- Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents
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Several members of the phenylamino-1,4-naphthoquinone series were prepared in order to investigate structure-activity relationships (SAR) and to explore the antitumor effects associated with this scaffold. The cytotoxic effects of the aminoquinones (ECsu
- Benites, Julio,Valderrama, Jaime A.,Bettega, Karina,Pedrosa, Rozangela Curi,Calderon, Pedro Buc,Verrax, Julien
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- Substituted 1,4-Naphthoquinones vs. the Ascitic Sarcoma 180 of Mice
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Twelve 1,4-naphthoquinones have been tested against the ascitic form of sarcoma 180 in Swiss mice.Statistical analysis shows that the most important molecular parameter determining their effectiveness in prolonging the life of mice bearing this tumor is their redox potentials.Although the toxicities of the compounds are also related to the redox potentials in the same way, the therapeutic indexes can be increased by adding substituents of greater lipophilicity.The naphthoquinones differ greatly in antitumor activities and may inhibit the growth of malignant cells by different mechanisms
- Hodnett, Ernest M.,Wongwiechintana, Chinda,Dunn, William J.,Marrs, Pam
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- Synthesis and characterization of nitrogen and sulfur containing 1,4-naphthoquinones
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New N,S-disubstituted naphthoquinones were synthesized by reactions of S- and N-nucleophiles with 2,3-dichloro-1,4-naphthoquinone. 2-(Hexadecylthio)-3- (phenylamino)-naphthalene-1,4-dione 5a was synthesized by reaction of 2-chloro-3-(phenylamino)-naphthal
- Sayil, Cigdem,Kurban, Semih,Ibis, Cemil
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- Crystallographic evidence for resonance assisted H-Bonding effect in selective colorimetric detection of cyanide by arylamino-naphthoquinones
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Five new chemo-receptors, based on arylamino-naphthoquinone, possessing electron donating and electron withdrawing substituents have been prepared by single step green method. These receptors are found to be highly selective and sensitive towards cyanide
- Rajalakshmi,Jayasudha,Ciattini, Samuele,Chelazzi, Laura,Elango, Kuppanagounder P.
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- Synthesis, antimicrobial properties, and inhibition of catalase activity of 1,4-naphtho-and benzoquinone derivatives containing N-, S-, O-substituted
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A series of new 1,4-naphtho-and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving
- Kurban, Semih,Deniz, Nahide Gulsah,Sayil, Cigdem,Ozyurek, Mustafa,Guclu, Kubilay,Stasevych, Maryna,Zvarych, Viktor,Komarovska-Porokhnyavet, Olena,Novikov, Volodymyr
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- Synthesis and Antimicrobial Evaluation of 1,4-Naphthoquinone Derivatives as Potential Antibacterial Agents
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1,4-Naphthoquinones are an important class of compounds present in a number of natural products. In this study, a new series of 1,4-naphthoquinone derivatives were synthesized. All the synthesized compounds were tested for in vitro antimicrobial activity.
- Ravichandiran, Palanisamy,Mas?yk, Maciej,Sheet, Sunirmal,Janeczko, Monika,Premnath, Dhanraj,Kim, Ae Rhan,Park, Byung-Hyun,Han, Myung-Kwan,Yoo, Dong Jin
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- Spectroscopic and theoretical studies on the nucleophilic substitution of 2,3-dichloronaphthoquinone with para-substituted anilines in solid state via initial charge transfer complexation
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Various spectroscopy techniques (UV-Vis, DRS, FT-IR, 1H NMR, LC-MS) and theoretical computations have been employed to investigate the mechanism of the nucleophilic substitution reaction of 2,3- dichloronaphthoquinone (DCNQ) with para-substitut
- Satheshkumar, Angupillai,Elango, Kuppanagounder P.
