Antitumor benzothiazoles. 7. Synthesis of 2-(4- acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines

Journal of Medicinal Chemistry

Volumn 42, Issue 3, 1999, Pages 381-392

  Chua, Mei Sze ^a   Shi, Dong Fang ^a   Wrigley, Samantha ^a   Bradshaw, Tracey D ^a   Hutchinson, Ian ^a   Shaw, P Nicholas ^a   Barrett, David A ^a   Stanley, Lesley A ^b   Stevens, Malcolm F G ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b DE MONTFORT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 ACYLAMINOPHENYL)BENZOTHIAZOLE DERIVATIVE; ACYLTRANSFERASE; ANTINEOPLASTIC AGENT; BENZOTHIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; DRUG ACETYLATION; DRUG METABOLISM; DRUG OXIDATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; DRUG UPTAKE; HUMAN; HUMAN CELL; NONHUMAN; PROSTATE CARCINOMA; RAT; TUMOR CELL LINE;

ACETYLATION; ACETYLTRANSFERASES; AMINES; ANIMALS; ANTINEOPLASTIC AGENTS; BIOTRANSFORMATION; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICROSCOPY, CONFOCAL; RATS; RATS, WISTAR; SPECTROPHOTOMETRY, INFRARED; THIAZOLES; TUMOR CELLS, CULTURED;

EID: 0032971926     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm981076x     Document Type: Article

References (25)

