EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
·
2022
·Vol. 2022
·期 33
·e202200316
·
IF 3.261
Yong Wang,Hui Wang,Qifan Yang,Shihua Xie,Hongjun Zhu
Graphical Herein, palladium(II)-catalyzed halogenation of 2-phenylquinazolines using N -halosuccinimides as halogen sources was described via C−H activation under mild reaction conditions. A series of halogen-substituted 2-arylquinazolines were synthesized through C−H functionalization. An efficient quinazoline-assisted ortho -halogenation of 2-arylquinazolines has been developed using N -halosuccinimides as halogen sources with Pd(II)-catalyzed C−H bond activation. No additional ligand and oxidant are required. This protocol is highly regioselective and applicable to a broad range of quinazoline substrates bearing different functional groups, giving yields of up to 98 %. The mechanism of the quinazoline ortho -halogenation was investigated by comprehensive experimentation.
研究领域:
有机化学
·
合成化学
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DOI
高影响因子
JOURNAL OF FOOD COMPOSITION AND ANALYSIS
·
2024
·
IF 4
Bin Li,Wenjing Gao,Ling Ling,Shaoning Yu,Liangqiang Chen,Fan Yang
Lactose is an important nutrient but its content in milk products poses concerns for people with lactose intolerance . Thus, a simple, rapid, and high-throughput assay for lactose determination is needed to maintain specified lactose levels during production and in final milk products. Here, we report a reactive matrix-assisted laser desorption/ionization mass spectrometry ( Re MALDI MS) method for the determination of lactose in milk products. The selective reactivity and the excellent laser absorption properties of 4-hydrazinoquinazoline (4-HQ) matrix increase the sensitivity of traditional MALDI MS analysis of lactose by 100 folds. After optimization of the method, lactose was detected distinctly in milk without pretreatment . Using xylobiose as an internal standard, the assay accurately quantified lactose in the concentration range of 1.00−700 μg/mL (R 2 = 0.994). Due to the high sensitivity and specificity, the lactose content in different types of milk samples was determined successfully, as well as the residual lactose in low-lactose and lactose-free milk.
研究领域:
食品科学
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分析化学
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产品关联
DOI
高影响因子
MONATSHEFTE FUR CHEMIE
·
2015
·Vol. 146
·期 8
·1343-1347
·
IF 1.222
Qiu Dezhi,Wang Yanyan,Lu Dongming,Zhou Lihong,Zeng Qingle
Abstract We have developed a KOH-promoted transition-metal-free synthesis of 2-substituted 4(3 H )-quinazolinones from anthranilamides and benzyl alcohols or cinnamyl alcohol with air as oxidant. The protocol is simple, practical, and cost saving. Graphical abstract
研究领域:
有机化学
·
药物化学
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DOI
高影响因子
JOURNAL OF MEDICINAL CHEMISTRY
·
2024
·
IF 6.8
Bo Wang,Shu-Wu Wang,Ying Zhou,Shao-Peng Wang,Ya Gao,Hui-Min Liu,Shi-Kun Ji,Sai-Qi Wang,Yi-Chao Zheng,Cheng Zhang,Adil Mardinoglu,Hong-Min Liu,Xiao-Bing Chen,Xing-Jie Dai
LSD1 (histone lysine-specific demethylase 1) has been gradually disclosed to act as an immunomodulator to enhance antitumor immune response. Despite the identification of numerous potent LSD1 inhibitors, there remains a lack of LSD1 inhibitors approved for marketing. Novel LSD1 inhibitors with different mechanisms are therefore needed. Herein, we reported a series of novel quinazoline-based LSD1 inhibitors. Among them, compound Z-1 exhibited the best LSD1 inhibitory activity (IC50 = 0.108 μM). Z-1 also acted as a selective and cellular active as an LSD1 inhibitor. Furthermore, Z-1 promoted response of gastric cancer cells to T-cell killing effect by decreasing PD-L1 expression and further attenuated the PD-1/PD-L1 interaction. In vivo, Z-1 exhibited significant suppression effect on the growth of gastric cancer cells without obvious toxicity. Therefore, Z-1 represents a potential novel immunomodulator that targets LSD1, providing a lead compound with new function mechanism for gastric cancer treatment.
研究领域:
肿瘤学
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免疫学
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药物化学
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产品关联
DOI
PubMed
高影响因子
Molecular Catalysis
·
2024
·
IF 3.9
Guiyu Chen,Wei Liu,Shiqiang Wang,Yongxiang Miao,Zhibin Song
Quinazolinone-based boron difluoride (BF 2 ) complexes were developed for the synthesis of dihydroisoquinolones, 2-phenylisoindolinone, 1-isochromanone and diarylketone through α-C(sp 3 )-H photooxidation. Seven selected quinazolinone-based BF 2 complexes exhibited good activity for photooxidation reaction using air as oxidant. It is worth noting that quinazolinone-based BF 2 as photocatalysts do not require the introduction of halogen heavy atoms to improve catalytic activity. Mechanism exploration indicated these BF 2 catalysts may involve a single electron transfer (SET) mediated photoredox catalysis to achieve α-C(sp3)-H oxidation. These quinazolinone-based BF 2 catalysts with facile preparation and structural modifiability would be good choice for organic oxidative transformation in the future.
