24137-17-5Relevant academic research and scientific papers
Synthetic enamine naphthoquinone derived from lawsone as cytotoxic agents assessed by in vitro and in silico evaluations
Carneiro, José Walkimar M.,Costa, Pedro Mikael S.,Filho, Eclair Venturini,Fiorot, Rodolfo G.,Gomes, Anne Caroline C.,Greco, Sandro J.,Guimar?es, Celina J.,Lemos, Bárbara C.,Pessoa, Claudia,Westphal, Regina,de Oliveira, Fátima C. E.
, (2021/11/11)
We synthesized ten enamine naphthoquinones with yields ranging from 43 to 76%. These compounds were screened for their in vitro antiproliferative activities by MTT assay against four types of human cancer cell lines: HCT116, PC3, HL60 and SNB19. The naphthoquinones bearing the picolylamine (7) and quinoline (12) moieties were the most actives (IC50 2–C3 internuclear repulsion and the molecular dipole moment, relate to the biological response. Furthermore, Molecular Docking simulations indicate that the synthetic compounds have the potential to act as anticancer molecules by inhibiting topoisomerase-II and thymidylate synthase.
Palladium catalyzed Carbon–Hydrogen bond activation on amino-substituted quinones under acidic condition
Huang, Peng-Hao,Hong, Rui-Yu,Hong, Fung-E
, p. 2337 - 2347 (2021/10/08)
In this study, 2-(benzylamino)naphthalene-1,4-dione (4a) was used as the starting material to carry out a one-pot catalytic reaction in acetic acid with divalent palladium metal Pd(OAc)2 in a nitrogen atmosphere. Two compounds, 5a and 6a, were observed unexpectedly. Both compounds were characterized by spectroscopic methods as well as X-ray single crystal determination. The crystal structure of 5a reveals that a nitrogen-containing six-membered ring is formed; while the crystal structure of 6a shows that both oxazole and pyridine ring are generated. The optimized condition for making 6a was pursued. Derivatives of 4a, such as 4b and 4c, were also used as starting materials to proceed under the aforementioned optimal reaction conditions. Although the yields are not satisfactory, obviously the same patterns of corresponding compounds can be synthesized. The reaction of a 4a-structural related compound 9 under similar condition, two unexpected oxazole-containing compounds, 10 and 11, were obtained. The diverse pathways for this type of reactions even starting with slightly different substituents on the quinone indeed provides chemists with a perpetual motivation for further studies.
Antibacterial Activity of 2-Amino-1,4-naphthoquinone Derivatives against Gram-Positive and Gram-Negative Bacterial Strains and Their Interaction with Human Serum Albumin
Chaves, Otávio A.,Echevarria, Aurea,Netto-Ferreira, José Carlos,Paiva, Rojane O.,da Costa, Gisela L.,da Silva, Carla C.
, p. 1838 - 1851 (2020/10/09)
A series of 2-amino-1,4-naphthoquinone derivatives (NQA-NQF) was synthesized by alternative methods (ultrasonication and microwave irradiation), with yields ranging from 40 to 71%, and without the need of further recrystallization. Each compound was evaluated against four Gram-positive (Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus and Bacillus cereus) and five Gram-negative (Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Acinetobacter baumannii and Klebsiella pneumoniae positive β-lactamase) bacteria strains. The NQF was the most active amino-naphthoquinone derivative with minimum inhibitory concentration (MIC) of 31.2 μg mL-1 against K. pneumoniae positive β-lactamase (a common intestinal bacteria which can cause life-threatening infections). On the other hand, NQA and NQC showed good activity as a potential antibiotic for the bacteria strains assayed, except for K. pneumoniae. In addition, the affinity of these three most active compounds (NQA, NQC, and NQF) for human serum albumin (HSA) was evaluated employing multiple spectroscopic techniques (steady-state, time-resolved, and synchronous fluorescence, as well as circular dichroism), combined with theoretical calculations (molecular docking). The interaction HSA:2-amino-1,4-naphthoquinones occurs spontaneously and moderately inside the subdomain IIA (Sudlow’s site I) via hydrogen bonding and van der Waals forces.
IDO inhibitor, preparation method and applications thereof
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Paragraph 0155-0158; 0317-0320, (2020/04/17)
The invention relates to an IDO inhibitor, a preparation method and applications thereof, and belongs to the technical field of medicinal chemistry. The IDO inhibitor with the characteristics of a structure represented by a general formula I or the pharma
Activity analysis and preliminary inducer screening of the chicken DAZL gene promoter
Zhang, Lei,Zhu, Rui,Zuo, Qisheng,Li, Dong,Lian, Chao,Tang, Beibei,Xiao, Tianrong,Zhang, Yani,Li, Bichun
, p. 6595 - 6605 (2015/04/14)
This study was aimed at identifying the active control area of chicken DAZL gene core promoter, to screen optimum inducers of the DAZL gene, thus to enhance the differentiation of embryonic stem cells into spermatogonial stem cells. Fragments of chicken DAZL gene promoter were cloned into fluorescent reporter plasmids and transfected into DF-1 cells. Then Dual-Luciferase Reporter Assay System was used to identify the activity of the DAZL gene under different inducers. Our studies showed that the DAZL core promoter region for the Suqin yellow chicken was 383 to 39 bp. The dual-luciferase reporter showed that all-trans retinoic acid (ATRA), a retinoic acid receptor alpha agonist (tamibarotene/Am80), or estradiol (E2) could significantly enhance DAZL transcription. The in vitro inductive culture of chicken ESCs demonstrated that, with ATRA treatment, DAZL transcription peaked at 6 days and then decreased slowly; whereas, DAZL transcription was continuous and peaked at 10 days with Am80 treatment. E E2 treatment significantly increased DAZL expression after 8 days. All three treatments were associated with the appearance of male germ cell (MGC)-like cells on day 10. These results provide the optimum inducer screening of the DAZL gene and lay the foundation for further screening of compounds that can induce the differentiation of ESCs into MGCs in vitro.