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- Synthesis of novel 2-(fluoroanilino)-3-(2,4-dinitroanilino) derivatives of 1,4-naphthoquinone
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Several novel 2-(fluoroanilino)-3-(2,4-dinitroanilino) derivatives of 1,4-naphthoquinone have been synthesized in good to excellent yields. First, 2-chloro-3-(2,4-dinitroanilino)-1,4-naphthoquinone was prepared in two steps beginning with the reaction of
- Leyva, Elisa,Baines, Kim M.,Espinosa-González, Claudia G.,López, Lluvia I.,Magaldi-Lara, Diego A.,Leyva, Socorro
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- Thermolysis of 2-azido-3-(R-anilino)-1,4-naphthoquinones. Nitrene insertion versus hydrogen abstraction
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2-chloro-3-(R-anilino)-1,4-naphthoquinones react with sodium azide upon refluxing in DMF. The thermochemistry of 2-azido-3-(R-anilino)-1,4-naphthoquinone is strongly modified by the substituent on aniline. Having an strong electron-donor like O-R results
- Cárdenas-Chaparro, Agobardo,Leyva, Elisa,Loredo-Carrillo, Silvia E.,Martínez-Richa, Antonio,Platz, Matthew S.
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supporting information
(2020/03/03)
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- Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber's Hereditary Optic Neuropathy (LHON)
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Leber's hereditary optic neuropathy (LHON) is a rare genetic mitochondrial disease and the primary cause of chronic visual impairment for at least 1 in 10 ?000 individuals in the U.K. Treatment options remain limited, with only a few drug candidates and therapeutic approaches, either approved or in development. Recently, idebenone has been investigated as drug therapy in the treatment of LHON, although evidence for the efficacy of idebenone is limited in the literature. NAD(P)H:quinone oxidoreductase 1 (NQO1) and mitochondrial complex III were identified as the major enzymes involved in idebenone activity. Based on this mode of action, computer-aided techniques and structure-activity relationship (SAR) optimization studies led to the discovery of a series naphthoquinone-related small molecules, with comparable adenosine 5′-triphosphate (ATP) rescue activity to idebenone. Among these, three compounds showed activity in the nanomolar range and one, 2-((4-fluoro-3-(trifluoromethyl)phenyl)amino)-3-(methylthio)naphthalene-1,3-dione (1), demonstrated significantly higher potency ex vivo, and significantly lower cytotoxicity, than idebenone.
- Varricchio, Carmine,Beirne, Kathy,Aeschlimann, Pascale,Heard, Charles,Rozanowska, Malgorzata,Votruba, Marcela,Brancale, Andrea
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p. 13638 - 13655
(2020/11/30)
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- A One-Pot Approach to 2-(N-Substituted Amino)-1,4-naphthoquinones with Use of Nitro Compounds and 1,4-Naphthoquinones in Water
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A one-pot synthesis of 2-(N-substituted amino)-1,4-naphthoquinones from 1,4-naphthoquinones and nitro compounds in water has been developed. This method features mild reaction conditions and provides aromatic nitro compounds with various functional groups such as halogens, methylthio, ester, amide, even allyl, propargyl, and heterocycles, as well as aliphatic nitro compounds that are well tolerated. This method can be scaled up and we conducted further transformation of the obtained 2-(N-substituted amino)-1,4-naphthoquinones to synthesize carbazolequinone derivatives.
- Chen, Xu-Ling,Dong, Yu,He, Shuai,Zhang, Rui,Zhang, Hua,Tang, Lei,Zhang, Xiao-Mei,Wang, Ji-Yu
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supporting information
p. 615 - 619
(2019/03/08)
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- Method for synthesizing 2-substituted amino-1,4-naphthoquinone derivative
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The invention discloses a method for synthesizing a 2-substituted amino-1,4-naphthoquinone derivative. The method comprises the following steps: mixing a nitro compound, 2-substituted 1,4-naphthoquinone, a catalyst, a metal and a solvent uniformly at 20-100 DEG C; adding an H source, stirring the components for reaction for 1-24h; performing a reduction-addition reaction between the nitro compoundand the 2-substituted 1,4-naphthoquinone; after the reaction, adding water to the reaction system for dilution; performing filtering; extracting filtrate with ethyl acetate; after organic phases arecombined, washing the mixture with saturated saline solution and drying the mixture with anhydrous sodium sulfate sequentially; subsequently, performing filtering, and performing vacuum concentrationto remove a solvent; and packing solids into a column, and performing separation through column chromatography (a ratio of petroleum ether to ethyl acetate is 5:1) to obtain red solids. Compared withan existing synthesis method, the synthesis method provided by the invention has a wide range of raw materials and the raw materials are easy to obtain; compared with amine compounds, nitro compoundshave better stability; and the synthesis method provided by the invention is simple to operate and mild in reaction condition.
