4-Aryldihydropyrimidines via the Biginelli Condensation: Aza-Analogs of Nifedipine-Type Calcium Channel Modulators
Abstract
:Introduction
The Mechanism of the Biginelli Reaction
Conformational Studies
Enantiomerically Pure Dihydropyrimidines
Synthetic Studies
Outlook
Acknowledgements
References and Notes
- Janis, R. A.; Silver, P. J.; Triggle, D. J. Adv. Drug Res. 1987, 16, 309.
- Bossert, F.; Vater, W. Med. Res. Rev. 1989, 9, 291. [CrossRef]
- Cho, H.; Ueda, M.; Shima, K.; Mizuno, A.; Hayashimatsu, M.; Ohnaka, Y.; Takeuchi, Y.; Hamaguchi, M.; Aisaka, K.; Hidaka, T.; Kawai, M.; Takeda, M.; Ishihara, T.; Funahashi, K.; Satah, F.; Morita, M.; Noguchi, T. J. Med. Chem. 1989, 32, 2399. [CrossRef]
- Atwal, K.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd, D. M. J. Med. Chem. 1990, 33, 1510. [CrossRef]
- Atwal, K. S.; Rovnyak, G. C.; Kimball, S. D.; Floyd, D. M.; Moreland, S.; Swanson, B. N.; Gougoutas, J. Z.; Schwartz, J.; Smillie, K. M.; Malley, M. F. J. Med. Chem. 1990, 33, 2629. [CrossRef]
- Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O´Reilly, B. C. J. Med. Chem. 1991, 34, 806. [CrossRef]
- Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O´Reilly, B. C.; Schwartz, J.; Malley, M. F. J. Med. Chem. 1992, 35, 3254. [CrossRef] [PubMed]
- Grover, G. J.; Dzwonczyk, S.; McMullen, D. M.; Normadinam, C. S.; Sleph, P. G.; Moreland, S. J. J. Cardiovasc. Pharmacol. 1995, 26, 289. Negwer, M. Organic-Chemical Drugs and their Synonyms; Akademie Verlag: Berlin, 1994; p. 2558. [Google Scholar]
- Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; DiMarco, J. D.; Gougoutas, J.; Hedberg, A.; Malley, M.; McCarthy, J. P.; Zhang, R.; Moreland, S. J. Med. Chem. 1995, 38, 119. Triggle, D. J.; Padmanabhan, S. Chemtracts: Org. Chem. 1995, 8, 191.
- For reviews of the Hantzsch synthesis and related reactions, see: Sausins, A.; Duburs, G. Heterocycles 1988, 27, 269. Stout, D. M.; Meyers, A. J. Chem. Rev. 1982, 82, 223. Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1.
- Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
- Kappe, C. O. Tetrahedron 1993, 49, 6937.
- O’Reilly, B. C.; Atwal, K. S. Heterocycles 1987, 26, 1185. Atwal, K S.; O’Reilley, B. C.; Gougoutas, J. Z.; Malley, M. F. Heterocycles 1987, 26, 1189. Atwal, K. S.; Rovnyak, G. C.; O’Reilly, B. C.; Schwartz, J. J. Org. Chem. 1989, 54, 5898. Zavyalov, S. I.; Kulikova, L. B. Khim.-Farm. Zh. 1992, 26, 116. Sár, C. P.; Hankovszky, O. H.; Jerkovich, G.; Pallagi, I.; Hideg, K. ACH - Models Chem. 1994, 131, 363. Gupta, R.; Gupta, A. K.; Paul, S.; Kachroo, P. L. Ind. J. Chem. 1995, 34B, 151. Hu, E. H.; Sidler, D. R.; Dolling, U. H. PCT WO 97 21,687.
- Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819. Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823. Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917. Robinett, L. D.; Yager, K. M.; Phelan, J. C. 211th National Meeting of the American Chemical Society, New Orleans, 1996; American Chemical Society: Washington, DC, 1996. ORGN 122.
