7427-09-0Relevant articles and documents
Bromine substituted aminonaphthoquinones: Synthesis, characterization, DFT and metal ion binding studies
Agarwal, Gunjan,Lande, Dipali N.,Chakrovarty, Debamitra,Gejji, Shridhar P.,Gosavi-Mirkute, Prajakta,Patil, Amit,Salunke-Gawali, Sunita
, p. 88010 - 88029 (2016)
Bromine substituted aminonaphthoquinone ligands viz. 2-(2′-aminomethylpyridyl)-3-bromo-naphthalene-1,4-dione; (2MPA), 2-(3′-aminomethylpyridyl)-3-bromo-naphthalene-1,4-dione; (3MPA), 2-(2′-aminoethylpyridyl)-3-bromo-naphthalene-1,4-dione; (2EPA) and 2-(2′-aminomethylthiophenyl)-3-bromo-naphthalene-1,4-dione (2AMT) and 2-(2′-aminoethylthiophenyl)-3-bromo-naphthalene-1,4-dione (2AET) have been synthesized and characterized by single-crystal X-ray diffraction experiments in conjunction with long range corrected density functional theory. The heterocyclic amines on the naphthoquinone ring render diverse crystal structures. It has been shown that bromine substitution influences the planarity and mutual orientation of naphthoquinone and heterocycles in aminonaphthoquinone ligands. The 2MPA, 3MPA, 2EPA, 2AET aminonaphthoquinone ligands crystallize in the monoclinic space group whereas 2AMT led to the triclinic space group P1. Furthermore, molecular packing of 2MPA and 2EPA revealed dimeric structures while 3MPA and 2AMT are rendered with 'stair-case' arrangements of molecules. 2AET, when viewed down c-axis, showed a 'butterfly like' arrangement. A broad charge transfer band (400-600 nm) was observed in the UV-visible spectra of these ligands. Besides 2MPA and 2EPA exhibit remarkable selectivity toward Cu2+ ions, accompanied by a color change from orange to blue in methanol and methanol-water mixture.
Synthesis, characterization and serum albumin binding studies of vitamin K3 derivatives
Suganthi, Murugesan,Elango, Kuppanagounder P.
, p. 126 - 135 (2017)
Synthesis, characterization and bovine serum albumin (BSA) binding properties of three derivatives of vitamin K3 have been described. Results of UV–Vis and fluorescence spectra indicate complexation between BSA and the ligands with conformational changes
Metal-free, base promoted sp2 C-H functionalization in the sulfonamidation of 1,4-naphthoquinones
Devenderan, Ramanathan,Kasi, Pitchumani
supporting information, p. 5294 - 5300 (2018/08/03)
A novel, metal-free, base promoted sp2 C-H functionalization in the sulfonamidation of 1,4-naphthoquinones via a [3 + 2] cycloaddition reaction using sulfonyl azides under mild reaction conditions is reported. In this straightforward atom- and step-economical protocol, the active alkene moiety of quinone undergoes a thermal azide-alkene [3 + 2] cycloaddition followed by proton abstraction, ring opening and elimination of a nitrogen molecule to form sulfonamidation products in good yield and all the synthesized sulfonamidation derivatives exhibit good absorption and emission characteristics. In addition, the electrochemical properties of both 1,4-naphthoquinone and menadione sulfonamidation derivatives are studied and significant redox potentials are observed. Other important features of this methodology are readily accessible and easy to handle starting materials, milder conditions, reaction with a wide range of substrates and shorter reaction times with good yields.
Highly Efficient Synthesis and Structure–Activity Relationships of a Small Library of Substituted 1,4-Naphthoquinones
Bao, Na,Ou, Jinfeng,Shi, Wei,Li, Na,Chen, Li,Sun, Jianbo
supporting information, p. 2254 - 2258 (2018/06/04)
A platform of highly efficient synthetic methodologies has been established to access a focused library of substituted 1,4-naphthoquinones derivatives functionalized with a diversity of amino/hydroxy/alkyl groups. Furthermore, the structure–activity relationship deduced from antiproliferative activities and toxicities of this 1,4-naphthoquinone library and intracellular reactive oxygen species (ROS) level detections might warrant future potential of plumbagin (2) and compound 13 as promising basic structures to develop novel anti-cancer agents.
