吖啶类衍生物的合成研究进展
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摘要
吖啶类衍生物具有良好的生物活性,在生物制药,功能材料和荧光标记物等领域有重要应用,但合成难度较大。综述了通过催化剂活化酰基的成环反应(分子内成环反应和分子间成环反应)合成吖啶衍生物的方法,并对其未来的发展进行了展望。参考文献19篇。
Acridine derivatives were widely used in biological pharmacy,function material,fluorescent mark,etc,due to its well bio-activities.However,the difficulties in synthesizing of acridine derivatives limited its application.The synthesis methods for acridine derivatives through catalyst-activited acyl cyclization,including intramolecular cyclization and intermolecular cyclization,were reviewed with nineteen references.The future development was prospected as well.
Acridine derivatives were widely used in biological pharmacy,function material,fluorescent mark,etc,due to its well bio-activities.However,the difficulties in synthesizing of acridine derivatives limited its application.The synthesis methods for acridine derivatives through catalyst-activited acyl cyclization,including intramolecular cyclization and intermolecular cyclization,were reviewed with nineteen references.The future development was prospected as well.
引文
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[2]Dollinger S,Lober S,Klingenstein R,et al.A chimeric ligand approach leading to potent antiprion active acridine derivatives:Design,synthesis,and biological investigations[J].J Med Chem,2006,49:659-6595.
[3]Ma Z,Choudhury J R,Saluta G,et al.A non-crosslinking platinum-acridine agent with potent activity in non-small-cell lung cancer[J].J Med Chem,2008,51:7574-7580.
[4]Denny W A.Acridine derivatives as chemotherapeutic agents[J].J Med Chem,2002,9:1655-1665.
[5]Goodell J R,Ougolkov A V,Hiasa H,et al.Acridine-based agents with topoisomerase II activity inhibit pancreatic cancer cell proliferation and induce apoptosis[J].J Med Chem,2008,51:179-182.
[6]Cheng M K,Modi C,Cookson J C,et al.Antitumor polycyclic acridines.Search for DNA quadruplex binding selectivity in a series of 8,13-dimethylquino[4,3,2-kl]acridinium salts:Telomere-targeted agents[J].J Med Chem,2008,51:963-975.
[7]Zhang D,Jiang X,Yang H,et al.Acridine-based macrocyclic fluorescent sensors:Self-assembly behavior characterized by crystal structures and a tunable bathochromic-shift in emission induced by H2PO4via adjusting the ring size and rigidity[J].Org Biomol Chem,2013,11:3375-3381.
[8]Ye X,Plessow P,Brinks M K,et al.Alcohol amination with ammonia catalyzed by an acridine-based ruthenium pincer complex:A mechanistic study[J].J Am Chem Soc,2014,136:5923-5929.
[9]Graham L A,Suryadi J,West T K,et al.Synthesis,aqueous reactivity,and biological evaluation of carboxylic acid ester-functionalized platinum-acridine hybrid anticancer agents[J].J Med Chem,2012,55:7817-7827.
[10]Tsvelikhovsky D,Buchwald S.Synthesis of heterocycles via Pd-ligand controlled cyclization of 2-chloroN-(2-vinyl)aniline:Preparation of carbazoles,indoles,dibenzazepines,and acridines[J].J Am Chem Soc,2010,132:14048-14051.
[11]Dubrovskiy A,Larock R.Synthesis of o-(dimethylamino)aryl ketones,acridones,acridinium salts,and1H-indazoles by the reaction of hydrazones and arynes[J].J Org Chem,2012,77:11232-11256.
[12]Li X A,Wang H L,Yang S D.Sc(OTf)3-catalyzed dehydrogenative cyclization for synthesis of N-methylacridones[J].Org Lett,2013,15(8):1794-1797.
[13]Zheng Z S,Dian L Y,Yuan Y C,et al.Ph I(OAc)2-mediated intramolecular oxidative aryl-aldehyde Csp2—Csp2bond formation:Metal-free synthesis of acridone derivatives[J].J Org Chem,2014,79(16):7451-7458.
[14]Su Q,Li P,He M N,et al.Facile synthesis of acridine derivatives by Zn Cl2-promoted intramolecular cyclization of o-arylaminophenyl Schiff bases[J].Org Lett,2014,16(1):18-21.
[15]Rogness D C,Larock R C.Synthesis of acridines by the[4+2]annulation of arynes and 2-aminoaryl ketones[J].J Org Chem,2010,75:2289-2295.
[16]Huang Z X,Yang Y,Xiao Q,et al.Auto-tandem catalysis:Synthesis of acridines by Pd-catalyzed C=C bond formation and C(sp2)-N cross-coupling[J].Eur J Org Chem,2012,33:6586-6593.
[17]Lian Y J,Hummel J R,Bergman R G,et al.Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade[J].J Am Chem Soc,2013,135(34):12548-12551.
[18]Pang X L,Lou Z B,Li M,et al.Tandem arylation/Friedel-Crafts reactions of o-acylanilines with diaryliodonium salts:A modular synthesis of acridine derivatives[J].Eur J Org Chem,2015,15:3361-3369.
[19]Wang T J,Chen W W,Li Y,et al.Facile synthesis of acridines via Pd(0)-diphosphine complex-catalyzed tandem coupling/cyclization protocol[J].Org Biomol Chem,2015,13:6580-6586.