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Journal articles on the topic 'Methylène quinone'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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1

Misran, M., D. Matthews, P. Valente, and A. Hope. "Photochemical Electron Transfer Between Methylene Blue and Quinones." Australian Journal of Chemistry 47, no. 2 (1994): 209. http://dx.doi.org/10.1071/ch9940209.

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Methylene Blue is a well known photochemical oxidant. In this paper we present results of cyclic voltammetry and laser flash photolysis experiments which demonstrate that Methylene Blue may function also as a photochemical reductant. Laser flash photolysis studies of Methylene Blue were carried out in aqueous solution at pH 10, in ethanol and in aqueous dispersions of lipid vesicles in the presence of benzoquinol , benzoquinone and the long-chain naphthoquinone Vitamin K1. Both the quinones and the quinol affected the transient of the decay of triplet Methylene Blue to its ground electronic st

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2

Zhang, Ling, Xiaoyan Lin, Dayun Huang, Xue Liu, and Xiangmei Wu. "Recent Advances in Triarylmethane Synthesis." Synthesis 52, no. 16 (2020): 2311–29. http://dx.doi.org/10.1055/s-0040-1707115.

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Triarylmethanes are important molecules in organic chemistry. This review discusses advances in their synthesis summarized in five categories according to the starting materials: (1) benzyl reagents with different leaving groups, such as benzyl alcohols, ethers, esters, phosphates, sulfones, thioethers, sulfonamide, 1,3-dicarbonyls, and ammonium salts; (2) reactions via para- or ortho-quinone methides; (3) arylation of benzyl halides; (4) C–H activation of methylenes; and (5) reactions of aldehydes or N-tosylhydrazones. Triarylmethane derivatives such as 9-arylxanthenones, 9-arylfluorenes, and

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3

Wan, Peter, Beverly Barker, Li Diao, Maike Fischer, Yijian Shi, and Cheng Yang. "1995 Merck Frosst Award Lecture Quinone methides: relevant intermediates in organic chemistry." Canadian Journal of Chemistry 74, no. 4 (1996): 465–75. http://dx.doi.org/10.1139/v96-051.

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ortho and para-Quinone methides (2-methylene-3,5-cyclohexadien-1-one and 4-methylene-2,5-cyclohexadien-1-one, respectively) are intermediates in a variety of important chemical systems. In particular, o-quinone methides are useful in synthesis for the construction of chroman ring systems. A brief account of the relevance of quinone methide chemistry will be provided. This is followed by a review of recent studies from our laboratory on efficient methods for the photogeneration of quinone methides, concentrating on the use of hydroxy-substituted benzyl alcohols in aqueous media. It is shown tha

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4

Tasqeeruddin, Syed, Yahya Asiri, and Jaber Abdullah Alsherhri. "An Efficient and Green Microwave-Assisted Synthesis of Quinoline DerivativesviaKnoevengal Condensation." Letters in Organic Chemistry 17, no. 2 (2020): 157–63. http://dx.doi.org/10.2174/1570178616666190618153721.

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:We have developed an efficient and green synthesis of quinoline derivatives using L-proline under Knoevenagel condensation. L-proline was found to be an efficient catalyst for the Knoevenagel condensation of substituted 2-aminoaryl ketones 1 with the active methylene compounds 2, affording quinolone derivatives 3. The reaction has been done under conventional as well as under microwave conditions. The latter procedure has been found to be much more efficient in terms of time and yield.

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5

Vartale, S. P., N. K. Halikar, and Y. D. Pawar. "Synthesis and Antimicrobial Activity of 3-Cyano-4-imino-9-methoxy-4H-pyrimido [2,1-b] pyrimido [4,5-b] quinoline and 2-Substituted Derivatives." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/862651.

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The 2-amino-7-methoxypyrimido[4,5-b]quinoline (1) on treatment with bis(methylthio)methylene malononitrile (2) in ethyl alcohol and catalytic amount of TEA gives 3-cyano-4-imino-9-methoxy-2-methythio-4H-pyrimido[2,1-b]pyrimido[4,5-b]quinoline (3). The latter were further reacted with selected N-, O-, and C-nucleophiles such as aryl amines, hetryl amines, substituted phenols, and compounds containing an active methylene group.

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6

Dong, Ying, Dong Liang, Jianjin Huang, and Peng Zhang. "Sesquiterpenes with Quinone Reductase-Inducing Activity from Liriodendron Chinense." Natural Product Communications 4, no. 4 (2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400403.

