Synthesis and Cytotoxicity of 1,4-Naphthoquinone Oxime Derivatives

Zhang, Q.; Dong, Junde; Meng, Qingqing; Huang, G.; Li, S.

doi:10.1134/s1070363218110221

Cited by 6 publications

(8 citation statements)

References 10 publications

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“…DSO-(6a–6c) were synthesized according to the reported procedures with minor modifications . In the nucleophilic substitution reaction between 2,2-dimethyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl) but-3-en-1-ol ( Compound-2 ) and protected bromohydrin, potassium iodine was used instead of iodine as the catalyst in order to avoid certain side reactions (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Discovery of Dimethyl Shikonin Oxime 5a, a Potent, Selective Bombesin Receptor Subtype-3 Agonist for the Treatment of Type 2 Diabetes Mellitus

Cui

Zhao

et al. 2023

J. Med. Chem.

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Bombesin receptor subtype-3 (BB3, BRS-3) is an orphan Gαq protein-coupled receptor. The characterization of novel synthetic ligands for BB3 is an alternative and attractive strategy to study its diverse physiological functions. Here, we uncovered the intimate pairing of DMAKO-00 and its derivatives with BB3. Dimethyl shikonin oxime 5a (DSO-5a) was identified as the most potent agonist for BB3 (pEC50 = 8.422 in IP-1 accumulation), which was 898-fold more potent than DMAKO-00. Importantly, without brain penetration, DSO-5a improved glucose tolerance in C57BL/6 mice through BB3 and ameliorated glucose homeostasis in diabetic db/db mice. We further revealed that DSO-5a upregulated PPAR-gamma activity via BB3 through a quantitative proteomics approach. Collectively, our study demonstrated that DSO-5a, a representative compound of DMAKO-00 derivatives, is a potent, selective, and low-brain-penetrating agonist for BB3, and BB3 is a promising treatment target for type 2 diabetes mellitus.

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Section: Resultsmentioning

confidence: 99%

Discovery of Dimethyl Shikonin Oxime 5a, a Potent, Selective Bombesin Receptor Subtype-3 Agonist for the Treatment of Type 2 Diabetes Mellitus

Cui

Zhao

et al. 2023

J. Med. Chem.

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“…52 The obtained 5-bromopentan-1-ol was then attached to tetrahydropyran (THP) group in the presence of ptoluenesulfonic acid in dichloromethane to attain tetrahydropyranyl ether functional group. 53 As a last step, 2-((5bromopentyl)oxy)tetrahydro-2H-pyran with magnesium formed a Grignard reagent, which reacted with phosphorous trichloride to furnish an alkyl-phosphine intermediate product.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The synthesis of THPPO began with a carboxylic acid reduction reaction of the commercially available 5-bromopentanoic acid by the borane–tetrahydrofuran complex to the corresponding primary alcohol . The obtained 5-bromopentan-1-ol was then attached to tetrahydropyran (THP) group in the presence of p -toluenesulfonic acid in dichloromethane to attain tetrahydropyranyl ether functional group . As a last step, 2-((5-bromopentyl)oxy)tetrahydro-2 H -pyran with magnesium formed a Grignard reagent, which reacted with phosphorous trichloride to furnish an alkyl-phosphine intermediate product.…”

Section: Resultsmentioning

confidence: 99%

Phosphine Oxide Derivative as a Passivating Agent to Enhance the Performance of Perovskite Solar Cells

Igci

Kim

Kanda

et al. 2021

ACS Appl. Energy Mater.

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Defects of metal-halide perovskites detrimentally influence the optoelectronic properties of the thin film and, ultimately, the photovoltaic performance of perovskite solar cells (PSCs). Especially, defect-mediated nonradiative recombination that occurs at the perovskite interface significantly limits the power conversion efficiency (PCE) of PSCs. In this regard, interfacial engineering or surface treatment of perovskites has become a viable strategy for reducing the density of surface defects, thereby improving the PCE of PSCs. Here, an organic molecule, tris(5-((tetrahydro-2H-pyran-2yl)oxy)pentyl)phosphine oxide (THPPO), is synthesized and introduced as a defect passivation agent in PSCs. The PO terminal group of THPPO, a Lewis base, can passivate perovskite surface defects such as undercoordinated Pb2+. Consequently, improvement of PCEs from 19.87 to 20.70% and from 5.84 to 13.31% are achieved in n−i−p PSCs and hole-transporting layer (HTL)-free PSCs, respectively.

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“…To demonstrate the microparticle platform could be constructed with different photocatalysts, we also synthesized an acrylate-functionalized ruthenium photocatalyst by modifying previously reported syntheses. [35][36][37][38] Microparticles were fabricated by the same method as the zinc porphyrin-based microparticles. As-synthesized Ru(bpy) 3 microparticles were uniform in size and distribution on the same scale as MP-1.…”

Section: Polymer Chemistry Papermentioning

confidence: 99%

Electrostatic loading and photoredox-based release of molecular cargo from oligoviologen-crosslinked microparticles

et al. 2022

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Synthesis and Cytotoxicity of 1,4-Naphthoquinone Oxime Derivatives

Cited by 6 publications

References 10 publications

Discovery of Dimethyl Shikonin Oxime 5a, a Potent, Selective Bombesin Receptor Subtype-3 Agonist for the Treatment of Type 2 Diabetes Mellitus

Discovery of Dimethyl Shikonin Oxime 5a, a Potent, Selective Bombesin Receptor Subtype-3 Agonist for the Treatment of Type 2 Diabetes Mellitus

Phosphine Oxide Derivative as a Passivating Agent to Enhance the Performance of Perovskite Solar Cells

Electrostatic loading and photoredox-based release of molecular cargo from oligoviologen-crosslinked microparticles

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