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Recent advances on the synthesis and application of tetrahydro-y-carbolines

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Chinese Chemical Letters 2023年第12期34卷 93-110页

作者： Haibo Mei Klara Aradi Lorand Kiss jianlin han jiangsu Co-lnnovation Center of Eficient Processing and Utilization of Forest Resources Nanjing Forestry UniversityNanjing 210037China Institute of Organic Chemistry Research Centre for Natural SciencesStereochemistry Research GroupMagyar Tudsok krt.2117 BudapestHungary

Tetrahydro-y-carbolines(THyCs)constitute one of the most important subtypes of indole *** addition to being substructures of natural products,these structural motifs and moieties can often be found in pharmaceuticals due to their diverse bioactivities such as antiviral,antibacterial,antifungal,antiparasitic,antitumor,anti-inflammatory,and neuropharmacological *** the pharmacological and biological aspects of these scaffolds,they have considerable synthetic applications for the construction of further bioactive compounds,*** aim of this review is to summarize recent developments in the synthesis of this compound class.

关键词： Tetrahydro-y-carbolines Synthetic methods Bioactive molecuels Asymmetric synthesis Indole Polycyclic compounds

Zinc-prolinamide complex catalyzed direct asymmetric aldol reactions in the presence of water

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Science China Chemistry 2010年第11期53卷 2291-2296页

作者： LU ZhiJin MEI HaiBo ZhanG GuangQian han jianlin PAN Yi School of Chemistry and Chemical Engineering Nanjing UniversityNanjing 210093China State Key Laboratory of Coordination Chemistry Nanjing UniversityNanjing 210093China

An efficient direct asymmetric aldol reaction with zinc triflate and prolinamides as combined catalysts is reported.A series of chiral prolinamides have been designed and used in the direct aldol reaction resulting in the desired products with excellent yields(up to 94% yield) and high enantioselectivities(up to 96% ee).Water was found to play a significant role in the formation of the aldol products,which suggests a new strategy in the design of new organic catalysts.

关键词： prolinamide Lewis acid aqueous media aldol reaction zinc

Recent Advances on the Electrochemical Difunctionalization of Alkenes/Alkynes

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Chinese Journal of Chemistry 2019年第3期37卷 292-301页

作者： Haibo Mei Zizhen Yin Jiang Liu Hailong Sun jianlin han College of Chemical Engineering Nanjing Forestry UniversityNanjingJiangsu 210037China Nanjing Research Institute of Sinopec Yangzi Petrochemical Co. Ltd.NanjingJiangsu 210048China Nanjing University University of Oklahoma Texas Tech University

Electroorganic synthesis is an emerging area of high impact research in organic chemistry, which is considered as one of the green and efficient methods and attracts growing research attention. In this review, we summarized comprehensively the recent literature reports on the electrochemical oxidative difunctionalization of unsaturated C—C bonds. The reaction types described in this review included electrochemical intermolecular cyclization, electrochemical intramolecular cyclization, and electrochemical difunctionalization of alkenes/alkynes. This review focuses on the discussion of its synthetic generality for the preparation of functionalized compounds and the related electrochemical oxidative reaction mechanism.

关键词： Electrochemical Difunctionalization Alkenes/Alkynes

Visible-light-irradiated tandem sulfonylation/cyclization of indole tethered alkenes for the synthesis of tetrahydrocarbazoles

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Chinese Chemical Letters 2022年第11期33卷 4886-4890页

作者： Yingjie Yu Aiyao Liu Jingrui He Chengting Wang Haibo Mei jianlin han Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources International Innovation Center for Forest Chemicals and MaterialsCollege of Chemical EngineeringNanjing Forestry UniversityNanjing 210037China

A visible-light-mediated reaction of indole derivatives employing arylsulfonyl chlorides as sulfonyl surrogates has been developed,which proceeds via the sequence of reduction of sulfonyl chloride,sulfonylation,and intramolecular *** mild protocol transforms a diverse array of indole tethered alkenes and simple sulfonyl chlorides into highly valuable functionalized tetrahydrocarbazoles in good *** reaction is also suitable for gram-scale synthesis,which provides an efficient and green access to multi-substituted tetrahydrocarbazoles.