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Bioassay-directed separation of the methylene chloride extracts from the wood of Liriodendron chinense led to the isolation of six sesquiterpenes, tulipinolide (1), α-liriodenolide (2), β-liriodenolide (3), lipiferolide (4), 11,13-dehydrolanuginolide (5), and tulipinolide diepoxide (6). Compounds 1-6 have not been found previously in L. chinense. The structures of the compounds were established on the basis of NMR spectroscopic data. All the compounds exhibited quinone reductase (QR)- inducing activity in Hepa lclc7 cells.

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7

Padilla-Montaño, Nayely, Leandro de León Guerra, and Laila Moujir. "Antimicrobial Activity and Mode of Action of Celastrol, a Nortriterpen Quinone Isolated from Natural Sources." Foods 10, no. 3 (2021): 591. http://dx.doi.org/10.3390/foods10030591.

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Species of the Celastraceae family are traditionally consumed in different world regions for their stimulating properties. Celastrol, a triterpene methylene quinone isolated from plants of celastraceas, specifically activates satiety centers in the brain that play an important role in controlling body weight. In this work, the antimicrobial activity and mechanism of action of celastrol and a natural derivative, pristimerin, were investigated in Bacillus subtilis. Celastrol showed a higher antimicrobial activity compared with pristimerin, being active against Gram-positive bacteria with minimum

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8

Liao, Xin, Jimin Fang, Lingling Yang, Zhijie Xu, and Xun Wang. "Fluorine-regulated surface chemical state of titanium dioxide (TiO2) and decolourisation mechanism of methylene blue." Environmental Chemistry 18, no. 2 (2021): 71. http://dx.doi.org/10.1071/en20163.

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Environmental contextAs a new type of photocatalytic material, nano-titanium dioxide can be applied in the field of energy and environmental protection. This research uses ammonium bifluoride to modify the titanium dioxide and analyses it in combination with interface chemistry theory, and finds that its photocatalytic efficiency has been greatly improved. This provides new ideas for wastewater treatment and pollutant degradation. AbstractTitanium dioxide (TiO2) was prepared by hydrothermally adjusting titanium sulfate with ammonium hydrogen fluoride. The UV-visible absorption spectra show tha

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9

Rogerio, Kamilla Rodrigues, Cedric Stephan Graebin, Luiza Helena Pinto Domingues, et al. "Novel Quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione Derivatives Against Chloroquine-resistant Plasmodium falciparum." Current Topics in Medicinal Chemistry 20, no. 2 (2020): 99–110. http://dx.doi.org/10.2174/1568026619666191019100711.

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Introduction: In this work DHPMs were combined with the quinoline nucleus to obtain new quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione compounds with improved antiplasmodial activity as well as decreased cytotoxicity. Nineteen quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione derivatives connected by a linker group to quinolone ring moieties with different substituents were synthesized and assayed against P. falciparum. Materials and Methods: Nineteen quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione derivatives connected by a linker group to quinoline ring moieties with different substituents were syn

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10

Yanni, Amal S. "Synthesis of some new indolizino[2,3-g]quinoline-5,12-dione derivatives." Collection of Czechoslovak Chemical Communications 56, no. 3 (1991): 695–701. http://dx.doi.org/10.1135/cccc19910695.

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Interaction of 6,7-dichloroquinoline-5,8-dione (I) with active methylene compounds and pyridine (or substituted pyridine) afforded indolizino[2,3-g]quinoline-5,12-diones (III, IV). When quinoline or isoquinoline was used instead of pyridine in the above reaction benzo[5,6]- or benzo[7,8]-indolizino[2,3-g]quinoline-5,12-diones (V, VI) were obtained. Their structure has been ascertained through elemental and spectral analysis.

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11

Kaukorat, Thomas, Ion Neda, Holger Thönnessen, Peter G. Jones та Reinhard Schmutzler. "The Reaction of 2-Hydro-2-oxo-5,6-benzo-l,3,2λ4-dioxaphosphorin-4-one with Imines and Carbonyl Compounds; Unusual Formation and First X-Ray Crystal Structure Determination of a Benzodioxaphosphepinone Ring System". Zeitschrift für Naturforschung B 51, № 10 (1996): 1501–10. http://dx.doi.org/10.1515/znb-1996-1022.

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On treatment of 2-hydro-2-oxo-5,6-benzo-1,3,2λ4-dioxaphosphorin-4-one (1) with the inline trimers trim ethyl- and tribenzyltriazine and the (monomeric) methylene-tert-butylimine, an insertion reaction of the imine molecule into the P-H bond of 1 took place, forming com pounds 2 -4 . Similar results were obtained when 1 was allowed to react with aldimines, asymmetric at carbon, leading to 5-7 . The diastereotopic properties of 5 - 7 were observed by 1H NMR spectroscopy. NMR and IR spectroscopic investigations on 5 - 7 indicated > C = O···H-N < interactions. Upon reaction of 1 with hexaflu

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12

Gazizov, M. B., A. L. Tarakanova, R. K. Ismagilov, L. P. Shamsutdinova, R. F. Karimova, and R. N. Burangulova. "Addition of phthalimide and acetone to phosphorylated methylene quinones." Russian Journal of General Chemistry 86, no. 2 (2016): 326–30. http://dx.doi.org/10.1134/s1070363216020213.

