An expedient, regioselective synthesis of novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their anticancer potential

Tetrahedron

Volumn 64, Issue 28, 2008, Pages 6711-6723

  Chakrabarty, Manas ^a   Kundu, Taraknath ^a   Arima, Shiho ^b   Harigaya, Yoshihiro ^b  

^a BOSE INSTITUTE   (India)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

Anticancer; Bromine in acetic acid; Indazolyl dithiocarbamates; Regioselective synthesis; Thiazolo 5,4 e and 4,5 g indazoles; Thioureidoindazoles

Indexed keywords

2 AMINOTHIAZOLO[4,5 G]INDAZOLE DERIVATIVE; 2 AMINOTHIAZOLO[5,4 E]INDAZOLE DERIVATIVE; 2 THIOTHIAZOLO[4,5 G]INDAZOLE DERIVATIVE; 2 THIOTHIAZOLO[5,4 E]INDAZOLE DERIVATIVE; 6 AMINOTHIAZOLO[4,5 G]INDAZOLE DERIVATIVE; 6 AMINOTHIAZOLO[5,4 E]INDAZOLE DERIVATIVE; 6 THIOTHIAZOLO[4,5 G]INDAZOLE DERIVATIVE; 6 THIOTHIAZOLO[5,4 E]INDAZOLE DERIVATIVE; 8 AMINOTHIAZOLO[4,5 G]INDAZOLE DERIVATIVE; 8 AMINOTHIAZOLO[5,4 E]INDAZOLE DERIVATIVE; 8 THIOTHIAZOLO[4,5 G]INDAZOLE DERIVATIVE; 8 THIOTHIAZOLO[5,4 E]INDAZOLE DERIVATIVE; ANTINEOPLASTIC AGENT; DITHIOCARBAMIC ACID DERIVATIVE; INDAZOLE DERIVATIVE; INDAZOLYL DITHIOCARBAMIC ACID DERIVATIVE; THIOUREIDOINDAZOLE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 45449090774     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.009     Document Type: Article

References (74)

