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Synthesis and Anti-Inflammatory Activity of N(2)-Arylindazol-3(2H)-One Derivatives: Copper-Promoted Direct N-Arylation via Chan-Evans-Lam Coupling.

ABSTRACT: Inflammatory-related diseases are becoming increasingly prevalent, leading to a growing focus on the development of anti-inflammatory agents, with a particular emphasis on creating novel structural compounds. In this study, we present a highly efficient synthetic method for direct N-arylation to produce a variety of N(2)-arylindazol-3(2H)-ones 3, which exhibit anti-inflammatory activity. The Chan-Evans-Lam (CEL) coupling of N(1)-benzyl-indazol-3-(2H)-ones 1 with arylboronic acids 2 in the presence of a copper complex provided the corresponding N(2)-arylindazol-3(2H)-ones 3 in good-to-excellent yields, as identified with NMR, MS, and X-ray crystallography techniques. The cell viability and anti-inflammatory effects of the synthesized compounds (3 and 5) were briefly assessed using the MTT method and Griess assay. Among them, compounds 5 exhibited significant anti-inflammatory effects with negligible cell toxicity.

SUBMITTER: Kim K

PROVIDER: S-EPMC10538006 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature

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Synthesis and Anti-Inflammatory Activity of N(2)-Arylindazol-3(2H)-One Derivatives: Copper-Promoted Direct N-Arylation via Chan-Evans-Lam Coupling.

Kim Kyungmin K Kim Jeong Ho JH Choi Heejae H Lee Byeongno B Lee Jihyun J Ok Kang Min KM Lee Tae Hoon TH Kim Hakwon H

Molecules (Basel, Switzerland) 20230920 18

Inflammatory-related diseases are becoming increasingly prevalent, leading to a growing focus on the development of anti-inflammatory agents, with a particular emphasis on creating novel structural compounds. In this study, we present a highly efficient synthetic method for direct N-arylation to produce a variety of N(2)-arylindazol-3(2H)-ones 3, which exhibit anti-inflammatory activity. The Chan-Evans-Lam (CEL) coupling of N(1)-benzyl-indazol-3-(2H)-one ...[more]

PMID: 37764482

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Project description:Development of heterogeneous catalysts from biomass-derived activated carbon is a challenging task. Biomass-derived activated carbon possesses a large specific surface area, highly porous structure, and good thermal/chemical stability. Magnetic copper catalysts based on biomass-derived activated carbon exhibited good catalytic activity in base-free Chan-Lam coupling and oxidations. Herein, biomass-derived activated carbon was prepared by the carbonization of neem dead leaves (abundant waste biomass) followed by chemical activation with KOH. Such a porous carbon material was used as a low cost and highly efficient support material for the preparation of inexpensive and environmentally benign magnetic catalysts [Cu@KF-C/MFe2O4, M = Co, Cu, Ni, and Zn]. In addition, KF modification was done to impart basic character to the catalyst that can perform C-N coupling under base-free conditions. Initially, Brunauer-Emmett-Teller (BET) analysis of the synthesized catalysts was carried out, which indicated that Cu@KF-C/CoFe2O4 possess more surface area as well as pore volume, and so accounting for the highest activity among the other synthesized catalysts. Further, X-ray photoelectron spectroscopy (XPS) analysis was performed, which inferred that Cu@KF-C/CoFe2O4 contains most of the copper in reduced form, i.e., Cu(0), which is the active species responsible for better catalytic activity toward Chan-Lam coupling reactions as well as oxidation of alcohols and hydrocarbons. The physiochemical properties of the most active catalyst, Cu@KF-C/CoFe2O4, was examined by BET, XPS, Fourier transform infrared Spectroscopy (FTIR), thermogravimetric analysis (TGA), field emission gun scanning electron microscopy (FEG-SEM), high-resolution transmission electron microscopy (HR-TEM), energy dispersive X-ray (EDX) mapping, energy dispersive X-ray (EDX), inductively coupled plasma atomic emission spectroscopy (ICP-AES), powder X-ray diffraction (XRD), and vibrating sample magnetometry (VSM). Moreover, Cu@KF-C/CoFe2O4 shows excellent stability as well as reusability and could be easily separated with the help of an external magnet.

Dataset Information

Synthesis and Anti-Inflammatory Activity of N(2)-Arylindazol-3(2H)-One Derivatives: Copper-Promoted Direct N-Arylation via Chan-Evans-Lam Coupling.

Publications

Synthesis and Anti-Inflammatory Activity of <i>N</i>(2)-Arylindazol-3(2<i>H</i>)-One Derivatives: Copper-Promoted Direct <i>N</i>-Arylation via Chan-Evans-Lam Coupling.

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