Novel 1H-pyrrolo[2,3-b]pyridine derivative nortopsentin analogues: Synthesis and antitumor activity in peritoneal mesothelioma experimental models

Journal of Medicinal Chemistry

Volumn 56, Issue 17, 2013, Pages 7060-7072

  Carbone, Anna ^a   Pennati, Marzia ^b   Parrino, Barbara ^a   Lopergolo, Alessia ^b   Barraja, Paola ^a   Montalbano, Alessandra ^a   Spanò, Virginia ^a   Sbarra, Stefania ^b   Doldi, Valentina ^b   De Cesare, Michelandrea ^b   Cirrincione, Girolamo ^a   Diana, Patrizia ^a   Zaffaroni, Nadia ^b  

^a UNIVERSITY OF PALERMO   (Italy)

^b NATIONAL CANCER INSTITUTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

[3 [2 (1H INDOL 3YL) 1,3 THIAZOL 4 YL] 1 METHYL 1H PYRROLO(2,3 B)PYRIDINE]; [3 [2 (5 FLUORO 1 METHYL 1H INDOL 3YL) 1,3 THIAZOL 4 YL] 1 METHYL 1H PYRROLO(2,3 B)PYRIDINE]; [3 [2 (5 FLUORO 1 METHYL 1H INDOL 3YL) 1,3 THIAZOL 4 YL] 1H PYRROLO(2,3 B)PYRIDINE]; ANTINEOPLASTIC AGENT; PACLITAXEL; PYRROLO[2,3 B]PYRIDINE DERIVATIVE; SURVIVIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG EFFECT; DRUG RESPONSE; DRUG SYNTHESIS; EXPERIMENTAL MODEL; FEMALE; HUMAN; HUMAN CELL; IC 50; NONHUMAN; PERITONEUM MESOTHELIOMA; TUMOR MODEL; TUMOR XENOGRAFT;

ANTINEOPLASTIC AGENTS; CELL LINE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MESOTHELIOMA; PERITONEAL NEOPLASMS; PYRIDINES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84884252001     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400842x     Document Type: Article

References (52)

