Synthesis of new N-[3-(Benzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)-ylidene] substituted benzamides

A series of novel N-[3-(2-benzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)-ylidene] substituted benzamides (2a--k) were efficiently synthesized by heterocyclization of the corresponding 1-(benzo[d]thiazol-2-yl)-3-aroylthioureas (1a--k). The cyclization was achieved by the reaction of a-bromoacteone produced in situ using bromine in dry acetone in the presence of triethylamine.

Anahtar Kelimeler:

N-[3-(2-Benzothiazolyl)-4-methylthiazol-2(3H)-ylidene] substituted benzamides, 1-(benzo[d] thiazol-2-yl)-3-aroylthioureas, 2-aminobenzothiazoles

Synthesis of new N-[3-(Benzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)-ylidene] substituted benzamides

Keywords:

N-[3-(2-Benzothiazolyl)-4-methylthiazol-2(3H)-ylidene] substituted benzamides, 1-(benzo[d] thiazol-2-yl)-3-aroylthioureas, 2-aminobenzothiazoles,

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Maeda, R.; Hirose K. United State Patent, US, 1977, 4, 018, 785.
Werbel, L. M.; Degnan, M. B.; Harger, G. F.; Capps, D. B. J. Med. Chem. 1972, 15, 955–963.
Boyce, R. J.; Mulqueen, G. C.; Pattenden, G. Tetrahedron Lett. 1994, 35, 5705–5708.
Wipf, P.; Fritch, P. C. Tetrahedron Lett. 1994, 35, 5397–5400.
Lai, J. Y.; Yu, J.; Mekonnen, B.; Falck, J. R. Tetrahedron Lett. 1996, 37, 7167–7170.
Acardi, A.; Attanasi, O. A.; Giorgi, G.; Fillippone, P.; Rossi, E.; Santeusanio, S. Tetrahedron Lett. 2003, 44, 8391–8394.
Fahmy, H. T. Y.; Bekhit, A. A. Pharmazie 2002, 57, 800–803.
Vittoria, D. M.; Mazzoni, O.; Piscopo, E.; Caligmano A.; Bolognese, A. J. Med. Chem. 1992, 35, 2910–2912.
Omar, A. M.; Eshba, N. H. J. Pharm. Sciences 1984, 73, 1166–1168.
Chaudhary, M.; Parmar, S. S.; Chaudhari S. K.; Ramasastry, B. V. J. Pharm. Sciences 1976, 65, 443–446.
Ulusoy, N. Arzneim.-Forsch./Drug Res. 2002, 52, 565–571.
K¨ u¸ c¨ ukg¨ uzel, G.; Kocatepe, A.; Clercq, E. D.; S ¸ahin F.; G¨ ull¨ uce, M. Eur. J. Med. Chem. 2006, 41, 353–359. b) Kucukbay, H.; Cetinkaya, E.; Durmaz, R. Arzneim.-Forsch./Drug Res. 1995, 45, 1331–1334.
Amin, K. M.; Rahman, A. D. E.; Al-Eryani, Y. A. Bioorg. Med. Chem. 2008, 16, 5377–5388.
Ragab, F. A.; Hussain, M. M.; Hanna, M. M.; Hassan, G. S. J. Pharm. Sciences 1993, 34, 387–390.
Rooney, C. S.; Rokach, J.; Cragoe, E. J. United States Patent, US, 1980, 4, 181, 661.
Walton, M. I.; Wilson, S. C.; Hardcastle, S. R.; Mirza, A. R. Workman, P. Mol. Cancer Ther. 2005, 4, 1369–1377. Sihgh, S. P.; Parmar, S. S.; Raman, K.; Stenherb, V. I. Chem. Pharm. Bulletin 1981, 81, 197.
Shih, M. H.; Ke, F. Y. Bioorg. & Med. Chem. 2004, 12, 4633–4643.
Jimonet, P.; Audiau, F.; Barreau, M.; Blanchard, J. C.; Boireau, A.; Bour, Y.; Col´ eno, M. A.; Doble, A.; Doerflinger, G.; Do Huu, C.; et al. J. Med. Chem. 1999, 42, 2828–2835.
Sawhney, S. N.; Arora, S. K.; Singh, J. V. Ind. J. Chem. 1978, 16B, 605–609.
Bensimon, G.; Lacomblez, L.; Meininger, V. New Engl. J. Med. 1994, 330, 585–591.
Foscolos, G.; Tsatsas, A.; Champagnac, A.; Pommier, M. Ann. Pharm. Fr. 1977, 35, 295–307.
Shirke, V. G.; Bobade, K.; Bhamaria, R. P.; Khadse, B. G.; Sengupta, S. R. Ind. Drugs 1990, 27, 350–356.
Paget, C. J.; Kinser, K.; Stone, R. L.; Delong, D. C. J. Med. Chem. 1969, 12, 1061–1066.
Piscitellia, F.; Ballatorea, C.; Smith A. B. Bioorg. Med. Chem. Lett. 2010, 20, 644–648.
Hutchinson, I.; Jennings, S. A.; Vishnuvajjala, B. R. J. Med. Chem. 2002, 45, 744–749.
Thanh, N. D. E-Journal of Chemistry 2012, 9, 55–62.
Saeed, A.; Rafique, H.; Hameed, A.; Rasheed, S. Pharm. Chem. J. 2008, 42, 191–195. a) Saeed, A.; Al-Masoudi, N. A.; Ahmed, A. A.; Pannecouque, C. Z. Naturforsch, 2011, 66b, 512–514. b) Saeed, A.; Zaman, S.; Bolte, M. Synthetic Commun. 2008, 38, 2185–2199. c) Saeed, A.; Shaheen, U.; Hameed, A.; Kazmi, F. J. Fluorine Chem. 2010, 131, 333–339.