JOURNAL OF ORGANIC CHEMISTRY
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2022
·
IF 4.198
Yueyue Zhu,Rupeng Dai,Chaoqun Huang,Wang Zhou,Xiaoyuan Zhang,Kundi Yang,Hongmei Wen,Wei Li,Jian Liu
In this study, we report a novel and efficient synthetic method to construct isoquinolone scaffold via the Rh(III)-catalyzed (4 + 2) annulation of benzamide with an unreported coupling reagent methyl 2-chloroacrylate. Accordingly, other valuable 1,2-benzothiazine and naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine derivatives are also obtained through a similar synthetic protocol. Thus, our developed method is highlighted by high yield and reaction versatility.
研究领域:
有机化学
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药物化学
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DOI
高影响因子
BIOLOGICAL & PHARMACEUTICAL BULLETIN
·
2017
·Vol. 40
·期 8
·1165-1173
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IF 1.683
Shuhua Mu,Huixian Liu,Lifang Zhang,Xiaoyang Wang,Feiqun Xue,Yue Zhang
To develop new pleuromutilin derivatives as veterinary antibiotic medicines, we designed and synthesized a series of new thioether pleuromutilin derivatives possessing acylthiazolyl moiety based on previously designed derivatives. The antibacterial properties of the prepared pleuromutilin derivatives were assessed in vitro by the broth dilution method against five kinds of bacteria and the mycoplasma Mycoplasma gallisepticum (MG). All of the tested compounds displayed moderate to good antibacterial activity to methicillin-sensitive Staphylococcus aureus (MSSA), methicillin-sensitive Staphylococcus epidermidis (MSSE), methicillin-resistant S. aureus (MRSA), Streptococcus agalactiae (S. aga) and MG. However, the activity to Pyogeniccoccus (Pyogens) was generally poor. Compounds 13i and l showed potent antibacterial activity against MSSE and MRSA which are better than that of valnemulin. The structural modification for pleuromutilin affected the antibacterial activity. Amino substituents in the benzene ring can effectively improve activity. Compared with the analogue 13a that possesses unsubstitution benzoyl group, the nitro, methoxy, hydroxy and dichloro substituent contributed little to antibacterial activity. Increasing a methylene between benzene moiety and carbonyl group decreased the bioactivity of derivative. The analogues that obtained by the reaction of amino acids and intermediate 9 showed moderate activity.
研究领域:
药理学
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微生物学
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兽医学
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DOI
PubMed
高影响因子
MOLECULES
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2021
·Vol. 26
·期 11
·3223
·
IF 4.412
Ji-Wei Zhang,Shao-Hua Xiang,Shaoyu Li,Bin Tan
NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation ofN-arylhydroxylamines orN-arylhydrazines with diaryliodonium salts and [3,3]-sigmatropic rearrangement. This reaction features mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols.Keywords:NOBIN;BINAM;arylation;sigmatropic rearrangement;copper-catalysis
研究领域:
有机化学
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合成化学
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PubMed
高影响因子
MOLECULES
·
2019
·Vol. 24
·期 18
·3223
·
IF 3.06
Xiu Liu,Linya Huang,Hongjun Chen,Na Li,Chao Yan,Chenzhong Jin,Hanhong Xu
To obtain highly selective toxic derivatives of fipronil, a series of Schiff bases with an alkynyl group (3a–3k) were designed and synthesized from 4-ethynylbenzaldehyde (2) and 4-substituted 5-amino-N-arylpyrazole (1a–1k) via a nucleophilic addition elimination reaction in ionic liquids. Utilization of ionic liquids was demonstrated to endow the yield of each compound beyond 50%, which was enhanced over 1.5 times of the synthetic productive rates comparing the conventional method by which longer reactive time was consumed. The derivatives were characterized via nuclear magnetic resonance hydrogen spectroscopy (1H-NMR), carbon-13 nuclear magnetic resonance spectroscopy (13C-NMR), and electrospray ionization high resolution mass spectrometry (ESI-HRMS). The cytotoxicity of these derivatives onTrichoplusia ni(Hi-5) cell andSpodoptera lituracell (SL cell) was evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) bioassays. The results indicated that several compounds had potential cytotoxicity on Hi-5 cell, especially a 4-ethyl substituted alkynyl Schiff base derivative (3f) that was demonstrated to possess high selective toxicity to the Hi-5 cell than the SL cell. In addition,3fexhibited comparable toxic activity to commercial fipronil on a Hi-5 cell while a little toxic effect on the SL cell, which satisfied the expectation for selective toxicity screening.Keywords:N-arylpyrazole derivatives;schiff base;cytotoxicity;fipronil derivatives