研究领域:
有机化学
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光化学
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催化科学
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产品关联
DOI
高影响因子
SYNTHETIC COMMUNICATIONS
·
2021
·
IF 2.007
Xiaoyun Ma,Daoping Wang,Gang Wei,Qingdi Zhou,Xiuhai Gan
Two series of quinoxaline–chalcone conjugates have been prepared by aldolic condensation and aromatic nucleophilic substitution reaction, and their anticancer activity against three cancer cell lines including benign prostatic hyperplasia epithelial cell (BPH-1), neuron-like rat pheochromocytoma cell line (PC12) and human breast cancer cell line (MCF-7) were evaluated in vitro. All of the synthesized compounds exhibited moderate to good activity against the cancer cell lines selected. Particularly, Compound A5 showed the excellent potent activity against BPH-1 and MCF-7 with IC50 values of 10.4 and 9.1 μM, respectively, which is similar to doxorubicin (14.1 and 9.2 μM, respectively). As well as compound B6 exhibited most excellent activity toward PC12 with IC50 values of 16.4 μM. Compound A10 exhibited 55.4, 36.8 and 54.5 folds higher selectivity for BPH-1, PC12 and MCF-7 cells than for HEK-293 cell, respectively. In addition, theoretical biological activities of compounds A5 and A10 were evaluated by SwissADME.
研究领域:
药物化学
·
肿瘤学
·
有机合成
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产品关联
DOI
高影响因子
JOURNAL OF CHEMICAL RESEARCH
·
2015
·
IF 0.633
Xiang Jiang,Guo-Wei Yu,Zu-Guang Li,Shi-Peng Chu,Shen-Peng Wang
2,2-Dichloro-4,4,6,6-bis[spiro(2′,2″-dioxy-1′,1″-biphenylyl)]cyclotriphosphazene was synthesised from the reaction of hexachlorocyclotriphosphazene with biphenyl-2,2′-diol. 2,2-Bis(4-formylphenoxy)-4,4,6,6-bis[spiro(2′,2″-dioxy-1′,1″-biphenylyl)]cyclotriphosphazene was obtained from the reaction of 2,2-dichloro-4,4,6,6-bis[spiro(2′,2″-dioxy-1′,1″-biphenylyl)] cyclotriphosphazene with 4-hydroxybenzaldehyde. 2,2-Bis[4-(4-quinazolinone)phenoxy]-4,4,6,6-bis[spiro(2′,2″-dioxy-1′,1″-biphenylyl)]cyclotriphosphazene was synthesised from the reaction of 2,2-bis(4-formylphenoxy)-4,4,6,6-bis[spiro(2′,2″-dioxy-1′,1″-biphenylyl)]cyclotriphosphazene with anthranilamide in N,N-dimethylformamide. The novel cyclophosphazene derivatives were synthesised under mild conditions from the reaction of 2,2-bis[4-(4-quinazolinone)phenoxy]-4,4,6,6-bis[spiro(2′,2″-dioxy-1′,1″-biphenylyl)]cyclotriphosphazene with 4-chlorobenzenemethanethiol, p-thiocresol, 4-aminothiophenol, and 4-chlorothiophenol in the presence of p-toluenesulfonyl chloride via C-OH bond activation under mild conditions. All products were generally obtained in high yields. Their structures were characterised by HRMS, IR and 1H, 13C spectroscopy.
研究领域:
有机化学
·
材料科学
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DOI
高影响因子
SYNTHESIS-STUTTGART
·
2013
·Vol. 45
·期 24
·3349-3354
·
IF 2.5
Haidong Wei,Tianbin Li,Yue Zhou,Lihong Zhou,Qingle Zeng
Alkyl halides, including heteroarylmethyl and arylmethyl halides, bromoacetate, and cinnamyl bromide, are readily prepared via halogenation from basic raw materials, even using green processes. It is essential to replace their downstream products with them to prepare medicinally important heterocycles quinazolin-4(3H)-ones. Copper(I) bromide catalyzed domino reaction of alkyl halides and anthranilamides under air affords 2-substituted quinazolin-4(3H)-ones in good to excellent yields and with wide functional group tolerance. A mechanism for a copper(I) bromide involved organometal-catalyzed reaction via a four-step domino reaction is proposed.
