Article
Chemistry, Organic
Jacques Renault, Christelle Bouvry, Jean-Francois Cupif, Jean-Pierre Hurvois
Summary: The syntheses of several alkaloids and nitrogen-containing compounds were described in this study, including N-Boc-coniine (14b), pyrrolizidine (1), 6-coniceine (2), and pyrrolo[1,2a]azepine (3). New C-C bonds in the alpha position relative to the nitrogen atom were formed through alkylation reactions. The pyrrolidine ring was formed in an aqueous medium, while the azepane ring was efficiently formed in N,N-dimethylformamide (DMF) as the solvent, using a 7-exo-tet cyclization process.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Biochemistry & Molecular Biology
Bin Li, Chen Chen, Jingjing Jia, Ling He
Summary: This article summarizes the research advances in different kinds of seven-membered heterocyclic compounds containing nitrogen, oxygen, and sulfur heteroatoms with antitumor, antisepsis, and anti-inflammation activities in the past ten years, which are expected to be beneficial to the development and design of novel drugs for the corresponding indications.
CURRENT MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Ajmir Khan, Luiz F. Silva, Muhammad Rabnawaz
Summary: This study presents a metal-free approach for the synthesis of seven-membered heterocycles (chromane, thiochromane) or rings fused with heterocycles (furan, indole, pyrrole, and thiophene) through the ring expansion of methylenic heterocycles mediated by the iodine(III) reagent HTIB in aqueous acetonitrile.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Yao Ting, Li Jiayan, Wang Jiaming, Zhao Changgui
Summary: Seven-membered rings are important in chemistry and pose a challenge for synthetic chemists. N-Heterocyclic carbene (NHC) organocatalysis is a powerful tool for quick construction of complex molecular structures, and this review highlights new advances in the synthesis of seven-membered rings catalyzed by NHC.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yujia Sun, Ziwei Wang, Yan Wang, Tongxiu Xu, Keqing Tian, Ping Zhang
Summary: Four kinds of 1,5-benzothiazepines with triazole moiety were designed and synthesized, with isomerization of triazole occurring during the conversion to target compounds. Two new compounds were isolated, showing potential for development of antifungal drugs due to their inhibitory effects on fungi, including C. neoformans.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kenta Mori, Midori Akiyama, Ko Inada, Yutaka Imamura, Yuichiro Ishibashi, Yusuke Takahira, Kyoko Nozaki, Takashi Okazoe
Summary: By introducing a seven-membered N-heterocyclic carbene (NHC) ligand, a significant increase in catalyst turnover number (TON) was achieved in the cross-metathesis of tetrafluoro-ethylene (TFE) and vinyl ethers. This study provides a new approach to enhance catalytic efficiency in such reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Keisuke Fujimoto, Seiichiro Izawa, Ayumu Takahashi, Toshiyasu Inuzuka, Kazutaka Sanada, Masami Sakamoto, Yasuo Nakayama, Masahiro Hiramoto, Masaki Takahashi
Summary: Synthesis of curved perylene diimides fused with seven-membered rings using regioselective bay-functionalization method and Pd-catalyzed intramolecular C-H/C-Br coupling reaction was achieved. X-Ray analysis and temperature-dependent NMR spectroscopy confirmed the curved molecular structure with conformational flexibility. The introduction of curved structure enabled removal of bulky N-substituents, enhancing solubility and power conversion efficiency in organic photovoltaic devices.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Yonghui Yang, Xiayu Shi, Zhuo Chen, Yufang Xu, Xuhong Qian, Weiping Zhu
Summary: In this study, a series of seven-membered ring-fused naphthalimide derivatives were designed and synthesized. Three derivatives, Y1, Y5, and Y9, showed similar cytotoxic activities to Amonafide against A549 and HL60 cells. Moreover, these derivatives exhibited high fluorescent quantum yields in water.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Jun-An Xiao, Huan Zhang, Xue-Ling Luo, Ru-Fang Meng, Wei Wang, Wei-dong Lu, Wei Su, Chenxiang Lin, Peng-Ju Xia, Hua Yang
Summary: A palladium-catalyzed ring-opening [3 + 2]-annulation reaction was developed for the synthesis of seven-membered benzosultams from spirovinylcyclopropanyloxindoles and cyclic N-sulfonylimines. The reaction yielded a wide range of compounds with both a quaternary center and axially chiral biaryl scaffolds, with an average yield of 87% and moderate to excellent diastereoselectivities. Enantioenriched benzosultams were also successfully synthesized in good yields with excellent atropoenantioselectivities using the Pd-2(dba)(3)/(S,S,S)-SKP ligand. The practical utility of this method was demonstrated through gram-scale reactions and diversified synthetic transformations.