研究领域:
有机化学
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农药学
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毒理学
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DOI
PubMed
高影响因子
Journal of Environmental Chemical Engineering
·
2025
·
IF 7.2
Zhiyi Xu,Zhuofeng Sheng,Shaojuan Chen,Shuhua Li,Yaojie Liu,Long Jiang,Weizhi Sun,Chao Xu,Mo Xian
There are bottlenecks in the synthesis and purification of fine chemicals, such as high energy consumption and complex processes. Process optimization and green separation technology innovation are the key challenges for green chemistry and sustainable production. (S)-2,2-dimethyl-4-(2-hydroxyethyl)-1,3-dioxolane (dioxolane), as an important pharmaceutical and chemical intermediate, has limited its market application due to technical bottlenecks such as low synthesis efficiency and low purity. In this study, an efficient and green synthesis of dioxolane was established for the first time to avoid the generation of toxic chelated borate esters, and the purity of the product reached 99 %. Firstly, to address the low efficiency issue in dioxolane synthesis, we developed a novel synthetic route utilizing a tetrahydropyranyl (THP) protecting group strategy with (L)-malic acid as the starting material. Through response surface optimization of the key-step reduction reaction, the yield improved from 54 % to 91 %. Secondly, to address the problem of reduced purity caused by byproduct dioxane, we leveraged the size-matching effect between dioxane and the material, preparing seven materials with diverse physical structures via Friedel-Crafts alkylation. Notably, DCE-3A achieved selective separation of dioxolane and dioxane with a selectivity coefficient of 103.07. Through adsorption separation, dioxolane exhibited a purity of 99 % and a yield of 94 %, markedly outperforming the traditional derivatization separation method (purity 98 %, yield 50 %). In summary, the synergistic effect of the innovative protecting group strategy and the novel adsorbent achieved the efficient synthesis of dioxolane, offering a technical approach for the green synthesis of analogous compounds.
研究领域:
化学工程
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绿色化学
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DOI
高影响因子
LANGMUIR
·
2024
·
IF 3.7
Bizhuo Wei,Huajing Li,Huan Chu,Huanhuan Dong,Yijun Zhang,Cai-Li Sun,Yuangang Li
This work presents a study of the thermally induced aggregation of perylene diimide (PDI) and naphthalene diimide (NDI) derivatives modified with oligo ethylene glycol (OEG) chains in aqueous solution. Water-soluble and flexible OEG side chains were introduced into the π-core of glutamate-modified NDI and PDI structures, and the aggregation process was modulated by heating or cooling in water. Interestingly, a rare opposite temperature response of fluorescent behavior from the two amphiphilic chromophores was revealed, in which the PDI exhibited fluorescent enhancement, while fluorescent quenching upon temperature increase was observed from the NDI assembly. The mechanism of thermally induced aggregation is clearly explained by studies with various spectroscopic techniques including UV–visible, fluorescence, 1H NMR, 2D NMR spectroscopy, and SEM observation as well as control experiments operated in DMSO solution. It is found that although similar J-aggregates were formed by both amphiphilic chromophores in aqueous solution, the temperature response of the aggregates to temperature was opposite. The degree of PDI aggregation decreased, while that of NDI increased upon temperature rising. This research paves a valuable way for understanding the complicated supramolecular behaviors of amphiphilic chromophores.
