Novel derivatives of benzo[b]thieno[2,3-c]quinolones: Synthesis, photochemical synthesis, and antitumor evaluation

Journal of Medicinal Chemistry

Volumn 46, Issue 21, 2003, Pages 4516-4524

  Koružnjak, Jasna Dogan ^a,d   Grdiša, Mira ^b   Slade, Neda ^b   Zamola, Branimir ^c   Pavelić, Krešimir ^b   Karminski Zamola, Grace ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

^b RUDER BO KOVI INSTITUTE   (Croatia)

^c UNIVERSITY OF ZAGREB   (Croatia)

^d PLIVA CROATIA LTD   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

5 [3 (DIMETHYLAMINO)PROPYL] 6 OXO 5,6 DIHYDRO[1]BENZOTHIENO[2,3 C]QUINOLINE 9 CARBOXANILIDE; BENZO[B]THIENO[2,3 C]QUINOLONE DERIVATIVE; METHYL 5 [3 (DIMETHYLAMINO)PROPYL] 6 OXO 5,6 DIHYDRO[1]BENZOTHIENO[2,3 C]QUINOLINE 9 CARBOXYLATE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CARCINOMA; CELL DEATH; COLON CARCINOMA; CONTROLLED STUDY; DRUG SYNTHESIS; FIBROBLAST; HUMAN; HUMAN CELL; LARYNX CARCINOMA; MELANOMA; PANCREAS CARCINOMA; PHOTOCHEMISTRY; UTERINE CERVIX CARCINOMA;

ALKYLATION; ANNEXIN A5; ANTINEOPLASTIC AGENTS; APOPTOSIS; DNA, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; FLOW CYTOMETRY; HUMANS; HYDROLYSIS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; QUINOLONES; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES;

EID: 10744232383     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0210966     Document Type: Article

References (45)

