Multicomponent Synthesis of
New Primaquine Thiazolidinone Derivatives

Patrícia D. Neuenfeldt; Bruna B. Drawanz; Anna Caroline C. Aguiar; Flávio Figueiredo Jr.; Antoniana U. Krettli; Wilson Cunico

doi:10.1055/s-0031-1289580

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Synthesis 2011(23): 3866-3870
DOI: 10.1055/s-0031-1289580

PAPER

Multicomponent Synthesis of New Primaquine Thiazolidinone Derivatives

Patrícia D. Neuenfeldt^a, Bruna B. Drawanz^a, Anna Caroline C. Aguiar^b,c, Flávio Figueiredo Jr.^b, Antoniana U. Krettli^b,c, Wilson Cunico*^a
^a Núcleo de Química Aplicada, Centro de Ciências Químicas, Farmacêuticas e de Alimentos, UFPel, Campus Universitário s/no, 96010-900, Pelotas, RS, Brazil
Fax: +55(53)32757454; e-Mail: wjcunico@yahoo.com.br;
^b Centro de Pesquisas René Rachou-Fiocruz, Laboratório de Malária, Av. Augusto de Lima 1715, 30190-002 Belo Horizonte, MG, Brazil
^c Universidade Federal de Minas Gerais, Programa de Pós Graduação em Medicina Molecular, Faculdade de Medicina, Av. Alfredo Balena, 30130-100 Belo Horizonte, MG, Brazil

Further Information

Publication History

Received 3 September 2011
Publication Date:
27 October 2011 (online)

Abstract
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Abstract

Primaquine thiazolidinone derivatives, potentially useful as antimalarial agents, were synthesized in good yields by multicomponent reactions of primaquine diphosphate, mercaptoacetic acid, and an optionally substituted benzaldehyde or cyclohexanone for two to four hours. All the products were characterized by ^¹H and ^¹³C NMR spectroscopy and by LC-MS.

Key words

heterocycles - multicomponent reactions - cyclocondensations - antimalarials

References

2 Cox-Singh J. Hiu J. Lucas SB. Divis PC. Zulkarnaen M. Chandran P. Wong KT. Adem P. Zaki SR. Singh B. Krishna S. Malar. J. 2010, 9: 10

Search in Google Scholar
3 Krettli AU. Expert Opin. Drug Discovery 2009, 4: 95

Search in Google Scholar
4 Baird JK. Clin. Microbiol. Rev. 2009, 22: 508

Search in Google Scholar
5 Vale N. Moreira R. Gomes P. Eur. J. Med. Chem. 2009, 44: 937

Search in Google Scholar
6 Valecha N. Adak T. Bagga AT. Asthana OP. Srivastava P. Joshi H. Sharma VP. Curr. Sci. 2011, 80: 561

Search in Google Scholar
7 Puri SK. Dutta GP. Exp. Parasitol. 2005, 111: 8

Search in Google Scholar
8 Cunico W. Gomes CRB. Vellasco WT. Mini-Rev. Org. Chem. 2008, 5: 336

Search in Google Scholar
9 Liesen AP. de Aquino TM. Góes AJS. de Lima JG. de Faria AR. Alves AJ. Quim. Nova 2008, 31: 369

Search in Google Scholar
10 Shah TJ. Desai VA. ARKIVOC 2007, (xiv): 218

Search in Google Scholar
11 Sharma A. Kumar V. Jain S. Sharma PC. J. Enzyme Inhib. Med. Chem. 2011, 26: 546

Search in Google Scholar
12 Gomes CRB. Moreth M. Facchinetti V. de Souza MVN. Vellasco WT. Lourenço MCS. Cunico W. Lett. Drug Des. Discovery 2010, 7: 353

Search in Google Scholar
13a Rawal RK. Tripathi R. Katti SB. Pannecouque C. De Clercq E. Eur. J. Med. Chem. 2008, 43: 2800

Search in Google Scholar
13b Ravichandran V. Prashantha Kumar BR. Sankar S. Agrawal RK. Eur. J. Med. Chem. 2009, 44: 1180

Search in Google Scholar
14 Neuenfeldt PD. Drawanz BB. Siqueira GM. Gomes CRB. Wardell SMSV. Flores AFC. Cunico W. Tetrahedron Lett. 2010, 51: 3106

Search in Google Scholar
15 Neuenfeldt PD. Duval AR. Drawanz BB. Rosales PF. Gomes CRB. Pereira CMP. Cunico W. Ultrason. Sonochem. 2011, 18: 65

Search in Google Scholar
16 Bolognese A. Correale G. Manfra M. Lavecchia A. Novellino E. Barone V. Org. Biomol. Chem. 2004, 2: 2809

Search in Google Scholar
17 Fraga-Dubreuil J. Bazureau JP. Tetrahedron 2003, 59: 6121

Search in Google Scholar
18 Pratap UR. Jawale DV. Bhosle MR. Mane RA. Tetrahedron Lett. 2011, 52: 1689

Search in Google Scholar
19 Solomon VR. Haq W. Srivastava K. Puri SK. Katti SB. J. Med. Chem. 2007, 50: 394

Search in Google Scholar

1

Dados Epidemiológicos de Malária, Por Estado. Amazônia Legal, Janeiro a Maio de 2009 e 2010; Ministério da Saúde: Brasilia. Available on: http://portal.saude.gov.br/portal/arquivos/pdf/avaliacao_malaria_jan_maio_19_07_2010.pdf. (Accessed: Aug. 24, 2011).