Identification of unusual C-Cl...π contacts in 2-(alkylamino)-3-chloro-1,4-naphthoquinones: Effect of N-substituents on crystal packing, fluorescence, redox and anti-microbial properties
Singh, Vinay K.,Verma, Sanjay K.,Kadu, Rahul,Mobin, Shaikh M.
, p. 43669 - 43686 (2015/05/27)
The chemo-selective reaction of 2,3-dichloro-1,4-naphthoquinone with different primary amines affords access to a series of derivatives, such as 2-(alkylamino)-3-chloro-1,4-naphthoquinone (1-6) and 2-(benzylamino)-1,4-naphthoquinone (7), in good yields. All the compounds 1-7 were characterized thoroughly by microanalysis, standard spectroscopy and thermogravimetric methods. The supramolecular structures of 1-4 and 7 were studied by means of single-crystal X-ray diffraction to gauge the influence of substituents that are present on the amine functionality on the association of molecules in the solid state. The study showed that the introduction of various amine N-substituents induces conformational changes that apparently modify the nature and number of donor-acceptor sites for noncovalent interactions, leading to diverse crystal packing patterns. Interestingly, the introduction of 2-(benzylamino)- and 2-(2-pyridylmethylamino)- substituents in 2 and 4 successfully switched on the C-Cl...π synthon, which is scarcely seen in the crystal packing of organic molecules. Compounds 1, 2, 4 and 5 fluoresced in the range of 350-620 nm with concomitant Stokes shifts of 81, 131, 141 and 131 nm, respectively, and their cyclic voltammograms evidenced two quasi-reversible single-electron waves. All the compounds (except 5) exhibited their first endothermic peak on the DTA curves without any mass loss due to the phase change, attributable to the melting points of the respective compounds. Remarkably, compound 5 exhibited an enhanced antibacterial activity against S. aureus and proved to be a more potent antibacterial agent than the well-known drug "ciprofloxacin".
Divergent and facile Lewis acid-mediated synthesis of N-alkyl 2-aminomethylene-1,3-indanediones and 2-alkylamino-1,4-naphthoquinones
Zhang, Qian,Chang, Cheng-Wei Tom
supporting information, p. 893 - 896 (2015/02/05)
N-Alkyl 2-aminomethylene-1,3-indanediones and 2-alkylamino-1,4-naphthoquinones are known for their diverse and versatile bioactivities and applications. Traditionally, these two compounds were synthesized in separate routes using different materials. By e
Development of quinone analogues as dynamin GTPase inhibitors
Macgregor, Kylie A.,Abdel-Hamid, Mohammed K.,Odell, Luke R.,Chau, Ngoc,Whiting, Ainslie,Robinson, Phillip J.,McCluskey, Adam
, p. 191 - 206 (2014/08/18)
Virtual screening of the ChemDiversity and ChemBridge compound databases against dynamin I (dynI) GTPase activity identified 2,5-bis-(benzylamino)-1,4- benzoquinone 1 as a 273 ± 106 μM inhibitor. In silico lead optimization and focused library-led synthesis resulted in the development of four discrete benzoquinone/naphthoquinone based compound libraries comprising 54 compounds in total. Sixteen analogues were more potent than lead 1, with 2,5-bis-(4-hydroxyanilino)-1,4-benzoquinone (45) and 2,5-bis(4-carboxyanilino)- 1,4-benzoquinone (49) the most active with IC50 values of 11.1 ± 3.6 and 10.6 ± 1.6 μM respectively. Molecular modelling suggested a number of hydrogen bonding and hydrophobic interactions were involved in stabilization of 49 within the dynI GTP binding site. Six of the most active inhibitors were evaluated for potential inhibition of clathrin-mediated endocytosis (CME). Quinone 45 was the most effective CME inhibitor with an IC50(CME) of 36 ± 16 μM.
COMPOSITIONS AND METHODS FOR TREATING NEUROLOGICAL DISEASES OR INJURY
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Paragraph 00219, (2014/05/24)
Provided are compounds for the treatment of neurological diseases or injuries, including neurodegenerative diseases, stroke, trauma, epilepsy, acute and chronic kidney injuries, diabetes mellitus, and/or seizures. In some embodiments, derivatives of vitamin K are provided.
INHIBITORS OF THE MITF MOLECULAR PATHWAY
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Paragraph 00369, (2015/01/09)
Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.
