26601-10-5Relevant articles and documents
Two new alkaloids from Crinum asiaticum var. sinicum
Kogure, Noriyuki,Katsuta, Noriko,Kitajima, Mariko,Takayama, Hiromitsu
, p. 1545 - 1548 (2011)
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.
A Nivalin industrial preparation method (by machine translation)
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Paragraph 0041; 0042, (2019/02/27)
The invention relates to a technical field of drug synthesis, in particular relates to a preparation method of the galanthamine hydrobromide. Preparation method of this invention comprises the following steps: (1) the racemate narwedine as raw materials, adding resolution solvent to get levorotation narwedine; (2) L narwedine [...] butyl boron lithium hydride reduction shall be galantamine free alkali, further and hydrobromic acid shall be galanthamine hydrobromide. (by machine translation)
An Eleven-Step Synthesis of Galanthamine from Commercially Available Materials
Nugent, Jeremy,Banwell, Martin G.
, p. 5862 - 5867 (2016/12/18)
Narwedine, an immediate precursor to the therapeutically valuable alkaloid (–)-galanthamine, has been synthesised by engaging an iodinated isovanillin derivative in an intermolecular Mitsunobu reaction with a 2-cyclohexen-1-ol derivative. The resulting aryl ether participated in an exceptionally efficient intramolecular Heck reaction to give a tetracyclic lactol after the hydrolysis of the primary cyclisation product. This last compound is an advanced intermediate associated with the Magnus synthesis of narwedine and could be elaborated to narwedine itself under reductive amination conditions. As a result, an eleven-step synthesis of galanthamine has been established.
Thiol-Reactive Analogues of Galanthamine, Codeine, and Morphine as Potential Probes to Interrogate Allosteric Binding within Nicotinic Acetylcholine Receptors
Gallagher, Ryan,Chebib, Mary,Balle, Thomas,McLeod, Malcolm D.
, p. 1834 - 1841 (2015/12/26)
Alkaloids including galanthamine (1) and codeine (2) are reported to be positive allosteric modulators of nicotinic acetylcholine receptors (nAChRs), but the binding sites responsible for this activity are not known with certainty. Analogues of galanthamine (1), codeine (2), and morphine (3) with reactivity towards cysteine thiols were synthesized including conjugated enone derivatives of the three alkaloids 4-6 and two chloro-alkane derivatives of codeine 7 and 8. The stability of the enones was deemed sufficient for use in buffered aqueous solutions, and their reactivity towards thiols was assessed by determining the kinetics of reaction with a cysteine derivative. All three enone derivatives were of sufficient reactivity and stability to be used in covalent trapping, an extension of the substituted cysteine accessibility method, to elucidate the allosteric binding sites of galanthamine and codeine at nAChRs.
