Design, synthesis and QSAR study of novel isatin analogues inspired Michael acceptor as potential anticancer compounds

Jiabing Wang; Di Yun; Jiali Yao; Weitao Fu; Fangyan Huang; Liping Chen; Tao Wei; Cuijuan Yu; Haineng Xu; Xiaoou Zhou; Yanqing Huang; Jianzhang Wu; Peihong Qiu; Wulan Li

doi:10.1016/j.ejmech.2017.12.043

journal article Jan 01, 2018

Design, synthesis and QSAR study of novel isatin analogues inspired Michael acceptor as potential anticancer compounds

Jiabing Wang

Di Yun

Jiali Yao Weitao Fu Fangyan Huang Liping Chen

Tao Wei

Cuijuan Yu Haineng Xu Xiaoou Zhou Yanqing Huang Jianzhang Wu Peihong Qiu Wulan Li

European Journal of Medicinal Chemistry Vol. 144 pp. 493-503 · Elsevier BV

View at Publisher Save 10.1016/j.ejmech.2017.12.043

Topics

No keywords indexed for this article. Browse by subject →

References

43

[1]

Ferlay "Cancer incidence and mortality worldwide: sources, methods and major patterns in GLOBOCAN 2012" Int. J. Canc. (2015) 10.1002/ijc.29210

[2]

Penny "The challenges for cancer chemoprevention" Chem. Soc. Rev. (2015) 10.1039/c5cs00705d

[3]

Luo "Systems pharmacology strategies for anticancer drug discovery based on natural products" Mol. Biosyst. (2014) 10.1039/c4mb00105b

[4]

Natural Products As Sources of New Drugs over the 30 Years from 1981 to 2010

David J. Newman, Gordon M. Cragg

Journal of Natural Products 2012 10.1021/np200906s

[5]

Mishra "Natural products: an evolving role in future drug discovery" Eur. J. Med. Chem. (2011) 10.1016/j.ejmech.2011.07.057

[6]

Gil-Turnes "Symbiotic marine bacteria chemically defend crustacean embryos from a pathogenic fungus" Science (1989) 10.1126/science.2781297

[7]

Sharma "Synthesis and anti-inflammatory activity evaluation of novel triazolyl-isatin hybrids" J. Enzym. Inhib. Med. Chem. (2016) 10.3109/14756366.2016.1151015

[8]

Swathi "Synthesis and screening of biologically significant 5-hydroxy isatin derivatives for antioxidant activity" Adv. Exp. Med. Biol. (2015) 10.1007/978-3-319-08927-0_14

[9]

Vine "Cytotoxic and anticancer activities of isatin and its derivatives: a comprehensive review from 2000-2008" Anti Canc. Agents Med. Chem. (2009) 10.2174/1871520610909040397

[10]

Griffith "Small molecule inhibitors of protein kinases in cancer-how to overcome resistance" Mini Rev. Med. Chem. (2006) 10.2174/138955706778560184

[11]

Garofalo "The combination of the tyrosine kinase receptor inhibitor SU6668 with paclitaxel affects ascites formation and tumor spread in ovarian carcinoma xenografts growing orthotopically" Clin. Canc. Res. (2003)

[12]

Shin "Zerumbone induces heme oxygenase-1 expression in mouse skin and cultured murine epidermal cells through activation of Nrf2" Canc. Prev. Res. (2011) 10.1158/1940-6207.capr-10-0354

[13]

Liu "Xanthohumol blocks proliferation and migration of vascular smooth muscle cells in vitro and reduces neointima formation in vivo" J. Nat. Prod. (2017) 10.1021/acs.jnatprod.7b00268

[14]

Liu "ERBB2 overexpression establishes ERBB3-dependent hypersensitivity of breast cancer cells to Withaferin A" Mol. Canc. Therapeut. (2016) 10.1158/1535-7163.mct-15-0932

[15]

Esatbeyoglu "Curcumin–from molecule to biological function" Angew. Chem. (2012) 10.1002/anie.201107724

[16]

Mahapatra "Anti-cancer chalcones: structural and molecular target perspectives" Eur. J. Med. Chem. (2015) 10.1016/j.ejmech.2015.05.004

[17]

