Specific nonpeptide inhibitors of puromycin-sensitive aminopeptidase with a 2,4(1H,3H)-quinazolinedione skeleton

Chemical and Pharmaceutical Bulletin

Volumn 51, Issue 11, 2003, Pages 1273-1282

  Kakuta, Hiroki ^a   Tanatani, Aya ^a   Nagasawa, Kazuo ^a   Hashimoto, Yuichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Inhibitor; Puromycin sensitive aminopeptidase; Quinazolinedione; Structure activity relationship

Indexed keywords

1 BENZYL 3 (2,6 DIETHYLPHENYL) 2,4(1H,3H)QUINAZOLINEDIONE; 1 BUTYL 3 (2,6 DIETHYLPHENYL) 2,4(1H,3H)QUINAZOLINEDIONE; 1 ETHYL 3 (2,6 DIETHYLPHENYL) 2,4(1H,3H)QUINAZOLINEDIONE; 1 METHYL 3 (2,6 DIETHYLPHENYL) 2,4(1H,3H)QUINAZOLINEDIONE; 1 PROPYL 3 (2,6 DIETHYLPHENYL) 2,4(1H,3H)QUINAZOLINEDIONE; 2 (2,6 DIETHYLPHENYL) 1,2,3,4 TETRAHYDRO 1,3 ISOQUINOLINEDIONE; 2 (2,6 DIETHYLPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE 1,3 DIONE; 2 (2,6 DIETHYLPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE 1,3,4 TRIONE; 2 (2,6 DIETHYLPHENYL) 4,4 DIFLUORO 1,2,3,4 TETRAHYDROISOQUINOLINE 1,3 DIONE; 2 AMINO N (2,6 DIETHYLPHENYL)BENZAMIDE; 2 AMINO N (2,6 DIETHYLPHENYL)BENZENEMETHANAMINE; 3 (2,6 DIETHYLPHENYL) 2,4(1H,3H)QUINAZOLINEDIONE; 3 (2,6 DIETHYLPHENYL) 3,4 DIHYDRO 2(1H)QUINAZOLINE; 3 (2,6 DIIETHYLPHENYL) 2 THIO 2,4(1H,3H)QUINAZOLINEDIONE; 3 (2,6 DIIETHYLPHENYL) 2,3 DIHYDRO 4(1H)QUINAZOLINONE; 3 (2,6 DIIETHYLPHENYL) 4 THIO 2,4(1H,3H)QUINAZOLINEDIONE; 3 (2,6 DIISOPROPYLPHENYL) 2H 1,3 BENZOXAZINE 2,4(3H)QUINAZOLINEDIONE; 6 AMINO 3 (2,6 DIETHYLPHENYL) 2,4(1H,3H)QUINAZOLINEDIONE; 6 NITRO 3 (2,6 DIETHYLPHENYL) 2,4(1H,3H)QUINAZOLINEDIONE; 7 NITRO 3 (2,6 DIETHYLPHENYL) 2,4(1H,3H)QUINAZOLINEDIONE; 8 NITRO 3 (2,6 DIETHYLPHENYL) 2,4(1H,3H)QUINAZOLINEDIONE; AMINOPEPTIDASE; BAQ 33; CARBENE; MATRIGEL; N (2,6 DIETHYLPHENYL) 2 HYDROXYBENZAMIDE; N (2,6 DIETHYLPHENYL) 2 NITROBENZAMIDE; N (2,6 DIETHYLPHENYL) 3,1 BENZOXAZIN 4 ONE; PAQ 00; PAQ 11; PAQ 22; PAQ 22B; PAQ 22BN; PAQ 22E; PAQ 22M; PAQ 22P; PAQ 33; PAZOX 22; PN 22; POQ 22; PUROMYCIN; QUINAZOLINE DERIVATIVE; THALIDOMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; 2,4(1H,3H) QUINAZOLINEDIONE; 2,4(1H,3H)-QUINAZOLINEDIONE; PROTEINASE INHIBITOR;