1. Antman, K.; Shemin, R.; Ryan, L.; Klegar, K.; Osteen, R.; Herman, T.; Lederman, G.; Corson, J. Malignant Mesothelioma: prognostic variables in a registry of 180 patients, the Dana-Farber Cancer Institute and Brigham and Women's Hospital experience over two decades, 1965-1985 J. Clin. Oncol. 1988, 6, 147-153
2. Baratti, D.; Kusamura, S.; Deraco, M. Diffuse malignant peritoneal Mesothelioma: systematic review of clinical management and biological research J. Surg. Oncol. 2011, 103, 822-831
3. Deraco, M.; Bartlett, D.; Kusamura, S.; Baratti, D. Consensus statement on peritoneal Mesothelioma J. Surg. Oncol. 2008, 98, 268-272
4. Yan, T. D.; Deraco, M.; Baratti, D.; Kusamura, S.; Elias, D.; Glehen, O.; Gilly, F. N.; Levine, E. A.; Shen, P.; Mohamed, F.; Moran, B. J.; Morris, D. L.; Chua, T. C.; Piso, P.; Sugarbaker, P. H. Cytoreductive surgery and hyperthermic intraperitoneal chemotherapy for malignant peritoneal Mesothelioma: multi-institutional experience J. Clin. Oncol. 2009, 27, 6237-6242
5. Baratti, D.; Kusamura, S.; Cabras, A. D.; Dileo, P.; Laterza, B.; Deraco, M. Diffuse malignant peritoneal Mesothelioma: failure analysis following cytoreduction and hyperthermic intraperitoneal chemotherapy (HIPEC) Ann. Surg. Oncol. 2009, 16, 463-472
6. Carteni, G.; Manegold, C.; Garcia, G. M.; Siena, S.; Zielinski, C. C.; Amadori, D.; Liu, Y.; Blatter, J.; Visseren-Grul, C.; Stahel, R. Malignant peritoneal Mesothelioma-results from the International Expanded Access Program using pemetrexed alone or in combination with a platinum agent Lung Cancer 2009, 64, 211-218
7. Barraja, P.; Diana, P.; Lauria, A.; Montalbano, A.; Almerico, A. M.; Dattolo, G.; Cirrincione, G. Pyrrolo[2,3- h ]quinolinones: synthesis and photo-chemotherapic activity Bioorg. Med. Chem. Lett. 2003, 13, 2809-2811
8. Barraja, P.; Diana, P.; Montalbano, A.; Carbone, A.; Cirrincione, C.; Viola, G.; Salvador, A.; Vedaldi, D.; Dall'Acqua, F. Thiopyrano[2,3- e ]indol-2-ones: Angelicin heteroanalogues with potent photoantiproliferative activity Bioorg. Med. Chem. 2008, 16, 9668-9683
9. Barraja, P.; Spanò, V.; Diana, P.; Carbone, A.; Cirrincione, G.; Vedaldi, D.; Salvador, A.; Viola, G.; Dall'Acqua, G. Pyrano[2,3- e ]isoindol-2-ones, a new angelicin heteroanalogue Bioorg. Med. Chem. Lett. 2009, 19, 1711-1714
10. Barraja, P.; Diana, P.; Montalbano, A.; Martorana, A.; Carbone, A.; Cirrincione, G. Synthesis of the new ring system 2-oxo-[1,4]oxazino[3,2- e ]indole heteroanalogue of angelicin Tetrahedron Lett. 2009, 50, 4182-4184
11. Barraja, P.; Spanò, V.; Diana, P.; Carbone, A.; Cirrincione, G. Synthesis of the new ring system 6,8-dihydro-5 H -pyrrolo[3,4- h ]quinazoline, heteroanalogue of angelicin Tetrahedron Lett. 2009, 50, 5389-5391
12. Barraja, P.; Caracausi, L.; Diana, P.; Carbone, A.; Montalbano, A.; Cirrincione, G.; Brun, P.; Palù, G.; Castagliuolo, I.; Dall'Acqua, F.; Vedaldi, D.; Salvador, A. Synthesis of pyrrolo[3,2- h ]quinolinones with good photochemotherapeutic activity and no DNA damage Bioorg. Med. Chem. 2010, 18, 4830-4843
13. Barraja, P.; Caracausi, L.; Diana, P.; Montalbano, A.; Carbone, A.; Salvador, A.; Brun, P.; Castagliuolo, I.; Tisi, S.; Dall'Acqua, F.; Vedaldi, D.; Cirrincione, G. Pyrrolo[3,2- h ]quinazolines as photochemotherapeutic agents ChemMedChem. 2011, 6, 1238-1248
14. Barraja, P.; Diana, P.; Montalbano, A.; Carbone, A.; Viola, G.; Basso, G.; Salvador, A.; Vedaldi, D.; Dall'Acqua, F.; Cirrincione, G. Pyrrolo[3,4- h ]quinolinones a new class of photochemotherapeutic agents Bioorg. Med. Chem. 2011, 19, 2326-2341
15. Barraja, P.; Diana, P.; Spanò, V.; Montalbano, A.; Carbone, A.; Parrino, B.; Cirrincione, G. An efficient synthesis of pyrrolo[3′, 2′:4,5]thiopyrano[3,2- b ]pyridin-2-one: a new ring system of pharmaceutical interest Tetrahedron 2012, 68, 5087-5094
