(±)-nornarwedine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: (±)-nornarwedine
• 英文别名: (1S,12S)-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-one
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: YDTYNIAJZIKMST-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-nornarwedine 在 甲酸 、 L-Selectride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 生成 加兰他敏
  参考文献：
  名称：

  Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids

  摘要：

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.

  DOI：

  10.1021/jo9807868
• 作为产物：
  描述：

  原儿茶酸 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 硫酸 、 sodium methylate 、 potassium carbonate 、 三氟乙酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 吡啶 、 甲醇 、 六甲基磷酰三胺 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 45.42h， 生成 (±)-nornarwedine
  参考文献：
  名称：

  Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids

  摘要：

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.

  DOI：

  10.1021/jo9807868

文献信息

• Two New Alkaloids from Crinum asiaticum var. sinicum
  作者：Noriyuki Kogure、Noriko Katsuta、Mariko Kitajima、Hiromitsu Takayama

  DOI：10.1248/cpb.59.1545

  日期：——

  Two new alkaloids (1, 2) were isolated from the whole plants of Crinum asiaticum var. sinicum together with seven known alkaloids. The structures of the new alkaloids were elucidated by spectroscopic analyses and chemical conversions from known alkaloids. New alkaloid 1 was isolated for the first time as a natural product, although it has been prepared as a synthetic product.

  从 Crinum asiaticum var. sinicum 的全株中分离出两种新生物碱（1，2）和七种已知生物碱。通过光谱分析和已知生物碱的化学转化，阐明了新生物碱的结构。新生物碱 1 是首次作为天然产物分离出来的，尽管它曾作为合成产物制备过。
• Seco-isopowellaminone: A new heterocycle from nornarwedine
  作者：Manfred Hirnschall、Johannes Froehlich、Ulrich Jordis、Kurt Mereiter

  DOI：10.1002/jhet.5570390622

  日期：2002.11

  crinine-type compounds by a reverse Michael- / Michael addition. Narwedine and bromonarwedine yield, as confirmed by X-ray structure determination, the known seco-powellaminone as well as the novel seco-isopowellaminone.

  众所周知，可以通过反向Michael- / Michael加成将Nornarwedine类型的分子转化为criinine类型的化合物。通过X-射线结构测定证实，已知的癸二-异戊二烯酮和新的癸二异-异戊二烯酮都可得到narwedine和bronarwedine的产量。
• CONSTRUCTS AND METHODS FOR BIOSYNTHESIS OF GALANTHAMINE
  申请人：Donald Danforth Plant Science Center

  公开号：US20190300892A1

  公开（公告）日：2019-10-03

  The present disclosure relates generally to the identification of biosynthetic pathway genes. In particular, it relates to the identification of enzymes within the Amaryllidaceae alkaloid biosynthetic pathway as well as to engineering transgenic organisms for the production of galanthamine and/or hemanthamine and/or lycorine.
• US8450365B2
  申请人：——

  公开号：US8450365B2

  公开（公告）日：2013-05-28
• Synthesis and evaluation of (−)- and (+)-[11C]galanthamine as PET tracers for cerebral acetylcholinesterase imaging
  作者：Hiroyuki Kimura、Tomoki Kawai、Yoshio Hamashima、Hidekazu Kawashima、Kenji Miura、Yuta Nakaya、Makoto Hirasawa、Kenji Arimitsu、Tetsuya Kajimoto、Yoshiro Ohmomo、Masahiro Ono、Manabu Node、Hideo Saji

  DOI：10.1016/j.bmc.2013.11.026

  日期：2014.1

  Improved radiopharmaceuticals for imaging cerebral acetylcholinesterase (AChE) are needed for the diagnosis of Alzheimer's disease (AD). Thus, C-11-labeled (-)-galanthamine and its enantiomers were synthesized as novel agents for imaging the localization and activity of AChE by positron emission tomography (PET). C-11 was incorporated into (-)- and (+)-[C-11] galanthamine by N-methylation of norgalanthamines with [C-11] methyl triflate. Simple accumulation of C-11 in the brain was measured in an in vivo biodistribution study using mice, whilst donepezil was used as a blocking agent in analogous in vivo blocking studies. In vitro autoradiography of rat brain tissue was performed to investigate the distribution of (-)-[C-11] galanthamine, and confirmed the results of PET studies in mice. The radiochemical yields of N-methylation of (-)- and (+)-norgalanthamines were 13.7% and 14.4%, respectively. The highest level of accumulation of C-11 in the brains of mice was observed at 10 min after administration (2.1% ID/g). Intravenous pretreatment with donepezil resulted in a 30% decrease in accumulation of (-)-[C-11] galanthamine in the striatum; however, levels in the cerebellum were unchanged. In contrast, use of (+)[ C-11] galanthamine led to accumulation of radioactivity in the striatum equal to that in the cerebellum, and these levels were unaffected by pretreatment with donepezil. In in vitro autoradiography of regional radioactive signals of brain sections showed that pretreatment with either (-)-galanthamine or donepezil blocked the binding of (-)-[C-11] galanthamine to the striatum, while sagittal PET imaging revealed accumulation of (-)-[C-11] galanthamine in the brain. These results indicate that (-)-[C-11] galanthamine showed specific binding to AChE, whereas (+)-[C-11]-galanthamine accumulated in brain tissue by nonspecific binding. Thus, optically pure (-)-[C-11] galanthamine could be a useful PET tracer for imaging cerebral AChE. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.