Sahu "Exploring pharmacological significance of chalcone scaffold: a review" Curr. Med. Chem. (2012) 10.2174/092986712803414132

[18]

Farombi "Curcumin attenuates dimethylnitrosamine-induced liver injury in rats through Nrf2-mediated induction of heme oxygenase-1" Food Chem. Toxicol. (2008) 10.1016/j.fct.2007.09.095

[19]

Shankaraiah "Synthesis of different heterocycles-linked chalcone conjugates as cytotoxic agents and tubulin polymerization inhibitors" Bioorg. Med. Chem. (2017) 10.1016/j.bmc.2017.07.031

[20]

Li "Hexamethoxylated monocarbonyl analogues of curcumin cause G2/M cell cycle arrest in NCI-H460 cells via Michael acceptor-dependent redox intervention" J. Agric. Food Chem. (2015) 10.1021/acs.jafc.5b02011

[21]

Raja "Anticancer activity of Celastrol in combination with ErbB2-targeted therapeutics for treatment of ErbB2-overexpressing breast cancers" Canc. Biol. Ther. (2011) 10.4161/cbt.11.2.13959

[22]

Gersch "Electrophilic natural products and their biological targets" Nat. Prod. Rep. (2012) 10.1039/c2np20012k

[23]

Gediya "Promise and challenges in drug discovery and development of hybrid anticancer drugs" Expet Opin. Drug Discov. (2009) 10.1517/17460440903341705

[24]

Kerru "Recent advances (2015-2016) in anticancer hybrids" Eur. J. Med. Chem. (2017) 10.1016/j.ejmech.2017.07.033

[25]

Shaveta "Singh, Hybrid molecules: the privileged scaffolds for various pharmaceuticals" Eur. J. Med. Chem. (2016) 10.1016/j.ejmech.2016.08.039

[26]

Baraldi "Design, synthesis, and biological evaluation of hybrid molecules containing alpha-methylene-gamma-butyrolactones and polypyrrole minor groove binders" J. Med. Chem. (2004) 10.1021/jm031104y

[27]

Fang "Hybrid molecules from xanomeline and tacrine: enhanced tacrine actions on cholinesterases and muscarinic M1 receptors" J. Med. Chem. (2010) 10.1021/jm901616h

[28]

Green "Rapid colorimetric assay for cell viability: application to the quantitation of cytotoxic and growth inhibitory lymphokines" J. Immunol. Meth. (1984) 10.1016/0022-1759(84)90190-x

[29]

Bradbury "Quantitative structure-activity relationships and ecological risk assessment: an overview of predictive aquatic toxicology research" Toxicol. Lett. (1995) 10.1016/0378-4274(95)03374-t

[30]

Amaratunga "Enriched random forests" Bioinformatics (2008) 10.1093/bioinformatics/btn356

[31]

De Lobel "A screening methodology based on random forests to improve the detection of gene-gene interactions" Eur. J. Hum. Genet. (2010) 10.1038/ejhg.2010.48

[32]

Astin "Competition amongst Eph receptors regulates contact inhibition of locomotion and invasiveness in prostate cancer cells" Nat. Cell Biol. (2010) 10.1038/ncb2122

[33]

Huang "Discovery of dehydroabietic acid sulfonamide based derivatives as selective matrix metalloproteinases inactivators that inhibit cell migration and proliferation" Eur. J. Med. Chem. (2017) 10.1016/j.ejmech.2017.07.020

[34]

Guggilapu "Synthesis of thiazole linked indolyl-3-glyoxylamide derivatives as tubulin polymerization inhibitors" Eur. J. Med. Chem. (2017) 10.1016/j.ejmech.2017.06.025

[35]

Xu "Enhancement of wound healing by the traditional Chinese medicine herbal mixture sophora flavescens in a rat model of perianal ulceration" In Vivo (2017)

[36]

Sri Ramya "Synthesis and biological evaluation of curcumin inspired indole analogues as tubulin polymerization inhibitors" Eur. J. Med. Chem. (2017) 10.1016/j.ejmech.2016.12.043

[37]

Wu "The possible FAT1-mediated apoptotic pathways in porcine cumulus cells" Cell Biol. Int. (2017) 10.1002/cbin.10695

