- Polymorphism in chloro derivatives of 1,4-naphthoquinone: Experiment and density functional theoretic investigations
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Molecular interactions underlying polymorphs of chlorine containing 1,4-naphthoquinone derivatives have been investigated by employing single crystal X-ray, 1H NMR, FTIR and electronic spectra experiments combined with density functional theory. Two polymorphs of 2,3-dichloro-1,4-naphthoquinone possessing (i) triclinic space group P-1(A1 and A3), and (ii) orthorhombic with Pb21a (A2) space group were obtained. The polymorph A3 has two molecules in its asymmetric unit which facilitate [Formula presented] interactions engendeing polymeric planar sheets. The two polymorphs of 2-amino-3-chloro-1,4-naphthoquinone reveal monoclinic forms with Pc (B1) and C2/C (B2) space groups. A tetramer of B2 molecule possess [Formula presented] interactions. The polymorphs of 2-chloro-3-hydroxy-1,4-naphthoquinone crystallizes in monoclinic space groups Pc (C1) and Pn (C2). Polymeric chain of C2 molecules results via [Formula presented] interactions and the chains further are connected through [Formula presented] and π-π stacking interactions those arise from benzenoid and quinonoid centroid. Moreover A3 facilitates the dimer via the halogen bonding interactions. Furthermore hydrogen bonding renders stability to the dimer C2. On the other hand compound B2 does not favor dimer formation. These inferences based on experimental observations are rationalized through the use of the dispersion corrected M06-2x functional based density functional theory. Further time dependent density functional theory has been used to assign the electronic transitions in UV–visible spectra of A3, B2 and C2.
- Chaudhari, Dinkar,Gejji, Shridhar P.,Lande, Dipali N.,Chakravarty, Debamitra,Salunke-Gawali, Sunita
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- Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone
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Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase.
- Stagliano, Kenneth W.,Emadi, Ashkan,Lu, Zhenhai,Malinakova, Helena C.,Twenter, Barry,Yu, Min,Holland, Louis E.,Rom, Amanda M.,Harwood, John S.,Amin, Ronak,Johnson, Allison A.,Pommier, Yves
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- Molecular structures and biological activities of (N)-n-alkylammonium 2-chloro-3-oxido-1,4-naphthoquinone salts
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Single crystal X-ray structures and vibrational spectra of (N)-n-alkylammonium 2-chloro-3-oxido-1,4-naphthoquinone salts (alkyl = methyl to octyl, CS-1 to CS-8) possessing X-H?Y (X = N, C and Y[dbnd]O, Cl) hydrogen bonding and diverse noncovalent interactions have been characterized. Except for the CS-2 and CS-7 rest of the compounds facilitate π?π and Cl?π interactions. The compound CS-3 showed the presence of Cl?O interactions. Electronic structure and spectral characteristics of obtained are in consonance with the density functional theory. These complexes showed remarkable antiproliferative and antifungal activities.
- Choudhari, Dinkar,Lande, Dipali N.,Bagade, Aditi,Gejji, Shridhar P.,Chakravarty, Debamitra,Kodam, Kisan M.,Salunke-Gawali, Sunita
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- Tridentate 3-Substituted Naphthoquinone Ruthenium Arene Complexes: Synthesis, Characterization, Aqueous Behavior, and Theoretical and Biological Studies
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A series of nine RuII arene complexes bearing tridentate naphthoquinone-based N,O,O-ligands was synthesized and characterized. Aqueous stability and their hydrolysis mechanism were investigated via UV/vis photometry, HPLC-MS, and density functional theory calculations. Substituents with a positive inductive effect improved their stability at physiological pH (7.4) intensely, whereas substituents such as halogens accelerated hydrolysis and formation of dimeric pyrazolate and hydroxido bridged dimers. The observed cytotoxic profile is unusual, as complexes exhibited much higher cytotoxicity in SW480 colon cancer cells than in the broadly chemo- (incl. platinum-) sensitive CH1/PA-1 teratocarcinoma cells. This activity pattern as well as reduced or slightly enhanced ROS generation and the lack of DNA interactions indicate a mode of action different from established or previously investigated classes of metallodrugs.