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13

SUZUKI, Takayoshi, Kan KUBOMURA, and Hiroaki TAKAYAMA. "Diels-Alder reaction of 4,6-dihydrothieno(3,4-c)furan-5,5-dioxide with quinones: Stereoselective synthesis of quinone-annelated 2,3-bis(methylene)-7-oxabicyclo(2.2.1)heptanes." CHEMICAL & PHARMACEUTICAL BULLETIN 39, no. 8 (1991): 2164–66. http://dx.doi.org/10.1248/cpb.39.2164.

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14

Akoachere, Monique, Kathrin Buchholz, Elisabeth Fischer, et al. "In Vitro Assessment of Methylene Blue on Chloroquine-Sensitive and -Resistant Plasmodium falciparum Strains Reveals Synergistic Action with Artemisinins." Antimicrobial Agents and Chemotherapy 49, no. 11 (2005): 4592–97. http://dx.doi.org/10.1128/aac.49.11.4592-4597.2005.

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ABSTRACT Methylene blue (MB) represents a promising antimalarial drug candidate for combination therapies against drug-resistant parasite strains. To support and facilitate the application of MB in future field trials, we studied its antiparasitic effects in vitro. MB is active against all blood stages of both chloroquine (CQ)-sensitive and CQ-resistant P. falciparum strains with 50% inhibitory concentration (IC50) values in the lower nanomolar range. Ring stages showed the highest susceptibility. As demonstrated by high-performance liquid chromatography-tandem mass spectrometry on different c

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15

Gupta, Tanu, Jay Bahadur Singh, Kalpana Mishra, and Radhey M. Singh. "Active methylene compounds (AMCs) controlled facile synthesis of acridine and phenanthridine from morita Baylis–Hillman acetate." RSC Advances 7, no. 86 (2017): 54581–85. http://dx.doi.org/10.1039/c7ra09447g.

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16

Vigalok, Arkadi, Linda J. W. Shimon, and David Milstein. "Methylene Arenium Cations via Quinone Methides and Xylylenes Stabilized by Metal Complexation." Journal of the American Chemical Society 120, no. 3 (1998): 477–83. http://dx.doi.org/10.1021/ja972321p.

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17

Milstein, D. "Challenging metal-based transformations. From single-bond activation to catalysis and metallaquinonoids." Pure and Applied Chemistry 75, no. 4 (2003): 445–60. http://dx.doi.org/10.1351/pac200375040445.

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Catalytic reactions resulting from our C–X (X = H, C, O, N, halide) bond activation studies are described. Aryl chlorides can react with aluminum alkyls in preference to bromides. Using PCP-type Pd catalysts, Heck reaction with aryl iodides and bromides can proceed without involvement of Pd(0). Ru-catalyzed oxidative coupling of arenes with alkenes using O2 was accomplished. Using specifically designed systems, the scope and mechanisms of C–C activation in solution was studied and compared to C–H activation. C–C activation by Rh(I), Ir(I), Ni(II),Pt(II), Ru(II), and Os(II) was observed. Metal

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18

Pascual, Aurélie, Maud Henry, Sébastien Briolant, et al. "In VitroActivity of Proveblue (Methylene Blue) on Plasmodium falciparum Strains Resistant to Standard Antimalarial Drugs." Antimicrobial Agents and Chemotherapy 55, no. 5 (2011): 2472–74. http://dx.doi.org/10.1128/aac.01466-10.

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ABSTRACTThe geometric mean 50% inhibitory concentration (IC50) for Proveblue, a methylene blue complying with the European Pharmacopoeia, was more active on 23P. falciparumstrains than chloroquine, quinine, mefloquine, monodesethylamodiaquine, and lumefantrine. We did not find significant associations between the Proveblue IC50and polymorphisms in thepfcrt,pfmdr1,pfmdr2,pfmrp, andpfnhe-1genes or the copy numbers of thepfmdr1andpfmdr2genes, all of which are involved in antimalarial resistance.

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19

SUZUKI, T., K. KUBOMURA, and H. TAKAYAMA. "ChemInform Abstract: Diels-Alder Reaction of 4,6-Dihydrothieno(3,4-c)furan 5,5-Dioxide with Quinones: Stereoselective Synthesis of Quinone-Annelated 2,3-Bis( methylene)-7-oxabicyclo(2.2.1)heptanes." ChemInform 23, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.199210078.

