Facile synthesis of 5, 6, 7, 8-tetrahydropyrimido [4, 5-b]-quinoline derivatives

Molecules

Volumn 11, Issue 11, 2006, Pages 890-903

  Elkholy, Yehya Mahmoud ^a   Morsy, Mohamed Abdelhamed ^a  

^a Helwan University   (Egypt)

Author keywords

Pyrimidine; Pyrimidoquinoline; Tetrahydroquinoline; Thioureide; X ray crystal structure

Indexed keywords

ANTIINFECTIVE AGENT; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; FUNGUS; MICROBIOLOGICAL EXAMINATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTI-BACTERIAL AGENTS; CRYSTALLOGRAPHY, X-RAY; FUNGI; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; PYRIMIDINES; QUINOLINES;

EID: 33845407219     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/11110890     Document Type: Article

References (30)

1. Joshi, A.A.; Viswanathan, C. L. Recent developments in antimalarials drug discovery. Anti-Infect. Agent. Med. Chem. 2006, 5, 105-122.
2. Dlugosz, A.; Dus, D. Synthesis and anticancer properties of pyrimido[4,5-b]quinolines. Farmaco 1996, 51, 364-374.
3. El-Sayed, O. A.; El-Bieh, F. M.; Al-Bassam B.A. Novel 4-aminopyrimido[4,5-b]quinoline derivatives as potential antimicrobial agents. Boll. Chim. Farm. 2002, 141, 461-465.
4. El-Sayed O. A.; Al-Bassam, B. A.; Hussein, M. E. Synthesis of some novel quinoline-3-carboxylic acids and pyrimidoquinoline derivatives as potential antimicrobial agents. Arch. Pharm. (Weinheim), 2002, 335, 403-410.
5. Gavrilov, M. Yu.; Mardanova, L.G.; Kolla V. E.; Konshin, M. E. Synthesis, Anti-inflammatory and analgesic activities of tetrahydroquini\oline-3- carboxamides. Pharm. Chem. J. 1988, 22, 554-556.
6. El-Sayed, O. A.; Al-Turki, T. M.; Al-Daffiri, H. M.; Al-Bassam, B. A.; Hussein, M. E. Pyrimidoquinoline derivatives as anti-inflammatory and antimicrobial agents, Boll. Chim. Farm. 2004, 143, 227-238.
7. Al-Mousawi, S. M.; Elkholy, Y.M.; Mohammed, M. A.; Elnagdi, M. H. Synthesis of new condensed 2-amino-4H-pyran-3-carbonitriles and of 2-Aminoquinoline-3-carbonitriles. Org. Prep. Proceed. Int. 1999, 31, 205-214.
8. Elassar, A. A.; Elkholy Y. M. Synthesis of 3,4,7-triazaacenaphthylene and pyrido[3,4,5-de]-cinnoline derivatives. Heteroatom Chem . 2003, 14, 427- 433.
9. Elkholy, Y. M. Studies with polyfunctionally substituted heterocycles. Chem. Heterocycl. Comp. 2002, 38, 1342-1347.
10. Elkholy, Y. M. Synthesis and antimicrobial of new polyfunctionally substituted pyridazines and their derivatives. Heterocycl. Commun. 2005, 11, 89-96.
11. Asolkar, R. N.; Schroder, D.; Heckmann, R.; Land, S.; Wagner-Dobler I.; Laatsch, H.; Helquinoline, a new tetrahydroquinoline antibiotic from Janibacter limosus Hel. J. Antibiotics 2004, 57, 17-23.
12. Schoenwald, R. D. Tetrahydroquinoline analogs for use in glaucoma treatment; U.S. Pat. 5776482, 1988.
13. Dimon, D. B.; Robert, W. Preparation of 4-carboxyamino-2-substituted tetrahydroquinoline derivatives as cholesteryl ester transfer protein inhibitors; JP 2001163859, 2001.
14. Shaaban, M. A.; Ghoneim, K.M.; Kalifa, M. Synthesis of certain 4-oxo-tetrahydroquinoline and benzauocine derivatives likely to possess analgesic activity. Pharmazie 1977, 32, 90-92.
15. Hashimoto, K.; Okaichi, Y.; Nomi, D.; Bando, M.; Minamikawa, J. A practical synthesis of (S)-(-)-nadifloxacin: Novel acid-catalyzed racemization of tetrahydroquinoline derivatives. Chem. Pharm. Bull. 1996, 44, 642-645.
16. Chakaravorty, P.K.; Grelnlee, W. P.C.T. Int. Appl WO 92, 20,687,156, 1992; [C.A. 1993, 118, 213104d].
17. Shujiang, T. U.; Fang, F.; Tuanjie, L.; Songlei, Z.; Xiaojing, Z. An efficient one-pot synthesis of novel pyrimidoquinoline derivative under microwave irradiation without catalyst, J Heterocycl. Chem, 2005, 42, 707-710.
18. Shimamure, H., Terajima, K., and Kawase, Y. Jpn. Kokai Tokyo Koho JP 05,112,559, 1993.
19. Gavrilov, M. Yu.; Konshin, M. E. Synthesis of Octahydroquinoline[4,5-b] quinoline-2,4-dione. Chem. Heterocycl. Comp. 1989, 25, 932-935.
20. Abdel-Gawad, S. M.; El-Gagy, M. S. A.; Heiba, H. I.; Aly, H. M.; Ghorab, M. M. Synthesis and radiation stability of some new biologically active hydroquinoline and pyrimido[4,5-b]quinoline derivatives. J. Chin. Chem. Soc. 2005, 52, 1227-1236.
21. Abu-Shanab, F. A.; Elkholy, Y. M.; Elnagdi, M. H. Enaminones as building blocks in organic Synthesis. Synth. Commun. 2002, 32, 3493-3502.
22. Leoncini, G.; Signorello, M. G.; Grossi, G. C.; Di Braccio, M. Mechanism of action of two new pyrimidoquinoline and isoquinoline derivatives in human platelets. Thromb. Res. 1997, 87, 483-492.
23. Omura, S.; Nakagawa, A. Structure of virantmycin, a novel antiviral antibiotic. Tetrahedron Lett. 1981, 2199-2202.
24. Nene Y. L.; Thapliyal P.N. Fungicides in plant disease control; Oxford & IBH Publ.: New Delhi, 1982 pp. 192-198.
25. CCDC 626536 and 626537 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
26. Mackay, S.; Gilmore, C. J.; Edwards, C.; Stewart, N.; Shankland, K. maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius: Delft, The Netherlands and Mac Science: Japan & The University of Glasgow, 1999.
27. Johnson, C. K. ORTEP - II. A Fortran Thermal - Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory: Oak Ridge, Tennessee, USA, 1976.
28. Otwinowski, Z.; Minor, W. In Methods in Enzymology; Carter, Jr.; C. W.; Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276, pp. 307-326.
29. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Cryst 1994, 27, 435.
30. Waasmaier, D.; Kirfel, A. Acta Cryst. 1995, A51, 416-431.