XinSheng Lei

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Name: 雷新胜; XinSheng Lei

Organization: Fudan University

Department: School of Pharmacy

Title: Associate Professor

Chemicals
References

Facile synthesis of fluorovinyl-containing lactams via ring-closing metathesis of N-substituted 2-fluoroallylamides

Co-reporter:Yang Li, Kai Li, Yue Wu, Qiaoning Ma, Xinsheng Lei

Tetrahedron 2016 Volume 72(Issue 32) pp:4845-4853

Publication Date(Web):11 August 2016

DOI:10.1016/j.tet.2016.06.054

A cost-efficient method for the preparation of a series of N-substituted 2-fluoroallylamines and their application in the synthesis of fluoroalkene-containing lactams are described. N-substituted 2-fluoroallylamine could be readily synthesized from methyl 2-fluoroacrylate via aminolysis and subsequently selective reduction of the amide group. These amines were further converted into the corresponding amides with diverse acids bearing a terminal double bond. The Ring-Closing Metathesis (RCM) of the resulting amides led to the formation fluorovinyl-containing lactams in good yields.

Synthesis and Evaluation of the Analogues of Penicillide against Cholesterol Ester Transfer Protein

Co-reporter:Qiao Zhang;Chunlin Deng;Lisong Fang;Wenwei Xu;Qun Zhao;Jiange Zhang;Yiping Wang

Chinese Journal of Chemistry 2013 Volume 31( Issue 3) pp:355-370

Publication Date(Web):

DOI:10.1002/cjoc.201200977

Abstract

A series of penicillide analogues, with modifications at C-3 and C-9 positions, are synthesized as potential cholesteryl ester transfer protein (CETP) inhibitors. The preliminary in vitro inhibition assay provided some valuable structure-activity relationship information about penicillide.

A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol and ent-Bakuchiol

Co-reporter:Qian-Qian Xu, Qun Zhao, Guang-Sheng Shan, Xi-Cheng Yang, Qi-Yuan Shi, Xinsheng Lei

Tetrahedron 2013 69(50) pp: 10739-10746

Publication Date(Web):

DOI:10.1016/j.tet.2013.10.064

A Convergent Approach to Dibenzodioxocinones: Synthesis of Racemic Penicillide

Co-reporter:Chun-Lin Deng;Qiao Zhang;Lisong Fang;Guoqiang Lin

Helvetica Chimica Acta 2012 Volume 95( Issue 4) pp:626-635

Publication Date(Web):

DOI:10.1002/hlca.201100405

Abstract

A convergent approach to dibenzodioxocinones was explored, thereby racemic penicillide ((±)-1a) could be obtained in 13 steps in 4.2% overall yield, based on 5-amino-2-methylphenol (5) (Schemes 2–4).

Tandem Amination/Cycloisomerization of Aryl Propargylic Alcohols with 2-Aminopyridines as an Expedient Route to Imidazo[1,2-a]pyridines

Co-reporter:Ping Liu;Chun-Lin Deng, ;Guo-qiang Lin

European Journal of Organic Chemistry 2011 Volume 2011( Issue 36) pp:7308-7316

Publication Date(Web):

DOI:10.1002/ejoc.201101053

Abstract

A new tandem route leading to imidazo[1,2-a]pyridines has been explored through the direct amination of aryl propargylic alcohols with 2-aminopyridines and their subsequent intramolecular cycloisomerization. A ZnCl₂/CuCl system has been developed to promote this transformation, which resulted in various imidazo[1,2-a]pyridines in moderate to good yields.

Regio-selective chlorination of vinca alkaloids catalyzed by Lewis acid

Co-reporter:LiSong Fang;Qiao Zhang;ChunLin Deng

Science China Chemistry 2011 Volume 54( Issue 7) pp:1039-1043

Publication Date(Web):2011 July

DOI:10.1007/s11426-011-4310-2

Novel C-17-chloro-substituted derivative of vinorelbine or vinflunine has been regio-selectively synthesized via the chlorination reaction in the presence of Lewis acid. The catalyst Cp2TiCl2 plays a key role in the chlorination reaction.

Discovery and synthesis of novel luteolin derivatives as DAT agonists

Co-reporter:Jiange Zhang, Xianbo Liu, Xinsheng Lei, Lei Wang, Lihe Guo, Gang Zhao, Guoqiang Lin

Bioorganic & Medicinal Chemistry 2010 Volume 18(Issue 22) pp:7842-7848

Publication Date(Web):15 November 2010

DOI:10.1016/j.bmc.2010.09.049

Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizing constructed Chinese hamster ovary (CHO) cell lines stably expressing rat DAT. Biological screening results demonstrated that luteolin derivatives 1d, 1e, and 4c carry great DAT agonistic potency (EC50 = 0.046, 0.869, and 1.375 μM, respectively) compared with luteolin 8 (EC50 = 1.45 ± 0.29 μM). Luteolin derivative 1d, notably, exhibited a 32-fold-higher DAT agonistic potency than luteolin. These luteolin derivatives represent a novel DAT agonist class, from which lead compounds useful for exploration of additional novel DAT agonists could be drawn.The synthesis of the novel dopamine transporter (DAT) agonist luteolin derivative 1d (EC50 = 0.046 μm) is reported.

Synthesis of imidazo[1,2a]pyridines via three-component reaction of 2-aminopyridines, aldehydes and alkynes

Co-reporter:Ping Liu, Li-song Fang, Xinsheng Lei, Guo-qiang Lin

Tetrahedron Letters 2010 Volume 51(Issue 35) pp:4605-4608

Publication Date(Web):1 September 2010

DOI:10.1016/j.tetlet.2010.05.139

A novel three-component reaction towards the synthesis of imidazo[1,2a]pyridines was independently developed based on 2-aminopyridines, aldehydes and alkynes, and thereby imidazo[1,2a]pyridines were obtained in acceptable yields by the CuSO4/TsOH catalyzed three-component reaction.A novel three-component reaction towards the synthesis of imidazo[1,2a]pyridines was independently developed based on 2-aminopyridines, aldehydes and alkynes, and thereby imidazo[1,2a]pyridines were obtained in acceptable yields by the CuSO4/TsOH catalyzed three-component reaction.

Synthesis of Racemic 3-2-Hydroxybakuchiol and Its Analogues

Co-reporter:Lei Shi;Jiange Zhang;Guoqiang Lin

Helvetica Chimica Acta 2010 Volume 93( Issue 3) pp:555-564

Publication Date(Web):

DOI:10.1002/hlca.200900243

Abstract

The first synthetic approach to (±)-Δ³-2-hydroxybakuchiol (=4-[(1E,5E)-3-ethenyl-7-hydroxy-3,7-dimethylocta-1,5-dien-1-yl]phenol; 14) and its analogues 13a–13f was developed by 12 steps (Schemes 2 and 3). The key features of the approach are the construction of the quaternary C-center bearing the ethenyl group by a Johnson–Claisen rearrangement (6); and of an (E)-alkenyl iodide via a Takai–Utimoto reaction (11); and an arylation via a Negishi cross-coupling reaction (12e–12f).