研究领域:
超分子化学
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材料科学
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物理化学
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DOI
PubMed
高影响因子
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
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2021
·
IF 1.571
Zhi-Ping Che,Jin-Ming Yang,Song Zhang,Di Sun,Yue-E Tian,Sheng-Ming Liu,Xiao-Min Lin,Jia Jiang,Gen-Qiang Chen
Endeavor to discover biorational natural products-based insecticides, two series (27) of novel 9R/S-acyloxy derivatives of cinchonidine and cinchonine were prepared and assessed for their insecticidal activity against Mythimna separata in vivo by the leaf-dipping method at 1 mg/mL. Among all the compounds, especially derivatives 6l and 6o exhibited the best insecticidal activity with final mortality rates of 75.0% and 71.4%, respectively. Overall, a free 9-hydroxyl group is not a prerequisite for insecticidal activity and C9-substitution is well tolerated; the configuration of C8/9 position is important for insecticidal activity, and 9S-configuration is optimal; 6’-OCH3 moiety is not necessary, removal of it is also acceptable.
研究领域:
有机化学
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植物保护学
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DOI
PubMed
高影响因子
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
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2021
·
IF 1.571
Yue-E Tian,Di Sun,Xiao-Xiao Han,Jin-Ming Yang,Song Zhang,Nan-Nan Feng,Li-Na Zhu,Zhong-Yuan Xu,Zhi-Ping Che,Sheng-Ming Liu,Xiao-Min Lin,Jia Jiang,Gen-Qiang Chen
Three series of sulfonate derivatives of paeonol were synthesized and screened in vitro for their anti-oomycete activity against P. capsici, respectively. Among all the compounds, 4m displayed the best promising and pronounced anti-oomycete activity against P. capsici than zoxamide, with the EC50 values of 24.51 and 26.87 mg/L, respectively. The results show that acetyl and 4-OCH3 are two necessary groups. The existence of these two sites is closely related to the anti-oomycete activity. Relatively speaking, hydroxyl group is well tolerated, and the results showed that after modification of hydroxyl group with sulfonyl, the anti-oomycete activity was significantly increased.
研究领域:
植物化学
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农药科学
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药物化学
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DOI
PubMed
高影响因子
JOURNAL OF MASS SPECTROMETRY
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2019
·Vol. 54
·期 3
·239-249
·
IF 2.267
Hua-Ming Xiao,Xian Wang,Xing Yang,Feng Zheng,Yu-Qi Feng
Hydralazine has been widely employed in the development of drugs, derivatization reagents, and ligands. In the present work, we reported a new type of dehydrogenated ion [M − H] + that was produced from the hydralazine derivative of hexanal in electrospray ionization mass spectrometry (ESI-MS). The formation of [M − H] + ions in the ESI-MS was found to be independent on the mobile phase composition of the liquid chromatography and ESI source parameters. A series of hydralazine derivatives of aldehyde were investigated to confirm this phenomenon. The results showed that hydralazine derivatives of aldehydes that contained an sp 3 hybridization carbon with a hydrogen at the α-position of aldehydes could form the unexpected [M − H] + ions, whereas hydralazine derivative of acetone could only generate [M + H] + ion in the ESI-MS. We proposed the possible formation mechanism of [M − H] + ion for the hydralazine derivatives of aldehydes: the [M − H] + ion was possibly formed by the loss a hydrogen molecule (H 2 ) from the protonated ion [M + H] + . The results obtained from density functional theory (DFT) calculations supported this proposed formation mechanism of [M − H] + ion.
