Synthesis and Antiproliferative Activities of Novel Substituted 5‐Anilino‐<i>α</i>‐Glucofuranose Derivatives

Zhang, Yaling; Wang, Lili; Baoli, Sun; Li, Xiabing; Hou, Qiaoli; Wang, Wei; Li, Baolin

doi:10.1002/cbdv.201900739

Cited by 3 publications

(6 citation statements)

References 23 publications

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“…Initially, nitroarene 12f was synthesized from 2-chloro-5-nitrobenzoic acid (12e) and phenyl ethyl ether via the Friedel−Crafts acylation reaction. 16 Further, nitroarene 12f was reduced to the corresponding amine 12g using tetrahydroxydiboron and 4,4′-bipyridine at room temperature in 95% yield. 17 Later, compound 12g is Arbutin is a phenolic O-glycoside extracted from the bearberry plant and used in skin lightening treatments.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…In this context, we attempted the synthesis of the dapagliflozin S -analogue 13 using the developed methodology. Initially, nitroarene 12f was synthesized from 2-chloro-5-nitrobenzoic acid ( 12e ) and phenyl ethyl ether via the Friedel–Crafts acylation reaction . Further, nitroarene 12f was reduced to the corresponding amine 12g using tetrahydroxydiboron and 4,4′-bipyridine at room temperature in 95% yield .…”

Section: Resultsmentioning

confidence: 99%

“…1-Chloro-2-(4-ethoxybenzyl)-4-nitrobenzene (12f). 16 Compound 12f was prepared using the literature procedure. 16 1 H NMR (500 MHz, CDCl 3 ) δ 7.93 (dt, J = 5.9, 2.6 Hz, 2H), 7.45 (d, J = 8.6 Hz, 1H), 7.03 (d, J = 8.6 Hz, 2H), 6.82−6.73 (m, 2H), 4.02 (s, 2H), 3.94 (q, J = 7.0 Hz, 2H), 1.33 (t, J = 7.0 Hz, 3H).…”

Section: -Methoxyphenyl-1-thio-β-d-glucopyranoside (12c) 6dmentioning

confidence: 99%

“…. 16 The reaction was carried out between substrate 12f (0.5 g, 1.71 mmol) and tetrahydroxydiboron (461 mg, 5.14 mmol) and 4,4′-bipy (13 mg, 5 mol %) in DMF (3 mL) stirred at RT for 5 min. Column chromatography purification was performed using 20% ethyl acetate in hexane, which furnished 12g as a colorless solid (426 mg, 95%).…”

Section: -Chloro-3-(4-ethoxybenzyl)aniline (12g)mentioning

confidence: 99%

“…The crude product was purified by column chromatography on silica gel (100−200 mesh) using 30% ethyl acetate in hexane to obtain compounds 15 (132 mg, 89%) and 16 (122 mg, 90%). (16). 6e The coupling reaction was carried out with 4-methoxy arylboronic acid (57 mg, 0.375 mmol).…”

Section: -Chloro-3-(4-ethoxybenzyl)aniline (12g)mentioning

confidence: 99%

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Copper(I)-Catalyzed Sandmeyer-Type S-Arylation of 1-Thiosugars with Aryldiazonium Salts under Mild Conditions

2022

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Preparation of S-aryl thioglycosides from 1-thiosugars via S-arylation was demonstrated under mild reaction conditions. A wide range of protected and unprotected 1-thiosugars derived from glucose, glucosamine, galactose, mannose, ribose, maltose, and lactose underwent cross-coupling reactions with functionalized aryldiazonium salts in the presence of copper(I) chloride and DBU. The desired products were obtained in 55–88% yields within 5 min. Various functional groups, including halogens, were tolerated under standard reaction conditions. Synthesis of the biologically relevant antidiabetic dapagliflozin S-analogue and arbutin S-analogues (tyrosinase inhibitors) was demonstrated.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: -Methoxyphenyl-1-thio-β-d-glucopyranoside (12c) 6dmentioning

confidence: 99%

Section: -Chloro-3-(4-ethoxybenzyl)aniline (12g)mentioning

confidence: 99%

Section: -Chloro-3-(4-ethoxybenzyl)aniline (12g)mentioning

confidence: 99%

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Copper(I)-Catalyzed Sandmeyer-Type S-Arylation of 1-Thiosugars with Aryldiazonium Salts under Mild Conditions