ANIMAL CELL; ARTICLE; CELL ASSAY; CYTOTOXICITY; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SPECIFICITY; DRUG STABILITY; ELECTRIC FIELD; ELECTRIC POTENTIAL; ELECTRICITY; ENZYME INHIBITION; MELANOMA CELL; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; ANIMAL; CANCER INVASION; CELL DIVISION; DOSE RESPONSE; DRUG ANTAGONISM; DRUG EFFECT; DRUG SCREENING; ELECTROCHEMISTRY; HUMAN; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PATHOLOGY; SYNTHESIS; TUMOR CELL LINE;

AMINOPEPTIDASES; ANIMALS; CELL DIVISION; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; ELECTROCHEMISTRY; HUMANS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; NEOPLASM INVASIVENESS; PROTEASE INHIBITORS; PUROMYCIN; QUINAZOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 2642559772     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.51.1273     Document Type: Article

References (49)

1. Filder I. J., Gersten D. M., Hart I. R., Adv. Cancer Res., 28, 149-250 (1978).
2. Liotta l. A., Tryggvason K., Garbisa S., Hart I., Foltz C. M., Shafie S., Nature (London), 284, 67-68 (1980).
3. Liotta l. A., Goldfarb R. H., Brundage R., Siegel G. P., Terenova V., Garbisa S., Cancer Res., 41, 4629-4636 (1981).
4. Sloane B. F., Honn K. V., Sadler J. G., Cancer Res., 42, 980-986 (1982).
5. Nagaoka I., Tamashita T., Biochim. Biophys. Acta, 598, 169-172 (1987).
6. Yoneda J., Saiki I., Fujii H., Abe F., Kojima Y., Azuma I., Clin. Exp. Metastasis, 10, 49-59 (1992).
7. Tsuruo T., Nagamura K., Iida H., Yamori T., Tsukagoshi S., Sakurai Y., J. Antibiot., 34, 1206-1209 (1981).
8. Saiki I., Murata J., Watanabe K., Fujii H., Abe F., Azuma I., Jpn. J. Cancer Res., 80, 873-878 (1989).
9. Look A. T., Ashmun R. A., Shapiro L. H., Peiper S. C., J. Clin. Invest., 83, 1299-1307 (1989).
10. Bowes M. A., Kenny A. J., J. Immunol., 60, 247-253 (1987).
11. Saiki I., Fujii H., Yoneda J., Abe F., Nakajima M., Tsuruo T., Azuma I., Int. J. Cancer, 54, 137-143 (1993).
12. Fujii H., Nakajima M., Aoyagi T., Tsuruo T., Biol. Pharm. Bull., 19, 6-10 (1996).
13. Umezawa H., Aoyagi T., Suda H., Hamada M., Takeuchi T., J. Antibiot., 29, 97-99 (1976).
14. Nicolson G. L., Cancer Res., 47, 1473-1487 (1987).
15. Moscattelli D., Rifkin D. B., Biochim. Biophys. Acta, 948, 67-85 (1988).
16. Hashimoto Y., Curr. Med. Chem., 5, 163-178 (1998).
17. Miyachi H., Azuma A., Kitamoto T., Hayashi K., Kato S., Koga M., Sato B., Hashimoto Y., Bioorg. Med. Chem. Lett., 7, 1483-1488 (1997).
18. Miyachi H., Azuma A., Hashimoto Y., Yakugaku Zasshi, 117, 91-107 (1997).
19. Hashimoto Y., Recent Res. Develop. Org. Chem., 4, 87-120 (2000).
20. Kakuta H., Takahashi H., Sou S., Kita T., Nagasawa K., Hashimoto Y., Recent Res. Devel. Medicinal Chem., 1, 189-211 (2001).
21. Kagechika H., Komoda M., Fujimoto Y., Koiso Y., Takayama H., Kadoya S., Miyata K., Kato F., Kato M., Hashimoto Y., Biol. Pharm. Bull., 22, 1010-1012 (1999).
22. Shimazawa R., Miyachi H., Takayama H., Kuroda K., Kato F., Kato M., Hashimoto Y., Biol. Pharm. Bull., 22, 224-226 (1999).
23. Miyachi H., Kato M., Kato F., Hashimoto Y., J. Med. Chem., 41, 263-265 (1998).