- Geisler, Heiko,Westermayr, Julia,Cseh, Klaudia,Wenisch, Dominik,Fuchs, Valentin,Harringer, Sophia,Plutzar, Sarah,Gajic, Natalie,Hejl, Michaela,Jakupec, Michael A.,Marquetand, Philipp,Kandioller, Wolfgang
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p. 9805 - 9819
(2021/06/30)
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- Merrifield resin-supported quinone as an efficient biomimetic catalyst for metal-free, base-free, chemoselective synthesis of 2,4,6-trisubstituted pyridines
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Metal-free, base-free, biomimetic and chemoselective synthesis of 2,4,6-trisubstituted pyridines was developed under mild conditions for the first time. The heterogeneous biomimetic catalyst-recoverable Merrifield resin-supported quinone-was fully characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray photoelectron spectrometry (XPS) and energy dispersive X-ray spectroscopy (EDX). This supported quinone catalyst exhibited excellent catalytic reactivity for chemoselective synthesis of 2,4,6-trisubstituted pyridines, providing an efficient and green method for the synthesis of pyridine derivatives under mild conditions. Mechanistic investigations were conducted to gain insights into the heterogeneous biomimetic catalyst as well as the resulting transformation. The successful capture of intermediates offered direct and clear evidence for the proposed mechanism.
- Yang, Qing,Zhang, Yilin,Zeng, Wei,Duan, Zheng-Chao,Sang, Xinxin,Wang, Dawei
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supporting information
p. 5683 - 5690
(2019/10/22)
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- NAPTHOQUINONES, PRO-DRUGS, AND METHODS OF USE THEREOF
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Provided herein are naphthoquinones compounds such as those with a hydrogen bond donating group of the formula (I): wherein: R1, R2, R3, R4, R5, and n are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.
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Paragraph 00156
(2017/07/06)
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- Design, synthesis and antimalarial activity of some new 2-hydroxy-1,4-naphthoquinone-4-hydroxyaniline hybrid mannich bases
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In this study, some novel 2-hydroxy-1,4-naphthoquinone-4-hydroxyaniline hybrid Mannich bases were designed, synthesized and evaluated for in vitro antimalarial activity. The design strategy of novel hybrid molecules involves fusion between the pharmacopho
- Sharma, Dipshikha,Chetia, Dipak,Rudrapal, Mithun
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p. 782 - 788
(2016/03/01)
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- Structure-activity relationships and colorimetric properties of specific probes for the putative cancer biomarker human arylamine N-acetyltransferase 1
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A naphthoquinone inhibitor of human arylamine N-acetyltransferase 1 (hNAT1), a potential cancer biomarker and therapeutic target, has been reported which undergoes a distinctive concomitant color change from red to blue upon binding to the enzyme. Here we describe the use of in silico modeling alongside structure-activity relationship studies to advance the hit compound towards a potential probe to quantify hNAT1 levels in tissues. Derivatives with both a fifty-fold higher potency against hNAT1 and a two-fold greater absorption coefficient compared to the initial hit have been synthesized; these compounds retain specificity for hNAT1 and its murine homologue mNat2 over the isoenzyme hNAT2. A relationship between pKa, inhibitor potency and colorimetric properties has also been uncovered. The high potency of representative examples against hNAT1 in ZR-75-1 cell extracts also paves the way for the development of inhibitors with improved intrinsic sensitivity which could enable detection of hNAT1 in tissue samples and potentially act as tools for elucidating the unknown role hNAT1 plays in ER+ breast cancer; this could in turn lead to a therapeutic use for such inhibitors.
- Egleton, James E.,Thinnes, Cyrille C.,Seden, Peter T.,Laurieri, Nicola,Lee, Siu Po,Hadavizadeh, Kate S.,Measures, Angelina R.,Jones, Alan M.,Thompson, Sam,Varney, Amy,Wynne, Graham M.,Ryan, Ali,Sim, Edith,Russell, Angela J.
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supporting information
p. 3030 - 3054
(2014/05/20)
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- Synthesis, chemical properties, and antimicrobial activity of 2- and 2,3-substituted [(tetrahydro-2,4-dioxopyrimidin-1(2H)-yl)phenoxy]naphthalene-1, 4-diones
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Mono- and disubstituted [(tetrahydro-2,4-dioxopyrimidin-1(2H)-yl)phenoxy] naphthalene-1,4-diones were synthesized by the reaction of dihydro-1-(3-hydroxy- and 4-hydroxyphenyl)pyrimidine-2,4(1H,3H)-diones and their 5- and 6-methyl derivatives with 2,3-dichloro-1,4-naphthoquinone. Their stability in alkaline and acidic media was investigated. Four of the compounds exhibited good antimicrobial activity against Staphylococcus aureus, Mycobacterium luteum, Candida tenuis, and Aspergillus niger. Graphical abstract: [Figure not available: see fulltext.]
