Synthesis and in vitro protein tyrosine kinase inhibitory activity of furan-2-yl(phenyl)methanone derivatives

Molecules

Volumn 16, Issue 6, 2011, Pages 4897-4911

  Zheng, Fei Lang ^a   Ban, Shu Rong ^a   Feng, Xiu E ^a   Zhao, Cheng Xiao ^a   Lin, Wenhan ^b   Li, Qing Shan ^a,b  

^a SHANXI MEDICAL UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

Furan 2 yl(phenyl)methanone; Halophenols; Protein tyrosine kinases inhibitor; Structure activity relationships (SAR)

Indexed keywords

FURAN DERIVATIVE; PROTEIN KINASE INHIBITOR; PROTEIN TYROSINE KINASE;

ANIMAL; ARTICLE; BRAIN; CHEMISTRY; DRUG ANTAGONISM; ENZYMOLOGY; NUCLEAR MAGNETIC RESONANCE; RAT; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; BRAIN; FURANS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PROTEIN KINASE INHIBITORS; PROTEIN-TYROSINE KINASES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79959621638     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16064897     Document Type: Article

References (20)

1. Li, K.; Li, X.M.; Ji, N.Y.; Wang, B.G. Natural bromophenols from the marine red alga Polysiphonia urceolata (Rhodomelaceae): Structural elucidation and DPPH radical-scavenging activity. Bioorg. Med. Chem. 2007, 15, 6627-6631. (Pubitemid 47385252)
2. Liu, Q.W.; Xu, H.; Zhang, T.; Fan, X.; Han, L.J. A new compound as PTP1B inhibitor from the red alga Polysiphonia urceolata. Chemistry 2006, 9, 708-710.
3. Han, L.J.; Xun, J.; Shi, J.G.; Yan, X.J.; Zeng, C.K. Isolation and pharmacological activities of bromophenols from Rhodomela confervoides. Chin. J. Oceanol. Limnol. 2005, 23, 226-229.
4. Shi, D.Y.; Li, J.; Guo, S.J.; Han, L.J. Antithrombotic effect of bromophenol, the alga-derived thrombin inhibitor. J. Biotechnol. 2008, 136S, S577-S588.
5. Oh, K.B.; Lee, J.H.; Lee, J.W.; Yoon, K.M.; Chung, S.C.; Jeon, H.B.; Shin, J.H.; Lee, H.S. Antimicrobial activities of the bromophenols from the red alga Odonthalia corymbifera and some synthetic derivatives. Bioorg. Med. Chem. Lett. 2008, 18, 104-108.
6. Popplewell, W.L.; Northcote, P.T. Colensolide A: A new nitrogenous bromophenol from the New Zealand marine red alga Osmundaria colensoi. Tetrahedron Lett. 2009, 50, 6814-6817.
7. Wang, W.; Okada, Y.; Shi, H.B.; Wang, Y.Q.; Okuyama, T. Structures and aldose reductase inhibitory effects of bromophenols from the red alga Symphyocladia latiuscula. J. Nat. Prod. 2005, 68, 620-622. (Pubitemid 40586334)
8. Xu, X.L.; Song, F.H.; Wang, S.J.; Li, S.; Xiao, F.; Zhao, J.L.; Yang, Y.C.; Shang, S.Q.; Yang, L.; Shi, J.G. Dibenzyl bromophenols with diverse dimerization patterns from the brown alga Leathesia nana. J. Nat. Prod. 2004, 67, 1661-1666. (Pubitemid 39426118)
9. Kurata, K.; Taniguchii, K.; Takashima, K.; Hayash, I.; Suzuki, M. Feeding-deterrent bromophenols from Odonthalia corymbifera. Phytochemistry 1997, 45, 485-487.
10. Abdel-Lateff, A. Chaetominedione, a new tyrosin kinase inhibitor isolated from the algicolous marine fungus Chaetomium sp. Tetrahedron Lett. 2008, 49, 6398-6400.
11. Oh, K.B.; Lee, J.H.; Lee, J.W.; Yoon, K.M.; Chung, S.C.; Jeon, H.B.; Shin, J.H.; Lee, H.S. Synthesis and antimicrobial activities of halogenated bis(hydroxyphenyl)methanes. Bioorg. Med. Chem. Lett. 2009, 19, 945-948.
12. Traxler, P.; Furet, P. Strategies toward the design of novel and selective protein tyrosine kinase inhibitors. Pharmacol. Ther. 1999, 82, 195-206. (Pubitemid 29255915)
13. Hori, H.; Nagasawa, H.; Uto, Y.; Ohkura, K.; Kirk, K.L.; Uehara, Y.; Shimamura, M. Design of hypoxia-targeting protein tyrosine kinase inhibitor using an innovative pharmacophore 2-methylene-4-cyclopentene-1,3-dione. Biochim. Biophys. Acta 2004, 1697, 29-38. (Pubitemid 38326759)
14. 60c-Src receptor tyrosine kinase and arylcarboxylic and arylacetic acid derivatives based on docking modes and in vitro activity. Biol. Pharm. Bull. 2004, 27, 61-65. (Pubitemid 41656674)
15. Zhao, W.Y.; Feng, X.E.; Ban, S.R.; Lin, W.H.; Li, Q.S. Synthesis and biological activity of halophenols as potent antioxidant and cytoprotective agents. Bioorg. Med. Chem. Lett. 2010, 14, 4132-4134.
16. Cui, Z.N.; Li, Y., Ling, Y.; Huang, J.; Cui, J.R.; Wang, R.Q.; Yang, X.L. New class of potent antitumor acylhydrazone derivatives containing furan. Eur. J. Med. Chem. 2010, 45, 5576-5584.
17. Patrick, G.L. An Introduction to Medicinal Chemistry, 3rd ed.; Oxford University Press: New York, NY, USA, 2005; pp. 271-298.
18. Kumar, D.; Kumar, N.M.; Chang, K.H. Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazoles. Eur. J. Med. Chem. 2010, 45, 4664-4668.
19. Joule, J.A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell Science Ltd: Oxford, UK, 2000; pp. 335-356.
20. Young, I.S.; Kerr, M.A. Total synthesis of (+)-nakadomarin. J. Am. Chem. Soc. 2007, 129, 1465-1469.