Gefitinib

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Gefitinib(cas 184475-35-2) is an anilinoquinazoline with antineoplastic activity. Gefitinib inhibits the catalytic activity of numerous tyrosine kinases including the epidermal growth factor receptor (EGFR), which may result in inhibition of tyrosine kinase-dependent tumor growth. Specifically, this agent competes with the binding of ATP to the tyrosine kinase domain of EGFR, thereby inhibiting receptor autophosphorylation and resulting in inhibition of signal transduction. Gefitinib may also induce cell cycle arrest and inhibit angiogenesis. It is marketed by AstraZeneca and Teva.


Catalog Number A000322
CAS Number 184475-35-2
Synonyms

ZD1839

Molecular Formula C₂₂H₂₄ClFN₄O₃
Purity ≥95%
Target EGFR
Solubility >22.3mg/mL in DMSO
Storage 3 years -20C powder
InChI InChI=1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)
InChIKey XGALLCVXEZPNRQ-UHFFFAOYSA-N
SMILES COC1=C(C=C2C(=C1)N=CN=C2NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4
Reference

1:Rationale design, synthesis, cytotoxicity evaluation, and molecular docking studies of 1,3,4-oxadiazole analogues. Ahsan MJ, Choupra A, Sharma RK, Jadav SS, Hassan MZ, Bakht MA, Padmaja P, Al-Tamimi ABS, Geesi MH.Anticancer Agents Med Chem. 2017 Apr 19. doi: 10.2174/1871520617666170419124702. [Epub ahead of print] PMID: 28425854
2:Synthesis and biological evaluation of novel tricyclic oxazine and oxazepine fused quinazolines. Part 2: Gefitinib analogs. Sun M, Zhao J, Chen X, Zong Z, Han J, Du Y, Sun H, Wang F.Bioorg Med Chem Lett. 2016 Oct 1;26(19):4842-5. doi: 10.1016/j.bmcl.2016.08.007. Epub 2016 Aug 4. PMID: 27524310
3:Combination of 4-anilinoquinazoline, arylurea and tertiary amine moiety to discover novel anticancer agents. Zuo SJ, Zhang S, Mao S, Xie XX, Xiao X, Xin MH, Xuan W, He YY, Cao YX, Zhang SQ.Bioorg Med Chem. 2016 Jan 15;24(2):179-90. doi: 10.1016/j.bmc.2015.12.001. Epub 2015 Dec 2. PMID: 26706113
4:Synthesis and biological evaluation of novel tricyclic oxazine and oxazepine fused quinazolines. Part 1: erlotinib analogs. Chen X, Du Y, Sun H, Wang F, Kong L, Sun M.Bioorg Med Chem Lett. 2014 Feb 1;24(3):884-7. doi: 10.1016/j.bmcl.2013.12.079. Epub 2013 Dec 25. PMID: 24411123

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