1. Shi, D.-F.; Bradshaw, T. D.; Wrigley, S.; McCall, C. J.; Lelieveld, P.; Fichtner, I.; Stevens, M. F. G. Antitumor benzothiazoles. 3. Synthesis and evaluation of their activities against breast cancer cell lines in vitro and in vivo. J. Med. Chem. 1996, 39, 3375-3384.
2. Bradshaw, T. D.; Chua, M.-S.; Shi, D.-F.; Wrigley, S.; Matthews, C. S.; Hiorns, L. R.; Leyland-Jones, B.; Stevens, M. F. G. Examination of mechanisms of aquired resistance to 2-(4-aminophenyl)benzothiazoles. Proc. Am. Assoc. Cancer Res. 1998, 39, 217.
3. von Angerer, A.; Strohmeier, J. 2-Phenylindoles. Relationship between structure, estrogen receptor affinity, and mammary tumor inhibiting activity in the rat. J. Med. Chem. 1984, 27, 1439-1447. von Angerer, E.; Erber, S. 3-Alkyl-2-phenylbenzo-[b]thiophenes: nonsteroidal estrogen antagonists with mammary tumor inhibiting activity. J. Steroid Biochem. Mol. Biol. 1992, 41, 557-562. Erber, S.; Ringshandl, R.; von Angerer, E. 2-Phenylbenzo[b]furans: relationship between structure, estrogen receptor affinity and cytostatic activity against mammary tumor cells. Anti-Cancer Drug Des. 1991, 6, 417-426.
4. von Angerer, A.; Strohmeier, J. 2-Phenylindoles. Relationship between structure, estrogen receptor affinity, and mammary tumor inhibiting activity in the rat. J. Med. Chem. 1984, 27, 1439-1447. von Angerer, E.; Erber, S. 3-Alkyl-2-phenylbenzo-[b]thiophenes: nonsteroidal estrogen antagonists with mammary tumor inhibiting activity. J. Steroid Biochem. Mol. Biol. 1992, 41, 557-562. Erber, S.; Ringshandl, R.; von Angerer, E. 2-Phenylbenzo[b]furans: relationship between structure, estrogen receptor affinity and cytostatic activity against mammary tumor cells. Anti-Cancer Drug Des. 1991, 6, 417-426.
5. von Angerer, A.; Strohmeier, J. 2-Phenylindoles. Relationship between structure, estrogen receptor affinity, and mammary tumor inhibiting activity in the rat. J. Med. Chem. 1984, 27, 1439-1447. von Angerer, E.; Erber, S. 3-Alkyl-2-phenylbenzo-[b]thiophenes: nonsteroidal estrogen antagonists with mammary tumor inhibiting activity. J. Steroid Biochem. Mol. Biol. 1992, 41, 557-562. Erber, S.; Ringshandl, R.; von Angerer, E. 2-Phenylbenzo[b]furans: relationship between structure, estrogen receptor affinity and cytostatic activity against mammary tumor cells. Anti-Cancer Drug Des. 1991, 6, 417-426.
6. Stevens, M. F. G.; McCall, C. J.; Lelieveld, P.; Alexander, P.; Richter, A.; Davies, D. E. Structural studies on bioactive compounds. 23. Synthesis of polyhydroxylated 2-phenylbenzothiazoles and a comparison of their cytotoxicities and phar-macological properties with genistein and quercetin. J. Med. Chem. 1994, 37, 1689-1695.
7. Yates, P. C.; McCall, C. J.; Stevens, M. F. G. Structural studies on benzothiazoles. Crystal and molecular structure of 5,6-dimethoxy-2-(4-methoxy-phenyl)benzothiazole and molecular orbital calculations on related compounds. Tetrahedron 1991, 47, 6493-6502.
8. Bradshaw, T. D.; Wrigley, S.; Shi, D.-F.; Schultz, R. J.; Paull, K. D.; Stevens, M. F. G. 2-(4-Aminophenyl)benzothiazoles: novel agents with selective profiles of in vitro anti-tumour activity. Br. J. Cancer 1998, 77, 745-752.
9. Weinstein, J. N.; Myers, T. G.; O'Connor, P. M.; Friend, S. H.; Fornace, A. J.; Kohn, K. W.; Fojo, T.; Bates, S. E.; Rubinstein, L. V.; Anderson, N. L.; Buolamwini, J. K.; van Osdol, W. W.; Monks, A. P.; Scudiero, D. A.; Sausville, E. A.; Zaharevitz, D. W.; Bunow, B.; Viswanadhan, V. N.; Johnson, G. S.; Wittes, R. E.; Paull, K. D. An information-intensive approach to the molecular pharmacology of cancer. Science 1997, 275, 343-349.
10. Akama, T.; Yasushi, S.; Ishida, H.; Gomi, K; Kasai, M. Novel 5-aminoflavone derivatives as specific antitumor agents in breast cancer. J. Med. Chem. 1996, 39, 3461-3469. Akama, T.; Ishida, H.; Kimura, U.; Gomi, K.; Saito, H. Structure-activity relation-ships of the 7-substituents of 5,4′-diamino-6,8,3′-trifluoroflavone, a potent antitumor agent. J. Med. Chem. 1998, 41, 2056-2087.
11. Akama, T.; Yasushi, S.; Ishida, H.; Gomi, K; Kasai, M. Novel 5-aminoflavone derivatives as specific antitumor agents in breast cancer. J. Med. Chem. 1996, 39, 3461-3469. Akama, T.; Ishida, H.; Kimura, U.; Gomi, K.; Saito, H. Structure-activity relation-ships of the 7-substituents of 5,4′-diamino-6,8,3′-trifluoroflavone, a potent antitumor agent. J. Med. Chem. 1998, 41, 2056-2087.
12. Hanna, P. E. Metabolic activation and deactivation of arylamines. Curr. Med. Chem. 1996, 3, 195-210.
13. Badawi, A. F.; Hirvonen, A.; Bell, D. A.; Lang, N. P.; Kadlubar, F. F. Role of aromatic amine acetyltransferases, NAT1 and NAT2, in carcinogen-DNA adduct formation in the human urinary bladder. Cancer Res. 1995, 55, 5230-5237.
14. Bamberger, E.; von Goldberger, A. Annalen 1899, 305, 339.
15. Fitton, E. O.; Smalley, R. K. Practical Heterocyclic Chemistry; Academic Press: London, 1968; pp 44-45.
16. Boyd, M. R.; Paull, K. D. Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Development Res. 1995, 34, 91-109.
17. Stanley, L. A.; Coroneos, E.; Cuff, R.; Hickman, D.; Ward, A.; Sim, E. Immunochemical detection of arylamine N-acetyltransferase in normal and neoplastic bladder. J. Histochem. Cytochem. 1996, 44, 1059-1067.
18. Bock, K. W. Metabolic polymorphisms affecting activation of toxic and mutagenic arylamines. Trends Pharm. Sci. 1992, 13, 223-226.
19. Bradshaw, T. D.; Shi, D.-F.; Schultz, R. J.; Paull, K. D.; Kelland, L.; Wilson, A.; Fiebig, H. H.; Wrigley, S.; Stevens, M. F. G. Influence of 2-(4-aminophenyl)benzothiazoles on growth of human ovarian carcinoma cells in vitro and in vivo. Br. J. Cancer 1998, 78, 421-429.
20. Double, J. A.; Bibby, M. C. Personal communication.
21. Scheler, S. Two component diazo material. Ger. Offen. 3,307,364, 1983; Chem. Abstr. 1985, 102, 158128g.
22. Stephen, F. F.; Bower, J. D. The preparation of benziminazole and benzoxazoles from Schiffs bases. Part 1. J. Chem. Soc. 1949, 2971-2972.
23. Feitelson, B. N.; Mamalis, P.; Moualim, R. J.; Petrow, V.; Stephenaon, O.; Sturgeon, B. Some benziminazole derivatives. J. Chem. Soc. 1952, 2389-2998.
24. Reese, J. A.; Byard, J. L. Isolation and culture of adult hepatocytes from liver biopsies. In Vitro 1981, 17, 935-940.
25. Greif, H.; Ben-Chaim, J.; Shimon, T.; Bechor, E.; Eldar, H.; Livneh, E. The protein kinase C-related PKC-L(η) gene product is localised in the cell nucleus. Mol. Cell. Biol. 1992, 12, 1304-1311.