Synthesis of tacrine analogs derived from N-Aryl-5-amino-4-cyanopyrazoles

Synthetic Communications

Volumn 38, Issue 24, 2008, Pages 4369-4378

  Rodrigues, Lígia M ^a   Francisco, Carla S ^a   Oliveira Campos, Ana M F ^a   Salaheldin, Abdellatif M ^a  

^a UNIVERSITY OF MINHO   (Portugal)

Author keywords

Alzheimer's disease; Aminocyanopyrazole; Friedl nder reaction; Nitrogen heterocycles; Tacrine analogs

Indexed keywords

KETONE; LEWIS ACID; N ARYL 5 AMINO 4 CYANOPYRAZOLE DERIVATIVE; NITRILE; PYRAZOLE DERIVATIVE; TACRINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 57349122062     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802331638     Document Type: Article

References (13)

1. Valenti, P.; Rampa, A.; Bisi, A.; Andrisano, V.; Cavrini, V.; Fin, L.; Buriani, A.; Giusti, A. Acetylcholinesterase inhibition by tacrine analogues. Bioorg. Med. Chem. Lett. 1997, 7, 2599.
2. Martinez-Grau, A.; Marco, J. L. Friedländer reaction on 2-amino-3-cyano-4H-pyrans: Synthesis of derivatives of 4H-pyran [2,3-b] quinoline, new tacrine analogues. Bioorg. Med. Chem. Lett. 1997, 7, 3165.
3. Marco-Contelles, J.; Leon, R.; Lopez, M. G.; Garcia, A. G.; Villarroya, M. Synthesis and biological evaluation of new 4H-pyrano[2,3-b] quinoline derivatives that block acetylcholinesterase and cell calcium signals, and cause neuroprotection against calcium overload and free radicals. Eur. J. Med. Chem. 2006, 41, 1464.
4. Chaki, H.; Yamabe, H.; Sugano, M.; Morita, S.; Bessho, T.; Tabata, R.; Saito, K. I.; Egawa, M.; Tobe, A.; Morinaka, Y. Design and syntheses of 4-acylaminopyridine derivatives: Novel high affinity choline uptake enhancers II. Bioorg. Med. Chem. Lett. 1995, 5, 1495.
5. Thomae, D.; Kirsch, G.; Seck, P. Synthesis of thiophene analogues of the tacrine series. Synthesis 2007, 1027.
6. Michalson, E. T.; D'Andrea, S.; Freeman, J. P.; Szmuszkovicz, J. The synthesis of 9-(1-azetidinyl)-1,2,3,4-tetrahydroacridine. Heterocycles 1999, 30, 415.
7. 2+ channels and nicotinic receptors. Bioorg. Med. Chem. 2004, 12, 2199.
8. Barreiro, E. J.; Câmara, C. A.; Verli, H.; Brazil-Más, L.; Castro, N. G.; Cintra, W. M.; Aracava, Y.; Fraga, C. A. M. Design, synthesis, and pharmacological profile of novel fused pyrazolo[4,3-d]pyridine and pyrazolo[ 3,4-b][1,8]naphthyridine isosteres: A new class of potent and selective acetylcholinesterase inhibitors. J. Med. Chem. 2003, 46, 1144.
9. Gupta, S.; Sivasubramanian, A.; Rodrigues, L. M.; Esteves, A. P.; Hrdina, R.; Oliveira-Campos, A. M. F. Synthesis of dyes derived from 1-aryl-5-amino-4-cyanopyrazoles. Dyes Pigments 2007, 75, 82-87.
10. Gupta, S.; Rodrigues, L. M.; Esteves, A. P.; Oliveira-Campos, A. M. F.; Nascimento, M. S. J.; Nazareth, N.; Cidade, H.; Neves, M. P.; Pinto, E. F. M.; Cerqueira, N. M. F.; Brás, N. Synthesis of N-aryl-5-amino-4- cyanopyrazole derivatives as potent xanthine oxidase inhibitors. Eur. J. Med. Chem. 2008, 43, 771.
11. Cheng, C. C.; Yan, S. J. Organic Reactions; John Wiley & Sons: New York, 1982; vol. 28, pp. 37-201.
12. Barbosa, S. L.; Dabdoub, M. J.; Hurtado, G. R.; Klein, S. I.; Baroni, A. C. M.; Cunha, C. Solvent-free esterification reactions using Lewis acids in solid phase catalysis. Appl. Catal. Gen. 2006, 313, 146.
13. Jacob, R. G.; Perin, G.; Loi, L. N.; Pinno, C. S.; Lenardão, E. J. Green synthesis of (-)-isopulegol from (+)-citronellal: Application to essential oil of citronella. Tetrahedron Lett. 2003, 44, 3605.