2022

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Palladium‐Catalyzed Reaction of Aryl Iodides and Glycal Enones: Application in the Preparation of Dapagliflozin Analogues

et al. 2022

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An efficient approach for the preparation of C‐1 aryl enones from aryl iodides and glycal enones by palladium‐catalyzed cross‐coupling reactions under ligand‐free conditions was developed. A wide range of aryl iodides bearing electron‐donating and withdrawing groups underwent oxidative C‐1 arylation with galactal, glucal and rhamnal enones in the presence of Pd(OAc)2 and AgNO3 under mild conditions. The protecting groups, including benzyl, acetyl, pivaloyl, and benzoyl groups, were found to be compatible under standard reaction conditions. The developed methodology was applied for the preparation of dapagliflozin analogues (SGLT‐2 inhibitors). Regioselective nitration of C‐1 aryl enones provides C‐2 nitro aryl enones in good yields.

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CD151 drives cancer progression depending on integrin α3β1 through EGFR signaling in non-small cell lung cancer

Zhu

Cai

Zhou

et al. 2021

J Exp Clin Cancer Res

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Background Tetraspanins CD151, a transmembrane 4 superfamily protein, has been identified participating in the initiation of a variety of cancers. However, the precise function of CD151 in non-small cell lung cancer (NSCLC) remains unclear. Here, we addressed the pro-tumoral role of CD151 in NSCLC by targeting EGFR/ErbB2 which favors tumor proliferation, migration and invasion. Methods First, the mRNA expression levels of CD151 in NSCLC tissues and cell lines were measured by RT-PCR. Meanwhile, CD151 and its associated proteins were analyzed by western blotting. The expression levels of CD151 in NSCLC samples and its paired adjacent lung tissues were then verified by Immunohistochemistry. The protein interactions are evaluated by co-immunoprecipitation. Flow cytometry was applied to cell cycle analysis. CCK-8, EdU Incorporation, and clonogenic assays were used to analyze cell viability. Wound healing, transwell migration, and matrigel invasion assays were utilized to assess the motility of tumor cells. To investigate the role of CD151 in vivo, lung carcinoma xenograft mouse model was applied. Results High CD151 expression was identified in NSCLC tissues and cell lines, and its high expression was significantly associated with poor prognosis of NSCLC patients. Further, knockdown of CD151 in vitro inhibited tumor proliferation, migration, and invasion. Besides, inoculation of nude mice with CD151-overexpressing tumor cells exhibited substantial tumor proliferation compared to that in control mice which inoculated with vector-transfected tumor cells. Noteworthy, we found that overexpression of CD151 conferred cell migration and invasion by interacting with integrins. We next sought to demonstrate that CD151 regulated downstream signaling pathways via activation of EGFR/ErbB2 in NSCLC cells. Therefore, we infer that CD151 probably affects the sensitivity of NSCLC in response to anti-cancer drugs. Conclusions Based on these results, we demonstrated a new mechanism of CD151-mediated tumor progression by targeting EGFR/ErbB2 signaling pathway, by which CD151 promotes NSCLC proliferation, migration, and invasion, which may considered as a potential target of NSCLC treatment.

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Synthesis and Antiproliferative Activities of Novel Substituted 5‐Anilino‐α‐Glucofuranose Derivatives

Cited by 3 publications

References 23 publications

Copper(I)-Catalyzed Sandmeyer-Type S-Arylation of 1-Thiosugars with Aryldiazonium Salts under Mild Conditions

Copper(I)-Catalyzed Sandmeyer-Type S-Arylation of 1-Thiosugars with Aryldiazonium Salts under Mild Conditions

Palladium‐Catalyzed Reaction of Aryl Iodides and Glycal Enones: Application in the Preparation of Dapagliflozin Analogues

CD151 drives cancer progression depending on integrin α3β1 through EGFR signaling in non-small cell lung cancer

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