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Stereoselective Synthesis of cis-2,5-Disubstituted pyrrolidines via Copper-Catalyzed Cyclization of Alkenes

Chinese Journal of Chemistry 2016年第11期34卷 1076-1080页

作者： Sai-Hu Cai Bing-Chao Da Jia-Hui Zhou Yun-He Xu Teck-Peng Loh Department of Chemistry University of Science and Technology of China Hefei Anhui 230026 China DiVision of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 637371 Singapore

An efficient methodology for the stereoselective synthesis of cis-2,5-disubstituted pyrrolidines using copper catalyst was developed. The corresponding cis-2,5-disubstituted pyrrolidines could be obtained in reasonable yields and with good stereoselectivities in the presence of 4,4＇-di-tert-butyl-2,2＇-bipyridine as ligand and l-methyl-2-pyrrolidinone as solvent.

关键词： stereoselectivity pyrrolidines copper-catalyzed cyclization

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Therapeutic effects of salidroside vs pyrrolidine dithiocarbamate against severe acute pancreatitis in rats

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Journal of Traditional Chinese Medicine 2022年第1期42卷 49-57页

作者： QIAN Jing WANG Xiaohong WEI Benzhong ZHOU Guoxiong ZHU Shunxing LIU Chun Department of General Surgery Yizheng Hospital of Nanjing Drum Tower Hospital GroupYizheng 211900China Department of Gastroenterology Yizheng Hospital of Nanjing Drum Tower Hospital GroupYizheng 211900China Department of Anesthesiology Yizheng Hospital of Nanjing Drum Tower Hospital GroupYizheng 211900China Department of Gastroenterology Affiliated Hospital of Nantong UniversityNantong 226001China Department of Laboratory Animal Center Nantong UniversityNantong 226001China

OBJECTIVE:To evaluate the therapeutic effectiveness of salidroside(Sal)and pyrrolidine dithiocarbamate(PDTC)against severe acute pancreatitis(SAP)in a rat ***:Rat models of SAP were established by retrograde infusion of sodium taurocholate *** rats were randomly divided into 6 groups:SAP 3 h group,SAP 24 h group,low-dose Sal treatment group(Sal L+S),middle-dose Sal treatment group(Sal M+S),high-dose Sal treatment group(Sal H+S)and PDTC treatment group(PDTC+S).The serum amylase,tumor necrosis factor-α(TNF-α),interleukin-1β(IL-1β)and interleukin-10(IL-10)levels were determined by optical turbidimetry and enzyme-linked immunosorbent *** expression of Beclin-1,microtubule-associated protein light chain 3Ⅱ(LC3Ⅱ),lysosome associated membrane protein 2(LAMP2),interleukin-1 receptor associated kinase 1(IRAK1),inhibitorαof nuclear transcription factor-κB(IκBα),nuclear transcription factor-κB 65(p65)in the pancreas tissues were detected by quantitative real-time polymerase chain reaction and Western blot,while the pIκBαand p-p65 levels were detected by Western *** changes of the pancreas and all the other indexes were observed at 3 and 24 h after ***:The serum IL-10 level,IκBαand LAMP2 levels in Sal M+S,Sal H+S and PDTC+S groups were higher than those in SAP 24 h group,while all the other indexes in these three groups were all lower significantly than those in SAP 24 h *** was no significant difference in all indexes between Sal H+S and PDTC+S ***:High-dose Sal has an effectively therapeutic effect on SAP in rats,which was similar to PDTC.

关键词： rhodioloside pyrrolidines ethylenebis(dithiocarbamates) pancreatitis autophagy NF-kappa B signal transduction

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First Total Synthesis of Hyacinthacine A_6 from the Protected Derivative of Polyhydroxylated Pyrrolidine

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Chemical Research in Chinese Universities 2008年第4期24卷 469-472页

作者： ZHANG Tao-xiang ZHOU Ling CAO Xiao-ping State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University Lanzhou 730000 P. R. China

（1S、2R、3R、5R、7aR）-1,2-Dihydroxy-3-hydroxy methyl-5-methylpyrrolizidine（hyacinthacine A6, I） was synthesized by Wittig＇s methodology via the reaction of aldehyde 6, prepared from the partially protected derivative of polyhydroxylated pyrrolidine, with appropriated ylides, followed by cyclization through the intemal reductive amination process of the resulting a,B-unsaturated ketone 7, and total deprotection.