1. Pozharskii A.F., Soldatenkov A.T., and Katritzky A.R. Heterocycles in Life and Society (1997), John Wiley, Chichester, UK
2. Grimmett M.R. Imidazoles. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1996), Pergamon, Oxford 77
3. Hartner F.W. Oxazoles. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1996), Pergamon, Oxford 261
4. Dondoni A., and Meerino P. Thiazoles. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1996), Pergamon, Oxford 373
5. Schofield K., Grimmett M.R., and Keene B.R.T. The Azoles (1976), Cambridge University Press, Cambridge
6. Zirngible L. Azoles. Antifungal Active Substances-Synthesis and Uses (1997), Wiley-VCH, London
7. Wu Y.-J., and Yang B.V. In: Gribble G.W., and Joule J.A. (Eds). Progress in Heterocyclic Chemistry Vol. 18 (2007), Elsevier, Oxford 247
8. Ulrich H. Benzothiazoles and related compounds. In: Schaumann E. (Ed). Science of Synthesis Vol. 11 (2001), Thieme, New York, NY 835
9. Smirnova N.G., Zavarzin I.V., and Krayushkin M.M. Chem. Heterocycl. Comp. 42 (2006) 144
10. Chakrabarty M., Ghosh N., and Harigaya Y. Heterocycles 62 (2004) 779
11. Chakrabarty M., Ghosh N., and Harigaya Y. Tetrahedron Lett. 45 (2004) 4955
12. Chakrabarty M., Kundu T., Arima S., and Harigaya Y. Tetrahedron Lett. 46 (2005) 2865
13. See Refs. 1-9 and 14-16 in Ref. 4b and Refs. 3-7 in Ref. 5a.
14. Elguero J. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 5 (1984), Pergamon, New York, NY 167
15. Kilpatrick G.J., Jones B.J., and Tyers M.B. Nature 330 (1987) 746
16. Schumann P., Collot V., Hommet Y., Gsell W., Dauphin F., Sopkova J., Mackenzie E.T., Duval D., Boulouard M., and Rault S. Bioorg. Med. Chem. Lett. 11 (2001) 1153
17. In: Budavari S. (Ed). The Merck Index. 11th ed. (1989), Merck, Rahway, NJ
18. Bendazac: p 161;
19. Benzydamine: p 175.
20. Ko F.N., Wu C.C., Kuo S.C., Lee F.Y., and Teng C.M. Blood 84 (1994) 4226
21. Chun Y.-S., Yeo E.-J., and Park J.-W. Cancer Lett. 207 (2004) 1
22. Chen C.-J., Hsu M.-H., Huang L.-J., Yamori T., Chung J.-G., Lee F.-Y., Teng C.-M., and Kuo S.-C. Biochem. Pharmacol. 75 (2007) 360
23. FS-32:. Yeu J.-P., Yeh J.-T., Chen T.-Y., and Uang B.-J. Synthesis (2001) 1775
24. WAY-169916:. Steffan R.J., Matelan E., Ashwell M.A., Moore W.J., Solvibile W.R., Trybulski E., Chadwick C.C., Chippari S., Kenney T., Eckert A., Borges-Marcucci L., Keith J.C., Xu Z., Mosayak L., and Harnish D.C. J. Med. Chem. 47 (2004) 6435
25. McBride C.M., Renhowe P.A., Gesner T.G., Jansen J.M., Lin J., Ma S., Zhou Y., and Shafer C.M. Bioorg. Med. Chem. Lett. 16 (2006) 3789
26. Fraley M.E., Steen J.T., Brnardic E.J., Arrington K.L., Spencer K.L., Hanney B.A., Kim Y., Hartman G.D., Stirdivant S.M., Drakas B.A., Rickert K., Walsh E.S., Hamilton K., Buser C.A., Hardwick J., Tao W., Beck S.C., Mao X., Lobell R.B., Sepp-Lorenzino L., Yan Y., Ikuta M., Munshi S.K., Kuo L.C., and Kreatsoulas C. Bioorg. Med. Chem. Lett. 16 (2006) 6049
27. Li X., Chu S., Feher V.A., Khalili M., Nie Z., Margosiak S., Nikulin V., Levin J., Sprankle K.G., Tedder M.E., Almassy R., Appelt K., and Yager K.M. J. Med. Chem. 46 (2003) 5663
28. Bouissance L., Kazzouli S.El., Léonce S., Pfeiffer B., Rakib E.M., Khouili M., and Guillaumet G. Bioorg. Med. Chem. 14 (2006) 1078
29. Yakaiah T., Lingaiah B.P.V., Narsaiah B., Shireesha B., Kumar B.A., Gururaj S., Parthasarathy T., and Sridhar B. Bioorg. Med. Chem. Lett. 17 (2007) 3445
30. Breitfelder, S.; Mailar, U.; Brandl, T.; Hoenke, C.; Grauert, M.; Pautsch, A.; Hoffmann, M.; Kalkbrenner, F.; Joergensen, A.; Schaenzle, G.; Peters, S.; Büttner, F.; Bauer, E. PCT Intl. Appl., 2006, WO-06040279;
