Design, synthesis and evaluation of novel non-ATP competitive CHK1 inhibitors as chemotherapy sensitizing agents

doi:10.5246/jcps.2016.10.081

Abstract

CLC Number:

R916

Supporting:

Yuanxin Li, Zifei Han, Chao Tian, Zhili Zhang, Junyi Liu. Design, synthesis and evaluation of novel non-ATP competitive CHK1 inhibitors as chemotherapy sensitizing agents[J]. Journal of Chinese Pharmaceutical Sciences, 2016, 25(10): 726-736.

References

[1] Mailand, N.; Falck, J.; Lukas, C.; Syljuasen, R.G.; Welcker, M.; Bartek, J.; Lukas, J. Science. 2000, 288, 1425-1429.
[2] Lopez-Girona, A.; Furnari, B.; Mondesert, O.; Russell, P. Nature. 1999, 397, 172-175.
[3 ] Soussi, T.; Béroud, C. Nat. Rev. Cancer. 2001, 1, 233-239.
[4] Gazzard, L.; Williams, K.; Chen, H.; Axford, L.; Blackwood, E.; Burton, B.; Chapman, K.; Crackett, P.; Drobnick, J.; Ellwood, C.; Epler, J.; Flagella, M.; Gancia, E.; Gill, M.; Goodacre, S.; Halladay, J.; Hewitt, J.; Hunt, H.; Kintz, S.; Lyssikatos, J.; Macleod, C.; Major, S.; Médard, G.; Narukulla, R.; Ramiscal, J.; Schmidt, S.; Seward, E.; Wiesmann, C.; Wu, P.; Yee, S.; Yen, I.; Malek, S. J. Med. Chem. 2015, 58, 5053-5074.
[5] Walton, M.I.; Eve, P.D.; Hayes, A.; Henley, A.T.; Valenti, M.R.; De Haven Brandon, A.K.; Box, G.; Boxall, K.J.; Tall, M.; Swales, K.; Matthews, T.P.; McHardy, T.; Lainchbury, M.; Osborne, J.; Hunter, J.E.; Perkins, N.D.; Aherne, G.W.; Reader, J.C.; Raynaud, F.I.; Eccles, S.A.; Collins, I.; Garrett, M.D. Oncotarget. 2016, 7, 2329-2342.
[6] Dietlein, F.; Kalb, B.; Jokic, M.; Noll, E.M.; Strong, A.; Tharun, L.; Ozretic, L.; Kunstlinger, H.; Kambartel, K.; Randerath, W.J.; Jungst, C.; Schmitt, A.; Torgovnick, A.; Richters, A.; Rauh, D.; Siedek, F.; Persigehl, T.; Mauch, C.; Bartkova, J.; Bradley, A.; Sprick, M.R.; Trumpp, A.; Rad, R.; Saur, D.; Bartek, J.; Wolf, J.; Buttner, R.; Thomas, R.K.; Reinhardt, H.C. Cell. 2015, 162, 146-159.
[7] Akinaga, S.; Gomi, K.; Morimoto, M.; Tamaoki, T.; Okabe, M. Cancer Res. 1991, 51, 4888-4892.
[8] Jimeno, A.; Rudek, M.A.; Purcell, T.; Laheru, D.A.; Messersmith, W.A.; Dancey, J.; Carducci, M.A.; Baker, S.D.; Hidalgo, M.; Donehower, R.C. Cancer Chemother. Pharmacol. 2008, 61, 423-433.
[9] Zabludoff, S.D.; Deng, C.; Grondine, M.R.; Sheehy, A.M.; Ashwell, S.; Caleb, B.L.; Green, S.; Haye, H.R.; Horn, C.L.; Janetka, J.W.; Liu, D.; Mouchet, E.; Ready, S.; Rosenthal, J.L.; Queva, C.; Schwartz, G.K.; Taylor, K.J.; Tse, A.N.; Walker, G.E.; White, A.M. Mol. Cancer Ther. 2008, 7, 2955-2966.
[10] Converso, A.; Hartingh, T.; Garbaccio, R.M.; Tasber, E.; Rickert, K.; Fraley, M.E.; Yan, Y.W.; Kreatsoulas, K.; Stirdivant, S.; Drakas, B.; Walsh, E.S.; Hamilton, K.; Buser, C.A.; Mao, X.Z.; Abrams, M.T.; Beck, S.C.; Tao, W.K.; Lobell, R.; Lorenzino, L.S.; Murphy, J.Z.; Sardana, V.; Munshi, S.K.; Jezequel-Sur, S.M.; Zuck, P.D.; Hartman, G.D. Bioorg. Med. Chem. Lett. 2009, 19, 1240-1244.
[11] Vanderpool, D.; Johnson, T.O.; Ping, C.; Bergqvist, S.; Alton, G.; Phonephaly, S.; Rui, E.; Luo, C.; Deng, Y.L.; Grant, S.; Quenzer, T.; Margosiak, S.; Register, J.; Brown, E.; Ermolieff, J. Biochemistry. 2009, 48, 9823-9830.
[12] Elliott, A.J.; Morris, P.E.; Petty, S.L.; Williams, C.H. J. Org. Chem. 1997, 62, 8071-8075.
[13] Tran, S.B.; Ekhato, I.V.; Rinehart, J.K. J. Label Compd. Radiopharm. 2009, 52, 485-489.
[14] Gangjee, A.; Vasudevan, A.; Queener, S.F. J. Med. Chem. 1997, 40, 3032-3039.
[15] Zegzouti, H.; Zdanovskaia, M.; Hsiao, K.; Goueli, S.A. Assay Drug Dev. Techn. 2009, 7, 560-572.
[16] Song, P.; Peng, P.; Han, M.; Cao, X.C.; Ma, X.D.; Liu, T.; Zhou, Y.B.; Hu, Y.Z. Bioorg. Med. Chem. 2014, 22, 4882-4892.

