Collect. Czech. Chem. Commun. 2000, 65, 1093-1108
https://doi.org/10.1135/cccc20001093

Synthesis and Analgesic Activity of Some Substituted 1-Benzofurans and 1-Benzothiophenes

Stanislav Rádl*, Petr Hezký, Petr Konvička and Ivan Krejčí

Research Institute of Pharmacy and Biochemistry, Kouřimská 17, 130 60 Prague 3, Czech Republic

References

1. Vaz Z. R., Cechinel-Filho V., Yunes R. A., Calixto J. B.: J. Pharmacol. Exp. Ther. 1996, 278, 304.
2. Cechinel-Filho V., Vaz Z. R., Zunino L., Calixto J. B., Yunes R. A.: Eur. J. Med. Chem. 1996, 31, 833. <https://doi.org/10.1016/0223-5234(96)83978-X>
3. Rádl S., Hezký P., Urbánková J., Váchal P., Krejčí I.: Collect. Czech. Chem. Commun. 2000, 65, 280. <https://doi.org/10.1135/cccc20000280>
4. Gewald K., Jansch H.-J.: J. Prakt. Chem. 1973, 315, 779. <https://doi.org/10.1002/prac.19733150423>
5. Vaidya V. P., Mahajan S. B., Agasimundin Y. S.: Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1981, 20, 391.
6. Lane C. F.: Synthesis 1975, 135. <https://doi.org/10.1055/s-1975-23685>
7. Borch R. F., Hassid A. I.: J. Org. Chem. 1972, 37, 1673. <https://doi.org/10.1021/jo00975a049>
8. McEvoy F. J., Allen G. R., Jr.: J. Med. Chem. 1974, 17, 281. <https://doi.org/10.1021/jm00249a005>
9. Regnier G. L., Canevari R. J., Le Douarec J. C., Holstorp S., Daussy J.: J. Med. Chem. 1972, 15, 295. <https://doi.org/10.1021/jm00273a600>
10. El-Mahdy S. A. M., Alhaider A. A., Mahgoub A. A.: J. Pharm. Pharmacol. 1990, 42, 522. <https://doi.org/10.1111/j.2042-7158.1990.tb06613.x>
11. Palaska E., Unlu S., Erdogan H., Safak C., Gumusel B., Sundal R.: Eur. J. Med. Chem. 1993, 28, 963. <https://doi.org/10.1016/0223-5234(93)90052-G>
12. Flouzat C., Bresson Y., Mattio A., Bonnet J., Guillaumet G.: J. Med. Chem. 1993, 36, 497. <https://doi.org/10.1021/jm00056a010>
13. Viaud M.-C., Jamoneau P., Flouzat C., Bizot-Espiard J.-G., Pfeiffer B., Renard P., Caignard D.-H., Adam G., Guillaumet G.: J. Med. Chem. 1995, 38, 1278. <https://doi.org/10.1021/jm00008a006>
14. Schlichtergroll A., Jakovlev V., Engel J.: Drugs Future 1982, 7, 806.
15. Engel J., Scheffler G., Nickel B., Thiemer K., Tibes U., Wermer U., Szelenyi I.: Drugs Future 1989, 14, 614. <https://doi.org/10.1358/dof.1989.014.07.95998>
16. Rádl S., Hafner W., Hezký P., Krejčí I., Proška J., Taimr J.: Collect. Czech. Chem. Commun. 1999, 64, 363. <https://doi.org/10.1135/cccc19990363>
17. Rádl S., Hafner W., Hezký P., Krejčí I., Proška J., Hájíček J.: Collect. Czech. Chem. Commun. 1999, 64, 377. <https://doi.org/10.1135/cccc19990377>
18. Rádl S., Hezký P., Proška J., Krejčí I.: Arch. Pharm. 1999, 332, 13. <https://doi.org/10.1002/(SICI)1521-4184(19991)332:1<13::AID-ARDP13>3.0.CO;2-L>
19. Rádl S., Kovářová L., Hezký P., Vosátka V., Königová O., Proška J., Krejčí I.: Arch. Pharm. 1999, 332, 208. <https://doi.org/10.1002/(SICI)1521-4184(19996)332:6<208::AID-ARDP208>3.0.CO;2-0>
20. Borowitz I. J., Parnes H.: J. Org. Chem. 1967, 32, 3560. <https://doi.org/10.1021/jo01286a060>
21. Clemo G. R., Morgan W. M., Raper R.: J. Chem. Soc. 1937, 965. <https://doi.org/10.1039/jr9370000965>
22. Dornow A., Machens H., Bruncken K.: Chem. Ber. 1951, 84, 147. <https://doi.org/10.1002/cber.19510840202>
23. Taurins A., Blaga A.: J. Heterocycl. Chem. 1970, 7, 1137. <https://doi.org/10.1002/jhet.5570070521>
24. Sabitha G., Rao A. V.: Synth. Commun. 1987, 17, 341. <https://doi.org/10.1080/00397918708077315>
25. Scheffler G., Engel J., Jakovlev V., Nickel B., Thiemer K. (Degussa AG): Eur. Pat. Appl. 149 088; Chem. Abstr. 1985, 103, 215189.
26. Eddy N. B., Leimbach D.: J. Pharmacol. Exp. Ther. 1953, 80, 385.
27. Koster R., Anderson M., De Beer J.: Fed. Proc. 1959, 18, 412.
28. D′Amour F. E., Smith D. L. J.: Pharmacol. Exp. Ther. 1941, 72, 74.