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20

Chakraborty, Gouri, Prasenjit Das, and Sanjay K. Mandal. "Quinoline-tagged fluorescent organic probes for sensing of nitro-phenolic compounds and Zn2+ ions at the ppb level." Materials Advances 2, no. 7 (2021): 2334–46. http://dx.doi.org/10.1039/d1ma00025j.

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The effect of flexible tetra-methylene vs. semi-rigid xylylene spacers appended in two quinoline tagged sensors bqbpbn (1) and bqbpxn (2) on the sensing of nitro-phenolic compounds and metal ions has been demonstrated.

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21

Chauncey, M. A., and M. F. Grundon. "Reactions of Heterocyclic Quinone Methides: 1-Methyl-3-methylene-2,4(1H,3H)-quinolinedione." Synthesis 1990, no. 11 (1990): 1005–7. http://dx.doi.org/10.1055/s-1990-27077.

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22

Gendrot, Mathieu, Priscilla Jardot, Océane Delandre, et al. "In Vitro Evaluation of the Antiviral Activity of Methylene Blue Alone or in Combination against SARS-CoV-2." Journal of Clinical Medicine 10, no. 14 (2021): 3007. http://dx.doi.org/10.3390/jcm10143007.

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A new severe acute respiratory syndrome coronavirus (SARS-CoV-2) causing coronavirus diseases 2019 (COVID-19), which emerged in Wuhan, China in December 2019, has spread worldwide. Currently, very few treatments are officially recommended against SARS-CoV-2. Identifying effective, low-cost antiviral drugs with limited side effects that are affordable immediately is urgently needed. Methylene blue, a synthesized thiazine dye, may be a potential antiviral drug. Antiviral activity of methylene blue used alone or in combination with several antimalarial drugs or remdesivir was assessed against inf

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23

Lopes, Andrey P., Bianca S. Bagatela, Paulo C. P. Rosa, et al. "Antioxidant and Cytotoxic Effects of Crude Extract, Fractions and 4-Nerolidylcathecol from Aerial Parts ofPothomorphe umbellataL. (Piperaceae)." BioMed Research International 2013 (2013): 1–5. http://dx.doi.org/10.1155/2013/206581.

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The crude ethanolic extract from aerial parts ofPothomorphe umbellataL. (Piperaceae) and fractions obtained by partitions sequentially among water-methanol, methylene chloride, and ethyl acetate, as well as the major constituent, 4-nerolidylcatechol, were, respectively, evaluated and evidenced for antioxidant and cytotoxic effects through fluorometric microplate and microculture tetrazolium assays in HL-60 cells. The crude ethanolic extract demonstrated the preeminent antioxidant activity (IC50=1.2 μg/mL) against exogenous cytoplasmic reactive oxygen species, followed by the water-methanolic (

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24

Hayashi, Maki, Hideaki Ohzeki, Haruo Shimada, and Tsutomu Unemoto. "NADPH-specific quinone reductase is induced by 2-methylene-4-butyrolactone in Escherichia coli." Biochimica et Biophysica Acta (BBA) - Bioenergetics 1273, no. 2 (1996): 165–70. http://dx.doi.org/10.1016/0005-2728(95)00138-7.

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25

Rabin, Oded, Arkadi Vigalok, and David Milstein. "A Novel Approach Towards Intermolecular Stabilization ofpara-Quinone Methides. First Complexation of the Elusive, Simplest Quinone Methide, 4-Methylene-2,5-cyclohexadien-1-one." Chemistry - A European Journal 6, no. 3 (2000): 454–62. http://dx.doi.org/10.1002/(sici)1521-3765(20000204)6:3<454::aid-chem454>3.0.co;2-q.

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26

Radini, Ibrahim Ali, Sameh Ramadan El-Gogary, Mohamed Sabri Mostafa, Bander Alnagei, Mohammed Mudarbish, and Shadad Dash. "Ecofriendly and simple synthesis of pyrano[3,2-c]quinolone in water via an efficient one-pot three-component reaction." European Journal of Chemistry 9, no. 1 (2018): 44–48. http://dx.doi.org/10.5155/eurjchem.9.1.44-48.1679.

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Pyrano[3,2-c]quinolones are commonly found in alkaloids, manifesting diverse biological activities. In this work, 2-amino-6-methyl-5-oxo-4-substituted-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitriles and ethyl 2-amino-4-(substituted)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylates have been synthesized efficiently from reaction of 4-hydroxy-1-methylquinolin-2(1H)-one, aldehydes and active methylene nitriles in one-pot three component reaction in aqueous medium, containing catalytic amount of ethanolamine resulting in 70-95% yields.