研究领域:
有机化学
·
药物化学
✓ 已验证
DOI
高影响因子
ACS Omega
·
2020
·
IF 2.87
Zhenghong Zhou,Kangfei Hu,Jiawei Wang,Zhibin Li,Yan Zhang,Zhenggen Zha,Zhiyong Wang
An electrochemical synthesis for quinazolines and quinazolinones was developed via a C(sp3)-H amination/C-N cleavage by virtue of the anodic oxidation. The reaction can be carried out in aqueous media under mild conditions to afford the desired products with high yields. The reaction mechanism was proposed after detailed investigation.
研究领域:
有机化学
·
电化学
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DOI
高影响因子
JOURNAL OF SOLID STATE ELECTROCHEMISTRY
·
2024
·
IF 2.6
Wang Pengna,Zheng Shengqing,Lin Bao-Ping
The potential use of n-type small organic molecules in electrodes has attracted significant attention in organic electronics owing to the easy, high-yield purification processes of organic compounds. However, only few studies have reported high-efficiency supercapacitors based on n-type organic materials. Nevertheless, most n-type organic compounds possess low capacitance and poor cycling efficiency. Therefore, it is crucial to develop n-type organic compounds that demonstrate good electrochemical properties for use in electrodes. Herein, both the (E)-N-(4-(diphenylamino)benzylidene)-6,6,10,10-tetramethyl-4-phenyl-6,7,8,9,10,10a-hexahydro-5H-6a,9-methanobenzo[H]quinazolin-2-amine (TPAB) and (E)-N-(4-(diphenylamino)benzylidene)-4-(4-(diphenylamino)phenyl)-6,6,10,10-tetramethyl-6,7,8,9,10,10a-hexahydro-5H-6a,9-methanobenzo [h]quinazolin-2-amine (TPANB) compounds containing electrochromic (EC) and aggregation-induced emission (AIE) groups were synthesized from triphenylamine (TPA) and quinazoline derivatives, and their structure and properties were investigated. These novel electrode materials demonstrate high EC and fluorescence performance just as a typical n-type semiconductor. The coloring time of a TPANB film is 4.00 s, whereas the bleaching time is 3.00 s. Compared with TPANB, TPAB electrode material demonstrate a high area-specific capacitance (2.38 mF cm −2 at 0.05 mA cm −2 ), outstanding the charge and discharge rate performance (93% with the current density of 0.05–0.25 mA cm −2 ), and excellent cycling performance (78.51%) after 300 cycles. Above all, the multifunctional materials hold good potential for intelligent display energy storage. Graphical Abstract
研究领域:
材料科学
·
有机电子学
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产品关联
DOI
高影响因子
RSC Advances
·
2015
·Vol. 5
·期 20
·15668-15673
·
IF 3.84
Xian-Dong Lang,Shuai Zhang,Qing-Wen Song,Liang-Nian He
An easily prepared amino acid ionic liquid (AAIL) i.e. [TBP][Arg] comprising a tetra-butylphosphonium cation and an arginine anion was found to be an efficient and recyclable catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from 2-aminobenzonitriles and CO2 under solvent-free conditions. As a result, various 2-aminobenzonitriles bearing electron-withdrawing or electron-donating substituents worked well to afford quinazoline-2,4(1H,3H)-diones in excellent yields. Notably, this type of AAIL showed good stability, and could be easily recovered and reused five times without significant loss of its catalytic activity. This process represents an alternative approach for greener chemical fixation of CO2 to afford valuable compounds.
研究领域:
有机化学
·
环境科学
✓ 已验证
DOI
高影响因子
CHEMISTRY & BIODIVERSITY
·
2018
·Vol. 15
·期 3
·e1700513
·
IF 1.617
Xiaoping Zhan,Yun Xu,Qi Qi,Yaolin Wang,Huiying Shi,Zhenmin Mao
A series of novel quinazolinone derivatives containing a substituted amino moiety were synthesized, evaluated for their cytotoxic and antibacterial activities. The results of MTT assay showed that all synthesized target compounds 5A – 5O showed potent cytotoxicity against SGC-7901 ( IC 50 , 0.72 – 1.41 μ m ). Moreover, the compounds 5D , 5I , and 5K showed better selectivity as compared with positive controls pemetrexed and MTX due to weak cytotoxicity against normal tissue cell line HUVSMC. Among synthesized compounds, the compounds 5E , 5J , 5L , and 5N showed broad-spectrum cytotoxic activities against at least four cancer cell lines at a micromolar level. The results of antibacteria evaluation revealed that all synthesized compounds showed good to moderate antibacterial activities against Gram -negative bacteria Escherichia coli . Among them, the MIC values of the compounds 5C , 5F , and 5M were 0.31 μg/mL. Graphical
研究领域:
药物化学
·
肿瘤学
·
微生物学
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）