹

  摘要：

  DOI：

  10.1021/ja01236a024
• 作为产物：
  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

文献信息

• Compounds and compositions for treating infection
  申请人：Chepkwony Paul Kiprono

  公开号：US20090069277A1

  公开（公告）日：2009-03-12

  Compounds from 14 Kenyan plants, including from the root of Dovyalis abyssinica and Clutia robusta have been characterized and isolated, and their uses are disclosed.

  来自14种肯尼亚植物的化合物，包括 Dovyalis abyssinica 和 Clutia robusta 的根部已经被鉴定和分离，它们的用途也被公开了。
• Fremy's salt oxidation of some isoquinoline alkaloids. Biogenetic considerations
  作者：Luis Castedo、Alberto Puga、José M. Saá、Rafael Suau

  DOI：10.1016/s0040-4039(01)90506-4

  日期：1981.1

  Fremy's salt oxidation of benzyl isoquinoline and aporphine alkaloids to isoquinolones and oxoaporphines is described. Aminium radicals are suggested to account for the observed results. Their possible involvement in alkaloid biosynthesis is considered.

  描述了苄基异喹啉和阿朴啡生物碱的弗雷米盐氧化为异喹诺酮和氧磷卟啉。建议使用氨基自由基来说明观察到的结果。考虑到它们可能参与生物碱的生物合成。
• Quaternary alkaloids of some species of the Papaveraceae family
  作者：Jiří Slavík、Karel Picka、Leonora Slavíková、Eva Táborská、František Věžník

  DOI：10.1135/cccc19800914

  日期：——

  Quaternary alkaloids of the following species of Papaveraceae were studied. From Hunnemannia fumariaefolia SWEET cyclanoline, escholidine and alkaloid HF3 were isolated, from Papaver atlanticum BALL magnoflorine, from P. caucasicum MARSCH.-BIEB., P. dubium L. and P. litwinowii FEDDE ex BORNM. aporheine methohydroxide, and from P. pseudo-orientale (FEDDE) MEDW. a new alkaloid, isothebaine methohydroxide were isolated. In P. confine JORD. magnoflorine was found and in two chemotypes of P. rhoeas L. β-stylopine methohydroxide and aporheine methohydroxide could be proved.

  研究了以下Papaveraceae物种的第四纪生物碱。从Hunnemannia fumariaefolia SWEET中分离出环烷烃、escholidine和生物碱HF3，从Papaver atlanticum BALL中分离出magnoflorine，从P. caucasicum MARSCH.-BIEB.、P. dubium L.和P. litwinowii FEDDE ex BORNM.中分离出aporheine methohydroxide，从P. pseudo-orientale (FEDDE) MEDW.中分离出一种新的生物碱isothebaine methohydroxide。在P. confine JORD.中发现了magnoflorine，在两种P. rhoeas L.的化学型中证明了β-stylopine methohydroxide和aporheine methohydroxide。
• COMPOUNDS AND COMPOSITIONS FOR TREATING INFECTION
  申请人：Chepkwony Paul Kiprono

  公开号：US20120190734A1

  公开（公告）日：2012-07-26

  Compounds from 14 Kenyan plants, including from the root of Dovyalis abyssinica and Clutia robusta have been characterized and isolated, and their uses are disclosed.

  来自14种肯尼亚植物的化合物已经被鉴定和分离，包括来自阿比西尼亚多维亚利斯和强健小簇花的根部，它们的用途已经被披露。
• Small molecule toll-like receptor (TLR) antagonists
  申请人：Lipford B. Grayson

  公开号：US20070232622A1

  公开（公告）日：2007-10-04

  The invention provides methods and compositions useful for modulating signaling through Toll-like receptors. The methods involve contacting a TLR-expressing cell with a small molecule having a core structure including at least two rings. Certain of the compounds are 4-primary amino quinolines. Many of the compounds and methods are useful specifically for inhibiting immune stimulation involving at least one of TLR9, TLR8, TLR7, and TLR3. The methods may have use in the treatment of autoimmunity, inflammation, allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer, and immunodeficiency.

  本发明提供了用于调节通过Toll样受体信号传导的方法和组合物。该方法涉及使用一个包含至少两个环的核心结构的小分子接触TLR表达的细胞。其中某些化合物是4-主氨基喹啉。许多化合物和方法特别适用于抑制至少一个TLR9、TLR8、TLR7和TLR3的免疫刺激。该方法可能在治疗自身免疫、炎症、过敏、哮喘、移植排斥、移植物抗宿主病、感染、败血症、癌症和免疫缺陷方面有用。