Article
Chemistry, Organic
Wei-Jun Wang, Meng-Yue Wang, Wen-Hua Xu, Bao-Yin Zhao, Hong-Xia Zhang, Ya-Ru Gao, Shi-Huan Guo, Yong-Qiang Wang
Summary: We have developed a direct Z-selective synthesis of 1,2-cis-dibromoalkenes from alkynes using Ag-CH3SO3H as the co-catalyst. Mechanistic studies revealed that the reaction proceeded through the formation of a silver allene cation intermediate, followed by sequential bromine free radical addition and substitution. This discovery has the potential to open up a new frontier in silver catalysis and allene chemistry. Additionally, we have also disclosed an efficient PPh3-promoted E-selective synthesis of 1,2-trans-dibromoalkenes from alkynes. Both protocols utilized N-bromosuccinimide as the sole brominating reagent, making the reactions milder and easier to handle.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Hana Pizova, Milan Malanik, Karel Smejkal, Michal Oravec, Pavel Bobal
Summary: An efficient and versatile synthesis method for the naturally occurring C-prenylated stilbenoid methyl ethers and their synthetic analogues is presented. The synthesis involves a six-step convergent process which includes an optimized C-prenylation method. Additionally, six new dihydro-benzopyranyl derivatives were obtained and isolated during the demethylation process.
Article
Chemistry, Organic
Avisikta Sinha, Mangalampalli Ravikanth
Summary: The benzofuran-embedded selena- and telluraporphyrins were synthesized through replacing the pyrrole ring with a benzofuran unit, resulting in altered electronic properties. The presence of the benzofuran moiety in the macrocycles led to distorted structures and hindered pi-electron delocalization. The absorption spectra showed strong bands in the visible range for the benzofuran-embedded selena- and telluraporphyrins, while the protonated derivatives exhibited strong absorption in the near-infrared region.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Bushra Adalat, Fazal Rahim, Muhammad Taha, Shawkat Hayat, Naveed Iqbal, Zarshad Ali, Syed Adnan Ali Shah, Abdul Wadood, Ashfaq Ur Rehman, Khalid Mohammed Khan
Summary: Inhibition of alpha-glucosidase and alpha-amylase enzymes is a significant approach in designing anti-diabetic drugs. A new series of benzofuran Schiff base compounds were designed and evaluated for their inhibitory potentials. The most potent analogues showed good accommodation in the enzyme's binding site.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Microbiology
Xuan Zhou, Ming-Yi Wang, Qian-Ping Cao, Ze Yang, Qing-Feng Meng, Shao-Bin Fu
Summary: In this study, the secondary metabolites of an endolichenic fungus were investigated, and compound 5 showed attractive antimicrobial activities on multiple pathogenic strains, likely affecting the permeability of the cell wall and cell membrane. These results enriched the library of active strains and metabolites resources of endolichenic microorganisms, and provided an alternative pathway to explore antimicrobial agents.
FRONTIERS IN MICROBIOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Abeer J. J. Ayoub, Ghewa A. A. El-Achkar, Sandra E. E. Ghayad, Layal Hariss, Razan H. H. Haidar, Leen M. M. Antar, Zahraa I. I. Mallah, Bassam Badran, Rene Gree, Ali Hachem, Eva Hamade, Aida Habib
Summary: The benzofuran and dihydrobenzofuran derivatives have been found to effectively inhibit inflammation and tumor growth in macrophages and colorectal adenocarcinoma cells. Six of these compounds showed anti-inflammatory effects by suppressing the expression of inflammatory genes and reducing the secretion of inflammatory mediators. Two compounds with fluorine, bromine, and ester or carboxylic acid groups also inhibited tumor cell proliferation and induced apoptosis. These findings suggest that these derivatives have potential applications in the treatment of chronic inflammation and cancer.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Lukas Fliegel, Jens Christoffers
Summary: Reacting beta-oxoesters with PIFA yields alpha-(iodophenyl) derivatives, which serve as starting materials for the preparation of [b] annulated benzofurane derivatives through copper-catalyzed C-O coupling reaction. The resulting scaffold shows great potential in medicinal chemistry and can be diversified to obtain various structurally different compounds.
