Literature DB >> 36238867

Efficient Synthesis of Aurone Mannich Bases and Evaluation of their Antineoplastic Activity in PC-3 Prostate Cancer Cells.

Antonina V Popova1, Mykhaylo S Frasinyuk1,2,3, Svitlana P Bondarenko4, Wen Zhang2,5, Yanqi Xie2,3, Zachary M Martin2,3, Xianfeng Cai2,5, Michael V Fiandalo6, James L Mohler6, Chunming Liu2,5, David S Watt2,3,5, Vitaliy M Sviripa3,7.   

Abstract

An efficient method for regioselective synthesis of C-7 Mannich bases of 6-hydroxyaurones was accomplished by the N,N-dialkylaminomethylation using aminals prepared from dimethylamine, dipropylamine, bis(2-methoxyethyl)amine, N-methylbutylamine, N-methylbenzylamine, morpholine, piperidine, and 1-methylpiperazine. Further transformation of 7-(N,N-dialkylamino)methyl group in these aurones led to formation of C-7 acetoxymethyl and methoxymethyl derivatives of 6-hydroxyaurones, some of which showed promising inhibition of PC-3 prostate cancer cell proliferation in the high nanomolar to low micromolar range that exceeded that of cisplatin.

Entities:  

Keywords:  6-hydroxyаurones; Mannich base; aminomеthylation; prostate cancer

Year:  2018        PMID: 36238867      PMCID: PMC9555813          DOI: 10.1007/s11696-018-0485-8

Source DB:  PubMed          Journal:  Chem Zvesti        ISSN: 0366-6352            Impact factor:   2.146


  16 in total

Review 1.  Aurones: a subclass of flavones with promising biological potential.

Authors:  Ahcène Boumendjel
Journal:  Curr Med Chem       Date:  2003-12       Impact factor: 4.530

2.  Influence of the skeleton on the cytotoxicity of flavonoids.

Authors:  Guy Lewin; Geneviève Aubert; Sylviane Thoret; Joëlle Dubois; Thierry Cresteil
Journal:  Bioorg Med Chem       Date:  2011-12-30       Impact factor: 3.641

3.  Synthesis of (Z)-2-((1H-indazol-3-yl)methylene)-6-[¹¹C]methoxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one as a new potential PET probe for imaging of the enzyme PIM1.

Authors:  Mingzhang Gao; Min Wang; Kathy D Miller; Qi-Huang Zheng
Journal:  Bioorg Med Chem Lett       Date:  2013-06-06       Impact factor: 2.823

4.  Design, synthesis and AChE inhibitory activity of indanone and aurone derivatives.

Authors:  Rong Sheng; Yu Xu; Chunqi Hu; Jing Zhang; Xiao Lin; Jingya Li; Bo Yang; Qiaojun He; Yongzhou Hu
Journal:  Eur J Med Chem       Date:  2008-03-16       Impact factor: 6.514

5.  Aurones as modulators of ABCG2 and ABCB1: synthesis and structure-activity relationships.

Authors:  Hong May Sim; Ker Yun Loh; Wee Kiang Yeo; Chong Yew Lee; Mei Lin Go
Journal:  ChemMedChem       Date:  2011-02-07       Impact factor: 3.466

6.  Synthesis and biological evaluation of a novel series of 2,2-bisaminomethylated aurone analogues as anti-inflammatory and antimicrobial agents.

Authors:  Babasaheb P Bandgar; Sachin A Patil; Balaji L Korbad; Satish C Biradar; Shivraj N Nile; Chandrahasya N Khobragade
Journal:  Eur J Med Chem       Date:  2010-04-03       Impact factor: 6.514

7.  Structure-based virtual screening approach to the discovery of p38 MAP kinase inhibitors.

Authors:  Hwanho Choi; Ho Jeong Park; Jong Chul Shin; Hyun Sun Ko; Jung Kyun Lee; Soyoung Lee; Hwangseo Park; Sungwoo Hong
Journal:  Bioorg Med Chem Lett       Date:  2012-02-02       Impact factor: 2.823

8.  Structure-based design and synthesis of 2-benzylidene-benzofuran-3-ones as flavopiridol mimics.

Authors:  Joseph Schoepfer; Heinz Fretz; Bhabatosh Chaudhuri; Lionel Muller; Egge Seeber; Laurent Meijer; Olivier Lozach; Eric Vangrevelinghe; Pascal Furet
Journal:  J Med Chem       Date:  2002-04-25       Impact factor: 7.446

9.  Nitrogen-containing flavonoids as CDK1/Cyclin B inhibitors: design, synthesis, and biological evaluation.

Authors:  Tao Liu; Zhongmiao Xu; Qiaojun He; Yanhong Chen; Bo Yang; Yongzhou Hu
Journal:  Bioorg Med Chem Lett       Date:  2006-11-07       Impact factor: 2.823

10.  Probing the aurone scaffold against Plasmodium falciparum: design, synthesis and antimalarial activity.

Authors:  Marta P Carrasco; Ana S Newton; Lídia Gonçalves; Ana Góis; Marta Machado; Jiri Gut; Fátima Nogueira; Thomas Hänscheid; Rita C Guedes; Daniel J V A dos Santos; Philip J Rosenthal; Rui Moreira
Journal:  Eur J Med Chem       Date:  2014-04-28       Impact factor: 6.514

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