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27

CHAUNCEY, M. A., and M. F. GRUNDON. "ChemInform Abstract: Reactions of Heterocyclic Quinone Methides: 1-Methyl-3-methylene-2,4( 1H,3H)-quinolinedione." ChemInform 22, no. 22 (2010): no. http://dx.doi.org/10.1002/chin.199122161.

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28

Hopper, David J., and Lisa Cottrell. "Alkylphenol Biotransformations Catalyzed by 4-Ethylphenol Methylenehydroxylase." Applied and Environmental Microbiology 69, no. 6 (2003): 3650–52. http://dx.doi.org/10.1128/aem.69.6.3650-3652.2003.

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ABSTRACT 4-Ethylphenol methylenehydroxylase from Pseudomonas putida JD1 acts by dehydrogenation of its substrate to give a quinone methide, which is then hydrated to an alcohol. It was shown to be active with a range of 4-alkylphenols as substrates. 4-n-Propylphenol, 4-n-butylphenol, chavicol, and 4-hydroxydiphenylmethane were hydroxylated on the methylene group next to the benzene ring and produced the corresponding chiral alcohol as the major product. The alcohols 1-(4′-hydroxyphenyl)propanol and 1-(4′-hydroxyphenyl)-2-propen-1-ol, produced by the biotransformation of 4-n-propylphenol and ch

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29

López-Carballeira, Diego, David Casanova, and Fernando Ruipérez. "Theoretical design of conjugated diradicaloids as singlet fission sensitizers: quinones and methylene derivatives." Physical Chemistry Chemical Physics 19, no. 44 (2017): 30227–38. http://dx.doi.org/10.1039/c7cp05120d.

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30

Knieß, Torsten, and Roland Mayer. "Synthese und Redoxverhalten schwefelsubstituierter Naphthochinone-1,4 / Synthesis and Redox Behaviour of Sulfur Substituted Naphthoquinones-1,4." Zeitschrift für Naturforschung B 51, no. 6 (1996): 901–4. http://dx.doi.org/10.1515/znb-1996-0624.

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Abstract Chloro substituted naphthoquinones-1,4 1 react with di-Na-4,5-dithio-1,3-dithiol-2-thiones 2 and other dithiolates to give new sulfur containing heterocyclic quinones 3 and 4 as possible preliminary states to synthesize tetrathiafulvalenes. The reaction of 1 with di-Li-2,2- bis(methylthio)-1,1-ethylendithiol 8 yields the appropriate bis-(methylthio)methylen substituted naphthoquinones 9. The redox behaviour of the new compounds was investigated by cyclic voltammetry

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31

Ma, Fei-Ping, Gui-Tian Cheng, Zhi-Guo He, and Zhan-Hui Zhang. "A New and Efficient Procedure for Friedländer Synthesis of Quinolines in Low Melting Tartaric Acid-Urea Mixtures." Australian Journal of Chemistry 65, no. 4 (2012): 409. http://dx.doi.org/10.1071/ch12025.

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A general, efficient and green method for the synthesis of quinoline derivatives via the Friedländer heteroannulation reaction of 2-aminoaryl ketones and α-methylene ketones has been developed, employing low melting mixtures of L-(+)-tartaric acid and urea derivatives as an inexpensive, non-toxic, easily biodegradable reaction medium. The melt acts as both the reaction medium and catalyst, furnishing quinolines in high to excellent yields.

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Ieva, Raffaele, Cristina Alaimo, Isabel Delany, Gunther Spohn, Rino Rappuoli, and Vincenzo Scarlato. "CrgA Is an Inducible LysR-Type Regulator of Neisseria meningitidis, Acting both as a Repressor and as an Activator of Gene Transcription." Journal of Bacteriology 187, no. 10 (2005): 3421–30. http://dx.doi.org/10.1128/jb.187.10.3421-3430.2005.

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ABSTRACT The crgA gene of Neisseria meningitidis, which codes for a LysR-type regulator, is divergently oriented with respect to the mdaB gene, which codes for a hypothetical NADPH-quinone oxidoreductase. Transcriptional studies of the intergenic region between crgA and mdaB showed that two overlapping and divergent promoters, P crgA and P mdaB , control transcription of these genes. Deletion of the crgA gene led to a strong increase in transcription from the P crgA promoter and a concomitant strong decrease in transcription from the P mdaB promoter, indicating that CrgA acts both as an autore

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33

da Silva, Gabriel, and Joseph W. Bozzelli. "Quantum Chemical Study of the Thermal Decomposition ofo-Quinone Methide (6-Methylene-2,4-cyclohexadien-1-one)." Journal of Physical Chemistry A 111, no. 32 (2007): 7987–94. http://dx.doi.org/10.1021/jp073335c.