关键词： Visible-light-irradiation Sulfonylation Tetrahydrocarbazoles Indoles Tandem radical reaction Sulfonyl chlorides

Facile synthesis of ( β -chlorodifluoroethyl)phosphonates via chlorination reaction of difluoroalkyl diazo derivatives with HCl

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Chinese Chemical Letters 2022年第5期33卷 2429-2432页

作者： Jiang Liu Romana Pajkert Li Wang Haibo Mei Gerd-Volker Röschenthaler jianlin han Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources International Innovation Center for Forest Chemicals and MaterialsCollege of Chemical EngineeringNanjing Forestry UniversityNanjing 210037China Department of Life Sciences and Chemistry Jacobs University Bremen gGmbHCampus Ring 1Bremen 28759Germany

An efficient chlorination reaction of in situ generated(β-diazo-α,α-difluoroethyl)phosphonates has been achieved with hydrochloric acid as a chlorine source under mild and operationally convenient *** reaction does not need any catalyst and tolerates a wide scope of substrates,which affords the(β-chlorodifluoroethyl)phosphonate products in good to excellent *** reaction represents the first example of the halogenation of difluoroalkyl diazo compounds,and also provides an easy way for the synthesis of difluoromethylenephosphonate-containing compounds.

关键词： Difluorodiazoethane (β-Diazo-α,α-difluoroethyl)phosphonates Halogenation reaction Difluoroalkyl diazo Hydrochloric acid Masked carbene

Fluorine-containing pharmaceuticals approved by the FDA in 2020:Synthesis and biological activity

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Chinese Chemical Letters 2021年第11期32卷 3342-3354页

作者： Yingjie Yu Aiyao Liu Gagan Dhawan Haibo Mei Wei Zhang Kunisuke Izawa Vadim A.Soloshonok jianlin han Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources International Innovation Center for Forest Chemicals and MaterialsCollege of Chemical EngineeringNanjing Forestry UniversityNanjing 210037China Department of Biomedical Science Acharya Narendra Dev CollegeUniversity of DelhiIndia Department of Chemistry University of Massachusetts Boston100 Morrissey BoulevardBostonMA 02125United States Hamari Chemical Ltd. 1-4-29 KunijimaHigashi-Yodogawa-kuOsaka 533-0024Japan Department of Organic Chemistry I Faculty of ChemistryUniversity of the Basque Country UPV/EHUPaseo Manuel Lardizabal 320018 San SebastianSpain IKERBASQUE Basque Foundation for ScienceMaría Díaz de Haro 3Plaza Bizkaia48013 BilbaoSpain

Thirteen new fluorine-containing drugs,which have been granted approval by the US Food and Drug Administration(FDA)in 2020,are profiled in this *** areas of these new fluorinated pharmaceuticals include medicines and diagnostic agents for Cushing's disease,neurofibromatosis,migraine,Alzheimer's disease,myelodysplastic syndromes,hereditary angioedema attacks,and various *** of these approved drugs feature aromatic fluorine(Ar-F)(11 compounds),aromatic Ar-CF_(3)(1),aliphatic CHF(1)and CF_(2)(1)*** each compound,we provide a spectrum of biological activity,medicinal chemistry discovery,and synthetic approaches.

关键词： Fluorine and compounds Blockbuster drugs Modern pharmaceuticals Synthesis Drug design and development Asymmetric synthesis

Fluorine-containing drugs approved by the FDA in 2019

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Chinese Chemical Letters 2020年第9期31卷 2401-2413页

作者： Haibo Mei Attila Mario Remete Yupiao Zou Hiroki Moriwaki Santos Fustero Lorand Kiss Vadim ASoloshonok jianlin han Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources College of Chemical EngineeringNanjing Forestry UniversityNanjing 210037China University of Szeged Institute of Pharmaceutical Chemistry6720 SzegedEotvos u.6Hungary Hamari Chemicals Ltd. 1-4-29 KunijimaHigashi-Yodogawa-kuOsaka 533-0024Japan Departamento de Quimica Organica Universidad de Valencia46100 BurjassotValenciaSpain Department of Organic Chemistry 1 Faculty of ChemistryUniversity of the Basque Country UPV/EHUPaseo Manuel Lardizabal 320018 San SebastianSpain IKERBASQUE Basque Foundation for Science.Maria Diaz de Haro 3Plaza Bizkaia48013 BilbaoSpain

Eleven new fluorine-containing FDA-approved drugs have been profiled and details of their discovery and preparation are *** areas include schizophrenia,migraine,multiple sclerosis,insomnia,rheumatoid arthritis,anti-tuberculosis,breast cancer,lymphoma kinase inhibitor,serotonin receptor *** pharmaceuticals feature four examples of aromatic fluorine,three aromatic CF3 group,three aliphatic CF3 and one compound with aromatic CF3O ***,among the new compounds,six are chiral and seven are derived from tailor-made amino acids.

