Synthesis of new pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines and their use in the preparation of tetraheterocyclic systems

Synthetic Communications

Volumn 40, Issue 6, 2010, Pages 877-887

  El Essawy, Farag A ^a  

^a Menoufia University   (Egypt)

Author keywords

Cyclocondensation; Dichloride; Pyrido 2',3':3,4 pyrazolo 1,5 a pyrimidin 2(1H) ones; Tetrahetrocyclic systems

Indexed keywords

1 BENZYL 2,3 DIHYDRO 4,6,8 TETRAMETHYL 1H PYRROLO[3,2 D]PYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDINE; 1 PHENYL 1,2,3,4 TETRAHYDRO 5,7,9 TRIMETHYLPYRIDAZINO[2,3 E]PYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDINE; 2 (2,3 DRIHYDRO 4,6,8 TRIMETHYL 1H PYRROLO[3,2 D]PYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDIN 1 YL)ETHANOL; 2,3 DIHYDRO 1 PHENYL 4,6,8 TETRAMETHYL 1H PYRROLO[3,2 D]PYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDINE; 2,3 DIHYDRO 1,4,6,8 TETRAMETHYL 1H PYRROLO[3,2 D]PYRIDO[20,30:3,4]PYRAZPYRAZOLO[1,5 A]PYRIMIDINE; 2,3 DIHYDRO 4,6,8 TRIMETHYLTHIENO[2,3 D]PYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDINE; 2,4 DIAZIDO 3 ETHYL 8,10 DIMETHYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDINE; 2,4 DIAZIDO 3,8,10 TRIMETHYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDINE; 2,4 DICHLORO 3 ETHYL 8,10 DIMETHYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDINE; 2,4 DICHLORO 3,8,10 TRIMETHYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDINE; 3 (2 HYDROXYETHYL) 2,8,10 TRIMETHYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDIN 4 OL; 3 [2 [(4,6 DIMETHYL 2H PYRAZOLO[3,4 B]PYRIDIN 3 YL)IMINO]PROPYL]DIHYDROFURAN 2(3H)ONE; 3 AMINE 4,6 DIMETHYL 1H PYRAZOLO[3,4 B]PYRIDINE; 3 BUTYL 4 HYDROXY 8,10 DIMETHYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDIN 2(1H)ONE; 3 ETHYL 4 HYDROXY 8,10 DIMETHYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDIN 2(1H)ONE; 4 AZIDO 3 (2 AZIDOETHYL) 2,8,10 TRIMETHYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDINE; 4 CHLORO 3 (2 CHLOROETHYL) 2,8,10 TRIMETHYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDINE; 4 HYDROXY 3,8,10 TRIMETHYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDIN 2(1H)ONE; 4 HYDROXY 8,10 DIMETHYL 3 PHENYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDIN 2(1H)ONE; 4 HYDROXY 8,10 DIMETHYLPYRIDO[20,30:3,4]PYRAZOLO[1,5 A]PYRIMIDIN 2(1H)ONE; ALPHA ACETYL GAMMA BUTYRLOLACTONE; ETHYL MALONATE DERIVATIVE; LACTONE DERIVATIVE; MALONIC ACID; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE;

EID: 77249146105     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903020783     Document Type: Article

References (27)