[38]

Ibrahim "Synthesis of spiro heterocyclic compounds" J. Chem. (2012)

[39]

Dandia "Facile one pot microwave enhanced multistep synthesis of novel biologically important scaffold spiro[indole-pyridopyrimidines]" Arkivoc (2005) 10.3998/ark.5550190.0006.d07

[40]

Zhao "Organocatalytic enantioselective cascade Aza-Michael/Michael addition sequence for asymmetric synthesis of chiral spiro[pyrrolidine-3,3'-oxindole]s" Am. J. Org. Chem. (2015)

[41]

Saroj "Photophysical study of some 3- benzoylmethyleneindol-2-ones and estimation of ground and excited states dipole moments from solvatochromic methods using solvent polarity parameters" J. Mol. Struct. (2012) 10.1016/j.molstruc.2011.12.043

[42]

Reddy "Synthesis and biological evaluation of spiro[cyclopropane-1,3'-indolin]-2'-ones as potential anticancer agents" Bioorg. Med. Chem. Lett (2015) 10.1016/j.bmcl.2015.08.056

[43]

M.S. Bedi, Preet, Process for Preparation of Aryl Pyridazino[3,4-b]indole Derivatives, Indian Patent Application, 2012DE02318, 2014.

Cited By

61

Synthesis of Isatin-derived Heterocycles with Promising Anticancer Activities

Bubun Banerjee, Aditi Sharma · 2025

Current Topics in Medicinal Chemist...

Thiazole, Isatin and Phthalimide Derivatives Tested in vivo against Cancer Models: A Literature Review of the Last Six Years

Aline Ferreira Pinto, Janine Siqueira Nunes · 2024

Current Medicinal Chemistry

Synthesis and Study of New Anticoagulant Candidates Based on 6-Aryl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones

A. A. Skoptsova, N. P. Novichikhina · 2023

Russian Journal of General Chemistr...

Metrics

61

Citations

43

References

Details

Published: Jan 01, 2018
Vol/Issue: 144
Pages: 493-503
License: View

Authors

Department of Children Health Care, Nanjing Maternity and Child Health Care Hospital Affiliated to Nanjing Medical University, Nanjing, China; Institute of Pediatrics, Nanjing Medical University, Nanjing, China

Department of Genetics, Harvard Medical School, and Department of Molecular Biology, Massachusetts General Hospital, Boston, MA 02114

Center for Cell and Gene Therapy, Baylor College of Medicine, Houston, TX 77030-2399, USA

Y

Yanqing Huang

Southwest Agricultural University, Chongqing Beibei, 400716, China.; Beijing Institute of Genomics of Chinese Academy of Sciences, Beijing Genomics Institute, Beijing Proteomics Institute, Beijing 101300, China.; James D. Watson Institute of Genome Sciences of Zhejiang University, Hangzhou Genomics Institute, Key Laboratory of Genomic Bioinformatics of Zhejiang Province, Hangzhou 310008, China.; University of Washington Genome Center, Department of Medicine, University of Washington, Seattle, WA 98195, USA.

J

Jianzhang Wu

General Surgery, Cancer Center, Department of Gastrointestinal and Pancreatic Surgery, Zhejiang Provincial People’s Hospital, Affiliated People’s Hospital, Hangzhou Medical College, Hangzhou, Zhejiang, China

Funding

National Natural Science Foundation of China Award: 81703766

ZheJiang Province Natural Science Fund of China Award: LY17H160059

The Opening Project of Zhejiang Provincial Top Key Discipline of Pharmaceutical Sciences, National Undergraduate Training Programs for Innovation and Entrepreneurship Award: 201710343004

Wenzhou Medical Universtiy Undergraduate Training Programs for Innovation and Entrepreneurship Award: wyx2017101038

Cite This Article

Jiabing Wang, Di Yun, Jiali Yao, et al. (2018). Design, synthesis and QSAR study of novel isatin analogues inspired Michael acceptor as potential anticancer compounds. European Journal of Medicinal Chemistry, 144, 493-503. https://doi.org/10.1016/j.ejmech.2017.12.043

Design, synthesis and QSAR study of novel isatin analogues inspired Michael acceptor as potential anticancer compounds

You May Also Like