Facile synthesis of isoquinolines, β-carbolines, and 3-deazapurines

Synthetic Communications

Volumn 37, Issue 13, 2007, Pages 2137-2143

  Huang, Wenhua ^a   Li, Jingyi ^a   Ou, Lihua ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

carboline; 3 deazapurine; Isoquinoline; Oxidative decarboxylation; Persulfate; Silver

Indexed keywords

3 DEAZAPURINE; ALPHA AMINO ACID; AMMONIUM SULFATE; BETA CARBOLINE; ISOQUINOLINE DERIVATIVE; PURINE DERIVATIVE; PYRIDINE DERIVATIVE; SILVER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DECARBOXYLATION; OXIDATION; SYNTHESIS;

EID: 34447114540     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701392459     Document Type: Article

References (22)

1. Ding, H.; Lu, W.; Li, H.; Yang, L.; Zhang, Q.; Zhou, C.; Wu, X.; Bandoin, O.; Cai, J.; Gueritte, F.; Zhao, Y. Synthesis and biological evaluation of novel compounds related to 1-arylnaphthalene lignans and isoquinolines. Chem. Biodiversity 2005, 2, 1217-1231.
2. Parker, C. A.; Anderson, N. J.; Robinson, E. S. J.; Price, R.; Tyacke, R. J.; Husbands, S. M.; Dillon, M. P.; Eglen, R. M.; Hudson, A. L.; Nutt, D. J.; Crump, M. P.; Crosby, J. Harmane and harmalan are bioactive components of classical clonidine-displacing substance. Biochem. 2004, 43, 16385-16392.
3. Cristalli, G.; Costanzi, S.; Lambertucci, C.; Taffi, S.; Vittori, S.; Volpini, R. Purine and deazapurine nucleosides: Synthetic approaches, molecular modeling and biological activity. Il Farmaco 2003, 58, 193-204.
4. Pari, K.; Sundari, C. S.; Chandani, S.; Balasubramanian, D. β-Carbolines that accumulate in human tissues may serve a protective role against oxidative stress. J. Biol. Chem. 2000, 275, 2455-2462.
5. Whaey, W. H.; Govindachari, T. R. The Pictet-Spengler synthesis of tetrahydroisoquinolines and related compounds. Org. React. 1951, 6, 151-206.
6. Song, Y.; Wang, J.; Teng, S. F.; Kesuma, D.; Deng, Y.; Duan, J.; Wang, J. H.; Qi, R. Z.; Sim, M. M. β-Carbolines as specific inhibitors of cyclin-dependent kinases. Bioorg. Med. Chem. Lett. 2002, 12, 1129-1132.
7. Hagen, T. J.; Skolnick, P.; Cook, J. M. Synthesis of 6-substituted β-carbolines that behave as benzodiazepine receptor antagonists or inverse agonists. J. Med. Chem. 1987, 30, 750-753.
8. Zelechonok, Y.; Silverman, R. B. Silver(I)/peroxydisulfate-induced oxidative decarboxylation of amino acids: A chemical model for a possible intermediate in the monoamine oxidase-catalyzed oxidation of amines. J. Org. Chem. 1992, 57, 5787-5790.
9. Bacon, R. G. R.; Hanna, W. J. W.; Stewart, D. Oxidation by persulphate, part V: Silver-catalysed oxidation of secondary aliphatic amines and α-amino-acids. J. Chem. Soc. C 1966, 1388-1399.
10. Cowden, C. J. Use of N-protected amino acids in the Minisci radical alkylation. Org. Lett. 2003, 5, 4497-4499.
11. Minisci, F.; Vismara, E.; Fontana, F. Recent developments of free-radical substituents of heteroaromatic bases. Heterocycles 1989, 28, 489-519.
12. Chao, W.; Weinreb, S. M. Radical-based methodology for efficient generation of acyclic N-acylimines. Tetrahedron Lett. 2000, 41, 9199-9204.
13. Renaud, P.; Giraud, L. 1-Amino- and 1-amidoalkyl radicals: Generation and stereoselective reactions. Synthesis 1996, 913-926.
14. Schiller, P. W.; Weltrowska, G.; Nguyen, T. M.-D.; Lemieux, C.; Chung, N. N.; Marsden, B. J.; Wilkes, B. C. Conformational restriction of the phenylalanine residue in a cyclic opioid peptide analogue: Effects on receptor selectivity and stereospecificity. J. Med. Chem. 1991, 34, 3125-3132.
15. Lippke, K. P.; Schunack, W. G.; Wenning, W.; Muller, W. E. β-Carbolines as benzodiazepine receptor ligands, I: Synthesis and benzodiazepine receptor interaction of esters of β-carboline-3-carboxylic acid. J. Med. Chem. 1983, 26, 499-503.
16. Snyder, H. R.; Hansch, C. H.; Katz, L.; Parmerter, S. M.; Spaeth, E. C. The synthesis of drivatives of β-carboline, II: Syntheses from dl-tryptophan and aldehydes. J. Am. Chem. Soc. 1948, 70, 219-222.
17. Guzman, F.; Cain, M.; Larscheid, P.; Hagen, T.; Cook, J. M.; Schweri, M.; Skolnick, P.; Paul, S. M. Biomimetic approach to potential benzodiazepine receptor agonists and antagonists. J. Med. Chem. 1984, 27, 564-570.
18. Krishnakumar, V.; Ramasamy, R. DFT studies and vibrational spectra of isoquinoline and 8-hydroxyquinoline. Spectrochim. Acta, Part A 2005, 61, 673-683.
19. Waston, C. Y.; Whish, W. J. D.; Threadgill, M. D. Synthesis of 3-substituted benzamides and 5-substituted isoquinolin-1(2H)-ones and preliminary evaluation as inhibitors of poly(ADP-ribose)polymerase (PARP). Bioorg. Med. Chem. 1998, 6, 721-734.
20. Parameswaran, P. S.; Naik, C. G.; Hegde, V. R. Secondary metabolites from the sponge tedania anhelans: Isolation and characterization of two novel pyrazole acids and other metabolites. J. Nat. Prod. 1997, 60, 802-803.
21. Kusurkar, R. S.; Goswami, S. K. Efficient one-pot synthesis of anti-HIV and anti-tumour β-carbolines. Tetrahedron 2004, 60, 5315-5318.
22. Katner, A. S.; Brown, R. F. A novel preparation of thiazolo[5,4-c] pyridine and the synthesis of some imidazo[4,5-c]pyridines and oxazolo[4,5-c]pyridine. J. Heterocycl. Chem. 1990, 27, 563-566.