Article
Chemistry, Organic
Shinji Harada, Juntaro Yamamoto, Akito Okabe, Shigeru Arai
Summary: We report the synthesis of seven-membered carbocycles through the dearomative intermolecular reaction of benzofurans with vinylcyclopropanes. The activation of benzofurans through energy transfer from an activated photocatalyst allows for the efficient construction of hydrocyclohepta[b]benzofurans with tetrasubstituted carbons as single diastereomers. This novel synthetic approach complements existing methodologies and introduces a new feedstock for the synthesis of carbocycles with diverse substitution patterns.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ryan J. Schwamm, Michael S. Hill, Han-Ying Liu, Mary F. Mahon, Claire L. McMullin, Nasir A. Rajabi
Summary: The study reports a seven-membered cyclic potassium alumanyl species with a dimeric structure that can be obtained through different reduction reactions or intermediate molecules. The potassium alumanyl species show different reactivity in chemical reactions, with different pathways when reacting with toluene, BPh3, and RN=C=NR. Additionally, different forms of potassium alumanyl species can be obtained through different encapsulation reactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Yiyang Fei, Yubin Fu, Xueqin Bai, Lili Du, Zichao Li, Hartmut Komber, Kam-Hung Low, Shengqiang Zhou, David Lee Phillips, Xinliang Feng, Junzhi Liu
Summary: The study focuses on the synthesis and characterization of three novel nanographenes with well-defined defects, demonstrating their unique physicochemical properties. Experimental and theoretical investigations showed that these defective nanographenes exhibit an anti-aromatic character and high stability under ambient conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Florent Bodinier, Youssouf Sanogo, Janick Ardisson, Marie-Isabelle Lannou, Geoffroy Sorin
Summary: This study presents a novel approach to access all-carbon or heterocyclic seven-membered ring frameworks using low-valent titanium(II) species, resulting in a broad range of cycloheptane, azepane or oxepane derivatives with moderate to good yields and excellent selectivity up to 95/5 d.r.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Jordi Vila, Miquel Sola, Anna Pla-Quintana, Anna Roglans
Summary: The synthesis of spiro compounds with seven- and six-membered rings was achieved through a cascade process involving a rhodium(I)-catalyzed cycloisomerization and a highly selective Diels-Alder homodimerization. The scope of the reaction was analyzed using synthetic substrates, and control experiments and DFT calculations were used to explain the observed degree of selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dimitrios Andreou, Nsikak B. Essien, Cristina Pubill-Ulldemolins, Michael A. Terzidis, Athanasios N. Papadopoulos, George E. Kostakis, Ioannis N. Lykakis
Summary: A copper-mediated method was developed for the synthesis of seven-membered-ring fused pyrroles, allowing for the tolerance of various functional groups in the derivatives and exhibiting high antioxidant activity in selected examples. These rare 7-mrFPs can now be accessed on a millimolar scale.
Article
Oncology
Rupinder Kaur Gill, Jyoti Kumari, Jitender Bariwal
ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY
(2017)
Article
Chemistry, Medicinal
Rupinder Kaur Gill, Virender Kumar, Stijn C. A. Robijns, Hans P. L. Steenackers, Erik V. Van der Eycken, Jitender Bariwal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2017)
Review
Chemistry, Multidisciplinary
Jitender Bariwal, Leonid G. Voskressensky, Erik V. Van der Eycken
CHEMICAL SOCIETY REVIEWS
(2018)
Article
Chemistry, Organic
Rupinder Kaur, Jitender Bariwal, Leonid G. Voskressensky, Erik V. Van der Eycken
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2018)
Review
Chemistry, Medicinal
Jitender Bariwal, Virender Kumar, Yuxiang Dong, Ram Mahato
MEDICINAL RESEARCH REVIEWS
(2019)
Review
Chemistry, Multidisciplinary
Jitender Bariwal, Rupinder Kaur, Leonid G. Voskressensky, Erik V. Van der Eycken
FRONTIERS IN CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Jitender Bariwal, Virender Kumar, Hao Chen, Rajan Sharma Bhattarai, Yang Peng, Wei Li, Ram Mahato
JOURNAL OF CONTROLLED RELEASE
(2019)
Article
Pharmacology & Pharmacy
Virender Kumar, Jitender Bariwal, Ajit S. Narang, Jerry Tso, Jonathan Cheong, Ram Mahato
INTERNATIONAL JOURNAL OF PHARMACEUTICS
(2020)
Review
Chemistry, Multidisciplinary
Jitender Bariwal, Hairong Ma, Guillermo A. Altenberg, Hongjun Liang
Summary: Cancer therapy faces challenges in drug delivery to cancer cells and non-selective killing of healthy cells. Nano-formulations show promising potential for targeted drug delivery. The shape and size of nanocarriers significantly impact their transport and internalization. Nanodiscs are desirable nano-formulations with enhanced anisotropic character and versatile functionalization potential.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Multidisciplinary Sciences
Yunjiang Jiang, Wan Zheng, Keith Tran, Elizabeth Kamilar, Jitender Bariwal, Hairong Ma, Hongjun Liang
Summary: This study demonstrates the antimicrobial activity and cytotoxicity of nanoparticle-pinched polymer brushes (NPPBs) composed of chemically inert silica nanospheres covalently grafted with hydrophilic polymer brushes. The antimicrobial potency of NPPBs against bacteria, including multidrug-resistant strains, depends critically on the size of the nanoparticles. Small nanoparticles enhance antimicrobial activity while large ones reduce it, with a threshold size identified for optimal membrane pore formation. Nanoengineering shows potential for developing nanoantibiotics that selectively kill bacteria while remaining nontoxic to mammalian cells.
NATURE COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Rupinder K. Gill, Harpreet Singh, Tilak Raj, Anuradha Sharma, Gagandeep Singh, Jitender Bariwal
CHEMICAL BIOLOGY & DRUG DESIGN
(2017)
Article
Oncology
Rupinder Kaur Gill, Virender Kumar, Mahendra Bishnoi, Kamalendra Yadav, Kanthi Kiran Kondepudi, Jitender Bariwal
ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY
(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)