1. Menezes, C. M. S.; Santa Anna, C. M. R.; Rodrigues, C. R.; Barreiro, E. J. J. Molecular modeling of novel 1H-pyrazolo[3,4-b]pyridine derivatives designed as isosters of the antimalarial mefloquine. Theochem. 2002, 579, 31-39.
2. Poreba, K.; Oplski, A.; Wietrezyk, J. Synthesis and antiproliferative activity in vitro of new 3-substituted aminopyrazolo[3,4-b]pyridines. Acta. Pol. Pharm. 2002, 59, 215.
3. Goda, F. E.; Abedl-Aziz, A. A. M.; Attef, O. A. Synthesis and antiproliferative activity in vitro of new 3-substituted aminopyrazolo[3,4-b] pyridines. Bioorg. Med. Chem. 2004, 12, 1845-1852.
4. Attaby, F. A.; Abdel-Fattah, A. M. A novel synthesis of thienopyridine, pyrroloquinoli-nothiophene, pyrazolopyridine-3-yl-phenylthiourea, and thiazolylpyrazolopyridine derivatives. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 155, 253-270.
5. Eleairy, M. A. A.; Attaby, F. A.; Elsayed, M. S. Synthesis of thiazole, triazole, pyrazolo[3,4-b]-pyridinyl-3-phenylthiourea, aminopyrazolo[3,4-b] pyridine derivatives and their biological evaluation. Phosphorus, Sulfur Silicon Relat. Elem. 2000, 167, 161-179.
6. Stasch, J. P.; Dembowsky, K.; Perzborn, E.; Stahl, E.; Br Schramm, M. Cardiovascular actions of a novel NO-independent guanylyl cyclase stimulator, BAY 41-8543: In vivo studies. Br. J. Pharmacol. 2002, 135, 344-355. (Pubitemid 34151166)
7. Boerrigter, G.; Costello-Boerrigter, L. C; Cataliotti, A.; Tsuruda, T.; Harty, G. J.; Lapp, H.; Stasch, J. P.; Burnett, J. C. Cardiorenal and humoral properties of a novel direct soluble guanylate cyclase stimulator BAY 41-2272 in experimental congestive heart failure. Circulation 2003, 107, 686-689.
8. Bawankule, D. U.; Stathishkumar, K.; Sardar, K. K.; Chanda, D.; Krishna, A. V.; Prakash, V. R.; Mishra, S. K. [5-Cyclopropyl-2-[1-(2-fluoro-benzyl)-1H- pyrazolo[3,4-b]pyridine-3-yl]pyrimidin-4-ylamine]-induced dilation in ovine pulmonary artery: Role of sodium pump. J. Pharmacol. Exp. Ther. 2005, 314, 207-213.
9. Attaby, F. A.; Elghandour, A. H. H.; Ali, M. A.; Ibrahim, Y. M. Synthesis, reactions, and antiviral activity of 1-(1H-pyrazolo[3,4-b]pyridin-5- yl)ethanone and pyrido[2',3':3,4] pyrazolo[5,1-c][1,2,4]triazine derivatives. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 1087-1102.
10. Attaby, F. A.; Elghandour, A. H. H.; Ali, M. A.; Ibrahim, Y. M. Synthesis, characterization, and antiviral activities of pyridopyrazolotriazines. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 133-149.
11. Azevedo, A. R.; Ferreira, V. F.; de Mello, H.; Leao-Ferreira, L. R.; Jabor, A. V.; Frugulhetti, I. C. P. P.; Pereira, H. S.; Moussatche, N.; Bernardino, A. M. R. Synthesis and biological evaluation of 1H-pyrazolo[3,4-b] pyridine-5-carboxylic acids against Vaccinia virus. Heterocycl. Commun. 2002, 8, 427-432.
12. De Mello, H.; Echevarria, A.; Bernardino, A. M.; Canto-Cavalheiro, M.; Leon, L. L. Antileishmanial pyrazolopyridine derivatives: Synthesis and structure\activity relationship analysis. J. Med. Chem. 2004, 47, 5427-5432.
13. Misra, R. N.; Xiao, H. Y.; Rawlins, D. B.; Shan, W.; Kellar, K. A.; Mulheron, J. G.; Sack, J. S.; Tokarski, J. S.; Kimball, S. D.; Webster, K. R. 1H-Pyrazolo[3,4-b]pyridine inhibitors of cyclin-dependent kinases: Highly potent 2,6-difluorophenacyl analogues. Biorg. Med. Chem. Lett. 2003, 13, 2405.
14. Poeba, K; Opolski, A.; Wietrzyk, J.; Kowalska, M. Synthesis and antiproliferative activity in vitro of new derivatives of 3-aminopyrazolo[3,4-b] pyridine, part 1: Reaction of 3-aminopyrazolo[3,4-b]pyridine with 1,3-, 1,4-diketones and a,b-unsaturated ketones. Arch. Pharm. 2001, 334, 219-223.
15. 0:1,5]pyrazolo[3,4-d]pyrimidines. Bioorg. Med. Chem. Lett. 2005, 15, 3778-3781. (Pubitemid 41038978)
16. Sekikawa, I.; Nishie, J.; Tono-Oka, S.; Tanaka, Y.; Kakimoto, S. Antituberculous compounds, XXVIII: Synthesis of pyrazolopyridines. J. Heterocycl. Chem. 1973, 10, 931-932.
17. Kukzynski, L.; Mrizikiewiez, A.; Banaszkiewicz, W.; Poreba, K. Synthesis and biological activity of pyrazo-[3,4-b]-pyridine derivatives, part I. Pol. J. Pharmacol. Pharm. 1979, 31, 217.
18. Kamal, A. M.; Atalla, A. A.; Mohamed, T. A.; Gies, A. A. Synthesis of some pyrazolo-pyridine sulphonamide derivatives. Z. Naturforsch. B: Chem. Sci. 1991, 46, 541-546.
19. 0-cyclic AMP phosphodiester-ase inhibitors. J. Med. Chem. 1974, 17, 645-648.
20. 0- monophosphate phosphodiesterase inhibitors, 2. 3-Substituted 5,7-dialkylpyrazolo[1,5-a]pyrimidines. J. Med. Chem. 1975, 18, 460-464.
21. Kirkpatrich, W. E.; Okabe, T.; Hillyard, I. W.; Robins, R. K.; Dren, A. T.; Novinson, T. 3-Halo-5,7-dimethylpyrazolo[1,5-A]pyrimidines, a nonbenzodiazepinoid class of antianxi-ety agents devoid of potentiation of central nervous system depressant effects of ethanol or barbiturates. J. Med. Chem. 1977, 20, 386-393.
22. 0:3,4]pyrazolo[1,5-a]pyrimidines. J. Flourine Chem. 1997, 86, 127-130.
23. 0:3,4]pyrazolo[1,5-a]pyrimidines. J. Flourine Chem. 2001, 109, 183-187.
24. 0:3,4] pyrazolo[1,5-a]pyrimidines=quinazolines. J. Flourine Chem. 2006, 127, 1211-1221.
25. 0:3,4]pyrazolo[1,5-a]pyrimidines. Can. J. Chem. 2007, 85, 592-599.
26. Hojo, M.; Masuda, R.; Kokuryo, Y.; Shioda, H.; Matsuo, S. Electrophilic substitutions of olefinic hydrogenes II: Acylation of vinyl ethers and N-vinyl amides. Chem. Lett. 1976, 499-502.
27. Hojo, M.; Masuda, R.; Okada, E. A convenient synthetic route to functionalized 5-trifluoroacetyl-6-trifluoromethyl-3,4-dihydro-2H-pyrans: Hetero-Diels-Alder reaction of b,b-bis(trifluoroacetyl)vinyl ethers with electron-rich alkenes. Synthesis 1990, 347-350.