31. Betzemeier, B.; Brandl, T.; Breitfelder, S.; Bruckner, R.; Gerstberger, T.; Gmachi, M.; Grauert, M.; Hilberg, F.; Hoenke, C.; Hoffmann, M.; Impagnatiello, M.; Kessler, D.; Klein, C.; Krist, B.; Mailer, U.; McConnell, D.; Reither, C.; Scheuer, S.; Schoop, A.; Schweifer, N.; Simon, O.; Steegmaier, M.; Steurer, S.; Waizenegger, I.; Weyer-cz-ernilofsky, V.; Zoephel, A. PCT Intl. Appl., 2006, WO-06040281.
32. Qian X., Li Z., and Yang Q. Bioorg. Med. Chem. 15 (2007) 6846
33. Boros E.E., Johns B.A., Garvey E.P., Koble C.S., and Miller W.H. Bioorg. Med. Chem. Lett. 16 (2006) 5668
34. Testard A., Logé C., Léger B., Robert J.-M., Lozach O., Blairvacq M., Meijer L., Thiéry V., and Besson T. Bioorg. Med. Chem. Lett. 16 (2006) 3419
35. Okafor C.O. J. Org. Chem. 38 (1973) 4383
36. Kitazawa, N.; Veno, K.; Takahashi, K.; Kimura, T.; Satyaki, A.; Kawaro, K.; Okabe, T.; Komatsu, M.; Matsunaga, M.; Kubota, A. Eur. Pat., 1998, 097672;
37. Chem. Abstr. 129 (1998) 302552
38. Grandolini G., Ricci A., Martini A., and Mezzeti T. J. Heterocycl. Chem. 3 (1966) 299
39. Hugershoff A. Ber. Dtsch. Chem. Ges. 36 (1903) 3121
40. Metzger J., and Plank H. Chim. Ind. (Milan) 75 (1956) 929
41. Chem. Abstr. 51 (1957) 4358
42. Ambati N.B., Anand V., and Hanumantha P. Synth. Commun. 27 (1997) 1487
43. Moghaddam M., and Boeini H.Z. Synlett (2005) 1612
44. Jacobson P. Ber. Dtsch. Chem. Ges. 19 (1886) 1067
45. Jackson Y.A., Lyon M.A., Townsend N., Bellabe K., and Soltanik F. J. Chem. Soc., Perkin Trans. 1 (2000) 205
46. Mu X.-J., Zou J.-P., Zeng R.-S., and Wu J.-C. Tetrahedron Lett. 46 (2005) 4345
47. Bose D.S., and Idrees M. J. Org. Chem. 71 (2006) 8261
48. Bose D.S., and Idrees M. Tetrahedron Lett. 48 (2007) 669
49. Appel R., Janssen H., Siray M., and Knoch F. Chem. Ber. 118 (1985) 1632
50. Chabane H., Lamazi C., Thiéry V., Guillaumet G., and Besson T. Tetrahedron Lett. 43 (2002) 2483
51. Alexandre F.-R., Berecibar A., Wrigglesworth R., and Besson T. Tetrahedron Lett. 44 (2003) 4455
52. Cottyn B., Vichard D., Terrier F., Nioche P., and Raman C.S. Synlett (2007) 1203
53. Monde K., Takasugi M., and Ohnishi T. J. Am. Chem. Soc. 116 (1994) 6650
54. Monde K., Tamura K., Takasugi M., Kobyashi K., and Somei M. Heterocycles 30 (1994) 263
55. Mehta R.G., Liu J., Constantinou A., Thomas C.F., Hawthorne M., You M., Gerhäuser, Pezzuto J.M., Moon R.C., and Moriarty R.M. Carcinogenesis 16 (1995) 399
56. Friedman S.G., and Golub D.K. Khim. Geterotsikl. Soedin. (1967) 481
57. Chem. Abstr. 68 (1968) 88182y
58. Friedman S.G., and Golub D.K. Chem. Heterocycl. Comp. 3 (1967) 385
59. Friedman S.G., and Kiprianov A.I. Zh. Org. Khim. 4 (1968) 696
60. Chem. Abstr. 69 (1968) 20394j
61. Bellavita N.C., Martani A., and Franolini A. Ann. Chim. (Rome) 58 (1968) 823
62. Chem. Abstr. 70 (1969) 37726n
63. Tarabasanu-mihaila C., Floru L., Balta E., and Predescu A. Rev. Roum. Chim. 18 (1973) 889
64. Chem. Abstr. 79 (1973) 127353d
65. Radulescu C., Tarabasanu-mihaila C., Hossu A.M., and Ionita I. Rev. Roum. Chim. 55 (2004) 1006
66. Chem. Abstr. 142 (2005) 465078
67. Mosman T. J. Immunol. Methods 65 (1983) 55
68. Wilson A.P. In: Masters J.R.W. (Ed). Cytotoxicity and Viability Assays in Animal Cell Culture: A practical Approach Vol. 1 (2000), Oxford University Press, Oxford 175
69. Commercially available (CAS no. 5228-49-9; Alfa-Aesar, item no. L16155);
70. Commercially available (CAS no. 5228-48-8; Alfa-Aesar, item no. L7724);
71. Kamel M. J. Prakt. Chem. (Leipzig) 31 (1966) 100 CAS no. 6850-23-3
72. Kametani T. J. Heterocycl. Chem. 14 (1977) 1175
73. Boyer J.H. J. Chem. Res., Synop. (1986) 416
74. Stankevicius A. Khim. Geterotsikl. Soedin. (1988) 491