Continuous flow synthesis of N,N-dimethyltryptamine (DMT) analogues with therapeutic potential.

IF 4.1 4区 医学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY RSC medicinal chemistry Pub Date : 2024-10-07 DOI:10.1039/d4md00562g
Andreas Simoens, Andreas Dejaegere, Marthe Vandevelde, Christian V Stevens
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Abstract

Herein, we describe the continuous flow synthesis and in-line extraction of N,N-dimethyltryptamine (DMT) and several of its analogues using a Fischer indole reaction, along with a larger gram scale synthesis (4.75 g) of the model compound. These products could then be quickly transformed into their respective fumarate salts, making them easier to handle and stable for long time storage using a straightforward batch procedure. Additionally, the commercially available drug rizatriptan benzoate could be synthesised with high purity using this setup. The presented method employs relatively green solvents both for the synthesis and purification of the target products.

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具有治疗潜力的 N,N-二甲基色胺 (DMT) 类似物的连续流合成。
在此,我们介绍了利用费舍尔吲哚反应连续流合成和在线萃取 N,N-二甲基色胺(DMT)及其几种类似物的方法,以及更大克级(4.75 克)的模型化合物合成方法。这些产品随后可迅速转化为各自的富马酸盐,从而使其更易于处理,并可通过简单的批处理程序长期稳定地储存。此外,利用该装置还可以合成高纯度的市售药物苯甲酸利扎曲普坦。所介绍的方法在合成和纯化目标产品时都使用了相对绿色的溶剂。
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来源期刊
CiteScore
5.80
自引率
2.40%
发文量
129
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Back cover Property-based optimisation of PROTACs. A practical guide for the assay-dependent characterisation of irreversible inhibitors. Adjuvant strategies to tackle mcr-mediated polymyxin resistance. Antibacterial activity of the structurally novel C-2 amine-substituted analogues based on quinoxaline.
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