Article
Construction & Building Technology
Hanshuai Zhang, Wenjing Xia, Zhihui Hu, Tao Xu
Summary: A composite anti-microbial aging agent has been developed to reduce microbial aging of asphalt pavement, inhibiting the reproduction of microbial consortia and maintaining the physicochemical properties of asphalt. The compounding scheme with specific ratios of ingredients shows a higher anti-microbial aging effect on the reproduction of microbial consortia on asphalt.
CONSTRUCTION AND BUILDING MATERIALS
(2021)
Article
Agriculture, Multidisciplinary
Jiming Li, Ru Wang, Yihai Wang, Jia Zeng, Zeyong Xu, Jingwen Xu, Xiangjiu He
Summary: This study explored the anti-inflammatory phytochemicals of Chinese olive fruit and discovered nine pairs of new benzofuran neolignans. These compounds exhibited pronounced inhibitory effects on nitric oxide production and some of them exerted anti-inflammatory effects by blocking the nuclear translocation of NF-kappa B.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2022)
Article
Chemistry, Organic
Yankun Li, Chen -Ho Tung, Zhenghu Xu
Summary: A novel method for synthesizing diverse benzofuran derivatives from easily obtained quinols and alkynyl esters has been reported. The method involves a gold-catalyzed intermolecular alkoxylation/Claisen rearrangement/condensation cascade. The introduction of difluorodiphenylsilane as a water-trapping reagent in the reaction leads to higher yield.
Article
Biochemistry & Molecular Biology
Fan Xu, Lisha Zhang, Changxin Zhou, Jianxia Mo, Shengnan Shen, Tian Zhang, Jie Li, Ligen Lin, Rihui Wu, Lishe Gan
Summary: Five new racemic alkyl-benzofuran dimers were isolated from the root tubers of Eupatorium chinense, with compound 1 exhibiting the best activity in enhancing insulin-stimulated glucose uptake. Some isolates showed promising inhibitory effects on nitric oxide (NO) in macrophages, with compound 1 also suppressing LPS-induced expression of inducible NO synthase and nuclear translocation of p65.
BIOORGANIC CHEMISTRY
(2021)
Review
Biotechnology & Applied Microbiology
Yiwen Jing, Yanxia Wang, Dawei Zhou, Jingnan Wang, Jiawen Li, Jingxiang Sun, Yifan Feng, Fengxue Xin, Wenming Zhang
Summary: This review paper introduces the properties and biosynthetic metabolism process of carotenoids, as well as the methods and strategies for microbial synthesis of carotenoids. The potential applications of carotenoids in food, medicine, cosmetic, and other fields are also discussed.
BIOTECHNOLOGY ADVANCES
(2022)
Article
Chemistry, Medicinal
Xiangyu Zhang, Hailan Huang, Ziheng Zhang, Jiangkun Yan, Tianxiao Wu, Wenbo Yin, Yixiang Sun, Xinran Wang, Yanting Gu, Dongmei Zhao, Maosheng Cheng
Summary: A series of novel LSD1 inhibitors were designed and synthesized, with compound 17i exhibiting excellent inhibitory effects and promising potential for further development. This compound showed robust in vivo antitumor efficacy without significant side effects, making it a promising lead compound for future studies.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Hongbo Qi, Kaiming Han, Shufeng Chen
Summary: This novel palladium-catalyzed aryl-furanylation of alkenes provides a straightforward route to various benzofuran-containing 3,3-disubstituted oxindole derivatives bearing a quarternary carbon center. In a single chemical operation, one C(sp(2))-O bond, two C(sp(2))C(sp(3)) bonds, an oxindole, and a furan ring are formed in the cascade process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Mohammad A. Ranjbari, Hossein Tavakol
Summary: Various benzofuran derivatives were synthesized through a catalyst-free reaction between nitroepoxides and salicylaldehydes under K2CO3 and DMF at 110 degrees C, resulting in yields ranging from 33-84% after 12 hours. The highest yields were achieved using 3-nitrosalicylaldehyde. A plausible mechanism was proposed for the reaction, supported by evidence such as the detection of released acetate anion using FTIR and the isolation and structure determination of a critical intermediate.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Sahishna Phaniraj, Zhe Gao, Digamber Rane, Blake R. Peterson
Article
Microbiology
Jennifer R. Klaus, Jacqueline Deay, Benjamin Neuenswander, Wyatt Hursh, Zhe Gao, Tiffany Bouddhara, Todd D. Williams, Justin Douglas, Kyle Monize, Patricia Martins, Charlotte Majerczyk, Mohammad R. Seyedsayamdost, Blake R. Peterson, Mario Rivera, Josephine R. Chandler
JOURNAL OF BACTERIOLOGY
(2018)
Article
Chemistry, Multidisciplinary
Kelsey E. Knewtson, Chamani Perera, David Hymel, Zhe Gao, Molly M. Lee, Blake R. Peterson
Article
Chemistry, Medicinal
Zhe Gao, Zhen Yang, Zheng Li, Kevin Burgess
Summary: Rucaparib-containing fluorescent probes (1-3) have been found to inhibit PARP1 activity in cell models. One of these probes (1) was tested in a murine model and shown to penetrate into implanted intracranial glioblastoma tumors and persist there for at least 24 hours.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Medicinal
Syed Muhammad Usama, Zhe Gao, Maritess Arancillo, Kevin Burgess
Summary: Conjugating tumor-seeking dyes with fragments can increase selective therapeutic delivery to tumors and drug residence by displacing meso-Cl with free cysteine residues of albumin. The significance of this strategy has recently been elevated as the first tumor-seeking dye-drug conjugate has entered clinical trials. Options for further clinical research include modifying the dye and using preformed albumin adducts instead of dyes alone.
