Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds

Twenty-two novel longifolene-derived diphenyl ether-carboxylic acid compounds 7a–7v were synthesized from renewable biomass resources longifolene, and their structures were confirmed by FT-IR, 1H NMR, 13C NMR, and HRMS. The preliminary evaluation of in vitro antifungal activity displayed that compound 7b presented inhibition rates of 85.9%, 82.7%, 82.7%, and 81.4% against Alternaria solani, Cercospora arachidicola, Rhizoctonia solani, and Physalospora piricola, respectively, and compound 7l possessed inhibition rates of 80.7%, 80.4%, and 80.3% against R. solani, C. arachidicola, P. piricola, respectively, exhibiting excellent and broad-spectrum antifungal activities. Besides, compounds 7f and 7a showed significant antifungal activities with inhibition rates of 81.2% and 80.7% against A.solani, respectively. Meanwhile, a reasonable and effective 3D-QSAR mode (r2 = 0.996, q2 = 0.572) has been established by the CoMFA method. Furthermore, the drug-loading complexes 7b/MgAl-LDH were prepared and characterized. Their pH-responsive controlled-release behavior was investigated as well. As a result, complex 7b/MgAl-LDH-2 exhibited excellent controlled-releasing performance in the water/ethanol (10:1, v:v) and under a pH of 5.7.

[1]  Jun Yu Li,et al.  Satisfactory Degradation of Tetracycline by a Ph-Universal Mnfe-Ldh@Bc Cathode in Electric Fenton Process: Performances, Mechanisms and Toxicity Assessments , 2022, SSRN Electronic Journal.

[2]  W. Duan,et al.  Synthesis of 3-Carene-derived Nanocellulose/1,3,4-Thiadiazole-Amide Complexes with Antifungal Activity for Plant Protection. , 2022, Pest management science.

[3]  W. Duan,et al.  Synthesis, Antifungal Activity, 3D-QSAR, and Molecular Docking Study of Novel Menthol-Derived 1,2,4-Triazole-thioether Compounds , 2021, Molecules.

[4]  W. Duan,et al.  Synthesis, Antifungal Activity and 3D‐QSAR Study of Novel ( E )‐Longifolene‐Derived Tetralone Oxime Ethers , 2021 .

[5]  Fuhou Lei,et al.  Design, Synthesis, and Antifungal Activity of Novel Longifolene-Derived Diacylhydrazine Compounds , 2021, ACS omega.

[6]  Zhong-Tian Fan,et al.  Synthesis, Antifungal Activity, and 3D-QSAR Study of Novel Nopol-Derived 1,3,4-Thiadiazole-Thiourea Compounds , 2021, Molecules.

[7]  Ying-zheng Zhao,et al.  Progress in the Application of Nano- and Micro-based Drug Delivery Systems in Pulmonary Drug Delivery , 2021, BIO Integration.

[8]  Yao.  Progress in the Application of Nano- and Micro-based Drug Delivery Systems in Pulmonary Drug Delivery , 2021 .

[9]  Byoung Choul Kim,et al.  Ceramic layered double hydroxide nanohybrids for therapeutic applications , 2020, Journal of the Korean Ceramic Society.

[10]  U. Riaz,et al.  Studies on conducting polymer intercalated layered double hydroxide nanocomposites: Antituberculosis drug delivery agents , 2020 .

[11]  W. Duan,et al.  Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety , 2020, Molecules.

[12]  J. Aubertot,et al.  Revisiting Sustainability of Fungicide Seed Treatments for Field Crops. , 2020, Plant disease.

[13]  R. Verma,et al.  Design, synthesis, evaluation, and molecular dynamic simulation of triclosan mimic diphenyl ether derivatives as antitubercular and antibacterial agents , 2020, Structural Chemistry.

[14]  Shifa Wang,et al.  Synthesis and Antiproliferative Activity of Isolongifolanone Pyrazoline Derivatives Inducing Intracellular ROS Accumulation , 2019, Pharmaceutical Chemistry Journal.

[15]  Zhengyun Wang,et al.  A review on electrochemical biosensing platform based on layered double hydroxides for small molecule biomarkers determination. , 2018, Advances in colloid and interface science.

[16]  B. Tang,et al.  Specific discrimination of gram-positive bacteria and direct visualization of its infection towards mammalian cells by a DPAN-based AIEgen. , 2018, Biomaterials.

[17]  Marian Rosaly Davolos,et al.  Eu(III) doped LDH intercalated with cinnamate anion as multifunctional sunscreens , 2018, Journal of Luminescence.

[18]  David G. Evans,et al.  A bottom-up synthesis of rare-earth-hydrotalcite monolayer nanosheets toward multimode imaging and synergetic therapy , 2018, Chemical science.

[19]  M. Fisher,et al.  Worldwide emergence of resistance to antifungal drugs challenges human health and food security , 2018, Science.

[20]  Min Wei,et al.  Monolayer Nanosheets with an Extremely High Drug Loading toward Controlled Delivery and Cancer Theranostics , 2018, Advanced materials.

[21]  Yan Wang,et al.  Development Strategies and Prospects of Nano-based Smart Pesticide Formulation. , 2017, Journal of agricultural and food chemistry.

[22]  Xiuhuan Li,et al.  Positive-Charge Functionalized Mesoporous Silica Nanoparticles as Nanocarriers for Controlled 2,4-Dichlorophenoxy Acetic Acid Sodium Salt Release. , 2017, Journal of agricultural and food chemistry.

[23]  You Liang,et al.  Development of Novel Urease-Responsive Pendimethalin Microcapsules Using Silica-IPTS-PEI As Controlled Release Carrier Materials , 2017 .

[24]  Xiaohui Xu,et al.  A Near-Infrared and Temperature-Responsive Pesticide Release Platform through Core-Shell Polydopamine@PNIPAm Nanocomposites. , 2017, ACS applied materials & interfaces.

[25]  E Benfenati,et al.  Predicting acute contact toxicity of pesticides in honeybees (Apis mellifera) through a k-nearest neighbor model. , 2017, Chemosphere.

[26]  P. Seuntjens,et al.  Application of biodegradation in mitigating and remediating pesticide contamination of freshwater resources: state of the art and challenges for optimization , 2016, Applied Microbiology and Biotechnology.

[27]  Cheng Fang,et al.  Receptor-based 3D-QSAR in Drug Design: Methods and Applications in Kinase Studies. , 2016, Current topics in medicinal chemistry.

[28]  Min Wei,et al.  TiO2@Layered Double Hydroxide Core–Shell Nanospheres with Largely Enhanced Photocatalytic Activity Toward O2 Generation , 2015 .

[29]  David G. Evans,et al.  Catalytic Applications of Layered Double Hydroxides: Recent Advances and Perspectives , 2014 .

[30]  Min Wang,et al.  Controlling Pesticide Loss through Nanonetworks , 2014 .

[31]  Shu-Jing Yu,et al.  Microwave-assisted synthesis of some novel 1,2,3-triazoles by click chemistry, and their biological activity , 2013, Research on Chemical Intermediates.

[32]  Hui‐Ming Cheng,et al.  α-Sulfur crystals as a visible-light-active photocatalyst. , 2012, Journal of the American Chemical Society.

[33]  Rickey Y. Yada,et al.  Nanotechnologies in agriculture: New tools for sustainable development , 2011 .

[34]  W. Luo,et al.  The Synthesis of Mg-Zn-Al LDH and the Sustained-Release Properties of Theophylline Intercalated LDH , 2011 .

[35]  G. Li,et al.  Synthesis of dehydroabietic acid-modified chitosan and its drug release behavior. , 2009, Carbohydrate research.