- Crambine alkaloids, see: Snider, B. B.; Shi, Z. J. Org. Chem. 1993, 58, 3828. and references cited therein. Batzelladine alkaloids, see: Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; DeBrosse, C.; Mai, S.; Truneh, A.; Faulkner, D. J.; Carte, B.; Breen, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westley, J. W.; Potts, B. C. M. J. Org. Chem. 1995, 60, 1182. Patil, A. D.; Freyer, A. J.; Taylor, P. B.; Carte, B.; Zuber, G.; Johnson, R.; Faulkner, D. J. J. Org. Chem. 1997, 62, 1814. Patil, A. D.; Freyer, A. J.; Cheng, J.; Snider, B. Tetrahedron Lett. 1996, 37, 6977. Rama Rao, A. V.; Gurjar, M. K.; Vasudevan, J. J. Chem. Soc., Chem. Commun. 1995, 1369. Ptilomycalin A and related alkaloids, see: Overman, L. E.; Rabinowitz, M. H. J. Org. Chem. 1993, 58, 3235. Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A. J. Am. Chem. Soc. 1995, 117, 2657. Palagiano, E.; De Marino, S.; Minale, L.; Riccio, R.; Zollo, F.; Iorizzi, M.; Carre, J. B.; Debitus, C.; Lucarain, L.; Provost, J. Tetrahedron 1995, 51, 3675.
- Folkers, K.; Johnson, T. B. J. Am. Chem. Soc. 1933, 55, 3784. [CrossRef]
- Sweet, F.; Fissekis, J. D. J. Am. Chem. Soc. 1973, 95, 8741. [CrossRef]
- Kappe, C. O. J. Org. Chem. 1997, 62, 7201. [CrossRef]
- Dixon, L. A. Encyclopedia of Reagents in Organic Chemistry; Wiley: New York, 1995; Vol. 6, p. 4166. [Google Scholar]
- Marson, C. M.; Grabowska, U.; Fallah, A.; Walsgrove, T.; Eggleston, D. S.; Baures, P. W. J. Org. Chem. 1994, 59, 291. [CrossRef]
- Falsone, S. F.; Kappe, C. O. unpublished results.
- Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803.
- Goldman, S.; Stoltefuss, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1559.
- Bikker, J. A.; Weaver, D. F. J. Mol. Struct. (Theochem) 1993, 281, 173. Bikker, J. A.; Weaver, D. F. Can. J. Chem. 1992, 70, 2249. Gaudio, A. C.; Korolkovas, A.; Takahata, Y. J. Mol. Struct. 1994, 303, 255. Shishkin, O. V.; Timofeeva, T. V.; Desenko, S. M.; Orlov, V. D.; Lindeman, S. V.; Struchkov, Y. T. Russ. Chem. Bull. 1993, 42, 1160. Langs, D. A.; Kwon, Y. W.; Strong, P. D.; Triggle, D. J. J. Comput.-Aided. Mol. Design 1991, 5, 95. Cozzi, P.; Carganico, G.; Fusar, D.; Grossoni, M.; Menichineri, M.; Pinciroli, V.; Tonani, R.; Vaghi, F.; Salvati, P. J. Med. Chem. 1993, 36, 2964. Palmer, R. B.; Andersen, N. H. Tetrahedron 1996, 52, 9665.
- Fabian, W. M. F.; Semones, M. A.; Kappe, C. O. J. Mol. Struct. (Theochem) 1998, in press.
- Kappe, C. O.; Peters, K.; Peters, E.-M. J. Org. Chem. 1997, 62, 2786. For related work on isomünchnones, see: Kappe, C. O. Tetrahedron Lett. 1997, 38, 3323.
- Kappe, C. O.; Uray, G.; Roschger, P.; Lindner, W.; Kratky, C.; Keller, W. Tetrahedron 1992, 26, 5473.
- Schulte, M.; Kinkel, J. N.; Nicoud, R.-M.; Charton, F. Chem. Ing. Tech. 1996, 68, 670. Stinson, S. C. Chem. Eng. News 1995, 44. ibid. 1994 September 19; issue. 38. Schulte, M.; Derwenskus, K.-H.; Ditz, R. Nachr. Chem. Tech. Lab. 1997, 45, 487.
- Kleidernigg, O. P.; Kappe, C. O. Tetrahedron: Asymmetry 1997, 8, 2057.
- Sausins, A.; Duburs, G. Heterocycles 1988, 27, 291.
- Kappe, C. O.; Roschger, P. J. Heterocycl. Chem. 1989, 26, 55. [CrossRef]
- Bossert, F.; Meyer, H.; Wehinger, E. Angew. Chem. Int. Ed. Engl. 1981, 20, 762. De Matteis, F.; Hollands, C.; Gibbs, A. H.; De Sa, N.; Rizzardini, M. FEBS Lett. 1982, 145, 87. Augusto, O.; Beilan, H. S.; De Montellano, O. P. R. J. Biol. Chem. 1982, 257, 1288. Böcker, R. H.; Guengerich, F. P. J. Med. Chem. 1986, 29, 1596. Mc Cluskey, S. A.; Riddick, D. S.; Mackie, J. E.; Kimmette, S. M.; Withney, R. A.; Marks, G. S. Can. J. Physiol. Pharmacol. 1992, 70, 1069.