16. Barraja, P.; Caracausi, L.; Diana, P.; Spanò, V.; Montalbano, A.; Carbone, A.; Parrino, B.; Cirrincione, G. Synthesis and antiproliferative activity of the ring system [1,2]ozaxolo[4,5- g ]indole ChemMedChem 2012, 7, 1901-1904
17. Shin, J.; Seo, Y.; Cho, K. W.; Rho, J. R.; Sim, C. J. New Bis(indole)alkaloids of the topsentin class from the sponge Spongosorites genitrix J. Nat. Prod. 1999, 62, 647-649
18. Casapullo, A.; Bifulco, G.; Bruno, I.; Riccio, R. Hamacanthin classes from the Mediterranean marina sponge Raphisia lacazei J. Nat. Prod. 2000, 63, 447-451
19. Bao, B.; Sun, Q.; Yao, X.; Hong, J.; Lee, C.; Sim, C. J.; Jung, J. H. Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp J. Nat. Prod. 2005, 68, 711-715
20. Gul, W.; Hamann, M. T. Indole alkaloid marine natural products: an established source of cancer drug leads with considerable promise for the control of parasitic, neurological and other diseases Life Sci. 2005, 78, 442-453
21. Shimizu, S.; Yamamoto, Y.; Inagaki, L.; Koshimura, S. Antitumor effect and structure-activity relationship of asterriquinone analogs Gann 1982, 73, 642-648
22. Kohmoto, S.; Kashman, Y.; McConnel, O. J.; Rinehart, K. L., Jr.; Wrigh, A.; Koehn, F. The first total synthesis of Dragmacidin D J. Org. Chem. 1988, 53, 3116-3118
23. Morris, S. A.; Andersen, R. J. Brominated bis(indole)alkaloids from the marine sponge Hexadella sp Tetrahedron 1990, 46, 715-720
24. Fahy, E.; Potts, B. C. M.; Faulkner, D. J.; Smith, K. 6-Bromotryptamine derivatives from the Gulf of California tunicate Didemnum candidum J. Nat. Prod. 1991, 54, 564-569
25. Wright, A. E.; Pomponi, S. A.; Cross, S. S.; McCarthy, P. A new bis-(indole)alkaloids from a deep-water marine sponge of the genus Spongosorites J. Org. Chem. 1992, 57, 4772-4775
26. Capon, R. J.; Rooney, F.; Murray, L. M.; Collins, E.; Sim, A. T. R.; Rostas, J. A. P.; Butler, M. S.; Carrol, A. R. Dragmacidins: New protein phosphatase inhibitors from a Southern Australian deep-water marine sponge Spongosorites sp J. Nat. Prod. 1998, 61, 660-662
27. Bokesch, H. R.; Pannell, L. K.; McKee, T. C.; Boyd, M. R.; Coscinamides, A. B, and C, three new bis indole alkaloids from the marine sponge Coscinoderma sp Tetrahedron Lett. 2000, 41, 6305-6308
28. Alvarez, M.; Salas, M. Marine, nitrogen-containing heterocyclic natural products-structures and syntheses of compounds containing indole units Heterocycles 1991, 32, 1391-1429
29. Sakem, S.; Sun, H. H. Nortopsentins A, B and C. Cytotoxic and antifungal imidazolediylbis[indoles] from the sponge Spongosorites ruetzleri J. Org. Chem. 1991, 56, 4304-4307
30. Kawasaki, I.; Yamashita, M.; Ohta, S. Total synthesis of nortopsentins A-D marine alkaloids Chem. Pharm. Bull. 1996, 44, 1831-1839
31. Jiang, B.; Gu, X. H. Synthesis and cytotoxicity evaluation of bis(indolyl)thiazole, bis(indolyl)pyrazinone and bis(indolyl)pyrazine: analogues of cytotoxic marine bis(indole)alkaloid Bioorg. Med. Chem. 2000, 8, 363-371
32. Jiang, B.; Yang, C. G.; Xiong, W. N.; Wang, J. Synthesis and cytotoxicity evaluation of novel indolylpyrimidines and indolylpyrazines as potential antitumor agents Bioorg. Med. Chem. 2001, 9, 1149-1154
33. Jiang, B.; Xiong, W. N.; Yang, C. G. Synthesis and antitumor evaluation of novel monoindolyl-4-trifluoromethylpyridines and bisindolyl-4- trifluoromethylpyridines Bioorg. Med. Chem. Lett. 2001, 11, 475-477
34. Xiong, W. N.; Yang, C. G.; Jiang, B. Synthesis of novel analogues of marine indole alkaloids: mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines as potential anticancer agents Bioorg. Med. Chem. 2001, 9, 1773-1780
35. Diana, P.; Carbone, A.; Barraja, P.; Montalbano, A.; Martorana, A.; Dattolo, G.; Gia, O.; Dalla Via, L.; Cirrincione, G. Synthesis and antitumor properties of 2,5-bis(3′-indolyl)thiophenes: analogues of marine alkaloid nortopsentin Bioorg. Med. Chem. Lett. 2007, 17, 2342-2346
