Literature DB >> 20961149

Design and synthesis of tetrahydropyridothieno[2,3-d]pyrimidine scaffold based epidermal growth factor receptor (EGFR) kinase inhibitors: the role of side chain chirality and Michael acceptor group for maximal potency.

Chia-Hsien Wu1, Mohane Selvaraj Coumar, Chang-Ying Chu, Wen-Hsing Lin, Yi-Rong Chen, Chiung-Tong Chen, Hui-Yi Shiao, Shaik Rafi, Sing-Yi Wang, Hui Hsu, Chun-Hwa Chen, Chun-Yu Chang, Teng-Yuan Chang, Tzu-Wen Lien, Ming-Yu Fang, Kai-Chia Yeh, Ching-Ping Chen, Teng-Kuang Yeh, Su-Huei Hsieh, John T-A Hsu, Chun-Chen Liao, Yu-Sheng Chao, Hsing-Pang Hsieh.   

Abstract

HTS hit 7 was modified through hybrid design strategy to introduce a chiral side chain followed by introduction of Michael acceptor group to obtain potent EGFR kinase inhibitors 11 and 19. Both 11 and 19 showed over 3 orders of magnitude enhanced HCC827 antiproliferative activity compared to HTS hit 7 and also inhibited gefitinib-resistant double mutant (DM, T790M/L858R) EGFR kinase at nanomolar concentration. Moreover, treatment with 19 shrinked tumor in nude mice xenograft model.

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Year:  2010        PMID： 20961149     DOI： 10.1021/jm100607r

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  17 in total

Review 1.  A Review on Fused Pyrimidine Systems as EGFR Inhibitors and Their Structure-Activity Relationship.

Authors:  Tanuja T Yadav; Gulam Moin Shaikh; Maushmi S Kumar; Meena Chintamaneni; Mayur Yc
Journal:  Front Chem       Date:  2022-06-13       Impact factor: 5.545

2.  Molecular mechanisms underlying the antitumor activity of 3-aminopropanamide irreversible inhibitors of the epidermal growth factor receptor in non-small cell lung cancer.

Authors:  Elena Galvani; Elisa Giovannetti; Francesca Saccani; Andrea Cavazzoni; Leticia G Leon; Henk Dekker; Roberta Alfieri; Caterina Carmi; Marco Mor; Andrea Ardizzoni; Pier Giorgio Petronini; Godefridus J Peters
Journal:  Neoplasia       Date:  2013-01       Impact factor: 5.715

3.  Anchor-based classification and type-C inhibitors for tyrosine kinases.

Authors:  Kai-Cheng Hsu; Tzu-Ying Sung; Chih-Ta Lin; Yi-Yuan Chiu; John T-A Hsu; Hui-Chen Hung; Chung-Ming Sun; Indrajeet Barve; Wen-Liang Chen; Wen-Chien Huang; Chin-Ting Huang; Chun-Hwa Chen; Jinn-Moon Yang
Journal:  Sci Rep       Date:  2015-06-16       Impact factor: 4.379

4.  Homology modeling of DFG-in FMS-like tyrosine kinase 3 (FLT3) and structure-based virtual screening for inhibitor identification.

Authors:  Yi-Yu Ke; Vivek Kumar Singh; Mohane Selvaraj Coumar; Yung Chang Hsu; Wen-Chieh Wang; Jen-Shin Song; Chun-Hwa Chen; Wen-Hsing Lin; Szu-Huei Wu; John T A Hsu; Chuan Shih; Hsing-Pang Hsieh
Journal:  Sci Rep       Date:  2015-06-29       Impact factor: 4.379

5.  QSAR based model for discriminating EGFR inhibitors and non-inhibitors using Random forest.

Authors:  Harinder Singh; Sandeep Singh; Deepak Singla; Subhash M Agarwal; Gajendra P S Raghava
Journal:  Biol Direct       Date:  2015-03-25       Impact factor: 4.540

6.  Design, Synthesis, and Biological Activity of Tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine Derivatives as Anti-Inflammatory Agents.

Authors:  Yuan Zhang; Lu Luo; Chao Han; Handeng Lv; Di Chen; Guoliang Shen; Kaiqi Wu; Suwei Pan; Faqing Ye
Journal:  Molecules       Date:  2017-11-13       Impact factor: 4.411

7.  High Potency of SN-38-Loaded Bovine Serum Albumin Nanoparticles Against Triple-Negative Breast Cancer.

Authors:  Hsin-Che Lin; Chih-Hung Chuang; Meng-Hsuan Cheng; Yu-Chih Lin; Yi-Ping Fang
Journal:  Pharmaceutics       Date:  2019-11-01       Impact factor: 6.321

8.  Molecular design, synthesis and in vitro biological evaluation of thienopyrimidine-hydroxamic acids as chimeric kinase HDAC inhibitors: a challenging approach to combat cancer.

Authors:  Mona M Abdel-Atty; Nahla A Farag; Rabah A T Serya; Khaled A M Abouzid; Samar Mowafy
Journal:  J Enzyme Inhib Med Chem       Date:  2021-12       Impact factor: 5.051

9.  Discovery of New Apoptosis-Inducing Agents for Breast Cancer Based on Ethyl 2-Amino-4,5,6,7-Tetra Hydrobenzo[b]Thiophene-3-Carboxylate: Synthesis, In Vitro, and In Vivo Activity Evaluation.

Authors:  Emad M Gad; Mohamed S Nafie; Elsayed H Eltamany; Magdy S A G Hammad; Assem Barakat; Ahmed T A Boraei
Journal:  Molecules       Date:  2020-05-28       Impact factor: 4.411

10.  Water-soluble chiral tetrazine derivatives: towards the application of circularly polarized luminescence from upper-excited states to photodynamic therapy.

Authors:  Tingchao He; Can Ren; Yu Luo; Qi Wang; Junzi Li; Xiaodong Lin; Chuanxiang Ye; Wenbo Hu; Junmin Zhang
Journal:  Chem Sci       Date:  2019-03-08       Impact factor: 9.825
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