24. Shimazawa R., Takayama H., Hashimoto Y., Jpn. J. Synth. Org. Chem., 57, 92-104 (1999).
25. Shimazawa R., Takayama H., Fujimoto Y., Komoda M., Dodo K., Yamasaki R., Shirai R., Koiso Y., Miyata K., Kato F., Kato M., Miyachi H., Hashimoto Y., J. Enzyme Inhibit., 14, 259-275 (1999).
26. Takahashi H., Komoda M., Kakuta H., Hashimoto Y., Yakugaku Zasshi, 120, 909-921 (2000).
27. Komoda M., Kakuta H., Takahashi H., Fujimoto Y., Kadoya S., Kato F., Hashimoto Y., Bioorg. Med. Chem., 9, 121-131 (2001).
28. Hersh L. B., McKelvy J. F., J. Neurochem., 36, 171-178 (1981).
29. Bauer W. O., Nanda I., Beck G., Schmid M., Jacob F., Cytogenet. Cell Genet., 92, 221-224 (2001).
30. Tobler A. R., Constam D. B., Schmitt-Graff A., Malipiero U., Schlabach R., Fontana A., J. Neurochem., 68, 889-897 (1997).
31. Johnson G. D., Hersh L. B., Arch. Biochem. Biophys., 276, 305-309 (1990).
32. Rawlings N. D., Barrett A. J., Biochem. J., 290, 205-218 (1993).
33. McLellan S., Dyer S. H., Rodriguenz G., Hersh L.B., J. Neurochem., 51, 1552-1559 (1988).
34. Constam D. B., Tobler A. R., Rensing-Ehl A., Kemler I., Hersh L. B., Fontana A., J. Biol. Chem., 270, 26931-26939 (1995).
35. de Gandarias J. M., Irazusta J., Gil J., Fernandez D., Varona A., Casis L., Brain Res. Bull., 50, 283-290 (1999).
36. Osada T., Ikegami S., Takiguchi-Hayashi K., Yamazaki Y., Katoh-Fukui Y., Higashinakagawa T., Sasaki Y., Takeuchi Y., J. Neurochem. 19, 6068-6078 (1999).
37. Kakuta H., Koiso Y., Takahashi H., Nagasawa K., Hashimoto Y., Heterocycles, 55, 1433-1438 (2001).
38. Kakuta H., Koiso Y., Nagasawa K., Hashimoto Y., Bioorg. Med. Chem. Lett., 13, 83-86 (2003).
39. Mallamo J. P., Pilling G. M., Wetzel J. R., Kowalczik P. J., Bell M. R., Kullnig R. K., Batzold F. H., Juniewiecz P. E., Winnecker R. C., Luss H. R., J. Med. Chem., 35, 1663-1670 (1992).
40. Kollman P., McKelvey J., Johansson A., Rothenberg S., J. Amer. Chem. Soc., 97, 955-965 (1975).
41. Weiner P. K., Langridge R., Blaney J. M., Schaefer R., Kollman P. A., Proc. Natl. Acad. Sci. U.S.A., 79, 3754-3758 (1982).
42. Naray-Szabo G., J. Mol. Graphics, 7, 76-81 (1989).
43. Rashkin M. J., Waters M. L., J. Amer. Chem. Soc., 124, 1860-1861 (2002).
44. Electrostatic potential surfaces were generated by mapping PM3 electrostatic potentials onto the surfaces of molecular electron density using Spartan (Wavefunction, Inc. Irvine, CA, U.S.A.). Potential energy range is -50 - 50 kcal/mol for all surfaces shown. Red indicates areas of greater electron density and blue indicates areas of less electron density.
45. Papadopoulas E. P., Torres C. D., J. Heterocycl. Chem., 19, 269-272 (1982).
46. Brown F. J., Bernstain P. R., Cronk L. A., Dosset D. L., Hebbel K. C., Maduskuie T. P., Jr., Shapiro H. S., Vacek E. P., Yee Y. K., Willard A. K., Krell R. D., Snyder D. W., J. Med. Chem., 32, 807-826 (1989).
47. Canonne P., Akssira M., Dahdouh A., Kasmi H., Boumzebra M., Heterocycles, 36, 1305-1313 (1993).
48. Sekine K., Fujii H., Abe F., Nishikawa K., Int. J. Cancer, 94, 485-491 (2001).
49. Albini A., Iwamoto Y., Kleinman H. K., Martin G. R., Aaronson S. A., Kozlowski J. M., McEwan R. N., Cancer Res., 47, 3239-3245 (1997).