- Voskiene, Ausra,Sapijanskaite, Birute,Mickevicius, Vytautas,Kantminiene, Kristina,Stasevych, Maryna,Komarovska-Porokhnyavets, Olena,Musyanovych, Rostyslav,Novikov, Volodymyr
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p. 529 - 537
(2011/12/22)
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- On the Reactions of 2,3-Dichloro-1,4-Naphthoquinone and 5-Chloro-6H-6-Oxoanthra[1,9-cd]isoxazole with Ketoximes and 1,2-Naphthaquinone Dioxime
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In the reaction of 2,3-dichloro-1,4-naphthoquinone and 5-chloro-6H-6-oxoanthra[1,9-cd]-isoxazole with ketoximes one of chlorine atoms is replaced by the oxime residue. In the reaction of 2,3-dichloro-1,4-naphthoquinone with 1,2-naphthoquinone dioxime 1,2-
- Timoshkova,Gornostaev
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p. 1486 - 1488
(2007/10/03)
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- Chlorination of quinonoid compounds using dichlorine monoxide
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Dichlorine monoxide is a selective reagent for the monochlorination at the active quinonoid position in benzoquinones and naphthoquinones.
- Thapliyal,Singh,Khanna
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p. 1079 - 1083
(2007/10/02)
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- Derivatives of 1,4-Naphthoquinone via 3-(Phenyliodonio)-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide
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The title compound 3 reacts with various electrophiles such as hydrogen halides, benzoyl chloride, iodomethane, and bromine to afford 3-halo derivatives of 2-hydroxy-1,4-naphthoquinone. 3 reacts also with dimethyl sulfide to give a trans-ylidation product; photochemically, furan derivatives are formed with 2-methyl-2-butene, styrene, and phenylacetylene.Carbon disulfide affords the 2-thioxo-1,3-oxathiole derivative 15.
- Hatzigrigoriou, Evangelia,Spyroudis, Spyros,Varvoglis, Anastasios
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p. 167 - 170
(2007/10/02)
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- OXYGENATION OF AROMATIC AND ALIPHATIC HYDROCARBONS BY A NEW REAGENT SYSTEM, Fe(CH3CN)6(2+)-H2O2-Ac2O: AN EFFECTIVE MODEL REAGENT FOR MONO-OXYGENASE
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Reactions of aromatic and aliphatic hydrocarbons with a new system, Fe(CH3CN)6(2+) - H2O2 - Ac2O in CH3CN, gave oxygenation products with fairly high reaction efficiency ( Tables I and II )compared to known to reagent systems used as enzyme models for mono-oxygenases.Investigations of the mechanism of these reactions indicated the involvement of either complex C.FeIV(OH)(OAc)(2+), or complex D, FeIV(OAc)(2+), dependig on the organic substrate.Keywords-oxygenation; aromatic hydrocarbon; aliphatic hydrocarbon; hexakisacetonitrile iron(II) perchlorate; hydrogen peroxide; enzyme model; mono-oxygenase
- Kotani, Eiichi,Kobayashi. Shigeki,Ishii, Yoko,Tobinaga, Seisho
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p. 4671 - 4679
(2007/10/02)
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- Quinone Chemistry. Reaction of 2,3-Dichloro-1,4-naphthoquinone with o-Aminophenols under Various Conditions
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The reaction of 2,3-dichloro-1,4-naphthochinone (1) and o-aminophenols (2) under various reaction conditions was reinvestigated.Despite earlier literature, 1 and 2a in alcohol react to give a mixture of 6-chloro-12a-hydroxy-5H-benzophenoxazin-5-one (4a), 6-chloro-12a-alkoxy-5H-benzophenoxazin-5-one (5), 6-chloro-5H-benzophenoxazin-5-one (7a), 2-amino-3H-phenoxazin-3-one (8) and triphenodioxazine (9a).Contradictory to earlier findings, 1 and 2a in MeOH/KOH afford 7a but the highest yield of the compound is achieved by using EtOH or MeOH and anhydrous potassium acetate.A probable mechanism for the formation of all reaction products is presented and detailed spectroscopic data of all compounds are given.
- Agarwal, Nand L.,Schaefer, Wolfram
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p. 2155 - 2161
(2007/10/02)
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