The thiazole derivative 3
was used for a series of heterocyclization reaction to produce pyran, pyridine
and thiazole derivatives. The cytotoxicity of the newly synthesized compounds
was studied against the six cancer cell lines namely NUGC, HR, DLD1, HA22T, HEPG2, MCF, HONE1 and
normal fibroblast cells (WI38). The results showed that most of the synthesized
compounds were of high potency. Among the tested compounds, 2-Amino-4-(4-chlorophenyl)-6-(4-phenylthiazol-2-yl)-4H-pyran-3,5-dicarbonitrile 17b showed the highest
potency among the tested compounds.
Cite this paper
Hamed, F. I. , Mohamed, A. A. and Abouzied, A. S. (2017). The Uses of 2-Amino-4-Phenylthiazole in the Synthesis of Coumarin, Pyran, Pyridine and Thiazole Derivatives with Antitumor Activities. Open Access Library Journal, 4, e3526. doi: http://dx.doi.org/10.4236/oalib.1103526.
Bharti, S.K., Nath, G.,
Tilak, R. and Singh, S.K. (2010) Synthesis, Anti-Bacterial and Anti-Fungal
Activities of Some Novel Schiff Bases Containing 2,4-Disubstituted Thiazole
Ring. European Journal of Medicinal Chemistry, 45, 651–660. https://doi.org/10.1016/j.ejmech.2009.11.008
Spector,
F.C., Liang, L., Giordano, H., Sivaraja, M. and Peterson, M.G. (1998) Inhibition
of Herpes Simplex Virus Replication by a 2-Amino Thiazole via Interactions with
the Helicase Component of the UL5-UL8-UL52 Complex. Journal of
Virology, 72, 6979-6987.
Fink,
B.E., Mortensen, D.S., Stauffer, S.R., Aron, Z.D. and Katzenellenbogen, J.A.
(1999) Novel Structural Templates for Estrogen-Receptor Ligands and Prospects
for Combinatorial
Synthesis of Estrogens. Cell Chemical Biology, 6, 205-219. https://doi.org/10.1016/s1074-5521(99)80037-4
Matteo,
B., Colin, P.L., Angelica, M. and Caberlotto, L. (2010) Synthesis and Structure-Activity
Relationship of N-(3-Azabicyclo[3.1.0]Hex-6-ylMethyl)-5-(2-Pyri- dinyl)-1,3-Tthiazol-2-Amines
Derivatives as NPY Y5 Antagonists. Bioorganic and Medicinal Chemistry
Letters, 20, 4741-4744. https://doi.org/10.1016/j.bmcl.2010.06.140
Tilburg,
E.W.V., Van der Klein, P.A.M., Groote, M.D.,
Beukers, M.W. and Jzerman, A.P.I. (2001) Substituted
4-Phenyl-2-(Phenylcarboxamido)-1,3-Thiazole Derivatives as Antagonists for the
AdenosineA1 Receptor. Bioorganic and Medicinal Chemistry Letters, 11, 2017-2019. https://doi.org/10.1016/S0960-894X(01)00356-0
Bhoga,
U. (2007) Novel Synthetic Approach to N-aryl-4-(3-Pyridyl)Thiazol-2- Amine and Analogues Using HMCM-41 as Catalyst,
and Their Biological
Evaluation as Human Platelet Aggregation Inhibitors. European Journal of
Medicinal Chemistry, 42,
1144-1150. https://doi.org/10.1016/j.ejmech.2007.01.016
Wilson,
K.J., Illig, C.R., Subasinghe, N. and Spurlino, J. (2001) Synthesis of Thiophene-2 -Carboxamidines Containing
2-Aminothiazoles and Their Biological Evaluation as Urokinase Inhibitors. Bioorganic
and Medicinal Chemistry Letters, 11,
915-918. https://doi.org/10.1016/S0960-894X(01)00102-0
Sekhiguchi,
A., Nishina, A., Kimura, H., Fukumoto, R.-H., Kanoh, K., Ishihara, H. and
Koketsu, M. (2005) Superoxide Anion-Scavenging Effect of 2-Amino-1,
3-Selenazoles. Chemical and Pharmaceutical Bulletin, 53, 1439-1442. https://doi.org/10.1248/cpb.53.1439
Koketsua,
M., Ishihara, H., Wu, W., Murakami, K. and Saiki, I. (1999)
1,3-Selena- zine
Derivatives Induce Cytotoxicity and DNA Fragmentation in Human HT-1080 Fibrosarcoma
Cells. European Journal of Pharmaceutical Sciences, 9, 157-161. https://doi.org/10.1016/S0928-0987(99)00058-5
Hantzsch,
A. and Weber, J.H. (1887) Ueber Verbindungen des Thiazols (Pyridins der Thiophenreihe). Berichte der deutschen chemischen Gesellschaft, 20, 3118- 3132. https://doi.org/10.1002/cber.188702002200