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34

Mahantheshappa, Santhosha Sangapurada, Harishkumar Shivanna, and Nayak Devappa Satyanarayan. "Synthesis, antimicrobial, antioxidant, and ADMET studies of quinoline derivatives." European Journal of Chemistry 12, no. 1 (2021): 37–44. http://dx.doi.org/10.5155/eurjchem.12.1.37-44.2038.

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The synthesis, antimicrobial, and antioxidant activities of new quinoline analogs were carried out with the aim to find possible hits/leads that can be taken up for future drug development. A series of 2-amino-N’-((2-chloroquinolin-3-yl)methylene)acetohydrazide derivatives (6a-h) have been synthesized by reacting 2-chloro-N’-((2-chloroquinolin-3-yl)methylene)acetohydrazide (5a) and N’-((6-bromo-2-chloroquinolin-3-yl)methylene)-2-chloroacetohydrazide (5b) with secondary amines (Morpholine, diethylamine, piperidine and 1-methylpiperazine). The characterization was achieved by FT-IR, 1H NMR, 13C

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35

Yanni, Amal S., and Zarif H. Khalil. "Synthesis and application of some new furoquinolinediones as bactericides." Collection of Czechoslovak Chemical Communications 56, no. 3 (1991): 706–11. http://dx.doi.org/10.1135/cccc19910706.

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Furo[3,2-g]quinoline-4,9-diones were prepared through the reaction of active methylene compounds with 6,7-dichloroquinoline-5,8-dione, either by one step or two step method. Benzo[b]- and naphtol[1,2-b or 2,1-b]furo[3,2-g]quinolinediones were also prepared through the reaction of 6,7-dichloroquinoline-5,8-dione with phenols and naphtols in presence of pyridine. The structure of the synthesized compounds was determined by elemental and spectral analysis.

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Chinh, Pham The, Pham Thi Tham, Duong Huong Quynh, et al. "Synthesis and Cytotoxic Activity of Several Novel N-Alkyl-Plinabulin Derivatives With Aryl Group Moieties." Natural Product Communications 16, no. 4 (2021): 1934578X2110100. http://dx.doi.org/10.1177/1934578x211010040.

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Seven novel N-alkyl-plinabulin derivatives with aryl groups moieties (nitroquinoline, 1,4-dihydroquinoline, 4-methoxybenzene, and 4-chlorobenzene) have been synthesized via aldol condensation and alkylation in one-pot, and tested for their cytotoxicity against 4 cancer cell lines (KB, HepG2, Lu, and MCF7). Compounds ( Z)−3-((6,8-dimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)piperazine-2,5-dione (5a), ( Z)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)−3-((1,6,8-trimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)piperazine-2,5-dione (5b), a

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37

Garavito, Giovanny, Stéphane Bertani, Miguel Quiliano, Alexis Valentin, Ignacio Aldana, and Eric Deharo. "The in vivo antimalarial activity of methylene blue combined with pyrimethamine, chloroquine and quinine." Memórias do Instituto Oswaldo Cruz 107, no. 6 (2012): 820–23. http://dx.doi.org/10.1590/s0074-02762012000600019.

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38

Polonik, Sergey, Galina Likhatskaya, Yuri Sabutski, et al. "Synthesis, Cytotoxic Activity Evaluation and Quantitative Structure-ActivityAnalysis of Substituted 5,8-Dihydroxy-1,4-naphthoquinones and Their O- and S-Glycoside Derivatives Tested against Neuro-2a Cancer Cells." Marine Drugs 18, no. 12 (2020): 602. http://dx.doi.org/10.3390/md18120602.

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Based on 6,7-substituted 2,5,8-trihydroxy-1,4-naphtoquinones (1,4-NQs) derived from sea urchins, five new acetyl-O-glucosides of NQs were prepared. A new method of conjugation of per-O-acetylated 1-mercaptosaccharides with 2-hydroxy-1,4-NQs through a methylene spacer was developed. Methylation of 2-hydroxy group of quinone core of acetylthiomethylglycosides by diazomethane and deacetylation of sugar moiety led to 28 new thiomethylglycosidesof 2-hydroxy- and 2-methoxy-1,4-NQs. The cytotoxic activity of starting 1,4-NQs (13 compounds) and their O- and S-glycoside derivatives (37 compounds) was d

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39

Delarmelina, Maicon, Sabrina B. Ferreira, Fernando de C. da Silva, Vitor F. Ferreira та José Walkimar de M. Carneiro. "Hetero-Diels–Alder Reactions of Quinone Methides: The Origin of the α-Regioselectivity of 3-Methylene-1,2,4-naphthotriones". Journal of Organic Chemistry 85, № 11 (2020): 7001–13. http://dx.doi.org/10.1021/acs.joc.0c00215.

