Novel synthesis and antitumor evaluation of polyfunctionally substituted heterocyclic compounds derived from 2-cyano-N-(3-cyano-4,5,6,7- tetrahydrobenzo[b]thiophen-2-yl)-acetamide

Molecules

Volumn 16, Issue 1, 2011, Pages 52-73

  Shams, Hoda Z ^a   Mohareb, Rafat M ^b,c   Helal, Maher H ^a   Mahmoud, Amira E ^a  

^a Helwan University   (Egypt)

^b October University for Modern Sciences and Arts   (Egypt)

^c CAIRO UNIVERSITY   (Egypt)

Author keywords

4,5,6,7 tetrahydrobenzo b thiophene; Antitumor; Pyrazole; Pyridine; Thiazole

Indexed keywords

ANTINEOPLASTIC AGENT; HETEROCYCLIC COMPOUND; THIOPHENE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; DRUG SCREENING; HUMAN; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CYCLIZATION; DRUG SCREENING ASSAYS, ANTITUMOR; HETEROCYCLIC COMPOUNDS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THIOPHENES;

EID: 79251527910     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16010052     Document Type: Article

References (35)

1. Chobot, V.; Vytlačilová, J.; Kubicová, L.; Opletal, L.; Jahodář, L.; Laaskso, I.; Vuorela, P. Phototoxic activity of a thiophene polyacetylene from Leuzea carthamoides. Fitoterapia 2006, 77, 194-198.
2. Tor, Y.; Valle, S. D.; Jaramillo, D.; Srivatsan, S. G.; Rios, A.; Weizman, H. Designing new isomorphic fluorescent nucleobase analogues: the thieno[3, 2-d]pyrimidine core. Tetrahedron 2007, 63, 3608-3614.
3. Okutan, M.; Yerli, Y.; San, S. E.; Yilmaz, F.; Günaydin, O.; Durak, M. Dielectric properties of thiophene based conducting polymers. Syn. Metals 2007, 157, 368-373.
4. Ogawa, S.; Muraoka, H.; Kikuta, K.; Saito, F.; Sato, R. Design of reversible multi-electron redox systems using benzochalcogenophenes containing aryl and/or ferrocenyl fragments. J. Organometal Chem. 2007, 692, 60-69.
5. Destri, S.; Giovanella, U.; Fazio, A.; Porzio, W.; Gabriele, B.; Zotti, G. Poly (bithiophene)-co-3, 4-di (methoxycarbonyl) methyl thiophene for LED. Org. Electron. 2002, 3, 149-156.
6. Bouachine, M.; Benaqqa, O.; Toufik, H.; Hamidi, M.; Lère-Porte, J.-P.; Serein-Spirau, F.; Amine, A. Experimental and quantum chemical investigation of new electroluminescent material based on thiophene, phenylene and antracene. Analele Universitatii din Bucuresti 2010, 19, 35-44.
7. Batista, R. M. F.; Costa, S. P. G; Belsley, M.; Lodeiro, C.; Raposo, M. M. M. Synthesis and characterization of novel (oligo) thienyl-imidazo- phenanthrolines as versatile π conjugated systems for several optical applications. Tetrahedron 2008, 64, 9230-9238.
8. Jarvest, R. L.; Pinto, I. L.; Ashman, S, M.; Dabrowski, C. E.; Fernandez, A. V.; Jennings, L. J.; Lavery, P.; Tew, D. G. Inhibition of herpes proteases and antiviral activity of 2-substituted thieno[2, 3-d]oxazinones. Bioorg. Med. Chem. Lett. 1999, 9, 443-448.
9. Wardakhan, WW.; Shams. H. Z.; Moustafa, H. E. Synthesis of polyfunctionally substituted thiophene, thieno [2, 3-b]pyridine and thieno[2, 3-d]pyrimidine derivatives. Phosph. Sulf. Silicon 2005, 180, 1815-1827.