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Paragraph 0134-0139
(2019/05/28)
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- A simple synthesis of 3,4-dihydrobenzo[f]quinoxalin-6(2H)-one derivatives substituted in the ring B
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[Figure not available: see fulltext.] We followed a simple, inexpensive, and efficient route to synthesize a series of 3,4-dihydrobenzo[f]quinoxalin-6(2H)-one derivatives substituted in the ring B, with the expectation that this scaffold might exhibit antineoplastic activity. 5-Chlorobenzo[f]quinoxalin-6-ylacetate and 4-benzylbenzo[f]quinoxalin-6(4H)-one were obtained for the first time.
- Castro-Castillo, Vicente,Suárez-Rozas, Cristian,Simpson, Sebastián,Barriga-González, Andrés
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p. 553 - 559
(2017/08/30)
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- Composition for Distructing Microalgae
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The present invention relates to a composition for destroying microalgae, more specifically, to a composition for destroying microalgae containing naphthoquinone compounds having a specific exchange group. The composition for destroying microalgae, according to the present invention, can prevent green tide and red tide by being processed in areas such as cultivation facilities for microalgae, areas in which the green tide or the red tide occur, or areas expected to occur the green tide or the red tide.
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Paragraph 0479-0482
(2017/09/05)
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- Synthesis and studies of the antifungal activity of 2-anilino-/2,3-dianilino-/2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinones
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Several synthetic and natural naphthoquinone derivatives have been associated with antifungal activity. Candida albicans is a fungus that is known to exist in the normal human flora, but under certain conditions it can cause mild to fatal infections. Its pathogenicity has been associated with fungus conversion from cellular yeast to filamentous form Y–M. Inhibition of this process by several anilino-, dianilino-, phenoxy-, and diphenoxy-1,4-naphthoquinones was investigated in order to find some correlation between structure, redox properties and biological activity.
- Leyva, Elisa,López, Lluvia I.,de la Cruz, Ramón F. García,Espinosa-González, Claudia G.
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p. 1813 - 1827
(2017/02/15)
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- NAPHTHAQUINONE METHYLTRANSFERASE INHIBITORS AND USES THEREOF
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Provided herein are compounds of (I), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, and prodrugs thereof. Also provided are pharmaceutical compositions and methods involving the inventive compounds for the treatment of proliferative diseases (e.g., cancer (e.g., leukemia, breast cancer, melanoma, metastatic cancer) and diseases associated with inappropriate SET8 activity. Also provided are methods for inhibiting SET8 and methods for labelling SET8.
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Page/Page column 87; 88; 90
(2015/11/27)
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- Synthesis and evaluation of 2-heteroaryl and 2,3-diheteroaryl-1,4- naphthoquinones that potently induce apoptosis in cancer cells
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This article describes the preparation of 2-heteroaryl and 2,3-diheteroaryl-1,4-naphthoquinones by an environmentally benign short synthetic route with the goal of finding 1,4-naphthoquinone derivatives that induce apoptosis in cancer cells. We have ident
- Tandon, Vishnu K.,Maurya, Hardesh K.,Kumar, Sandeep,Rashid, Aijaz,Panda, Dulal
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p. 12441 - 12447
(2014/03/21)
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- Synthesis, anticancer activity and QSAR study of 1,4-naphthoquinone derivatives
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A series of 2-substituted amino-3-chloro-1,4-naphthoquinone derivatives (3-12) were synthesized as anticancer agents and tested against four cancer cell lines including HepG2, HuCCA-1, A549 and MOLT-3. The most potent cytotoxic activity against the HepG2,
- Prachayasittikul, Veda,Pingaew, Ratchanok,Worachartcheewan, Apilak,Nantasenamat, Chanin,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
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p. 247 - 263
(2014/08/05)
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- Charge transfer facilitated direct electrophilic substitution in phenylaminonaphthoquinones: Experimental, theoretical and electrochemical studies
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A simple and effective synthetic protocol to introduce electron withdrawing substitutents (Br and NO2) in the phenyl ring of 2-(p-R-phenylamino)-3-chloro-1,4-naphthoquinones (where R = H, Me, OMe, F and Cl; 1a-e) has been demonstrated using the
- Satheshkumar,Ganesh,Elango, Kuppanagounder P.