36. Diana, P.; Carbone, A.; Barraja, P.; Martorana, A.; Gia, O.; Dalla Via, L.; Cirrincione, G. 3,5-bis(3′-indolyl)pyrazoles, analogues of marine alkaloid nortopsentin: synthesis and antitumor properties Bioorg. Med. Chem. Lett. 2007, 17, 6134-6137
37. Diana, P.; Carbone, A.; Barraja, P.; Kelter, H. H.; Fiebig, G.; Cirrincione, G. Synthesis and antitumor activity of 2,5-bis(3′-indolyl)- furans and 3,5-bis(3′-indolyl)-isoxazoles, nortopsentin analogues Bioorg. Med. Chem. 2010, 18, 4524-4529
38. Carbone, A.; Parrino, B.; Spanò, V.; Barraja, P.; Cirrincione, G.; Diana, P.; Maier, A.; Kelter, G.; Fiebig, H.-H. Synthesis and antiproliferative activity of 2,5-bis(3′-indolyl)pyrroles, analogues of the marine alkaloid nortopsentin Mar. Drugs 2013, 11, 643-654
39. Kumar, D.; Kumar, N. M.; Chang, K. H.; Gupta, R.; Shah, K. Synthesis and in vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles Bioorg. Med. Chem. Lett. 2011, 21, 5897-5900
40. Jacquemard, U.; Dias, N.; Lansiaux, C.; Bailly, C.; Logè, C.; Robert, J. M.; Lozach, O.; Meijer, L.; Merour, J. Y.; Routier, S. Synthesis of 3,5-bis(2-indolyl)pyridine and 3-[(2-indolyl)-5-phenyl]pyridine derivatives as CDK inhibitors and cytotoxic agents Bioorg. Med. Chem. 2008, 16, 4932-4953
41. Diana, P.; Carbone, A.; Barraja, P.; Montalbano, A.; Parrino, B.; Lopergolo, A.; Pennati, M.; Zaffaroni, N.; Cirrincione, G. Synthesis and antitumor activity of 3-(2-phenyl-1,3-thiazol-4-yl)-1 H -indoles and 3-(2-phenyl-1,3-thiazol-4-yl)-1 H -7-azaindoles ChemMedChem. 2011, 6, 1300-1309
42. Gu, X. H.; Wan, X. Z.; Jiang, B. Syntheses and biological activities of bis(3-indolyl)thiazoles, analogues of marine bis(indole)alkaloid nortopsentin Bioorg. Med. Chem. Lett. 1999, 9, 569-572
43. Senderowicz, A. M. Small-molecule cyclin-dependent kinase modulators Oncogene 2003, 22, 6609-6620
44. Zaffaroni, N.; Costa, A.; Pennati, M.; De Marco, C.; Affini, E.; Madeo, M.; Erdas, R.; Cabras, A.; Kusamura, S.; Baratti, D.; Deraco, M.; Daidone, M. G. Survivin is highly expressed and promotes cell survival in malignant peritoneal mesothelioma Cell Oncol. 2007, 29, 453-466
45. Pennati, M.; Folini, M.; Zaffaroni, N. Targeting survivin in cancer therapy Expert Opin. Ther. Targets 2008, 12, 463-476
46. O'Connor, D. S.; Wall, N. R.; Porter, A. C.; Altieri, D. C. A p34(cdc2) survival checkpoint in cancer Cancer Cell. 2002, 2, 43-54
47. 34 by flavopiridol enhances tumor cell apoptosis Cancer Res. 2003, 63, 230-235
48. Pennati, M.; Campbell, A. J.; Curto, M.; Binda, M.; Cheng, Y.; Wang, L. Z.; Curtin, N.; Golding, B. T.; Griffin, R. J.; Hardcastle, I. R.; Henderson, A.; Zaffaroni, N.; Newell, D. R. Potentiation of paclitaxel-induced apoptosis by the novel cyclin-dependent kinase inhibitor NU6140: a possible role for survivin down-regulation Mol. Cancer Ther. 2005, 4, 1328-1337
49. Zaffaroni, N.; Pennati, M.; Colella, G.; Perego, P.; Supino, R.; Gatti, L.; Pilotti, S.; Zunino, F.; Daidone, M. G. Expression of the anti-apoptotic gene survivin correlates with taxol resistance in human ovarian cancer Cell. Mol. Life Sci. 2002, 59, 1406-1412
50. Chou, T. C.; Talalay, P. Quantitative analysis of dose-effect relationships: the combined effects of multiple drugs or enzyme inhibitors Adv. Enzyme Reg. 1984, 22, 27-55
51. Kirchberg, S.; Frohlich, R.; Studer, A. Stereoselective palladium-catalyzed carboaminoxylations of indoles with arylboronic acids and TEMPO Angew. Chem., Int. Ed. 2009, 48, 4235-4238
52. Soledade, M.; Pedras, C.; Liu, J. Designer phytoalexins: probing camalexin detoxification pathways in the phytopathogen Rhizoctonia solani Org. Biomol. Chem. 2004, 2, 1070-1076