THERMOCHIMICA ACTA
·
2017
·
IF 2.236
Jing Liu,Rujuan Li,Mengya Guo,Hairong Tao,Donglan Sun,Chengxing Zong,Chunjing Liu,Fengzhi Fu
We recently found that the introduction of benzene ring as connection block improved the thermal stability of glycerol carbonate derivatives. To further explore how polysubstitution on benzene influences their thermal stability, another two derivatives, benzene-1,3,5-tricarboxylic acid tris-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (BATE1) and benzene-1,2,4,5-tetracarboxylic acid tetrakis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (BATE2), were synthesized and characterized by a combined TG–FTIR and theoretical calculation. TG results showed that both BATE1 and BATE2 had three weight loss stages. FTIR spectra of evolved gases and the bond dissociation energy for the two compounds indicated that during the pyrolysis process, the C C, C O bonds of five-membered cyclic carbonate fractured preferentially to produce volatile carbonates and CO 2 , and then the nearby C O bond of esters continued to crack to produce more fragments. Finally, benzene ring still remains in the solid pyrolysis products. Therefore, improving the thermal stability of compound cannot be achieved simply by increasing the number of substituents on the benzene ring.
研究领域:
化学
·
材料科学
✓ 已验证
产品关联
DOI
高影响因子
FITOTERAPIA
·
2024
·
IF 2.5
Ye-Fang Lu,Chuang Liu,Juan Ma,Hu-Ri Piao,Changhao Zhang,Xuejun Jin,Cheng-Hua Jin
Hypoxia-inducing factor-1α (HIF-1α) is overexpressed in variety of tumor patients and plays an important role in the regulation of hypoxia response in tumor cells. Therefore, its inhibitors have become one of the targets for the treatment of a variety of cancers. Two series of panaxadiol (PD) ester derivatives containing pyrazole ( 18a–j ) and pyrrole ( 19a–n ) moiety were synthesized and their HIF-1α inhibitory activities were evaluated. Among all the target compouds, compounds 18c , 19d , and 19n (IC 50 = 8.70 – 10.44 μM) showed better HIF-1α inhibitory activity than PD (IC 50 = 13.35 μM). None of these compounds showed cytotoxicity above 100 μM and inhibited HIF-1α transcription in a dose-dependent manner. These compounds showed good antitumor activity and provide lead compounds for further design and activity study of PD ester derivatives.
研究领域:
药理学
·
肿瘤学
·
药物化学
✓ 已验证
DOI
PubMed
高影响因子
Food & Function
·
2024
·Vol. 15
·期 11
·5785-5796
·
IF 5.1
Li-sha Hao,Meng-meng Zhang,Xiao-Feng Li,Xuan Xin,Guang-lei Zhao
In this study, we developed a multi-site acylation strategy to improve the lipophilicity and cellular uptake of troxerutin, a natural flavonoid with many health-promoting bioactivities. By clarifying the acylation properties of troxerutin catalyzed by lipases from different sources, a series of troxerutin ester derivatives acylated at different sites was synthesized, including troxerutin dipropyl (TDP), tripropyl (TTP), tetrapropyl (TEP), dibutyl (TDB), monohexyl (TMH), monooctyl (TMO) and monodecyl (TMD) esters. Interestingly, the troxerutin esters acylated at multiple sites with shorter fatty chains (TDP, TTP and TEP) had similar lipophilicity to the mono-acylated esters bearing longer fatty chains (TMH, TMO and TMD, respectively) and meanwhile demonstrated surprisingly lower cytotoxicity than that of the long fatty-chain mono-esters. In particular, the multi-acylated esters with shorter fatty chains showed remarkably higher cellular uptake than the mono-esters with long fatty chains. In vitro gastrointestinal digestion suggested that the multi-acylated esters of troxerutin were more resistant to gastrointestinal degradation than the mono-esters. These results indicated that multi-site acylation with short fatty chains could be an effective alternative to introducing one-site mono-acylation for the modification of troxerutin and other flavonoid compounds.
研究领域:
生物化学
·
药理学
·
食品科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
·
2021
·
IF 4.291
Miao Yao,Shaohui Liu,Chen Huang,Jun Nie,Yong He
Five ester derivatives from hydroxyalkyl of 2-hydroxy-2-methyl-1-phenyl propanone, one of the most successfully applied α-hydroxyalkyl acetophenone photoinitiators, are synthesized. From the spectroscopy results and theory calculation, it is proved that the much lower photocleavage rates of the directly linked unsaturated ester derivatives are due to that the strong electron withdrawing effect of carbonyl increase the bond strength between the benzoyl and quaternary carbon and the effective energy transfer from benzoyl to double bond because of the existence of p-σ-π hyperconjugation, which consequently decreased their initiating ability. Excitingly, simple introduction of two-methylene spacer between the carbonyl and alkoxyl can effectively block the hyperconjugation and significantly increase the photocleavage rate up to the same level of their mother commercial photoinitiator, which can open a gate for design of new high efficiency and polymerizable type I photoinitiators.