关键词： Hyacinthacine A6 pyrrolidines Wittig reaction Cyclization

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N-Alkoxyl Templates for Diastereoselective Pyrrolidine Synthesis

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Chinese Chemical Letters 2004年第1期15卷 1-4页

作者： SongQingWANG OmarA.IBRAHIMI PanLI KangZHAO CollegeofPharmaceuticalsandBiotechnology TianjinUniversityTianjin300072 DepartmentofChemistry NewYorkUniversityNewYorkNY10003USA

Intramolecular cyclization of N-alkoxyl amines are studied for the stereoselective preparation of 2, 4-disubstituted pyrrolidine derivatives. Reduction of oximes under acidic conditions by NaBH3CN afforded the corresponding nucleophilic hydroxylamine derivatives, which subsequently cyclized via SN2' mechanism to give the desired N-alkoxyl pyrrolidines.

关键词： SN' reaction pyrrolidines oxime hydroxylamine.

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Skeletal contraction:A novel strategy to access multisubstituted cyclobutane

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Green Synthesis and Catalysis 2022年第1期3卷 1-3页

作者： Chunfa Xu V.U.Bhaskara Rao Fen-Er Chen Institute of Pharmaceutical Science and Technology College of ChemistryFuzhou UniversityFuzhou 350108China Department of Chemical Biology Max Planck Institute for Molecular PhysiologyDortmund 44227Germany Engineering Center of Catalysis and Synthesis for Chiral Molecules Department of ChemistryFudan UniversityShanghai 200433China Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs Fudan UniversityShanghai 200433China

The polysubstituted and spirocyclic cyclobutanes were efficiently constructed by the utilization of a novel skeletal contraction strategy which only took one-step synthesis from the readily accessible *** mechanistic studies indicated that a key intermediate N-aminated pyrrolidine was formed initially and subsequent extrusion of a nitrogen via a radical pathway completed the *** practical methodology was further highlighted by the concise,formal synthesis of the cytotoxic natural product piperarborenine B.

关键词： Cyclobutane Skeletal contraction Hypervalent iodine pyrrolidines Piperarboreine B

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Mechanisms mediating cholinergic antral circular smooth muscle contraction in rats

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World Journal of Gastroenterology 2004年第22期10卷 3292-3298页

作者： HelenaFWrzos TarunTandon AnnOuyang DivisionofGastroenterologyandHepatology DepartmentofMedicineCollegeofMedicinePennsylvaniaStateUniversityUSA

AIM:To investigate the pathway(s)mediating rat antral circular smooth muscle contractile responses to the cholinomimetic agent,bethanechol and the subtypes of muscarinic receptors mediating the cholinergic contraction. METHODS:Circular smooth muscle strips from the antrum of Sprague-Dawley rats were mounted in muscle baths in Krebs *** tension was *** concentration-response curves were obtained for(+)-cis- dioxolane(cD),a nonspecific muscarinic agonist,at 10^(-8)- 10^(-4)mol/L,in the presence of tetrodotoxin(TTX,10^(-7)mol/L). Results were normalized to cross sectional area.A repeat concentration-response curve was obtained after incubation of the muscle for 90 min with antagonists for M1(pirenzepine), M2(methoctramine)and M3(darifenadn)muscarinic receptor *** sensitivity to PTX was tested by the ip injection of 100 mg/kg of PTX 5 d before the *** antral circular smooth muscles were removed from PTX-treated and non-treated rats as strips and dispersed smooth muscle cells to identify whether PTX-linked pathway mediated the contractility to bethanechol. RESULTS:A dose-dependent contractile response observed with bethanechol,was not affected by *** pretreatment of rats with pertussis toxin decreased the contraction induced by *** of calcium as well as the presence of the L-type calcium channel blocker,nifedipine,also inhibited the cholinergic contraction,with a reduction in response from 2.5±0.4 g/mm^2 to 1.2±0.4 g/mm^2(Pmethocramine(M_2)>pirenzepine(M_1). CONCLUSION:The muscarinic receptors-dependent contraction of rat antral circular smooth muscles was linked to the signal transduction pathway(s)involving pertussis-toxin sensitive GTP-binding proteins and to extracellular calcium via L-type voltage gated calcium *** presence of the residual contractile respo

关键词： Anesthetics, Local Animals Benzofurans Bethanechol Calcium Calcium Channel Blockers Cholinergic Agonists Dose-Response Relationship, Drug GTP-Binding Proteins In Vitro Male Muscarinic Antagonists Muscle Contraction Muscle, Smooth Nifedipine Pertussis Toxin Pirenzepine Pyloric Antrum pyrrolidines Rats Rats, Sprague-Dawley Receptor, Muscarinic M1 inhibitors Receptor, Muscarinic M2 Receptor, Muscarinic M3 Signal Transduction Tetrodotoxin

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