10. Isabel C. F. R., Ricardo C. C, Letícia M. E., Maria-João R. P. Q. Screening of antimicrobial activity of diarykamines in the 2, 3, 5-trimethylbenzo[b]thiopheneseries: a structure-activity evaluation study. Bioorg. Med. Chem. Lett. 2004, 14, 5831-5833.
11. Pinto, E.; Queiroz, M.-J. R. P.; Vale-Silva, L. A.; Oliveira, J. F.; Begouin, A.; Begouin, J.-M.; Kirsch, G. Antifungal activity of synthetic di (hetero) arylamines based on the benzo[b]thiophene moiety. Bioorg. Med. Chem. 2008, 16, 8172-8177.
12. Dannhardt, G.; Kiefer, W.; Krämer, G.; Maehrlein, S.; Nowe, U.; Fiebich, B. The pyrrole moiety as a template for COX-1/COX-2 inhibitors. Eur. J. Med. Chem. 2000, 35, 499-510.
13. Brault, L.; Migianu, E.; Néguesque, A.; Battaglia, E.; Bagrel, D.; Kirsch, G. New thiophene analogues of kenpaullone: synthesis and biological evaluation in breast cancer cells. Eur. J. Med. Chem. 2005, 40, 757-763.
14. Starčevic, K.; Karminski-Zamola, G.; Piantanida, I.; Zinic, M.; Suman, L.; Kralj, M. Photoinduced switch of a DNA/RNA inactive molecule into a classical intercalator. J. Am. Chem. Soc. 2005, 127, 1074-1075.
15. Romagnoli, R.; Baraldi, P. G.; Carrion, M. D.; Cara, C. L.; Cruz-Lopez, O.; Preti, D.; Tolomeo, M.; Grimaudo, S.; Cristina, A. D.; Zonta, N.; Balzarini, J.; Brancale, A.; Sarkar, T.; Hamel, E. Design, synthesis and biological evaluation of thiophene analogues of chalcones. Bioorg. Med. Chem. 2008, 16, 5367-5376.
16. Ferreira, I. C. F. R.; Queiroz, M. R. P.; Vilas-Boas, M.; Estevinho, L. M.; Begouin, A.; Kirsch G Evaluation of the antioxidant properties of diarylamines in benzo[b]thiophene series by free radical scavenging activity and reducing power, Bioorg. Med. Chem. Lett. 2006, 16, 1384-1387.
17. Pinto, I. L.; Jarvest, R. L.; serafinowska, H. T. The synthesis of 5-alkoxy and 5-amino substituted thiophenes. Tetrahedron Lett. 2000, 41, 1597-1600.
18. Baraldi, P. G; Pavani, M. G.; Shryock, J. C.; Moorman, A. R.; Iannotta, V.; Borea, PA.; Romagnoli, R. Synthesis of 2-amino-3-heteroaroylthiophenes and evaluation of their activity as potential allosteric enhancers at the human A1 receptor. Eur. J. Med. Chem. 2004, 39, 855-865.
19. Pillai, A. D.; Rathod, P. D.; Xavier, F. P.; Vasu, K. K.; Padh, H.; Sudarsanam, V. Design, synthesis, and pharmacological evaluation of some 2-[4-morpholino]-3-aryl-5-substituted thiophenes as novel anti-inflammatory agents: generation of a novel anti-inflammatory pharmacophore. Bioorg. Med. Chem. 2004, 12, 4667-4671.
20. Moghaddam, F. M.; Zali-Boinee, H. A versatile one-pot synthesis of 2, 3, 5-tri-substituted thiophenes from thiomorpholides. Tetrahedron Lett. 2003, 44, 6253-6255.
21. Jones, R. J.; Cava, M. P. Photocyclisation strategy for the synthesis of antitumour agent CC-1065: synthesis of thiophene analogues of PDE-I and PDE-II. J. Chem. Soc. Chem. Commun. 1986, 826-827.
22. Starčevic, K.; Kralj, M.; Piantanida, I.; Šuman, L.; Pavelic, K.; Karminski-Zamola, G. Synthesis, photochemical synthesis, DNA binding and antitumor evaluation of novel cyano-and amidinosubstituted derivatives of naphtho-furans, naphtho-thiophenes, thieno-benzofurans, benzodithiophenes and their acyclic precursors. Eur. J. Med. Chem. 2006, 41, 925-939.