研究领域:
有机化学
·
材料科学
·
光化学
✓ 已验证
产品关联
DOI
高影响因子
Marine Drugs
·
2019
·Vol. 17
·期 6
·332
·
IF 3.772
Zhongbin Cheng,Yuanli Li,Wan Liu,Lijun Liu,Jie Liu,Wangjun Yuan,Zhuhua Luo,Wei Xu,Qin Li
Three new butenolide derivatives, namely aspernolides N–P (1–3), together with six known analogues (4–9), were isolated from the ethyl acetate (EtOAc) extract of the deep sea-derived fungusAspergillus terreusYPGA10. The structures of compounds1–3were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of1and2were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compound1represents the rare example ofAspergillus-derived butenolide derivatives featured by a monosubstituted benzene ring. Compounds6–9exhibited remarkable inhibitory effects againstα-glucosidase with IC50values of 3.87, 1.37, 6.98, and 8.06 μM, respectively, being much more active than the positive control acarbose (190.2 μM).Keywords:Aspergillus terreusYPGA10;deep-sea-derived fungus;butenolide derivatives;α-glucosidase
研究领域:
微生物学
·
药物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
·
2021
·
IF 1.571
Gen-Qiang Chen,Di Sun,Jin-Ming Yang,Song Zhang,Yue-E Tian,Zhi-Ping Che,Sheng-Ming Liu,Jia Jiang,Xiao-Min Lin
Two series of sulfonate derivatives of carvacrol and thymol were synthesized and screened in vitro for their anti-oomycete activity against Phytophthora capsici, respectively. Among all of 32 derivatives, five compounds 3a, 4a, 4k, 3n, and 4n exhibited more potent anti-oomycete activity against P. capsici with EC50 values of 66.66, 62.94, 68.65, 61.24, and 52.91 mg/L, respectively. This suggested that introduction of different substitutions at the hydroxyl position of 1/2 could have remarkable effect on anti-oomycete activity. Overall, when R1 = isopropyl and R2 = methyl, the anti-oomycete activities of the compounds were higher than that of the corresponding compounds of R1 = methyl and R2 = isopropyl.
研究领域:
植物化学
·
农药科学
·
微生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CHEMICAL PHYSICS LETTERS
·
2021
·
IF 2.328
Chunhua Ni,Guobo Chen,Xia Li,Haizhou Zhao,Liangmin Yu
Two new indole ester derivatives containing acrylamide group were synthesized by Michael addition reaction and Friedel-Crafts reaction based on 5-bromo-1 H -indole. The synthesized compounds were characterized by 1 H Nuclearmagnetic Resonance Spectroscopy ( 1 HNMR) and Fourier Transform Infrared spectroscopy (FTIR). In the step of the Friedel-Crafts reaction, the optimum process conditions were determined as that the catalyst was AlCl 3 , the reaction time was 3 days and the reaction temperature was 25 °C. The results of minimal inhibitory concentration (MIC) of synthesized compounds showed that the two synthesized compounds have better antibacterial activity than reference. Algal inhibiting experiment shows that indole derivatives have better algae inhibition performance. Anti-protein adsorption experiment of antifouling paints with indole derivative and chlorothalonil as antifouling agents proves that indole derivatives exhibit better protein resistance behaviors. The antifouling paints using indole derivatives as antifouling agents have excellent antifouling properties after 24 months marine field test.
研究领域:
有机化学
·
材料科学
·
海洋生物学
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
·
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
·
农药科学
·
药物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
COLLOID AND POLYMER SCIENCE
·
2021
·Vol. 299
·期 11
·1743-1755
·
IF 1.931
Liu Zhaowen,Chen Xiuqiong,Wen Yanshi,Liu Chunyang,Cao Shirui,Yan Huiqiong,Lin Qiang
Due to the presence of abundant carboxyl and hydroxyl groups on the molecular chain, the raw alginate is too hydrophilic to achieve effective entrapment and controlled release of hydrophobic drug. To broaden the application range of alginate, 1-bromodecane was covalently grafted onto sodium alginate (SA) via bimolecular nucleophilic substitution (S N 2) reaction to synthesize decyl alginate ester derivative (DAED). The structure and self-assembly behavior of DAED were characterized by means of FT-IR, 1 H NMR, thermogravimetric analysis (TGA), XRD, fluorescence spectrum (FM), surface tension (SFT), TEM, atomic force microscope (AFM), and dynamic light scattering (DLS). Furthermore, the loading and in vitro release of hydrophobic ibuprofen for the self-assembled DAED microcapsules and their cytotoxicity against the murine macrophage RAW264.7 cell were investigated. The FT-IR and 1 H NMR analyses showed that the decyl groups were successfully grafted onto the alginate backbone. The results of TGA and XRD showed that due to the grafting decyl side chains, the intramolecular hydrogen bond of DAED was broken, thus resulting in the decrease of its thermal stability and the change of its microcrystalline structure, which improved its molecular flexibility and self-assembly behavior. Therefore, the DAED could reveal good amphiphilic property with the critical aggregation concentration (CAC) of 0.08 g/L, and form micelle-like aggregates with the average hydrodynamic diameter of 185.1 nm (PDI = 0.615) and zeta potential at about −39.2 mV. In addition, from TEM and AFM observation, DAED could generate spherical drug-loaded microcapsules through its self-assembly behavior, which exhibited excellent sustained-release property ascribed to the enhanced affinity of DAED to hydrophobic ibuprofen. And the prepared DAED microcapsules also displayed low cytotoxicity to the murine macrophage RAW264.7 cells. Therefore, it was the good self-assembly behavior of DAED that made it have great potentials as the hydrophobic drug carriers in pharmaceutical field.
