Design and biological evaluation of novel hybrids of 1, 5-diarylpyrazole and Chrysin for selective COX-2 inhibition

Bioorganic & Medicinal Chemistry - Tập 26 - Trang 4264-4275 - 2018
Shen-Zhen Ren1, Zhong-Chang Wang1, Xiao-Hua Zhu1, Dan Zhu1, Zhang Li1, Fa-Qian Shen1, Yong-Tao Duan2, Han Cao1, Jing Zhao3, Hai-Liang Zhu1
1State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210023, PR China
2Henan Provincial Key Laboratory of Children's Genetics and Metabolic Diseases, Zhengzhou Children's Hospital, Zhengzhou, 450018, PR China
3State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210023, PR China

Tài liệu tham khảo

Cai, 2016, Discovery of novel hybrids of diaryl-1,2,4-triazoles and caffeic acid as dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase for cancer therapy, Eur J Med Chem, 108, 89, 10.1016/j.ejmech.2015.11.013 Grivennikov, 2010, Immunity, inflammation, and cancer, Cell, 140, 883, 10.1016/j.cell.2010.01.025 Fiorucci, 2001, Dual inhibitors of cyclooxygenase and 5-lipoxygenase. A new avenue in anti-inflammatory therapy, Biochem Pharmacol, 62, 1433, 10.1016/S0006-2952(01)00747-X Jana, 2008, NSAIDs and apoptosis, Cell Mol Life Sci, 65, 1295, 10.1007/s00018-008-7511-x Abbas, 2012, New quinazolinone–pyrimidine hybrids: synthesis, anti-inflammatory, andulcerogenicity studies, Eur J Med Chem, 53, 141, 10.1016/j.ejmech.2012.03.050 Dadiboyena, 2011, Recent methodologies toward the synthesis of valdecoxib: a potential 3,4-diarylisoxazolyl COX-II inhibitor, Eur J Med Chem, 42, 4697 Bali, 2012, Synthesis, evaluation and docking studies on 3-alkoxy-4-methanesulfonamido acetophenone derivatives as non ulcerogenic anti-inflammatory agents, Eur J Med Chem, 49, 397, 10.1016/j.ejmech.2012.01.018 Grover, 2014, Synthesis, biological evaluation, molecular docking and theoretical evaluation of ADMET properties of nepodin and chrysophanol derivatives as potential cyclooxygenase COX-1, COX-2 inhibitors, Eur J Med Chem, 80, 47, 10.1016/j.ejmech.2014.04.033 Kawamori, 1998, Chemopreventive activity of celecoxib, a specific cyclooxygenase-2 inhibitor, against colon carcinogenesis, Cancer Res, 58, 409 Wang, 2007, Cyclooxygenases, prostanoids, and tumor progression, Cancer Metastasis Rev, 26, 525, 10.1007/s10555-007-9096-5 Sever, 2016, Indomethacin based new triazolothiadiazine derivatives: synthesis, evaluation of their anticancer effects on T98 human glioma cell line related to COX-2 inhibition and docking studies, Eur J Med Chem, 113, 179, 10.1016/j.ejmech.2016.02.036 Abouzid, 2010, Structure-based molecular design, synthesis, and in vivo anti-inflammatory activity of pyridazinone derivatives as nonclassic COX-2 inhibitors, Med Chem Res, 19, 629, 10.1007/s00044-009-9218-4 Bandgar, 2011, Synthesis and biological evaluation of orally active prodrugs of indomethacin, J Med Chem, 54, 1191, 10.1021/jm101085j Liebman, 2013, Cyclooxygenase-2 inhibitors for chemoprevention of nonmelanoma skin cancer: is there a role for these agents, J Am Acad Dermatol, 68, 173, 10.1016/j.jaad.2012.06.037 Regulski, 2017, Synthesis, in vitro and in silico evaluation of novel trans -stilbene analogues as potential COX-2 inhibitors, Bioorg Med Chem, 26, 141, 10.1016/j.bmc.2017.11.027 Wuest, 2008, Synthesis and evaluation in vitro and in vivo of a C-labeled cyclooxygenase-2 (COX-2) inhibitor, Bioorg Med Chem, 16, 7662, 10.1016/j.bmc.2008.07.016 Elsayed, 2011, Design, synthesis, and biological evaluation of substituted hydrazone and pyrazole derivatives as selective COX-2 inhibitors: molecular docking study, Bioorg Med Chem, 19, 3416, 10.1016/j.bmc.2011.04.027 Norouzi, 2015, Apoptotic effects of two COX-2 inhibitors on breast adenocarcinoma cells through COX-2 independent pathway, J Cell Biochem, 116, 81, 10.1002/jcb.24944 Qiu, 2015, Synthesis of dihydropyrazole sulphonamide derivatives that act as anti-cancer agents through COX-2 inhibition, Pharmacol Res, 104, 86, 10.1016/j.phrs.2015.12.025 Sun, 2016, Synthesis of phenylpiperazine derivatives of 1,4-benzodioxan as selective COX-2 inhibitors and anti-inflammatory agents, Bioorg Med Chem, 24, 5626, 10.1016/j.bmc.2016.09.023 Zhu, 2016, Design, synthesis and evaluation of benzenesulfonamide-substituted 1,5-diarylpyrazoles containing phenylacetohydrazide derivatives as COX-1/COX-2 agents against solid tumors, RSC Adv, 6, 22,917, 10.1039/C6RA02168A Lu, 2016, Coumarin sulfonamides derivatives as potent and selective COX-2 inhibitors with efficacy in suppressing cancer proliferation and metastasis, Bioorg Med Chem Lett, 26, 3491, 10.1016/j.bmcl.2016.06.037 Yu, 2013, Chrysin activates Notch1 signaling and suppresses tumor growth of anaplastic thyroid carcinoma in vitro and in vivo, Cancer, 119, 774, 10.1002/cncr.27742 Wang, 2014, Anti-enterovirus 71 effects of chrysin and its phosphate ester, PLoS One, 9, 1 Singh, 2015, Triblock conjugates: identification of a highly potent antiinflammatory agent, J Med Chem, 58, 5989, 10.1021/acs.jmedchem.5b00952 Müller-Schiffmann, 2010, Combining independent drug classes into superior, synergistically acting hybrid molecules, Angew Chem Int Ed Engl, 49, 8743, 10.1002/anie.201004437