Bavachinin analogues as agonists of pan-peroxisome proliferator-activated receptors

Du, Guoxin; Zhao, Yuanyuan; Zhang, Liuqiang; Лі, Бо; Zhu, Weiliang; Huang, Cheng; Li, Yiming; Guo, Fujiang

doi:10.1007/s00044-018-2197-6

Cited by 6 publications

(4 citation statements)

References 24 publications

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“…The coupling of compounds 11 and 8 resulted in compound 12 via the Suzuki coupling reaction, which was deeply explored under different reaction systems. We were only afforded compound 12 with a 40% yield under the conditions of Pd(OAc) 2 /MeOH/Na 2 CO 3 ( Table 1 , entry 1) [ 17 ]. The yield of the reaction has not been significantly improved by changing the solvent and base (entries 2 and 3).…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis and Anti-Inflammatory Evaluation of Osajin, Scandenone and Analogues

Wang,

Ma,

Feng

et al. 2024

Pharmaceuticals

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In this study, the total synthesis of osajin, scandenone and their analogues have been accomplished. The key synthetic steps include aldol/intramolecular iodoetherification/elimination sequence reactions and a Suzuki coupling reaction to assemble the tricyclic core, chemoselective propargylation and Claisen rearrangement reactions to obtain natural compounds. In addition, we also designed and synthesized twenty-five natural product analogues. All synthetic compounds were screened for anti-inflammatory activity against tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Collectively, Compound 39e and 39d were considered as promising lead compounds for further development.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis and Anti-Inflammatory Evaluation of Osajin, Scandenone and Analogues

Wang,

Ma,

Feng

et al. 2024

Pharmaceuticals

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“…We first tested phosphine-free cross-coupling conditions that used Pd(OAc) 2 as a precatalyst, methanol as a solvent, polyethylene glycol (PEG-10000) as an additive, and Na 2 CO 3 as a base (entry 1). These conditions had previously been used for the Suzuki coupling of several 3-iodochromones 14 with para -phenolboronic acid ( 15a ), ,− including the bis-MOM-protected derivative 14a . However, when we applied these conditions to the cross-coupling of 14a and 15a , an inseparable mixture of products was obtained.…”

Section: Resultsmentioning

confidence: 99%

“…The application of this Pd-catalyzed cross-coupling reaction to the synthesis of flavonoids in general, including isoflavones, has been reviewed . The examples discussed therein and an independent literature search by us revealed that most syntheses of isoflavones using the Suzuki–Miyaura coupling start from 3-halochromones and methoxy-substituted arene boronic acids or MOM-protected phenolboronic acids. ,− Some examples for the protecting-group-free cross-coupling of phenolboronic acids have been reported using Pd/C, Pd(0)–phosphine ligands, − or Pd(OAc) 2 /polyethylene glycols (PEG) − as catalyst systems. In particular the latter variant, originally developed as an “extremely active catalyst” for the phosphine-free synthesis of biaryls through Suzuki couplings, appears to be the preferred method in the literature when unprotected phenolboronic acids are the coupling partners.…”

Section: Introductionmentioning

confidence: 99%

The Suzuki–Miyaura Cross-Coupling–Claisen Rearrangement–Cross-Metathesis Approach to Prenylated Isoflavones

et al. 2023

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Isoflavones were synthesized via Suzuki−Miyaura coupling of 3-iodochromones and para-methoxybenzene-and paraphenolboronic acid. In our hands, conditions commonly used for similar cross couplings turned out to be unsuccessful or difficult to reproduce, for example, due to the unplanned partial cleavage of MOM-protecting groups. Using Pd(dba) 2 as a precatalyst and tricyclohexylphosphine as an activating ligand, reliable cross-coupling conditions were identified. In all cases, notably higher yields of isoflavones were obtained with para-phenolboronic acid than with para-methoxybenzene boronic acid. This observation and the commercial availability of para-phenolboronic acid suggest that for the synthesis of the important 3′-prenyl-or 3′,5′-diprenylisoflavone substitution pattern a synthetic route that introduces the prenyl substituents after the Pd-catalyzed cross-coupling step, thereby avoiding laborious and protecting-group-intensive multistep syntheses of C-prenylated arene boronic acids, is advantageous.

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“…When compared to bavachinin, Analog 41 is a powerful pan-PPAR agonist with significantly higher PPAR α/β agonistic potential and similar PPAR-γ agonistic potential. [ 116 ].…”

Section: Recent Developments In the Medicinal Chemistry Of Pparsmentioning

confidence: 99%

Development of Heterocyclic PPAR Ligands for Potential Therapeutic Applications

et al. 2022

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The family of nuclear peroxisome proliferator-activated receptors (PPARα, PPARβ/δ, and PPARγ) is a set of ligand-activated transcription factors that regulate different functions in the body. Whereas activation of PPARα is known to reduce the levels of circulating triglycerides and regulate energy homeostasis, the activation of PPARγ brings about insulin sensitization and increases the metabolism of glucose. On the other hand, PPARβ when activated increases the metabolism of fatty acids. Further, these PPARs have been claimed to be utilized in various metabolic, neurological, and inflammatory diseases, neurodegenerative disorders, fertility or reproduction, pain, and obesity. A series of different heterocyclic scaffolds have been synthesized and evaluated for their ability to act as PPAR agonists. This review is a compilation of efforts on the part of medicinal chemists around the world to find novel compounds that may act as PPAR ligands along with patents in regards to PPAR ligands. The structure–activity relationship, as well as docking studies, have been documented to better understand the mechanistic investigations of various compounds, which will eventually aid in the design and development of new PPAR ligands. From the results of the structural activity relationship through the pharmacological and in silico evaluation the potency of heterocycles as PPAR ligands can be described in terms of their hydrogen bonding, hydrophobic interactions, and other interactions with PPAR.

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Bavachinin analogues as agonists of pan-peroxisome proliferator-activated receptors

Cited by 6 publications

References 24 publications

Total Synthesis and Anti-Inflammatory Evaluation of Osajin, Scandenone and Analogues

Total Synthesis and Anti-Inflammatory Evaluation of Osajin, Scandenone and Analogues

The Suzuki–Miyaura Cross-Coupling–Claisen Rearrangement–Cross-Metathesis Approach to Prenylated Isoflavones

Development of Heterocyclic PPAR Ligands for Potential Therapeutic Applications

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