研究领域:
分析化学
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药物化学
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计算化学
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DOI
PubMed
高影响因子
CARBOHYDRATE POLYMERS
·
2023
·
IF 11.2
Fan Wang,Weiqi Wang,Yuqing Wang,Lili Zhang,Yoshio Okamoto,Jun Shen
Two novel cellulose and amylose derivatives bearing bulky tris(2-benzothienylformate) pendants ( Cel - 3 and Amy - 3 ) were expeditiously prepared by one-step esterification . The fluorescent sensing performance of six polysaccharide derivatives, including Cel - 3 / Amy - 3 , and other four previously prepared benzothienyl- or benzofuranyl-phenylcarbamates of cellulose and amylose ( Cel-1 / Amy-1 , Cel-2 / Amy-2 ), were carefully evaluated using eight metal ions , including Co 2+ , K + , Na + , Li + , Hg 2+ , Ni 2+ , Ca 2+ and Fe 3+ . All six derivatives exhibited excellent fluorescence quenching property to Fe 3+ ions with high sensitivity and selectivity. Especially, the limit of detection of Amy - 2 with benzofuranylphenylcarbamates for Fe 3+ was 3.0 μM, much lower than the maximum contaminant level for Fe 3+ in the drinking water . Additionally, the six bulky derivatives displayed the interesting fluorescence “turn-off” and “turn-on” observation, indicating a desirable reversibility for Fe 3+ detection. The high anti-interference ability was also observed for detection of Fe 3+ on the benzothienyl/benzofuranyl derivatives of cellulose and amylose in the combined system containing Co 2+ , K + , Na + , Li + , Hg 2+ , Ni 2+ and Ca 2+ . It suggested that the obtained polysaccharide derivatives with bulky chromophores possessed good potentials for detection of Fe 3+ as high-efficient fluorescent sensors in diverse applications. The sensing mechanism for detection of Fe 3+ was further proposed based on the Stern-Volmer plots and fluorescence titration analysis.
研究领域:
材料科学
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分析化学
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产品关联
DOI
PubMed
高影响因子
NATURAL PRODUCT RESEARCH
·
2022
·
IF 2.488
Zhibo Hu,Jannu Vinay Gopal,Lan Liu,Zhizeng Gao
A new tyrosine derivative (1), and two new terezine derivatives (2 and 3) were discovered from a marine-sponge-derived fungus Phoma herbarum YG5839. Those compounds were identified by comprehensive spectroscopic analysis, and antifungal activities were conducted against Fusarium oxysporum, Fusarium graminearum, Penicillium italicum, Colletotrictum gloeosporioides and Colletotrichum musae.
研究领域:
海洋生物学
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药物化学
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真菌学
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DOI
PubMed
高影响因子
RSC Advances
·
2017
·Vol. 7
·期 28
·17030-17037
·
IF 3.108
Xiangfei Kong,Liting Xia,Haifeng Zhang,Shengping Dai,Caili Yu,Zheng Liu,Linping Mu,Guixia Wang,Zhiqun He
Four novel mesogenic dyads consisting of a hexa(alkoxy)triphenylene donor that was linked to a perylene tetracarboxylic esters acceptor by the bridges (O–(CH2)2–O), (O–(CH2)6–O), (O–(CH2)10–O) and (O–(CH2)12–O), had been synthesized. Their structures were characterized by 13C and 1H nuclear magnetic resonance (NMR), infrared spectroscopy (IR) and elemental analysis (EA). The experimental results of cyclic voltammetry and UV/Vis showed the aliphatic linkage of the donor–acceptor dyads preserved the genuine electrochemical behaviors and light absorption properties of the donor and acceptor units, and the energy level difference between the HOMO of the donor and the LUMO of the acceptor is about 1.94 eV. The differential scanning calorimetry (DSC) traces and polarizing optical microscopy (POM) textures confirmed that all dyads had mesophase. When excited at 443 nm, fluorescence quenching process of the acceptor unit was ascribed to a intramolecular ground-state charge transfer from the donor to it. And the fluorescence quenching varying with the bridge lengths were understood by Dexter-type energy transfer theory. These behaviors of photoinduced intramolecular charge transfer and forming columnar liquid crystal phase made these dyads candidates of new active materials in organic solar cells.
研究领域:
材料科学
·
化学
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DOI
高影响因子
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