Synthesis of 4-(3'-[125I]iodoanilino)-6,7-dialkoxyquinazolines: Radiolabeled epidermal growth factor receptor tyrosine kinase inhibitors

被引：0
|
作者：
Lim, John K. [1 ,2 ]
Negash, Kitaw [1 ,3 ]
Hanrahan, Stephen M. [1 ]
Vanbrocklin, Henry F. [1 ]
机构：
[1] Lawrence Berkeley National Laboratory, University of California, MS 55-121, 1 Cyclotron Rd., Berkeley, CA 94720, United States
[2] Department of Radiology, University of California, San Francisco, CA 94143, United States
[3] American Cyanamide Co., Agricultural Research Division, Princeton, NJ 08543, United States
来源：
Journal of Labelled Compounds and Radiopharmaceuticals | 2000年 / 43卷 / 12期
关键词：
Amino acids - Enzyme inhibition;
D O I：
10.1002/1099-1344(20001030)43:123.0.CO;2-N
中图分类号：
学科分类号：
摘要：
The preparation of two radioiodinated analogs of the epidermal growth factor receptor tyrosine kinase (EGFrTK) inhibitor PD153035 (4-(3'-bromoanilino)-6,7-dimethoxyquinazoline) are reported herein. The two analogs, 4-(3'-[125I]iodoanilino)-6,7-dimethoxyquinazoline and 4-(3'-[125I]iodoanilino)-6,7-diethoxyquinazoline, were synthesized via iododestannylation of the corresponding 4-(3'-trimethylstannylanilino)-6,7-dialkoxyquinazolines to form the desired I-125 labeled products in good yield, high radiochemical purity (>99%) and high specific activity.
引用
收藏
页码：1183 / 1191
相关论文
共 50 条
  • [31] 3D-QSAR and docking studies on 4-anilinoquinazoline and 4-anilinoquinoline epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors
    Haregewein Assefa
    Shantaram Kamath
    John K. Buolamwini
    Journal of Computer-Aided Molecular Design, 2003, 17 : 475 - 493
  • [32] 3D-QSAR and docking studies on 4-anilinoquinazoline and 4-anilinoquinoline epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors
    Assefa, H
    Kamath, S
    Buolamwini, JK
    JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 2003, 17 (08) : 475 - 493
  • [33] Tyrosine kinase inhibitors .13. Structure-activity relationships for soluble 7-substituted 4-[(3-bromophenyl)amino]pyrido[4,3-d]pyrimidines designed as inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor
    Thompson, AM
    Murray, DK
    Elliott, WL
    Fry, DW
    Nelson, JA
    Showalter, HDH
    Roberts, BJ
    Vincent, PW
    Denny, WA
    JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (24) : 3915 - 3925
  • [34] Optimization of 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity
    Tsou, HR
    Overbeek-Klumpers, EG
    Hallett, WA
    Reich, MF
    Floyd, MB
    Johnson, BD
    Michalak, RS
    Nilakantan, R
    Discafani, C
    Golas, J
    Rabindran, SK
    Shen, R
    Shi, XQ
    Wang, YF
    Upeslacis, J
    Wissner, A
    JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (04) : 1107 - 1131
  • [35] Design, synthesis and anti-inflammatory activity of pyrimidine scaffold benzamide derivatives as epidermal growth factor receptor tyrosine kinase inhibitors
    Thirumurugan, K.
    Lakshmanan, Sivalingam
    Govindaraj, Dharman
    Prabu, D. Sam Daniel
    Ramalakshmi, N.
    Antony, S. Arul
    JOURNAL OF MOLECULAR STRUCTURE, 2018, 1171 : 541 - 550
  • [36] Synthesis and biological evaluation of novel 2,4′-bis substituted diphenylamines as anticancer agents and potential epidermal growth factor receptor tyrosine kinase inhibitors
    Abou-Seri, Sahar Mahmoud
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (09) : 4113 - 4121
  • [37] Benzofuran-appended 4-aminoquinazoline hybrids as epidermal growth factor receptor tyrosine kinase inhibitors: synthesis, biological evaluation and molecular docking studies
    Mphahlele, Malose J.
    Maluleka, Marole M.
    Aro, Abimbola
    McGaw, Lyndy J.
    Choong, Yee Siew
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2018, 33 (01) : 1516 - 1528
  • [38] Tyrosine kinase inhibitors.: 18.: 6-substituted 4-anilinoquinazolines and 4-anilinopyrido [3,4-d]pyrimidines as soluble, irreversible inhibitors of the epidermal growth factor receptor
    Smaill, JB
    Showalter, HDH
    Zhou, HR
    Bridges, AJ
    McNamara, DJ
    Fry, DW
    Nelson, JM
    Sherwood, V
    Vincent, PW
    Roberts, BJ
    Elliott, WL
    Denny, WA
    JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (03) : 429 - 440
  • [39] 4-Aminoindazolyl-dihydrofuro[3,4-d]pyrimidines as non-covalent inhibitors of mutant epidermal growth factor receptor tyrosine kinase
    Hanan, Emily J.
    Baumgardner, Matt
    Bryan, Marian C.
    Chen, Yuan
    Eigenbrot, Charles
    Fan, Peter
    Gu, Xiao-Hui
    La, Hank
    Malek, Shiva
    Purkey, Hans E.
    Schaefer, Gabriele
    Schmidt, Stephen
    Sideris, Steve
    Yen, Ivana
    Yu, Christine
    Heffron, Timothy P.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (02) : 534 - 539
  • [40] Synthesis of a prodrug designed to release multiple inhibitors of the epidermal growth factor receptor tyrosine kinase and an alkylating agent: A novel tumor targeting concept
    Banerjee, R
    Rachid, Z
    McNamee, J
    Jean-Claude, BJ
    JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (25) : 5546 - 5551
12345