Scaffold-hopping strategy toward calanolides with nitrogen-containing heterocycles

Chinese Chemical Letters

Volumn 24, Issue 4, 2013, Pages 295-298

  Guo, Xiao Yong ^a   Liu, Gang ^a,b  

^a INSTITUTE OF MATERIA MEDICA   (China)

^b Tsinghua University   (China)

Author keywords

Calanolides; Nitrogen containing heterocycles; Scaffold hopping

Indexed keywords

EID: 84876678137     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2013.03.007     Document Type: Article

References (20)

1. A. Kumar, R.A. Maurya, and S. Sharma Pyranocoumarins: a new class of anti-hyperglycemic and anti-dyslipidemic agents Bioorg. Med. Chem. Lett. 19 2009 6447 6451
2. G. Cebrian-Torrejon, S. Assad Kahn, and N. Lagarde Antiproliferative activity of trans-avicennol from Zanthoxylum chiloperone var. angustifolium against human cancer stem cells J. Nat. Prod. 75 2012 257 261
3. S. Srinivasan, and D.V.L. Sarada Antifungal activity of phenyl derivative of pyranocoumarin from Psoralea corylifolia L. seeds by inhibition of acetylation activity of trichothecene 3-O-acetyltransferase (Tri101) J. Biomed. Biotechnol. 2012 8 10.1155/2012/310850 Article ID 310850
4. C.R. Su, S.F. Yeh, and C.M. Liu Anti-HBV and cytotoxic activities of pyranocoumarin derivatives Bioorg. Med. Chem. 17 2009 6137 6143
5. Y. Kashman, K.R. Gustafson, and R.W. Fuller The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum J. Med. Chem. 35 1992 2735 2743
6. D.A. Eiznhamer, T. Creagh, and J.L. Ruckle Safety and pharmacokinetic profile of multiple escalating doses of (+)-calanolide A, a naturally occurring nonnucleoside reverse transcriptase inhibitor, in healthy HIV-negative volunteers HIV Clin. Trials 3 2002 435 450
7. Z.Q. Xu, W.W. Barrow, and W.J. Suling Anti-HIV natural product (+)-calanolide A is active against both drug-susceptible and drug-resistant strains of Mycobacterium tuberculosis Bioorg. Med. Chem. 12 2004 1199 1207
8. T. Ma, L. Liu, and H. Xue Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents J. Med. Chem. 51 2008 1432 1446
9. H. Xue, X.F. Lu, and P.R. Zheng Highly suppressing wild-type HIV-1 and Y181C mutant HIV-1 strains by 10-chloromethyl-11-demethyl-12-oxo-calanolide A with druggable profile J. Med. Chem. 53 2010 1397 1401
10. W.J. Burman, K. Gallicano, and C. Peloquin Therapeutic implications of drug interactions in the treatment of human immunodeficiency virus-related tuberculosis Clin. Infect. Dis. 28 1999 419 430
11. G.L. Dean, S.G. Edwards, and N.J. Ives Treatment of tuberculosis in HIV-infected persons in the era of highly active antiretroviral therapy AIDS 16 2002 75 83
12. H.M. Sun, G. Tawa, and A. Wallqvist Classification of scaffold hopping approaches Drug Discov. Today 17 2012 310 324
13. B. Chenera, M.L. West, and J.A. Finkelstein Total synthesis of (±)-calanolide A, a non-nucleoside inhibitor of HIV-1 reverse transcriptase J. Org. Chem. 58 1993 5605 5606
14. M.E. Fox, I.C. Lennon, and G. Meek A novel synthesis of 5-hydroxy-2, 2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one Tetrahedron Lett. 43 2002 2899 2902
15. J.T. Zhang, E.W. Kirchhoff, and D.E. Zembower Automated process research. An example of accelerated optimization of the Friedel-Crafts acylation reaction, a key step for the synthesis of anti-HIV (+)-calanolide A Org. Process Res. Dev. 4 2000 577 580
16. P.P. Deshpande, F. Tagliaferri, and S.F. Victory Synthesis of optically active calanolides A and B J. Org. Chem. 60 1995 2964 2965
17. A. Lilienkampf, J.L. Mao, and B.J. Wan Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculosis J. Med. Chem. 52 2009 2109 2118
18. A. Lilienkampf, M. Pieroni, and B.J. Wan Rational design of 5-phenyl-3-isoxazolecarboxylic acid ethyl esters as growth inhibitors of Mycobacterium tuberculosis. A potent and selective series for further drug development J. Med. Chem. 53 2010 678 688
19. Q.Q. Huang, J.L. Mao, and B.J. Wan Searching for new cures for tuberculosis: design, synthesis, and biological evaluation of 2-methylbenzothiazoles J. Med. Chem. 52 2009 6757 6767
20. X.K. Li, N. Liu, and H.N. Zhang Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis Bioorg. Med. Chem. Lett. 20 2010 6306 6309