1. Li, L.; Wang, H.-K.; Kuo, S.-C.; Wu, T.-S.; Lednicer, D.; Lin, C. M.; Hamel, E.; Lee, K.-H. Antitumor Agents. 150.2′,3′,4′,5′ ,5,6,7-Substituted 2-Phenyl-4-quinolones and Related Compounds: Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization. J. Med. Chem. 1994, 37, 1126-1135.
2. Li, L.; Wang, H.-K.; Kuo, S.-C.; Wu, T.-S.; Mauger, A.; Lin, C. M.; Hamel, E.; Lee, K.-H. Antitumor Agents. 155. Synthesis and Biological Evaluation of 3′,6,7-Substituted 2-Phenyl-4-quinolones as Antimicrotubule Agents. J. Med. Chem. 1994, 37, 3400-3407.
3. Chen, K.; Kuo, S.-C.; Hsieh, M.-C.; Mauger, A.; Lin, C. M.; Hamel, E.; Lee, K.-H. Antitumor Agents. 174. 2′,3′,4′,5′ ,5,6,7-Substituted 2-Phenyl-1,8-naphthyridin-4-ones: Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization. J. Med. Chem. 1997, 40, 2266-2275.
4. Zhang, S.-X.; Bastow, K. F.; Tachibana, Y.; Kuo, S.-C.; Hamel, E.; Mauger, A.; Narayanan, V. L.; Lee, K.-H. Antitumor Agents. 196. Substituted 2-Thienyl-1,8-naphthyridin-4-ones: Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization. J. Med. Chem. 1999, 42, 4081-4087.
5. Zhang, S.-X.; Feng, J.; Kuo, S.-C.; Brossi, A.; Hamel, E.; Tropsha, A.; Lee, K.-H. Antitumor Agents. 199. Three-Dimensional Quantitative Structure-Activity Relationship Study of the Colchicine Binding Site Ligands Using Comparative Molecular Field Analysis. J. Med. Chem. 2000, 43, 167-176.
6. Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K. F.; Nakanishi, Y.; Hamel, E.; Lee, K.-H. 6-Alkylamino- and 2,3-Dihydro-3′ -methoxy-2-phenyl-4-quinazolinones and Related Compounds: Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization. J. Med. Chem. 2000, 43, 4479-4487.
7. Wang, H.-K.; Bastow, K. F.; Cosentino, M. L.; Lee, K.-H. Antitumor Agents. 166. Synthesis and Biological Evaluation of 5,6,7,8-Substituted-2-phenylthiochromen-4-ones. J. Med. Chem. 1996, 39, 1975-1980.
8. Xia, Y.; Yang, Z.-Y.; Xia, P.; Bastow, K. F.; Tachibana, Y.; Kuo, S.-C.; Hamel, E.; Hackl, T.; Lee, K.-H. Antitumor Agents. 181. Synthesis and Biological Evaluation of 6,7,2′,3′,4′ -Substituted-1,2,3,4-tetrahydro-2-phenyl-4-quinolones as a New Class of Antimitotic Antitumor Agents. J. Med. Chem. 1998, 41, 1155-1162.
9. Tabarrini, O.; Cecchetti, V.; Fravolini, A.; Nocentini, G.; Barzi, A.; Sabatini, S.; Miao, H.; Sissi, C. Design and Synthesis of Modified Quinolones as Antitumoral Acridones. J. Med. Chem. 1999, 42, 2136-2144.
10. Sit, S.-Y.; Ehrgott, F. J.; Gao, J.; Meanwell, N. A. 3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine Binding to the Site Associated with the NMDA Receptor. Bioorg. Med. Chem. Lett. 1996, 6 (5), 499-504.
11. El-Subbagh, H. I.; Abadi, A. H.; Al-Khawad, I. E.; Al-Rashood, K. A. Synthesis and Antitumor Activity of some New Substituted Quinolin-4-one and 1,7-Naphthyridin-4-ones Analogues. Arch. Pharm. Pharm. Med. Chem. 1999, 332, 19-24.
12. Oleson, J. J.; Calderella, L. A.; Mjos, K. J.; Reith, A. R.; Thie, R. S. ; Toplin, I. The Effects of Streptonigrin on Experimental Tumors. Antibiot. Chemother. 1961, 11, 158-164.
13. Teller, M. N.; Wagshul, S. F.; Wolley, G. W. Transplantable Human Tumors in Experimental Chemotherapy. Effects of Streptonigrin on HS-1 and Hep-3 in the Rat. Antibiot. Chemother. 1961, 11, 165-173.
14. Reilly, H. C.; Sigura, K. An Antitumor Spectrum of Streptonigrin. Antibiot. Chemother. 1961, 11, 174-177.
