A Novel 6-(2-methyl-2-alkylsubstituted-2H-chromen-6-yl)-amine Derivatives and Pharmacophore Model as 5-Lipoxygenase Inhibitors

Gong, Young‐Dae; Cheon, Hyae-Gyeong; Lee, Tae‐Ho; Bae, Mi-Seon; Kang, Nam Sook

doi:10.5012/bkcs.2011.32.10.3752

Cited by 4 publications

(1 citation statement)

References 22 publications

(7 reference statements)

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“…The drug-like small molecule library with variously substituted benzopyrans was constructed by Gong and co-workers [79,80]. An orally active 5-LO [81,82,83,84,85,86,87] inhibitor KRH-102140 [30,31] with the benzopyran moiety (see Figure 1) was discovered as a lead compound on the drug discovery program via HTS of in-house small molecule library by Gong et al [88].…”

Section: Solid-phase Synthesis Of Substituted Benzopyran Compoundsmentioning

confidence: 99%

Solid-Phase Parallel Synthesis of Drug-Like Artificial 2H-Benzopyran Libraries

Lee

Gong

2012

Molecules

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This review covers the construction of drug-like 2H-benzopyrans and related libraries using solid-phase parallel synthesis. In this context, the preparation of substituted benzopyrans such as mono-, di-and trisubstituted benzopyran derivatives and additional ring-fused benzopyrans such as benzopyranoisoxazoles, benzopyranopyrazoles, six-membered ring-fused benzopyrans, and polycyclic benzopyrans are highlighted.

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Section: Solid-phase Synthesis Of Substituted Benzopyran Compoundsmentioning

confidence: 99%

Solid-Phase Parallel Synthesis of Drug-Like Artificial 2H-Benzopyran Libraries

Lee

Gong

2012

Molecules

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Development for a new 5‐lipoxygenase inhibitors of N‐((6‐(substituted‐amino)‐2‐methyl‐2H‐chromen‐2‐yl)methyl)‐N‐methyl benzenesulfonamide derivatives

Kim

Abdildinova

Shin

et al. 2023

Bulletin Korean Chem Soc

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Abstract5‐Lipoxygenase (5‐LO) is one of the significant drug targets for the development of various anti‐inflammatory drugs. Herein, we designed, optimized, and synthesized a novel N‐((6‐(substituted‐amino)‐2‐methyl‐2H‐chromen‐2‐yl)methyl)‐N‐methylbenzenesulfonamide derivatives as potential 5‐LO inhibitors. Among the synthesized compounds, 10a, 10b, and 10g exhibited inhibitory activity toward 5‐LO according to the in vitro studies including enzyme activity assay (≥78% inhibition rate at 1 μM) and cell‐based assay (≥72% inhibition rate at 1 μM). 10b was selected for further in vivo efficiency using an ear edema mouse model, which was induced by arachidonic acid. Oral administration of 10b successfully suppressed ear edema and myeloperoxidase activity (MPO activity). Molecular docking studies showed alkyl and pi‐alkyl interactions of compound 10b with Ile126 and Val110 of 5‐LO as well as a hydrogen bonding with Arg138 as key protein‐ligand interactions.

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Solid-phase Parallel Synthesis of a Novel N-[Alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted Amide and Amine Drug-like Libraries

Kim¹,

Gong

Lee³

et al. 2012

Bulletin of the Korean Chemical Society

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We report the solid-phase library construction of 222 number of a novel N-[alkyl sulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B derivatives. The polymer-bound N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 9 and amine 10 derivatives were obtained by first diversity generation with various acid chlorides and alkyl halides. Further reactions on the resins 9 and 10 with substituted sulfonyl chlorides produced the desired N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B analogues.

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A Novel 6-(2-methyl-2-alkylsubstituted-2H-chromen-6-yl)-amine Derivatives and Pharmacophore Model as 5-Lipoxygenase Inhibitors

Cited by 4 publications

References 22 publications

Solid-Phase Parallel Synthesis of Drug-Like Artificial 2H-Benzopyran Libraries

Solid-Phase Parallel Synthesis of Drug-Like Artificial 2H-Benzopyran Libraries

Development for a new 5‐lipoxygenase inhibitors of N‐((6‐(substituted‐amino)‐2‐methyl‐2H‐chromen‐2‐yl)methyl)‐N‐methyl benzenesulfonamide derivatives

Solid-phase Parallel Synthesis of a Novel N-[Alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted Amide and Amine Drug-like Libraries

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