23. [4, 8]]undeca-9, 11-diones and the formation of fascinating novel cage compounds with pyrrole and thiophene using Montmorillonite K-10. Tetrahedron Lett. 2007, 48, 6059-6063.
24. Kondolff, I.; Doucet, H.; Santelli, M. Synthesis of biheteroaryl derivatives by tetraphosphine/palladium-catalysed Suzuki coupling of heteroaryl bromides with heteroarylboronic acids. J. Mol. Catal. A: Chem. 2007, 269, 110-118.
25. Queiroz, M.-J. R. P.; Ferreira, I. C. F. R.; Gaetano, Y. D.; Kirsch, G; Calhelha, R. C.; Estevinho, L. M. Synthesis and antimicrobial activity studies of orthochlorodiarylamines and heteroaromatic tetracyclic systems in the benzo[b]thiophene series. Bioorg. Med. Chem. 2006, 14, 6827-6831.
26. Quèiroz, M.-J. R. P.; Ferreira, I. C. F. R.; Calhelha, R. C.; Estevinho, L. M. Synthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2, 3-dimethylbenzo[b]thiophenes obtained by Buchwald-Hartwig C-N cross-coupling. Bioorg. Med. Chem. 2007, 15, 1788-1794.
27. Rodriguez, J. G.; Esquivias, J.; Lafuente, A.; Rubio, L. Synthesis of conjugated 2 and 2, 5-(ethenyl) and (ethynyl) phenylethynyl thiophenes: fluorescence properties. Tetrahedron 2006, 62, 3112-3122.
28. Raju, S.; Kumar, P. R.; Mukkanti, K.; Annamalai, P.; Pal, M. Facile synthesis of substituted thiophenes via Pd/C-mediated sonogashira coupling in water. Bioorg. Med. Chem. Lett. 2006, 16, 6185-6189.
29. Shams, H. Z.; Elkholy, Y. M.; Azzam, R, A.; Mohareb, R. M. Synthetic potentialities of thiophene systems in heterocyclic synthesis: Anovel synthesis of thieno[2, 3-b]pyridine derivatives. Phosph. Sulf. Silicon 1999, 155, 215-233.
30. Shams, H. Z.; Mohareb, R. M.; Helal, M. H.; Mahmoud, A. E. Synthesis, structure elucidation, and biological evaluation of some fused and/or pendant thiophene, pyrazole, imidazole, thiazole, triazole, triazine, and coumarin systems based on cyanoacetic 2-[(benzoylamino) thioxomethyl]-hydrazide. Phosph. Sulf. Silicon 2007, 182, 237-263.
31. Sherif, S. M.; Mohareb, R. M.; Shams, H. Z.; Gaber, H. M. A convenient synthesis of polyfunctionally substituted benzo[b]thiophen-2-yl-pyrimidine,- pyrazole,-isoxazole andpyridazine derivatives. J. Chem. Res. 1995, (S), 434-435; (M) 2658-2674.
32. Gewald, K.; Schindler, R. Cyclisierungen mit Cyanthioacetamid in Gegenwart von Schwefel. J. Prakt. Chem. 1990, 332, 223-228.
33. Mohareb, R. M.; Aziz, S. I.; Sayed, N. I. A.; Shams, H. Z. Reactions of benzoyl isothiocyanate with active methylene reagents: A novel synthesis of thiophene, thiazoline and thieno[2, 3-d]pyrimidine derivatives. J. Chin. Chem. Soc. 1992, 39, 181-187.
34. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; Gray-Goodrich, M.; Campbell, H.; Mayo, J.; Boyd, M. Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines. J. NCI. J. Natl. Cancer Inst. 1991, 83, 757-766.
35. Li, L.; Yu, F.-H. Transcriptional specificities of adriamycin. Biochem. Mol. Biol. Int. 1993, 31, 879-887. (Pubitemid 24013442)