15. Hackethal, C. A.; Golbey, R. B.; Tan, C. T. C.; Karnofsky, D. A.; Burchenal, J. H. Clinical Observation on the Effects of Streptonigrin in Patients wizh Neoplastiv Disease. Antibiot. Chemother. 1961, 11, 178-183.
16. Rivers, S. L.; Whittington, R. M.; Medrek, T. J. Treatment of Malignant Lymphomas with Methyl Ester of Streptonigrin (NSC 45384). Cancer 1966, 19 (10), 1377-1385.
17. Kaung, D. T.; Whittington, R. M.; Spencer, H. H.; Patno, M. E. Comparison of Chlorambucil and Streptonigrin (NSC-45383) in the Treatment of Chronic Lymphocytic Leukemia. Cancer 1969, 23 (3), 597-600.
18. Kaung, D. T.; Whittington, R. M.; Spencer, H. H.; Patno, M. E. Comparison of Chlorambucil and Streptonigrin (NSC-45383) in the Treatment of Malignant Lymphomas. Cancer 1969, 23 (6), 1280-1283.
19. Banzet, P.; Jacquillat, C.; Civatte, J.; Puissant, A.; Maral, J.; Chastang, C.; Israel, L.; Belaich, S.; Jourdain, J.-C.; Weil, M.; Auclere, G. Adjuvant Chemotherapy in the Management of Primary Malignant Melanoma. Cancer 1978, 41 (4), 1240-1248.
20. Forcier, R. J.; McIntyre, O. R.; Nissen, N. I.; Pajak, T. F.; Glidewell, O.; Holland, J. F. Combination Chemotherapy of non-Hodgkin Lymphoma. Med. Pediatr. Oncol. 1978, 4 (4), 351-362.
21. Fryatt, T.; Goroski, D. T.; Nilson, Z. D.; Moody, C. J.; Beall, H. D. Novel Quinolinequinone Antitumor Agents: Structure-Metabolism Studies with NAD(P)H: Quinone Oxidoreductase (NQO1). Bioorg. Med. Chem. Lett. 1999, 9, 2195-2198.
22. Yang, Z.-Y.; Xia, Y.; Xia, P.; Tachibana, Y.; Bastow, K. F.; Lee, K.-H. Antitumor Agents. 187. Synthesis and Cytotoxicity of Substituted 8,8-Dimethyl-2H,8H-pyrano[6,5-h]quinoline-2-one and Related Compounds. Bioorg. Med. Chem. Lett. 1999, 9, 713-716.
23. Xia, Y.; Yang, Z.-Y.; Hour, M.-J.; Kuo, S.-C.; Xia, P.; Bastow, K. F.; Nakanishi, Y.; Nampoothiri, P., Hackl, T.; Hamel, E.; Lee, K.-H. Antitumor Agents. Part 204: Synthesis and Biological Evaluation of Substituted 2-Aryl Quinazolinones. Bioorg. Med. Chem. Lett. 2001, 11, 1193-1196.
24. Edwards, J. P.; Higuchi, R. I.; Winn, D. T.; Pooley, C. L. F.; Caferro, T. R.; Hamann, L. G.; Zhi, L.; Marschke, K. B.; Goldman, M. E.; Jones, T. K. Nonsteroidal Androgen Receptor Agonists Based on 4-(Trifluoromethyl)-2H-pyrano[3, 2-g]quinolin-2-one. Bioorg. Med. Chem. Lett. 1999, 9, 1003-1008.
25. Dogan Koruznjak, J.; Slade, N.; Zamola, B.; Pavelić, K.; Karminski-Zamola, G. Synthesis, photochemical synthesis and antitumor evaluation of novel derivatives of thieno[3′,2′ :4,5]thieno[2,3-c]quinolones. Chem. Pharm. Bull. 2002, 50, 656-660.
26. Ried, W.; Oremek, G.; Ocakcioglu, B. Synthese von Substituierten Benzo[b]thiophenen. Liebigs Ann. Chem. 1980, 1424-1427.
27. Krubsack, A. J.; Higa, T. Mechanism of the Abnormal Reaction of Thionyl Chloride with Carboxylic Acids. Tetrahedron Lett. 1968, 49, 5149-5152.
28. Dogan, J.; Karminski-Zamola, G.; Boykin, D. W. Synthesis and Photosynthesis of Substituted Benzo[b]thieno[3, 2-c]quinolones. Heterocycl. Commun. 1996, 2, 213-217.
29. Dogan, J.; Karminski-Zamola, G.; Boykin, D. W. Photosynthesis of Some New Heteropolycyclic Quinolones. Heterocycles 1995, 41, 1659-1667.
30. Baum, E. Brenzschleimsäurechlorid als Acrylirungsmittel. Synthese der Pyromycursäure. Ber. 1904, 2949-2961.
