Literature DB >> 33727979

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity.

Zbigniew Malinowski1, Emilia Fornal2, Agata Sumara2, Renata Kontek3, Karol Bukowski3, Beata Pasternak4, Dariusz Sroczyński5, Joachim Kusz6, Magdalena Małecka7, Monika Nowak1.   

Abstract

Amino- and polyaminophthalazinones were synthesized by the palladium-catalyzed amination (alkyl- and arylamines, polyamines) of 4-bromophthalazinones in good yields. The coordinating properties of selected aminophthalazinones towards Cu(II) ions were investigated and the participation of the nitrogen atoms in the complexation of the metal ion was shown. A biological screening of the potential cytotoxicity of selected synthesized compounds on HT-29 and PC-3 cell lines, as well as on the L-929 cell line, proved that some amino derivatives of phthalazinone show interesting anticancer activities. The detailed synthesis, spectroscopic data, and biological assays are reported.
Copyright © 2021, Malinowski et al.

Entities:  

Keywords:  Pd cross-coupling; amination; complexes; cytotoxicity; phthalazinone

Year:  2021        PMID: 33727979      PMCID: PMC7934800          DOI: 10.3762/bjoc.17.50

Source DB:  PubMed          Journal:  Beilstein J Org Chem        ISSN: 1860-5397            Impact factor:   2.883


  29 in total

1.  Metabolism and disposition of vatalanib (PTK787/ZK-222584) in cancer patients.

Authors:  Lorenz M Jost; Hans-Peter Gschwind; Tarja Jalava; Yongyu Wang; Clemens Guenther; Claire Souppart; Antje Rottmann; Karsten Denner; Felix Waldmeier; Gerhard Gross; Eric Masson; Dirk Laurent
Journal:  Drug Metab Dispos       Date:  2006-08-01       Impact factor: 3.922

2.  Design of Phthalazinone Amide Histamine H1 Receptor Antagonists for Use in Rhinitis.

Authors:  Panayiotis A Procopiou; Alison J Ford; Paul M Gore; Brian E Looker; Simon T Hodgson; Duncan S Holmes; Sadie Vile; Kenneth L Clark; Ken A Saunders; Robert J Slack; James E Rowedder; Clarissa J Watts
Journal:  ACS Med Chem Lett       Date:  2017-04-21       Impact factor: 4.345

3.  Palladium-catalyzed synthesis of 4-aminophthalazin-1(2H)-ones by isocyanide insertion.

Authors:  Tjøstil Vlaar; Eelco Ruijter; Anass Znabet; Elwin Janssen; Frans J J de Kanter; Bert U W Maes; Romano V A Orru
Journal:  Org Lett       Date:  2011-11-15       Impact factor: 6.005

Review 4.  Phthalazin-1(2H)-one as a remarkable scaffold in drug discovery.

Authors:  Noemí Vila; Pedro Besada; Tamara Costas; M Carmen Costas-Lago; Carmen Terán
Journal:  Eur J Med Chem       Date:  2014-11-25       Impact factor: 6.514

5.  Discovery of highly selective and potent p38 inhibitors based on a phthalazine scaffold.

Authors:  Brad Herberich; Guo-Qiang Cao; Partha P Chakrabarti; James R Falsey; Liping Pettus; Robert M Rzasa; Anthony B Reed; Andreas Reichelt; Kelvin Sham; Maya Thaman; Ryan P Wurz; Shimin Xu; Dawei Zhang; Faye Hsieh; Matthew R Lee; Rashid Syed; Vivian Li; David Grosfeld; Matthew H Plant; Bradley Henkle; Lisa Sherman; Scot Middleton; Lu Min Wong; Andrew S Tasker
Journal:  J Med Chem       Date:  2008-09-26       Impact factor: 7.446

6.  Phase II trial of vatalanib in patients with advanced or metastatic pancreatic adenocarcinoma after first-line gemcitabine therapy (PCRT O4-001).

Authors:  T Dragovich; D Laheru; F Dayyani; V Bolejack; L Smith; J Seng; H Burris; P Rosen; M Hidalgo; P Ritch; A F Baker; N Raghunand; J Crowley; D D Von Hoff
Journal:  Cancer Chemother Pharmacol       Date:  2014-06-18       Impact factor: 3.333

7.  Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-Imidazolyl)alkyl]-1(2H)-phthalazinones.

Authors:  M Yamaguchi; K Kamei; T Koga; M Akima; T Kuroki; N Ohi
Journal:  J Med Chem       Date:  1993-12-10       Impact factor: 7.446

8.  Synthesis and pharmacological investigation of azaphthalazinone human histamine H(1) receptor antagonists.

Authors:  Panayiotis A Procopiou; Christopher Browning; Paul M Gore; Sean M Lynn; Stephen A Richards; Robert J Slack; Steven L Sollis
Journal:  Bioorg Med Chem       Date:  2012-08-31       Impact factor: 3.641

9.  Antioxidant activity and inhibitory effects of hydralazine on inducible NOS/COX-2 gene and protein expression in rat peritoneal macrophages.

Authors:  José M Leiro; Ezequiel Alvarez; Juan A Arranz; Ernesto Cano; Francisco Orallo
Journal:  Int Immunopharmacol       Date:  2004-02       Impact factor: 4.932

10.  Regioselective Synthesis of Substituted 4-Alkylamino and 4-Arylaminophthalazin-1(2H)-ones.

Authors:  Subramaniam Krishnananthan; Daniel Smith; Dauh-Rurng Wu; Shiuhang Yip; Prashantha Gunaga; Arvind Mathur; Jianqing Li
Journal:  J Org Chem       Date:  2016-02-08       Impact factor: 4.354

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