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Haghighijoo, Zahra, Rezaei, Zahra, Taheri, Samaneh, Jani, Meysam, Khabnadideh, Soghra. (1394). A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives. سامانه مدیریت نشریات علمی, 1(3), 173-178.
Zahra Haghighijoo; Zahra Rezaei; Samaneh Taheri; Meysam Jani; Soghra Khabnadideh. "A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives". سامانه مدیریت نشریات علمی, 1, 3, 1394, 173-178.
Haghighijoo, Zahra, Rezaei, Zahra, Taheri, Samaneh, Jani, Meysam, Khabnadideh, Soghra. (1394). 'A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives', سامانه مدیریت نشریات علمی, 1(3), pp. 173-178.
Haghighijoo, Zahra, Rezaei, Zahra, Taheri, Samaneh, Jani, Meysam, Khabnadideh, Soghra. A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives. سامانه مدیریت نشریات علمی, 1394; 1(3): 173-178.

A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives

Trends in Pharmaceutical Sciences
مقاله 8، دوره 1، شماره 3، آذر 2015، صفحه 173-178    اصل مقاله (360.58 K)
نوع مقاله: Research(Original) Article
نویسندگان
Zahra Haghighijoo1؛ Zahra Rezaei؛ Samaneh Taheri2؛ Meysam Jani2؛ Soghra Khabnadideh* 2
1Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, I.R.Iran. Department of Medicinal Chemistry, Faculty of Pharmacy Mazandaran University of Medical Sciences, Sari, I.R.Iran
2Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, I.R.Iran.
چکیده
4-Anilinoquinazolines have been widely studied as anticancer agents. Despite the widespread utility of this class of compounds, the reported syntheses of 4-anilinoquinazolines require multistep and low-yielding pathways. A novel strategy to prepare 4-anilinoquinazoline derivatives based on the cyclization of anthranilic acid is described. By using of dichloro anthranilic acid we could etherified the quinazoline ring in order to mimic the erlotinib structure as a tyrosine kinase inhibitor. Our new compounds contain different substitutions at the meta-positions of the quinazoline ring instead of the ortho-positions of erlotinib. We synthesized ten new 4-anilinoquinazoline derivatives (17-26) in only 4 steps with desirable yields. Key words: Synthesis, Erlotinib, Anilinoquinazolines, EGFR.
مراجع
  1. Shi D-Q, Dou G-L, Li Z-Y, Ni S-N, Li X-Y, Wang X-S, et al. An efficient synthesis of quinazoline-2,4-dione derivatives with the aid of a low-valent titanium reagent. Tetrahedron. 2007;63(39):9764-73.
  2. Chilin A, Marzaro G, Zanatta S, Guiotto A. A microwave improvement in the synthesis of the quinazoline scaffold. Tetrahedron Letters. 2007;48(18):3229-31.
  3. Chandrika PM, Yakaiah T, Rao AR, Narsaiah B, Reddy NC, Sridhar V, et al. Synthesis of novel 4,6-disubstituted quinazoline derivatives, their anti-inflammatory and anti-cancer activity (cytotoxic) against U937 leukemia cell lines. Eur J Med Chem. 2008;43(4):846-52. Epub 2007/08/11.
  4. Kabri Y, Azas N, Dumetre A, Hutter S, Laget M, Verhaeghe P, et al. Original quinazoline derivatives displaying antiplasmodial properties. Eur J Med Chem. 2010;45(2):616-22. Epub 2009/11/21.
  5. Li G, Kakarla R, Gerritz SW, Pendri A, Ma B. A facile one-step synthesis of 5-chloro-imidazo[1,5-a]quinazoline by microwave irradiation. Tetrahedron Letters. 2009;50(44):6048-52.
  6. Mizuno T, Iwai T, Ishino Y. The simple solvent-free synthesis of 1H-quinazoline-2,4-diones using supercritical carbon dioxide and catalytic amount of base. Tetrahedron Letters. 2004;45(38):7073-5.
  7. Marzaro G, Guiotto A, Pastorini G, Chilin A. A novel approach to quinazolin-4(3H)-one via quinazoline oxidation: an improved synthesis of 4-anilinoquinazolines. Tetrahedron. 2010;66(4):962-8.
  8. Yang S, Li Z, Jin L, Song B, Liu G, Chen J, et al. Synthesis and bioactivity of 4-alkyl(aryl)thioquinazoline derivatives. Bioorg Med Chem Lett. 2007;17(8):2193-6. Epub 2007/02/24.
  9. Chen KF, Pao KC, Su JC, Chou YC, Liu CY, Chen HJ, et al. Development of erlotinib derivatives as CIP2A-ablating agents independent of EGFR activity. Bioorg Med Chem. 2012;20(20):6144-53. Epub 2012/09/18.
  10. Harris CS, Kettle JG, Williams EJ. Facile synthesis of 7-amino anilinoquinazolines via direct amination of the quinazoline core. Tetrahedron Letters. 2005;46(43):7381-4.
  11. Zheng QZ, Zhang F, Cheng K, Yang Y, Chen Y, Qian Y, et al. Synthesis, biological evaluation and molecular docking studies of amide-coupled benzoic nitrogen mustard derivatives as potential antitumor agents. Bioorg Med Chem. 2010;18(2):880-6. Epub 2009/12/17.
  12. Luo Q, Gu Y, Zheng W, Wu X, Gong F, Gu L, et al. Erlotinib inhibits T-cell-mediated immune response via down-regulation of the c-Raf/ERK cascade and Akt signaling pathway. Toxicology and applied pharmacology. 2011;251(2):130-6.
  13. Zuliani V, Carmi C, Rivara M, Fantini M, Lodola A, Vacondio F, et al. 5-Benzylidene-hydantoins: synthesis and antiproliferative activity on A549 lung cancer cell line. Eur J Med Chem. 2009;44(9):3471-9. Epub 2009/03/10.
  14. Huether A, Höpfner M, Sutter AP, Schuppan D, Scherübl H. Erlotinib induces cell cycle arrest and apoptosis in hepatocellular cancer cells and enhances chemosensitivity towards cytostatics. Journal of hepatology. 2005;43(4):661-9.
  15. Barghi L, Aghanejad A, Valizadeh H, Barar J, Asgari D. Modified synthesis of erlotinib hydrochloride. Adv Pharm Bull. 2012;2(1):119-22.
  16. Ku GY, Chopra A, Lopes Jr GdL. Successful treatment of two lung cancer patients with erlotinib following gefitinib-induced hepatotoxicity. Lung Cancer. 2010;70(2):223-5.
  17. Mizuno T, Ishino Y. Highly efficient synthesis of 1H-quinazoline-2, 4-diones using carbon dioxide in the presence of catalytic amount of DBU. Tetrahedron. 2002;58(16):3155-8.
  18. Wu X, Yu Z. Metal and phosgene-free synthesis of 1H-quinazoline-2,4-diones by selenium-catalyzed carbonylation of o-nitrobenzamides. Tetrahedron Letters. 2010;51(11):1500-3.
  19. Phoujdar MS, Kathiravan MK, Bariwal JB, Shah AK, Jain KS. Microwave-based synthesis of novel thienopyrimidine bioisosteres of gefitinib. Tetrahedron Letters. 2008;49(7):1269-73.
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