研究领域:
材料科学
·
药学
·
生物学
✓ 已验证
产品关联
DOI
高影响因子
NATURAL PRODUCT RESEARCH
·
2024
·
IF 1.9
Xiaofang Zhang,Xiaolong Guo,Wanying Yin,Ruiguang Wang,Yuee Tian,Huilu Sun,Shaobin Xu,Shaoyan Shuang,Xiaobo Huang,Genqiang Chen,Zhiping Che
To discover biorational natural product-based pesticides, a series of paeonol ester derivatives containing a Schiff base (6a-j, 7i,j, 8i,j, and 9i,j) were prepared, and their structures were well characterised by 1H NMR and HRMS. Furthermore, bioactivities of these compounds as anti-oomycete and anti-fungal agents against two serious agricultural diseases, Phytophthora capsici and Fusarium graminearum we assessed. Amongst evaluated compounds, 1) Compounds 6a and 6e displayed good anti-oomycete against P. capsici, with EC50 values of 116.50 and 88.86 mg/L, respectively. 2) Compounds 6e and 7i exhibited prominent anti-fungal against F. graminearum, with EC50 values of 66.73 and 29.33 mg/L, respectively. 3) This study suggested that the introduction of nitro at the C5 position of paeonol could improve its bioactivity against P. capsici and F. graminearum. The results of this study pave the way for further design and development of paeonol derivatives as plant anti-oomycetes and anti-fungal agents in crop protection.
研究领域:
植物化学
·
农药学
·
植物病理学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
·
2025
·
IF 4.7
Ting Yang,Xinhui Huang,Liangbin Lin,Hongyu Guo,Fafu Yang
As Al 3+ is an important ion in industry and daily life, the fluorescence sensor with high sensing selectivity and sensitivity for Al 3+ in rapid, simple and in-situ way was always anticipated. In this work, a “turn-on” fluorescence sensor ( CBC ) based on a crown ether-bridged biscyanostilbene carboxylic derivative exhibited excellent fluorescence response for Al 3+ with obvious fluorescence change from dark blue to bright blue-green color. The high sensing selectivity for Al 3+ was observed among 28 kinds of metallic cations and anions. The detecting limitation was as low as 1.68 × 10 −8 M. The sensing mechanism was proposed as that Al 3+ was bound by two carboxyl groups, resulting in the rotating restriction of aromatic groups and strong fluorescence. This sensing ability of CBC for Al 3+ was evaluated by TLC analysis, stamp experiment and simulated water samples, suggesting the excellent application potential on simple, rapid and in-situ detection of Al 3+ in real environments.
研究领域:
化学传感
·
分析化学
✓ 已验证
产品关联
DOI
高影响因子
RENEWABLE ENERGY
·
2024
·
IF 9
Kai Zhang,Zhengyong Huang,Jian Li
Natural polyphenols are commonly used as antioxidants in oil-based systems due to their strong antioxidant activity and safety profile. However, their hydrophilic nature limits their solubility in oils, a limitation that can be addressed by converting them into hydrophobic lipophenols through esterification. In this study, the antioxidant activity and oxidative stability of gallic acid and its ester derivatives in natural ester oils were investigated. Density functional theory and molecular dynamics simulations were conducted to elucidate the antioxidant mechanisms of gallic acid esters. The results indicate that gallic acid esters form stable hydrogen-bonded complexes with natural ester molecules, and the lower reaction barrier with ROO• radicals facilitates effective interactions between the antioxidants and oil molecules, thereby enhancing antioxidant efficacy. Among the derivatives, C2-GA demonstrates superior antioxidant activity due to its lowest reaction barrier with ROO• radicals and the stability of its hydrogen-bonded complexes with natural esters. This aligns well with experimental findings, as differential scanning calorimetry (DSC) tests show that C2-GA increases the oxidation induction time (OIT) of natural ester oils by 119 %, significantly enhancing oxidative stability. Additionally, C2-GA exhibits strong radical scavenging ability in the DPPH radical assay, further supporting its high antioxidant potential. These results demonstrate that this computational approach can effectively predict the antioxidant potential of gallic acid esters, facilitating the rational design of new polyphenolic antioxidants for applications in oil-based systems.
研究领域:
食品科学
·
计算化学
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）