An Efficient One‐Step Synthesis of Piperidin‐2‐yl and Pyrrolidin‐2‐yl Flavonoid Alkaloids through Phenolic Mannich Reactions

Nguyen, Thanh Binh; Wang, Qian; Guéritte, Françoise

doi:10.1002/ejoc.201101312

Cited by 27 publications

(12 citation statements)

References 24 publications

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“…Due to the comparatively higher flexibility of flavan molecules, the substitution on the 6-,8-positions had a lack of selectivity, even when different solvent systems were tried including MeOH, EtOH, H 2 O/MeOH, H 2 O/THF. Yet, this substitution selectivity was observed and reported in flavonone and flavone groups, indicating that carbonyl groups at position 4 can impact the nucleophilic activities of positions 6 and 8 [ 9 , 10 ].…”

Section: Resultsmentioning

confidence: 80%

Total Synthesis of Novel Skeleton Flavan-Alkaloids

Jing

Simon

2020

Molecules

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The first total synthesis of novel skeleton natural compounds kinkeloids A and B, a group of newly discovered flavan alkaloids isolated from the African plant Combretum micranthum, are described in this study. The key and final step are achieved by Mannich reaction, through which the piperidine moiety couples to the flavan moiety. The identities of synthesized kinkeloids were further confirmed through a comparison with the ones in the plant leaves extract using LC/MS.

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Section: Resultsmentioning

confidence: 80%

Total Synthesis of Novel Skeleton Flavan-Alkaloids

Jing

Simon

2020

Molecules

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“…Nucleophilic attack of the isocyanide ( 13 ) may then come from the bottom face (equatorial attack, in red), leading to an disfavored twist‐boat conformation I , or from the top face (axial attack, in green), leading directly to a more favorable chair conformation ( II ). Consequently, the kinetic barrier for an axial attack is much lower than for an equatorial attack, providing exclusively the trans ‐product , …”

Section: Resultsmentioning

confidence: 99%

Efficient Diastereoselective Three‐Component Synthesis of Pipecolic Amides

et al. 2019

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An efficient Ugi‐type three‐component reaction (U‐3CR) for the synthesis of pipecolic amides is reported. The U‐3CR between electronically diverse isocyanides, carboxylic acids and 4‐substituted Δ1‐piperideines proceeds in a highly diastereoselective fashion. The Δ1‐piperideines are obtained by NCS‐mediated oxidation of the corresponding 4‐substituted piperidines, which in turn are generated by an efficient two‐step procedure involving the alkylation of 4‐picoline and subsequent catalytic hydrogenation of the pyridine ring. We demonstrate the utility of this U‐3CR, in combination with the convertible isocyanide 2‐bromo‐6‐isocyanopyridine, in the synthesis of the anticoagulant argatroban.

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“…In order to enhance water-solubility, bioavailability, and tumor inhibitory activities of ISL, we used ISL as lead compound while remaining its hydroxyl and modifying side chains in A ring of chalcone with nitrogen heterocyclic ring compounds and open-chain amino through Mannich reaction [19][20][21]. We chose the Mannich reaction in our study, because the reaction products Mannich alkaline compounds have a quite wide range of biological activity, such as antibacterial, anticonvulsive, anti-inflammatory, anti-tumor activities [22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-Tumor Activity of Novel Aminomethylated Derivatives of Isoliquiritigenin

Zhang

Wang

et al. 2014

Molecules

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A series of new aminomethylated derivatives of isoliquiritigenin was synthesized. The structures of the compounds were confirmed by IR, MS, NMR, 13 C-NMR and elemental analyses. Cytotoxic activities of these derivatives towards the human prostatic cell line PC-3, human mammary cancer cell line MCF-7 and human oophoroma cell line HO-8910 in vitro were tested. The IC50 values showed cytotoxic activities of some of these new derivatives were relatively strong. Furthermore, tumor growth inhibition in vivo of aminomethylated derivatives of isoliquiritigenin 15 was superior to that of isoliquritigenin and reached inhibition rates of 71.68%. The detailed synthesis, spectroscopic data, biological and pharmacologicalactivities of the synthesized compounds were provided.

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An Efficient One‐Step Synthesis of Piperidin‐2‐yl and Pyrrolidin‐2‐yl Flavonoid Alkaloids through Phenolic Mannich Reactions

Cited by 27 publications

References 24 publications

Total Synthesis of Novel Skeleton Flavan-Alkaloids

Total Synthesis of Novel Skeleton Flavan-Alkaloids

Efficient Diastereoselective Three‐Component Synthesis of Pipecolic Amides

Synthesis and Anti-Tumor Activity of Novel Aminomethylated Derivatives of Isoliquiritigenin

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