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p. 993 - 1003
(2014/03/21)
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- Novel naphthoquinone derivatives: Synthesis and activity against human African trypanosomiasis
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A series of naphthoquinone derivatives has been synthesized and tested for its biological activity against human African trypanosomiasis. The use of reverse micellar medium not only enhanced the conversion rate, but also showed selectivity towards mono-co
- Samant, Bhupesh S.,Chakaingesu, Chikomborero
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supporting information
p. 1420 - 1423
(2013/03/14)
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- 'On water': unprecedented nucleophilic substitution and addition reactions with 1,4-quinones in aqueous suspension
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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
- Tandon, Vishnu K.,Maurya, Hardesh K.
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experimental part
p. 5896 - 5902
(2010/01/11)
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- Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents
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A series of 2-Arylamino-3-chloro-1,4-naphthoquinones (3), 2-Amino-3-arylsulfanyl-1,4-naphthoquinones (5), 2-Arylamino-3-arylsulfanyl-1,4-naphthoquinones (6), Dihydrobenzo[f]naphtho[2,3-b][1,4]thiazepine-6,11-diones (9) (via Pictet-Spengler cyclization), Isoindoline-1,3-dione derivatives of 1,4-naphthoquinone (13), 2,2′-(1,4-Dioxo-1,4-dihydronaphthalene-2,3-diyl)bis(methylene)dibenzonitrile (14), 13-Amino-12-substituted-6H-benzo[e]naphtho [2,3-b][1,4]diazepine-6,11(12H)-diones (15-16), 2-Chloro-3-arylsulfanyl-1,4-naphthoquinones (17-18) and 3-Methyl-6H-benzo[b]phenothiazine-6,11(12H)-dione (19) were synthesized and studied for their antifungal and antibacterial activities. The results indicate that compounds 3b, 5a and 5b have potent antifungal activity. Amongst the most promising antifungal compounds, 3b showed better antifungal activity than clinically prevalent antifungal drug Fluconazole (MIC50 = 2.0 μg/mL) against Sporothrix schenckii (MIC50 = 1.56 μg/mL), significant profile against Candida albicans (MIC50 = 1.56 μg/mL), Cryptococcus neoformans (MIC50 = 0.78 μg/mL) and Trichophyton mentagraphytes (MIC50 = 1.56 μg/mL) and same antifungal activity when compared with Amphotericin-B against C. neoformans (MIC50 = 0.78 μg/mL). Compounds 3b, 5a and 5b also showed promising antibacterial activity.
- Tandon, Vishnu K.,Maurya, Hardesh K.,Mishra, Nripendra N.,Shukla, Praveen K.
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experimental part
p. 3130 - 3137
(2009/10/17)
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- NEW IMIDAZOLE DERIVATIVES, PREPARATION METHOD THEREOF AND ORGANIC ELECTRONIC DEVICE USING THE SAME
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The present invention relates to a new imidazole derivative, a method for preparing the derivative, and an organic electronic device using the derivative. The imidazole derivative according to the invention can perform functions of hole injection, hole tr
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Page/Page column 22
(2010/11/25)
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- Direct nitration of 3-arylamino-2-chloro-1,4-naphthoquinones
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A convenient two-step synthesis of mononitro and dinitro derivatives of the title compounds is reported. The Michael type addition of aromatic amines to 2,3-dichloro-1,4-naphthoquinone, is followed by mixed acids nitration to yield nitro aromatic quinones
- Win, Thida,Yerushalmi, Sarit,Bittner, Shmuel
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p. 1631 - 1634
(2007/10/03)
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- Diamine derivatives of quinone and uses thereof
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Diamine derivatives of quinones, and related compounds, including salts thereof, that modulate the levels of gene expression in cellular systems, such as cancer cells, are disclosed, along with methods for preparing such compounds and derivatives, as well as pharmaceutical compositions containing these compounds and derivatives as active ingredients. Methods of using these as compounds and derivatives as therapeutic agents are also described.