[1]	Mingna Li, Xing Wu, Liangren Zhang, Zhenming Liu. Evaluating reverse docking on general and selective inhibitors: a case study about glide [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(10): 679-688.
[2]	Peili Jiao, Yiyan Li, Xing Wu, Yuxi Wang, Beibei Mao, Hongwei Jin, Lihe Zhang, Liangren Zhang, Zhenming Liu. Structure-based design and biological evaluation of novel mTOR inhibitors as potential anti-cervical agents [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(9): 603-616.
[3]	Hui Liu, Lei Liang, Lan Yuan, Fengrong Xu, Yan Niu, Chao Wang, Ping Xu. Design and synthesis of nitrogen-fused pyridazinone fluorescent probes and their application in biological imaging [J]. Journal of Chinese Pharmaceutical Sciences, 2019, 28(5): 298-315.
[4]	Beidou Zhou, Xin Wang, Zhimin Weng, Baocheng Huang, Zetong Ma, Bo Yu, Liqin Ruan, Dongbao Hu. Synthesis and antitumor, antityrosinase, and antiplatelet aggregation activities of xanthone [J]. Journal of Chinese Pharmaceutical Sciences, 2019, 28(4): 247-256.
[5]	Xintong Wang, Wenxing Zou, Haoran Xiao, Wenjun Xie, Xin Li, Xiling Bian, Qi Sun, Kewei Wang. Electrophysiological characterization of furo[3,2-b]pyridine derivatives as negative allosteric modulator of a7 nicotinic acetylcholine receptor [J]. Journal of Chinese Pharmaceutical Sciences, 2019, 28(3): 160-166.
[6]	Ming He, Baohua Xie, Pei He, Haibing Zhou, Shengtang Huang, Chune Dong. Design, synthesis and biological evaluation of novel quinoline [4,3-b]chromene derivatives as AChE inhibitors through an efficient one-pot, four-component microwave-mediated reaction [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(11): 735-752.
[7]	Olatunde S. Oladeji, Monisola I. Ikhile, Carine M. D. Fotsing, Messai Mamo, Patrick G. Ndungu, Derek T. Ndinteh. Synthesis of 4-aminoantipyrine Schiff bases and their antimicrobial activities [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(11): 753-766.
[8]	Can Li, Hongyue Li, Jing Sun, Dandan Xi, Chao Wang, Lei Liang, Fengrong Xu, Yan Niu, Ping Xu. Structure-based design and synthesis of 5-benzyl-2-phenylpyrimidin-4(3H)-one derivatives as novel MEK1 inhibitors [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(10): 686-695.
[9]	Dini Kesuma, Siswandono, Bambang Tri Purwanto, Marcellino Rudyanto. Synthesis of N-(phenylcarbamothioyl)-benzamide derivatives and their cytotoxic activity against MCF-7 cells [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(10): 696-702.
[10]	Yucui Ma, Liang Xu, Cui Wu, Zhimao Chao. Crystal structure of trans-3-phenyl-2-propenoic acid [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(9): 644-648.
[11]	Zongze Huang, Xintong Wang, Ying Meng, Xin Li, Haoran Xiao, Xiling Bian, KeWei Wang, Qi Sun. The design, synthesis and α7 nicotinic acetylcholine receptors positive allosteric modulative evaluation of 3H-quinazolin-4-one derivatives [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(8): 540-552.
[12]	Huixia Huang, Huixue Liu, Xiaojie Ma, Hui Guan, Xiaogai Yang. Lanthanum chloride or citrate is absorbed mainly via M cells in gastrointestinal tracts with lanthanum phosphates as the transformed species [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(8): 553-564.
[13]	Yibo Li, Xin Zhou, Zhenming Liu, Liangren Zhang. Designing natural product-like virtual libraries using deep molecule generative models [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(7): 451-459.
[14]	Ying Meng, Wenxing Zou, Zongze Huang, Xintong Wang, Wenxuan Jiao, Wenjun Xie, Xiling Bian, KeWei Wang, Qi Sun. Development of palladium-catalyzed Suzuki carbonylation reaction without external ligand and its application in modification of novel series of α7 nAChR PAMs [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(7): 460-468.
[15]	Yunqi Liu, Xixi Li, Xiaodong Dou, Chao Tian, Zhili Zhang, Junyi Liu, Xiaowei Wang. Similar pyridinone compounds with different activities of anti-HIV-1 reverse transcriptase [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(7): 469-477.