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Brucine

About: Brucine is a research topic. Over the lifetime, 586 publications have been published within this topic receiving 6866 citations. The topic is also known as: 10,11-dimethoxy strychnine.


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Journal ArticleDOI
TL;DR: Brucine recognized specifically m-substituted benzoic acid derivatives among other geometrical isomers by Brucine 1 as mentioned in this paper, and the results of complex formation by combination of substituted Vol. 8, No. 3, 2002 was summarized in the Table.
Abstract: Brucine recognized specifically m-substituted benzoic acid derivatives among other geometrical isomers. Crystalline clathrates were produced as single crystals from the reaction mixture solutions. The search for new building blocks and structural motifs for crystal engineering has been growing as an intensive research area in recent several years [1]. The optical resolution of enantio mixtures of acids by an optically active basic compound was often reported [2] from mid-20 century. For example, brucine 1 known as an alkaloid derivative is essential compound for an optical resolution agent [3]. However, the molecular recognition of geometrical isomers of mono-substituted benzoic acids by brucine 1. has not been known. We examined the molecular recognition of mono-substituted benzoic acid derivatives 2 with brucine 1_. Mono-substituted benzoic acid derivatives used were ortho, metha, and para isomers with chloro-, bromo-, or nitro-substituent. After equimolar amount mixture of enantiomerically pure brucine 1 and a m-substituted benzoic acid was completely dissolved in methanol, the solution was allowed to stand quietly (without stirring) at room temperature. The precipitation of a solid material was observed from the initial complete solution after 0.5-3 hours. The results of complex formation by combination of substituted Vol. 8, No. 3, 2002 Molecular recognition and resolution of constitutional isomer of benzoic acids by brucine benzoic acids 2 with brucine 1_ is summarized in the Table. In the case of only m-nitrobenzoic acid 2b (entry 2 in Table), the crystal ot the clathrate compound 3b immediately precipitated. Surprisingly, the crystal of the clathrate compound from the reaction mixture in methanol formed a good single crystal. Compounds 3je and 3h (entries 5 and 8 in Table) afforded single crystals similarly under the same conditions as described above. Thus, the specific self-assembling between m-substituted benzoic acid 2 and brucine 1 was confirmed, however, attempts to obtain crystalline clathrate compounds of oand p-substituted benzoic acids with brucine 1 were all unsuccessful as shown in the Table.

5 citations

Journal ArticleDOI
TL;DR: The structures of the brucine complexes with (+)-(1R,2S,4R)-bicyclo[2.2.1] and 7-oxa derivatives have been determined in this article.
Abstract: The structures of the brucine complexes with (+)-(1R,2S,4R)-bicyclo[2.2.1]hept-5-ene-2-cyanohydrin and (+)-(1R,2R,4R)-7-oxabicyclo[2.2.1]hept-5-ene-2-cyanohydrin {(6) 2,3-dimethoxystrychnidine-2-hydroxybicyc-lo[2.2.1]hept-5-ene-2-carbonitr ile (1/1) and (7) 2,3-dime-thoxystrychnidine-2-hydroxy-7-oxabicyclo[2.2. I]hept-5-ene-2-carbonitrile (1/1)} have been determined. The primary interaction in the complexes is a hydrogen bond between the OH group of the cyanohydrin and the most basic N atom of brucine. Molecular-mechanics calculations on the 7-oxa derivative indicate that the enantiomeric cyanohydrin will fit into the same cavity in the brucine matrix at the cost of ca 71 kJ mol-1

5 citations

Journal ArticleDOI
TL;DR: One of the two adjacent methoxyl groups attached to the aromatic ring of brucine was found to be demethylated selectively in rabbits, and the predominant monophenolic metabolite was identified as 2-methoxy-3-hydroxystrychnine and excreted mostly as conjugated forms in the urine, mainly the β-glucuronide.

4 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20235
202224
202117
20208
201912
201812