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40

Cayabyab, F. S., and E. E. Daniel. "K+ channel opening mediates hyperpolarizations by nitric oxide donors and IJPs in opossum esophagus." American Journal of Physiology-Gastrointestinal and Liver Physiology 268, no. 5 (1995): G831—G842. http://dx.doi.org/10.1152/ajpgi.1995.268.5.g831.

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The ionic mechanisms by which nitric oxide (NO) or a related compound mediates the inhibitory junction potentials (IJPs) of the opossum esophageal circular smooth muscle were studied using microelectrodes and double sucrose gap. The NO donors, 3-morpholino-sydnonimine hydrochloride and sodium nitroprusside, induced 15- to 20-mV hyperpolarizations that reversed near the potassium equilibrium potential as did the IJPs. They inhibited the IJPs and decreased electrotonic potentials (increased conductance) even during restoration of the resting membrane potential by application of depolarizing curr

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41

Takahashi, Hiroaki, Yoshiki Watanabe, Makoto Sakai, and Masanori Tachikawa. "Photoinduced Intramolecular Hydrogen Transfer Reaction of Ortho Nitrobenzyl Compounds." Laser Chemistry 19, no. 1-4 (1999): 357–62. http://dx.doi.org/10.1155/1999/29456.

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Time-resolved resonance Raman and absorption spectra have revealed that the photoinduced intramolecular hydrogen transfer reaction of ortho nitrobenzyl compounds is initiated by the abstraction of methylene hydrogen by the ortho nitro group to generate the ortho aci-nitro acid isomer. In polar solvents the ortho aci-nitro acid is dissociated into the aci-nitro anion and a proton, and the proton is captured by other hydrogen accepting sites, such as 2-pyridyl, 4-pyridyl and 4-nitro groups to generate the ortho N—H quinoid, para N—H quinoid and para aci-nitro acid isomers, respectively. For 2-ni

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42

Idrees, M., Naqui J. Siddiqui, Yogita G. Bodkhe, and Satish Kola. "Synthesis and Characterization of Novel 1,3,5-Thiadiazine Derivatives Integrated with Quinoline Moiety as Potent Antimicrobial Agents." Asian Journal of Organic & Medicinal Chemistry 5, no. 2 (2020): 149–55. http://dx.doi.org/10.14233/ajomc.2020.ajomc-p262.

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An expeditious synthesis of series of novel 1,3,5-thiadiazine (5a-f) and (6a-f) derivatives have been described. These compounds were synthesized by reaction of 1-(N-((6-methyl-2-(p-tolyloxy)quinoline- 3-yl)methylene)carbamimidoyl)-3-arylthiourea (3a-b) derivatives with N-aryl isocyanodichloride (4a-c) in chloroform followed by basification with dilute NH4OH to give the target compounds 5a-f; which were acetylated further to afford six novel 1,3,5-thiadiazin-3-(6H)-yl)ethanone (6a-f) derivatives. Synthesis of intermediate compounds 3a-b was obtained by reacting 6-methyl-2-(p-tolyloxy)quinoline

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43

Pradeep, P. S., S. Naveen, M. N. Kumara, K. M. Mahadevan, and N. K. Lokanath. "Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one." Acta Crystallographica Section E Structure Reports Online 70, no. 9 (2014): 153–56. http://dx.doi.org/10.1107/s1600536814019254.

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In the title compound, C14H17FN2O, the 1,2,3,4-tetrahydropyridine ring of the quinoline moiety adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation with the central methylene C atom as the flap. The pyrrolidine ring lies in the equatorial plane and its mean plane is normal to the mean plane of the quinoline ring system, with a dihedral angle value of 88.37 (9)°. The bridging N—C bond distance [1.349 (3) Å] is substantially shorter than the sum of the covalent radii (dcov: C—N = 1.47 Å and C=N = 1.27 Å), which indicates partial double-bond character for this

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44

Kashiwagi, Yukiyasu, Koji Kubono, and Toshiyuki Tamai. "Crystal structure of 7,7′-[(pyridin-2-yl)methylene]bis(5-chloroquinolin-8-ol)." Acta Crystallographica Section E Crystallographic Communications 76, no. 8 (2020): 1271–74. http://dx.doi.org/10.1107/s2056989020009317.