31. Kerr, J. F. R.; Harmon, B. V. Definition and incidence of apoptosis and historical perspective. In Apoptosis: The molecular biology of cell death; Tomei, L. D.; Cope, F. O., Eds.; Cold Spring Harbor Laboratory Press: Plainview, New York, 1991; pp 5-30.
32. Lazebnik, Y. A.; Cole, S.; Cook, C. A.; Nelson, G. W.; Earnshaw, W. C. Nuclear events of apoptosis in vitro in cell-free mitotic extracts: a model system for analysis of the active phase of apoptosis. J. Cell Biol. 1993, 123, 7-22.
33. Evans, D. L.; Dive, C. Effects of cisplatin on the induction of apoptosisin proliferating hepatoma cells and nonproliferating immature thymocytes. Cancer Res. 1993, 53, 2133-2139.
34. Kuribayashi, N.; Sakagami, H.; Sakagami, T.; Niimi, E. I.; Shiokawa, D.; Ikekita, M., Takeda, M.; Tanuma, S. T. Induction of DNA fragmentation in human myelogenous leukemic cell lines by sodium 5,6-benzylidene-L-ascorbate and its related compounds. Anticancer Res. 1994, 14, 969-976.
35. Grdiša, M.; Lopotar, N.; Pavelić, K. Effect of 17-member azalide on tumor cells growth. Exp. Chemother. 1998, 44, 331-336.
36. Zhao, S.; Smith, K. S.; Deveau, A. M.; Dickhaus, C. M.; Johnson, M. A.; Macdonald, T. L.; Cook, J. M. Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines. J. Med Chem. 2002, 45, 1559-1562.
37. Kanthou, C.; Tozer, G. M. The tumor vascular targeting agent combretastatin A-4-phosphate induces reorganization of the actin cytoskeleton and early membrane blebbing in human endothelial cells. Blood 2002, 99, 2060-2069.
38. Li, Q.; Wooda, K. W.; Claiborne, A.; Gwaltney, S. L.; Barr, K. J.; Liu, G.; Gehrke, L.; Credo, R. B.; Hui, Y. H.; Lee, J.; Warner, R. B.; Kovar, P.; Nukkala, M. A.; Zielinski, N. A.; Tahir, S. K.; Fitzgerald, M.; Kim, K. H.; Marsh, K.; Frost, D.; Mg, S. C.; Rosenberg, S.; Sham, H. L. Synthesis and biological evaluation of 2-indolyloxazolines as a new class of tubulin polymerization inhibitors. Discovery of A-289099 as an orally active antitumot agent. Bioorg., Med. Chem. Lett. 2002, 12, 465-469.
39. Bacher, G.; Beckers, T.; Emig, P.; Klenner, T.; Kutscher, B.; Nickel, B. New smal molecule tubulin inhibitors. Pure Appl. Chem. 2001, 73, 1459-1464.
40. Ried, W.; Ochs, W. Umsetzung Asymmetrisch Substituierter Alkine mit Dischwefeldichlorid. Chem. Ber. 1974, 107, 1334-1343.
41. Kanaoka, Y.; Itoh, K.; Hatanaka, Y.; Flippen, J. L.; Karle, I. L.; Witkop, B. Synthetic Photochemistry with Heterocyclic Anilides. Stereochemistry of the Intramolecular 1,5-Hydrogen Shifts in Nonoxidative Photocyclization of Benzo[b]thiophene-2-carboxanilides. J. Org. Chem. 1975, 40 (20), 3001-3003.
42. Gronowitz, S.; Timari, G. Some reactions of Thieno-fused Quinoline N-oxides. J. Heterocycl. Chem. 1990, 27, 1501-1504.
43. Slater, T. F.; Sawyer, B.; Sträuli, U. Studies on Succinate-tetrazolium Reductase Systems. III Points of Coupling of Four Different Tetrazolium Salts. Biochim. Biophys. Acta 1963, 77, 383-393.
44. Mickisch, G.; Fajta, S.; Keilhauer, G.; Schlick, E.; Tschada, R.; Alken, P. Chemosensitivity Testing on Primary Human Cell Carcinoma by a Tetrazolium Based Microculture Assay (MTT). Urol. Res. 1990, 18, 131-136.
45. Herrmann, M.; Lorenz, H. M.; Voll, R.; Grunke, M.; Woith, W.; Kalden, J. R. A rapid and simple method for isolation of apoptotic DNA fragments, Nucl. Acids Res. 1994, 22, 5506-5507.