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Page/Page column 12
(2010/02/10)
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- Identification of compounds for the treatment or prevention of proliferative diseases
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The invention features compounds for the treatment of cancer and other proliferative diseases. These compounds were identified in screening assays that contact candidate compounds with a cell containing a nucleic acid that includes a HER2 regulatory element and a reporter sequence. The invention further features compounds structurally related to those identified by the screening assays. Finally, the invention features methods of treating or preventing a proliferative disease using the compounds of the invention.
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- Synthesis and Structure of Chlorine-Containing 2-Amino-1,4-naphthoquinone Derivatives
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Exhaustive chlorination of 2-amino-1,4-naphthoquinone derivatives yields 3,3-dichloro-2-imino-2,3-dihydro-1,4-naphthoquinones.
- Litvin, B. L.,Gubrii, Z. V.,Shermolovich, Yu. G.,Novikov, V. P.
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p. 377 - 383
(2007/10/03)
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- Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of 2-substituted 3-chloro-1,4-naphthoquinone derivatives
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A series of 2-substituted 3-chloro-1,4-naphthoquinones was synthesized, and the antiplatelet, antiinflammatory, and antiallergic activities of these compounds were evaluated. The structure-activity relationships in this series were also examined. Most of the 2-alkyl/arylcarboxamido derivatives of 3-chloro-1,4-naphthoquinone showed potent activities with similar trends in each of the activities evaluated.
- Lien, Jin-Cherng,Huang, Li-Jiau,Wang, Jih-Pyang,Teng, Che-Ming,Lee, Kuo-Hsiung,Kou, Sheng-Chu
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p. 2111 - 2120
(2007/10/03)
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- Iodination and chlorination of 2-/4-arylamino-1,4-/1,2-naphthoquinones with alkylhalides and DMSO
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2-/4-Arylamino-1,4-/1,2-naphthoquinones 10/13 are chlorinated with tert-butylbromide, DMSO and calcium chloride to give 2-/4-arylamino-3-chloro-1,4-/1,2-naphthoquinones 11A/14A. The iodination with tert-butylbromide, DMSO and potassium iodide give 2-/4-arylamino-3-iodo-1,4-/1,2-naphthoquinones 11C/14C.
- Kallmayer,Doerr
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p. 479 - 485
(2007/10/03)
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- Angular Heterocycles. A Convenient Synthesis of 6-N-(Acetylanilino)-5H-benzophenothiazin-5-one, 6-N-(Acetylanilino)-5H-benzophenoxazin-5-ones and Their Derivatives
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The reaction of 2-N-(acetylanilino)-3-chloro-1,4-naphthoquinone (2) with bifunctional aromatic amines afforded angular heterocycles 6 and 7.Reductive acetylation of 7 provided O-acyl 9 and O,N-diacyl 10 derivatives depending upon the reaction conditions.T
- Agarwal, N. L.,Ghosh, S.,Tripathi, A. K.,Atal, C. K.
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p. 509 - 512
(2007/10/02)
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- Quinone Chemistry. Reaction of 2,3-Dichloro-1,4-naphthoquinone with Arylamines in Pyridine
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2,3-Dichloro-1,4-naphthoquinone (1) reacts with arylamines (2) in pyridine to afford 2-(arylamino)-3-chloro-1,4-naphthoquinone (6), 2-(arylamino)-1,4-naphthoquinone (5), 2-(arylamino)-1,4-naphthoquinone-3-pyridinium perchlorate (4), and 2-amino-1,4-naphth
- Agarwal, Nand L.,Schaefer, Wolfram
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p. 5139 - 5143
(2007/10/02)
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