Article
Biochemistry & Molecular Biology
Zhe Gao, Krishna K. Sharma, Angelo E. Andres, Brandon Walls, Fadel Boumelhem, Zachary R. Woydziak, Blake R. Peterson
Summary: Fluorinated analogues of pyronin B, a fluorophore, were synthesized and shown to react reversibly with primary amines. These analogues undergo oxidation in the presence of proteins, yielding fluorescent pyronins, and this oxidation step can be enhanced by blue light irradiation. The fluorinated analogue 2,7-difluoropyronin B was found to localize in mitochondria in living HeLa cells and depolarize the mitochondria upon blue laser excitation. This photochemical control of mitochondrial biology is attributed to the enhanced cellular production of reactive oxygen species.
RSC MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Chen-Ming Lin, Zhengyang Jiang, Zhe Gao, Maritess Arancillo, Kevin Burgess
Summary: The study explored the potential disruption of the NEDD8·NAE interaction using various chemotype designs through EKO evaluation. A compound was identified from a targeted library for its ability to bind NAE, inhibit NEDDylation, and induce cytotoxicity in leukemia cells. It represents a first-in-class inhibitor of NEDDylation and demonstrates the utility of EKO in evaluating chemotypes as potential PPI inhibitors.
Article
Chemistry, Multidisciplinary
Molly M. Lee, Zhe Gao, Blake R. Peterson
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Medicinal
Shuang Mei, Su Jiang, Yuting Wang, Han Jing, Peng Yang, Miao-Miao Niu, Jindong Li, Kai Yuan, Yan Zhang
Summary: This study identifies a dual-targeting peptide, AP-1, that effectively inhibits variants of concern (VOCs) of SARS-CoV-2 without impairing host cell viability. The findings suggest that AP-1 could be a promising broad-spectrum agent for treating emerging VOCs of SARS-CoV-2.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Hyeonjun Lee, Ju Yeon Lee, Hyunsoo Jang, Hye Young Cho, Minhee Kang, Sang Hyun Bae, Suin Kim, Eunji Kim, Jaebong Jang, Jin Young Kim, Young Ho Jeon
Summary: By using liquid chromatography-tandem mass spectrometry and nuclear magnetic resonance experiments, we identified new chemical moieties that bind to the target sites of the protein of interest, allowing for reversible binding and protein degradation. This method has the potential to expand the application of PROTAC technology.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Yingying Li, Xiyou Du, Xinru Kong, Yuelin Fang, Zhijing He, Dongzhu Liu, Hang Wu, Jianbo Ji, Xiaoye Yang, Lei Ye, Guangxi Zhai
Summary: This study proposes a novel nanoplatform based on the autophagy cascade to overcome the obstacles in chemo-immunotherapy. The platform combines chemotherapy and starvation therapy to initiate pro-death autophagy and enhance antigen presentation, while also remodeling the immunosuppressive tumor microenvironment. Furthermore, the study discovers a new therapeutic direction for the respiration inhibitor 3-bromopyruvic acid (3BP) in cancer treatment. Overall, this study offers an opportunity to improve antitumor efficacy and boost immune responses.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Bingsi Wang, Mingxu Ma, Yusen Dai, Pengfei Yu, Liang Ye, Wenyan Wang, Chunjie Sha, Huijie Yang, Yingjie Yang, Yunjing Zhu, Lin Dong, Shujuan Wei, Linlin Wang, Jingwei Tian, Hongbo Wang
