Copper-mediated trimethylsilyl azide in amination of bromoflavonoids to synthesize unique aminoflavonoids

Shih, Tzenge‐Lien; Chou, Chien-Hsing; Liao, Wen-Yu; Hsiao, Chih-Ang

doi:10.1016/j.tet.2014.04.022

Cited by 11 publications

(11 citation statements)

References 41 publications

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“…Shih and co‐workers developed a strategy for aminoflavanoid synthesis by the amination of bromoflavanoid via copper catalysis . The amination was effectively carried out using Cu‐powder in DMA [N,N‐dimethylacetamide], trimethylsilyl azide and 2‐aminoethanol at 120 °C.…”

Section: Amination Using Azidesmentioning

confidence: 99%

Recent Advances and Perspectives in the Copper‐Catalysed Amination of Aryl and Heteroaryl Halides

et al. 2020

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Section: Amination Using Azidesmentioning

confidence: 99%

Recent Advances and Perspectives in the Copper‐Catalysed Amination of Aryl and Heteroaryl Halides

et al. 2020

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“…mp 134–135 °C (ref. [ 46 ] m.p. 129–131 °C); 1 H-NMR (600 MHz, CDCl 3 ): δ (ppm) 13.63 (s, 1H, -OH), 7.98 (d, J = 2.4 Hz, 1H, H-6′), 7.92 (d, J = 15.0 Hz, 1H, Hb), 7.87 (d, J = 2.4 Hz, 1H, H-4′), 7.48 (d, J = 1.8 Hz, 1H, H-2), 7.39 (d, J = 15.0 Hz, 1H, Ha), 7.33 (dd, J = 8.4, 1.2 Hz, 1H, H-6), 7.22 (d, J = 8.4 Hz, 1H, H-5), 5.31 (br, 4H, 2 × -O-CH 2 -O-), 3.56 (s, 3H, -OCH 3 ), 3.53 (s, 3H, -OCH 3 ).…”

Section: Methodsmentioning

confidence: 99%

“…The novel chalcones were prepared via Claisen–Schmidt condensation in alkaline media (Method A: 20% w/v KOH, EtOH, Method B: 60% w/w NaH, DMF). Chalcones 3f – 3g and 3i – 3l , were prepared through the Claisen–Schmidt condensation reaction between appropriately substituted 2′-hydroxy-acetophenones and benzaldehydes carried out using aqueous KOH in ethanol, as previously reported in the literature [ 41 , 46 , 47 , 48 , 49 ]. Aurones 6b and 7b were synthesized via oxidative cyclization of the corresponding chalcones using mercury (II) acetate in pyridine followed by deprotection of the methoxylated aurone using BBr 3 in CH 2 Cl 2 , respectively.…”

Section: Introductionmentioning

confidence: 99%

Exploring the 2′-Hydroxy-Chalcone Framework for the Development of Dual Antioxidant and Soybean Lipoxygenase Inhibitory Agents

et al. 2021

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2’-hydroxy-chalcones are naturally occurring compounds with a wide array of bioactivity. In an effort to delineate the structural features that favor antioxidant and lipoxygenase (LOX) inhibitory activity, the design, synthesis, and bioactivity profile of a series of 2’-hydroxy-chalcones bearing diverse substituents on rings A and B, are presented. Among all the synthesized derivatives, chalcone 4b, bearing two hydroxyl substituents on ring B, was found to possess the best combined activity (82.4% DPPH radical scavenging ability, 82.3% inhibition of lipid peroxidation, and satisfactory LOX inhibition value (IC50 = 70 μM). Chalcone 3c, possessing a methoxymethylene substituent on ring A, and three methoxy groups on ring B, exhibited the most promising LOX inhibitory activity (IC50 = 45 μM). A combination of in silico techniques were utilized in an effort to explore the crucial binding characteristics of the most active compound 3c and its analogue 3b, to LOX. Α common H-bond interaction pattern, orienting the hydroxyl and carbonyl groups of the aromatic ring A towards Asp768 and Asn128, respectively, was observed. Regarding the analogue 3c, the bulky (-OMOM) group does not seem to participate in a direct binding, but it induces an orientation capable to form H-bonds between the methoxy groups of the aromatic ring B with Trp130 and Gly247.

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“…Therefore, kaempferol is used commonly as a chemosensitizer in combination with other chemotherapy drugs, such as 5-fluorouracil and cisplatin, to enhance antitumor efficacy and reduce side effects. , Although kaempferol shows numerous potential health benefits, its low bioavailability has been associated with challenges to its application . Kaempferol is usually modified by methylation, alkylation, and sulfation to ameliorate its solubility and bioavailability. − For example, kaempferol-SO 3 -Ga, a sulfonate kaempferol–gallium complex, showed greater water solubility and antioxidant activity than free kaempferol . Kaempferol–piperidine, a primary aminomethyl derivative, exhibited more potential cytotoxic activity than kaempferol in HeLa cells …”

mentioning

confidence: 99%

Dual-Targeting Antiproliferation Hybrids Derived from 1-Deoxynojirimycin and Kaempferol Induce MCF-7 Cell Apoptosis through the Mitochondria-Mediated Pathway

Zhang

Xin

et al. 2021

J. Nat. Prod.

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1-Deoxynojirimycin, an α-glucosidase inhibitor, possesses various biological activities such as antitumor, antidiabetic, and antiviral effects. However, the application of 1-deoxynojirimycin is restricted by its poor lipophilicity and low bioavailability. In this study, three 1-deoxynojirimycin derivatives (8−10) comprising 1-deoxynojirimycin and kaempferol were designed and synthesized to modify their pharmacokinetics and improve their antitumor efficacy. Among them, compound 10, a conjugate of 1-deoxynojirimycin and kaempferol linked through an undecane chain, exhibited excellent lipophilicity, antiproliferative effects, and α-glucosidase inhibitory activity. Compared with 1-deoxynojirimycin, kaempferol, and their combination, compound 10 downregulated cyclooxygenase-2 (COX-2) expression, arrested the cell cycle at the S phase, induced cellular apoptosis, and inhibited the migration of MCF-7 cells. Moreover, further investigation indicated that compound 10 induced MCF-7 cell apoptosis through a mitochondrial-mediated pathway via the loss of mitochondrial membrane potential. This led to increasing intracellular levels of reactive oxygen species (ROS) and Ca 2+ , the downregulation of Bcl-2 expression, and the upregulation of Bax levels.

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Copper-mediated trimethylsilyl azide in amination of bromoflavonoids to synthesize unique aminoflavonoids

Cited by 11 publications

References 41 publications

Recent Advances and Perspectives in the Copper‐Catalysed Amination of Aryl and Heteroaryl Halides

Recent Advances and Perspectives in the Copper‐Catalysed Amination of Aryl and Heteroaryl Halides

Exploring the 2′-Hydroxy-Chalcone Framework for the Development of Dual Antioxidant and Soybean Lipoxygenase Inhibitory Agents

Dual-Targeting Antiproliferation Hybrids Derived from 1-Deoxynojirimycin and Kaempferol Induce MCF-7 Cell Apoptosis through the Mitochondria-Mediated Pathway

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