Copper-catalyzed Direct 2-Arylation of Benzoxazoles and Benzoimidazoles with Aryl Bromides and Cytotoxicity of Products

Jia, Nan-Nan; Tian, Xin‐Chuan; Qu, Xin; Chen, Xingxiu; Cao, Yanan; Yao, Yunxin; Gao, Feng; Zhou, Xian‐Li

doi:10.1038/srep43758

Cited by 25 publications

(6 citation statements)

References 46 publications

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“…This transformation typically involves in situ metalation of an aryl C–H bond and subsequent coupling with an aryl donor. Many different transition metals have been found to catalyze this transformation, including Rh, Ru, Ir, Co, Cu, Fe, and Au, but the most frequently used continues to be Pd …”

Section: Introductionmentioning

confidence: 99%

Ag/Pd Cocatalyzed Direct Arylation of Fluoroarene Derivatives with Aryl Bromides

et al. 2020

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Diverse C−H functionalizations catalyzed by Pd employ Ag(I) salts added as halide abstractors or oxidants. Recent reports have shown that Ag can also perform the crucial C−H activation step in several of these functionalizations. However, all of these processes are limited by the wasteful requirement for (super)stoichiometric Ag(I) salts. Herein, we report the development of a Ag/Pd cocatalyzed direct arylation of (fluoroarene) chromium tricarbonyl complexes with bromoarenes. The small organic salt, NMe 4 OC(CF 3 ) 3 , added as a halide abstractor, enables the use of a catalytic amount of Ag, reversing the rapid precipitation of AgBr. We have shown through H/D scrambling and kinetic studies that a (PR 3 )Ag-alkoxide is responsible for C−H activation, a departure from previous studies with Ag carboxylates. Furthermore, the construction of biaryls directly from the simple arene is achieved via a one-pot chromium tricarbonyl complexation/C−H arylation/decomplexation sequence using (pyrene)Cr(CO) 3 as a Cr(CO) 3 donor.

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Section: Introductionmentioning

confidence: 99%

Ag/Pd Cocatalyzed Direct Arylation of Fluoroarene Derivatives with Aryl Bromides

et al. 2020

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“…The cells showed a slightly greater sensitivity to the change of concentration when exposed to 24 hours, with a tiny steep slope, compared to a long exposure time (Figure 4). According to existing reports, 23,24 PTX caused less than 50% survival of HCT116 cell saturation doses around 2.5 nanomoles after 1 or 3 days. Therefore, hybrid 11b does not possess antiproliferative activity at similar dose.…”

Section: Resultsmentioning

confidence: 97%

Design, Synthesis, and Anticancer Activity of Natural Product Hybrids With Paclitaxel Side Chain Inducing Apoptosis in Human Colon Cancer Cells

Zheng

Wen

Yao

et al. 2020

Natural Product Communications

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Based on the strong activity dependence of paclitaxel (PTX; Taxol) or docetaxel (Taxotere) on the C-13 side chain, a small library of dehydroepiandrosterone, cholesterol, vitamin D2, and alkaloids talatisamine and songorine-PTX hybrids have been synthesized and evaluated for in vitro anticancer activity by MTT assay against human breast (MCF-7), colon (HCT116), lung carcinoma (A549), and renal adenocarcinoma (786-0) cancer cell lines. Most hybrids (11b, 12b, 13b, 15b, and 18b) reduced the growth of MCF-7 and 786-0 cells with low PTX sensitivity in vitro. Among the synthesized compounds, hybrid 11b was better in inhibiting the growth of the 4 cells than PTX. A relatively low IC50 value of compound 11b (8.16 ± 0.04 μM) was also examined after exposure for 48 hours. Hybrid 11b showed a proapoptotic effect in HCT116 cells evaluated by Annexin V/propidium iodide binding assay. The level of hybrid 11b leading to protective cell death in HCT116 cells was detected using western blot and not easily observed in our basic examinations.

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“…Fortunately, cheap copper is an efficient counterpart of palladium in the direct arylation of benzoheterocyclic compounds [23][24][25][26][27][28]. Previously, we have reported that Cu/PPh3 directly catalyzed the 2-arylation of benzoxazoles with economical aryl bromides [29], and the same catalysis system has been used in our further research. In this work, a series of 2-aryl-Nalkylbenzimidazole derivatives were prepared via copper-catalyzed direct arylation of Nalkylbenzimidazoles with aryl bromides, and their in vitro neuroprotective activities were evaluated.…”

Section: Introductionmentioning

confidence: 91%

Copper-Catalyzed Synthesis, Bio-Evaluation, and in Silico Studies of 2-Aryl-N-alkylbenzimidazoles as Neuroprotective Agents

et al. 2018

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2-aryl-N-alkylbenzimidazole derivatives synthesized by CuI/PPh3 promoted direct coupling of N-alkylbenzimidazoles with aryl bromides. In vitro neurotoxicities of 20 compounds were evaluated, and the neuroprotective abilities of low-neurotoxic compounds (3b, 3g, 3h, 3i, 3j, 3k, 3o, 3q, 3s and 3t) were investigated against toxicity induced by 1-methyl-4-phenylpyridinium ion (MPP+) in SH-SY5Y neuronal cells. In silico studies revealed that compound 3g could have molecule docking with the following proteins: the bone morphogenetic protein receptor type 1B (BMPR1B), human cytochrome P450 1B1(CYP1B1), Metabotropic glutamate receptor 7 (GRM7), histone deacetylase 6 (HDAC6), 5-hydroxytryptamine receptor 5A (HTR5A), human topoisomerase II beta (TOP2B). A molecular docking simulation of model compound 3g and model protein CYP1B1 has been shown.

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Copper-catalyzed Direct 2-Arylation of Benzoxazoles and Benzoimidazoles with Aryl Bromides and Cytotoxicity of Products

Cited by 25 publications

References 46 publications

Ag/Pd Cocatalyzed Direct Arylation of Fluoroarene Derivatives with Aryl Bromides

Ag/Pd Cocatalyzed Direct Arylation of Fluoroarene Derivatives with Aryl Bromides

Design, Synthesis, and Anticancer Activity of Natural Product Hybrids With Paclitaxel Side Chain Inducing Apoptosis in Human Colon Cancer Cells

Copper-Catalyzed Synthesis, Bio-Evaluation, and in Silico Studies of 2-Aryl-N-alkylbenzimidazoles as Neuroprotective Agents

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