Synthesis, anti-proliferative activity evaluation and 3D-QSAR study of naphthoquinone derivatives as potential anti-colorectal cancer agents
Acu?a, Julio,Piermattey, Jhoan,Caro, Daneiva,Bannwitz, Sven,Barrios, Luis,López, Jairo,Ocampo, Yanet,Vivas-Reyes, Ricardo,Aristizábal, Fabio,Gaitán, Ricardo,Müller, Klaus,Franco, Luis
, (2018/02/06)
Colorectal cancer (CRC) is a disease with high incidence and mortality, constituting the fourth most common cause of death from cancer worldwide. Naphthoquinones are attractive compounds due to their biological and structural properties. In this work, 36 naphthoquinone derivatives were synthesized and their activity evaluated against HT-29 cells. Overall, high to moderate anti-proliferative activity was observed in most members of the series, with 15 compounds classified as active (1.73 50 2 = 0.99 and q2 = 0.625). This model allowed proposing five new compounds with two-fold higher theoretical anti-proliferative activity, which would be worthwhile to synthesize and evaluate. Further investigations will be needed to determine the mechanism involved in the effect of most active compounds which are potential candidates for new anticancer agents.
COMPOSITIONS AND METHODS FOR TREATING NEUROLOGICAL DISEASES OR INJURY
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Paragraph 00209, (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 00375, (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.
Structure-activity relationship study of vitamin K derivatives yields highly potent neuroprotective agents
Josey, Benjamin J.,Inks, Elizabeth S.,Wen, Xuejun,Chou, C. James
, p. 1007 - 1022 (2013/03/28)
Historically known for its role in blood coagulation and bone formation, vitamin K (VK) has begun to emerge as an important nutrient for brain function. While VK involvement in the brain has not been fully explored, it is well-known that oxidative stress plays a critical role in neurodegenerative diseases. It was recently reported that VK protects neurons and oligodendrocytes from oxidative injury and rescues Drosophila from mitochondrial defects associated with Parkinson's disease. In this study, we take a chemical approach to define the optimal and minimum pharmacophore responsible for the neuroprotective effects of VK. In doing so, we have developed a series of potent VK analogues with favorable drug characteristics that provide full protection at nanomolar concentrations in a well-defined model of neuronal oxidative stress. Additionally, we have characterized key cellular responses and biomarkers consistent with the compounds' ability to rescue cells from oxidative stress induced cell death.
Synthesis using microwave irradiation and antibacterial evaluation of new N,O-acetals and N,S-acetals derived from 2-amino-1,4-naphthoquinones
Jord?o, Alessandro K.,Novais, Juliana,Leal, Bruno,Escobar, Ana C.,Dos Santos Júnior, Helvécio M.,Castro, Helena C.,Ferreira, Vitor F.
, p. 196 - 201 (2013/07/27)
This paper describes a novel series of N,O-acetals and N,S-acetals (7a-o) derived from 2-amino-1,4-naphthoquinones that were synthesized and evaluated as potential antimicrobial agents. These compounds were obtained in good yields using microwave irradiation, and several of them showed promising antibacterial profiles. Three of our biologically active 2-amino-1,4-naphthoquinone N,O-acetals and N,S-acetals tested against hospital bacterial strains were identified as potential lead compounds. Characterization of all compounds was performed using one-dimensional NMR techniques (1H, 13C-APT), IR spectra, elemental analyses and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS).
3-Arylamino and 3-alkoxy-nor-β-lapachone derivatives: Synthesis and cytotoxicity against cancer cell lines
Da Silva Jr., Eufranio N.,De Deus, Clara F.,Cavalcanti, Bruno C.,Pessoa, Cláudia,Costa-Lotufo, Letícia V.,Montenegro, Raquel C.,De Moraes, Manoel O.,Pinto, Maria Do Carmo F. R.,De Simone, Carlos A.,Ferreira, Vitor F.,Goulart, Marilia O. F.,Andrade, Carlos Kleber Z.,Pinto, Ant?nio V.
scheme or table, p. 504 - 508 (2010/05/02)
Several 3-arylamino and 3-alkoxy-nor-β-lapachone derivatives were synthesized in moderate to high yields and found to be highly potent against cancer cells SF295 (central nervous system),HCT8 (colon), MDA-MB435 (melanoma), and HL60 (leukemia), with ICsub