Summary: Breast cancer is a common malignant tumor in women, and drug resistance remains a clinical challenge. In this study, a novel compound, G-5b, was developed with potent antagonistic and degradation activities comparable to the current drug fulvestrant. G-5b also showed improved stability and solubility. Mechanistically, G-5b engages the proteasome pathway to degrade ER, inhibiting the ER signaling pathway and inducing apoptosis and cell cycle arrest. In animal models, G-5b exhibited superior pharmacokinetics and pharmacodynamics properties. Overall, G-5b is a promising long-acting SERD worthy of further investigation and optimization.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Karoline B. Waitman, Larissa C. de Almeida, Marina C. Primi, Jorge A. E. G. Carlos, Claudia Ruiz, Thales Kronenberger, Stefan Laufer, Marcia Ines Goettert, Antti Poso, Sandra V. Vassiliades, Vinicius A. M. de Souza, Monica F. Z. J. Toledo, Neuza M. A. Hassimotto, Michael D. Cameron, Thomas D. Bannister, Leticia Costa-Lotufo, Joa o A. Machado-Neto, Mauricio T. Tavares, Roberto Parise-Filho
Summary: A series of hybrid inhibitors combining pharmacophores of known kinase inhibitors and benzohydroxamate HDAC inhibitors were synthesized and evaluated for their anticancer activity and pharmacokinetic properties. Compounds 4d-f exhibited promising cytotoxicity against hematological cells and moderate activity against solid tumor models. Compound 4d showed potent inhibition of multiple kinase targets and had stable interactions with HDAC and members of the JAK family. These compounds showed selective cytotoxicity with minimal effects on non-tumorigenic cells and favorable pharmacokinetic profiles.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Michal Sulik, Diana Fontinha, Dietmar Steverding, Szymon Sobczak, Michal Antoszczak, Miguel Prudencio, Adam Huczynski
Summary: This study describes the synthesis of the first-in-class ivermectin derivatives obtained through derivatization of the C13 position, along with the unexpected rearrangement of the macrolide ring. These derivatives show potential for antiparasitic activity and are important for the development of new antiparasitic agents.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Jun Liu, Qiu-Xian Chen, Wen-Fu Wu, Dong Wang, Si -Yu Zhao, Jia-Hao Li, Yi-Qun Chang, Shao-Gao Zeng, Jia-Yi Hu, Yu-Jie Li, Jia-Xin Du, Shu-Meng Jiao, Hai-Chuan Xiao, Qiang Zhang, Jun Xu, Jian-Fu Zhao, Hai -Bo Zhou, Yong-Heng Wang, Jian Zou, Ping-Hua Sun
Summary: A new anti-infective drug strategy has been discovered to attenuate virulence and modulate inflammation caused by drug-resistant Pseudomonas aeruginosa infections. Compound 5f inhibits biofilm formation, macrophage migration, and inflammatory response induced by P. aeruginosa, showing potential as a novel candidate against drug-resistant infections.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Liuzeng Chen, Ke Wang, Lingyun Wang, Wei Wang, Lifan Wang, Jia Li, Xiaohan Liu, Mengya Wang, Banfeng Ruan
Summary: In this study, a series of novel anti-inflammatory compounds were designed and synthesized based on the natural product pterostilbene skeleton. Among them, compound 8 showed the highest activity and exhibited its effects through inhibition of pro-inflammatory cytokines by blocking the NF-KB/MAPK signaling pathway. Compound 8 also demonstrated a good relieving effect on acute colitis in mice and showed good safety in acute toxicity experiments.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Si-Min Liang, Gui-Bin Liang, Hui-Ling Wang, Hong Jiang, Xian-Li Ma, Jian-Hua Wei, Ri-Zhen Huang, Ye Zhang
Summary: A series of novel multi-target antitumor agents were designed, synthesized, and evaluated. Some compounds exhibited significant antitumor activity and one compound showed excellent efficacy, limited toxicity, and low resistance. Further mechanism studies revealed that the compound exerted antitumor effects through multiple pathways.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