- Vanden Eynde, J. J.; Audiart, N.; Canonne, V.; Michel, S.; van Haverbeke, Y.; Kappe, C. O. Heterocycles 1997, 45, 1967.
- Khromov-Borisov, N. V.; Savchenko, A. M. Zh. Obschch. Khim. 1952, 22, 1680.
- Kappe, C. O.; Wagner, U. G. Heterocycles 1989, 29, 761.
- Kappe, C. O. Liebigs Ann. Chem. 1990, 505.
- Kappe, C. O.; Färber, G. J. Chem. Soc., Perkin Trans. 1 1991, 1342.
- For a review on the chemistry of geminal diazides, see: Kappe, T.; Kappe, C. O. Progress in Heterocyclic Chemistry; Suschitzky, H., Gribble, G. W., Eds.; Pergamon Press: Oxford, 1996; Vol. 8, Chapter 1. [Google Scholar]
- Nagarathanm, D.; Chiu, G.; Dhar, T. G. M.; Wong, W. C.; Marzabadi, M. R.; Gluchowski, C. L.; Lagu, B.; Miao, S. W. PCT Int. Appl. WO 96 14,846. Kettmann, V.; Drimal, J.; Svetlik, J. Pharmazie 1996, 51, 10. Kattmann, V.; Svetlik, J. Acta Cryst. 1996, C52, 1496. Alajarin, R.; Vaquero, J. J.; Alvarez- Builla, J.; De Casa-Juana, M. F.; Sunkel, C.; Priego, J. G.; Gomez-Sal, P.; Torres, R. Bioorg. Med. Chem. 1994, 2, 323. Alajaran, R.; Jordan, P.; Vaquero, J. J.; Alvarez-Builla, J. Synthesis 1995, 389. Gupta, R.; Sudan, S.; Kachroo, P. L. Ind. J. Chem. 1996, 35B, 985. Sudan, S.; Gupta, R.; Bani, S.; Singh, G. B.; Jain, S. M.; Kachroo, P. L. J. Ind. Chem. Soc. 1996, 73, 431. Ghorab, M. M.; Mohamed, Y. A.; Mohamed, S. A.; Ammar, Y. A. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 108, 249. Sharaf, M. A. F.; Aal, F. A. A.; Fattah, A. M. A.; Khalik, A. M. R. A. J. Chem. Res. (S) 1996, 354. Rehani, R.; Shah, A. C.; Arya, V. P. Ind. J. Chem. 1994, 33B, 775. Sherif, S. M.; Youssef, M. M.; Mobarak, K.; Abdel-Fattah, A.-S. M. Tetrahedron 1993, 49, 9561. Remmenikov, G. Ya.; Shavaran, S. S.; Boldyrev, I. V.; Kurilenko, L. K.; Klebanov, B. M.; Kukhar, V. P. Khim.-Farm. Zh. 1991, 25, 35. Remennikov, G. Ya.; Boldyrev, I. V.; Kravchenko, S. A.; Pirozhenko, V. V. Khim. Geterotsikl. Soedin. 1993, 1290. Remnenikov, G. Y.; Boldyrev, I. V.; Krachenko, S. A.; Pirozhenko, V. V. Khim. Geterotsikl. Soedin. 1993, 1398. Schleifer, K.-J. Pharm. Pharmacol. Lett. 1995, 5, 162.
Biographical Sketch
- Sample Availability: Available from MDPI.
© 1998 MDPI. All rights reserved
Share and Cite
Kappe, C.O. 4-Aryldihydropyrimidines via the Biginelli Condensation: Aza-Analogs of Nifedipine-Type Calcium Channel Modulators. Molecules 1998, 3, 1-9. https://doi.org/10.3390/30100001
Kappe CO. 4-Aryldihydropyrimidines via the Biginelli Condensation: Aza-Analogs of Nifedipine-Type Calcium Channel Modulators. Molecules. 1998; 3(1):1-9. https://doi.org/10.3390/30100001
Chicago/Turabian StyleKappe, C. Oliver. 1998. "4-Aryldihydropyrimidines via the Biginelli Condensation: Aza-Analogs of Nifedipine-Type Calcium Channel Modulators" Molecules 3, no. 1: 1-9. https://doi.org/10.3390/30100001