6305-23-3Relevant academic research and scientific papers
Novel 2,3-disubstituted 1,4-naphthoquinone derivatives and their metal complexes - Synthesis and in vitro cytotoxic effect against mouse fibrosarcoma L929 cells
Niculescu, Violeta-Carolina,Muresan, Nicolae,Salageanu, Aurora,Tucureanu, Catalin,Marinescu, Gabriela,Chirigiu, Liviu,Lepadatu, Costinel
, p. 13 - 19 (2012)
Quinones have various pharmacological properties including antibacterial, antifungal, antiviral, anti-inflammatory, antipyretic and anticancer activity. Two novel 2,3-disubstituted 1,4-naphthoquinones and their metal complexes were synthesised, characterized and tested. The cytotoxic potential of the novel 2,3-disubstituted 1,4-naphthoquinones and their metal complexes was studied against L929 murine fibroblasts cells grown in vitro. The treatment resulted in a concentration-dependent cytotoxicity as indicated by MTT assay.
Synthesis of amino acid-naphthoquinones and in vitro studies on cervical and breast cell lines
Rivera-ávalos, Ernesto,De Loera, Denisse,Araujo-Huitrado, Jorge Gustavo,Escalante-García, Ismailia Leilani,Mu?oz-Sánchez, Miguel Antonio,Hernández, Hiram,López, Jesús Adrián,López, Lluvia
, (2019/12/23)
We performed an extensive analysis about the reaction conditions of the 1,4-Michael addition of amino acids to 1,4-naphthoquinone and substitution to 2,3-dichloronaphthoquinone, and a complete evaluation of stoichiometry, use of different bases, and the p
Synthesis, anticancer activity, and molecular modeling of 1,4-naphthoquinones that inhibit MKK7 and Cdc25
Schepetkin, Igor A.,Karpenko, Alexander S.,Khlebnikov, Andrei I.,Shibinska, Marina O.,Levandovskiy, Igor A.,Kirpotina, Liliya N.,Danilenko, Nadezhda V.,Quinn, Mark T.
, (2019/09/30)
Cell division cycle 25 (Cdc25) and mitogen-activated protein kinase kinase 7 (MKK7) are enzymes involved in intracellular signaling but can also contribute to tumorigenesis. We synthesized and characterized the biological activity of 1,4-naphthoquinones structurally similar to reported Cdc25 and(or) MKK7 inhibitors with anticancer activity. Compound 7 (3-[(1,4-dioxonaphthalen-2-yl)sulfanyl]propanoic acid) exhibited high binding affinity for MKK7 (Kd = 230 nM), which was greater than the affinity of NSC 95397 (Kd = 1.1 μM). Although plumbagin had a lower binding affinity for MKK7, this compound and sulfur-containing derivatives 4 and 6–8 were potent inhibitors of Cdc25A and Cdc25B. Derivative 22e containing a phenylamino side chain was selective for MKK7 versus MKK4 and Cdc25 A/B, and its isomer 22f was a selective inhibitor of Cdc25 A/B. Docking studies performed on several naphthoquinones highlighted interesting aspects concerning the molecule orientation and hydrogen bonding interactions, which could help to explain the activity of the compounds toward MKK7 and Cdc25B. The most potent naphthoquinone-based inhibitors of MKK7 and/or Cdc25 A/B were also screened for their cytotoxicity against nine cancer cell lines and primary human mononuclear cells, and a correlation was found between Cdc25 A/B inhibitory activity and cytotoxicity of the compounds. Quantum chemical calculations using BP86 and ωB97X-D3 functionals were performed on 20 naphthoquinone derivatives to obtain a set of molecular electronic properties and to correlate these properties with cytotoxic activities. Systematic theoretical DFT calculations with subsequent correlation analysis indicated that energy of the lowest unoccupied molecular orbital E(LUMO), vertical electron affinity (VEA), and reactivity index ω of these molecules were important characteristics related to their cytotoxicity. The reactivity index ω was also a key characteristic related to Cdc25 A/B phosphatase inhibitory activity. Thus, 1,4-naphthoquinones displaying sulfur-containing and phenylamino side chains with additional polar groups could be successfully utilized for further development of efficacious Cdc25 A/B and MKK7 inhibitors with anticancer activity.
Non-peptide proteasomal inhibitor, its pharmaceutical composition, preparation method and application
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Paragraph 0082-0085, (2018/06/28)
The invention discloses a non-peptide proteasome inhibitor as well as a medicine composition, a preparation method and application thereof. The non-peptide proteasome inhibitor disclosed by the invention is novel in structure and has the property of in vi
Design, synthesis and biological evaluation of novel non-peptide boronic acid derivatives as proteasome inhibitors
Ge, Ying,Li, Aibo,Wu, Jianwei,Feng, Haiwei,Wang, Letian,Liu, Hongwu,Xu, Yungen,Xu, Qingxiang,Zhao, Li,Li, Yuyan
, p. 180 - 191 (2017/02/15)
A novel series of non-peptide proteasome inhibitors bearing the 1, 4-naphthoquinone scaffold and boronic acid warhead was developed. In the biological evaluation on the chymotrypsin-like activity of human 20S proteasome, five compounds showed IC50/s
'On water': unprecedented nucleophilic substitution and addition reactions with 1,4-quinones in aqueous suspension
Tandon, Vishnu K.,Maurya, Hardesh K.
experimental part, p. 5896 - 5902 (2010/01/11)
Unique nucleophilic substitution and addition reactions of 1,4-quinones in aqueous suspension with aromatic amines, primary aliphatic amines, amino acid, ester of amino acid, heterocyclic amines, hydrazine, amide, and thioethers are described in absence o