关键词： Fluorine Pharmaceuticals Synthesis Medicinal chemistry Marketed medicinal drugs

Fluorine-containing drugs approved by the FDA in 2021

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Chinese Chemical Letters 2023年第1期34卷 29-38页

作者： Jingrui He Ziyi Li Gagan Dhawan Wei Zhang Alexander E.Sorochinsky Greg Butler Vadim A.Soloshonok jianlin han Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources International Innovation Center for Forest Chemicals and MaterialsCollege of Chemical EngineeringNanjing Forestry UniversityNanjing 210037China Department of Biomedical Science Acharya Narendra Dev CollegeUniversity of DelhiNew Delhi 110019India Department of Chemistry University of Massachusetts BostonBostonMA 02125United States V.P.Kukhar Institute of Bioorganic Chemistry and Petrochemistry The National Academy of Sciences of UkraineKyiv 02094Ukraine Oakwood Chemical Inc.EstillSC 29918United States Department of Organic Chemistry I Faculty of ChemistryUniversity of the Basque Country UPV/EHU20018 San SebastiánSpain IKERBASQUE Basque Foundation for SciencePlaza Bizkaia48013 BilbaoSpain

Nine new fluorine-containing drugs have been approved by the US Food and Drug Administration(FDA)in 2021,which are presented in this review *** small molecular drugs feature aromatic fluorine,trifluoromethyl and chlorodifluoro *** therapeutic areas of these fluorine-containing drugs include multiple myeloma,lymphoma,HIV,chronic heart failure,chronic myeloid leukemia,(ANCA)-associated vasculitis,migraines,von Hippel-Lindau disease,and non-small cell lung *** brief biological activities and the synthetic methods have been discussed in this review for each of these nine drugs.

关键词： Fluorine-containing compounds Blockbuster drugs Pharmaceuticals Anti-cancer Drug design and development Asymmetric synthesis

FDA approved fluorine-containing drugs in 2023

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Chinese Chemical Letters 2024年第11期35卷 111-122页

作者： Qian Wang Yeping Bian Gagan Dhawan Wei Zhang Alexander E.Sorochinsky Ata Makarem Vadim A.Soloshonok jianlin han Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources College of Chemical EngineeringNanjing Forestry UniversityNanjing 210037China Jiangsu Province Geriatric Hospital Nanjing 210024China School of Allied Medical Sciences Delhi Skill and Entrepreneurship Universityand Department of Biomedical ScienceAcharya Narendra Dev CollegeUniversity of DelhiNew Delhi 110019India Department of Chemistry University of Massachusetts BostonBostonMA 02125United States V.P.Kukhar Institute of Bioorganic Chemistry and Petrochemistry The National Academy of Sciences of UkraineKyiv 02094Ukraine Department of Chemistry University of HamburgMartin-Luther-King-Platz 6Hamburg 20146Germany Department of Organic Chemistry I Faculty of ChemistryUniversity of the Basque Country UPV/EHUPaseo Manuel Lardizábal 3San Sebastián 20018Spain IKERBASQUE Basque Foundation for ScienceMaría Díaz de Haro 3Plaza BizkaiaBilbao 48013Spain

This review profiles twelve fluorine-containing drugs approved by the US Food and Drug Administration(FDA) for the clinic in *** small molecule drugs represent such therapeutic areas as cancer,neuromuscular disorder,immunodeficiency,virology,and infectious *** chemistry discovery,biological activity,and synthetic routes have been discussed for each ***,new trends in structural positioning,functionality,and degree of fluorination are *** fluorination,the importance of amino acid residues and chirality in the design of new pharmaceuticals is highlighted.

关键词： Fluorine-containing compounds Blockbuster drugs Pharmaceuticals Anti-cancer Drug design and development Asymmetric synthesis