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In the title compound, C24H15Cl2N3O2, one quinoline ring system is essentially planar and the other is slightly bent. An intramolecular O—H...N hydrogen bond involving the hydroxy group and a pyridine N atom forms an S(5) ring motif. In the crystal, two molecules are associated into an inversion dimer with two R 2 2(7) ring motifs through intermolecular O—H...N and O—H...O hydrogen bonds. The dimers are further linked by an intermolecular C—H...O hydrogen bond and four C—H...π interactions, forming a two-dimensional network parallel to (001).

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45

Poirel, Laurent, Laurent Dortet, Sandrine Bernabeu, and Patrice Nordmann. "Genetic Features ofblaNDM-1-Positive Enterobacteriaceae." Antimicrobial Agents and Chemotherapy 55, no. 11 (2011): 5403–7. http://dx.doi.org/10.1128/aac.00585-11.

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ABSTRACTGenetic features associated with theblaNDM-1gene were investigated in 6Escherichia coli, 7Klebsiella pneumoniae, 1Citrobacter freundii, 1Proteus mirabilis, and 1Providencia stuartiiisolate of worldwide origin. Clonal diversity was observed for bothE. coliandK. pneumoniae. TheblaNDM-1gene was carried by different plasmid types (IncA/C, IncF, IncL/M, or untypeable) and was likely chromosome borne in two isolates. TheblaNDM-1plasmids coharbored a variety of resistance determinants, including β-lactamase genes, quinolone resistance genes, and 16S RNA methylase genes.

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46

Erguc, Ali, Mehlika Dilek Altintop, Ozlem Atli, et al. "Synthesis and Biological Evaluation of New Quinoline-Based Thiazolyl Hydrazone Derivatives as Potent Antifungal and Anticancer Agents." Letters in Drug Design & Discovery 15, no. 2 (2018): 193–202. http://dx.doi.org/10.2174/1570180814666171003145227.

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Background: In medicinal chemistry, thiazoles have gained great importance in antifungal and anticancer drug design and development. Objectives: The aim of this study was to synthesize new quinoline-based thiazolyl hydrazone derivatives and evaluate their anticandidal and anticancer effects. Methods: New thiazolyl hydrazone derivatives were evaluated for their anticandidal effects using disc diffusion method. Ames MPF assay was carried out to determine the genotoxicity of the most effective antifungal derivative. MTT assay was also performed to assess the cytotoxic effects of the compounds on

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47

Takeuchi, Mio, Yoichi Kamagata, Kenshiro Oshima, et al. "Methylocaldum marinum sp. nov., a thermotolerant, methane-oxidizing bacterium isolated from marine sediments, and emended description of the genus Methylocaldum." International Journal of Systematic and Evolutionary Microbiology 64, Pt_9 (2014): 3240–46. http://dx.doi.org/10.1099/ijs.0.063503-0.

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An aerobic, methane-oxidizing bacterium (strain S8T) was isolated from marine sediments in Kagoshima Bay, Japan. Phylogenetic analysis based on 16S rRNA gene sequences indicated that this strain is closely related to members of the genus Methylocaldum (97.6–97.9 % similarity) within the class Gammaproteobacteria . Strain S8T was a Gram-staining-negative, non-motile, coccoid or short rod-shaped organism. The temperature range for growth of strain S8T was 20–47 °C (optimum growth at 36 °C). It required NaCl (>0.5 %), tolerated up to 5 % NaCl and utilized methane and methanol. The major cellul

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48

Gao, Wentao, Jia Liu, Yun Jiang, and Yang Li. "First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives." Beilstein Journal of Organic Chemistry 7 (February 15, 2011): 210–17. http://dx.doi.org/10.3762/bjoc.7.28.

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A facile and inexpensive synthesis of a series of novel methylenedioxy-bearing 2-(benzofuran-2-yl)-quinoline-3-carboxylic acid derivatives 3a–h via the one-pot reaction of ethyl 2-chloromethyl-6,7-methylenedioxyquinoline-3-carboxylate (5) with various substituted salicylaldehydes 6a–g as well as 2-hydroxy-1-naphthaldehyde (6h) is described. Substrate 5 was synthesized by the Friedländer condensation reaction of 2-amino-4,5-methylenedioxybenzaldehyde (4) with ethyl 4-chloro-3-oxobutanoate using KHSO4 as catalyst under ultrasound irradiation conditions. The targeted compounds 3a–h were obtained

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49

Gautam, Daman R., Konstantinos E. Litinas, Konstantina C. Fylaktakidou та Demetrios N. Nicolaides. "Reactions ofo-quinones with α-methyl- (or methylene) substituted phosphorus ylides. Synthesis of benzo[b]furan derivatives". Journal of Heterocyclic Chemistry 40, № 3 (2003): 399–404. http://dx.doi.org/10.1002/jhet.5570400301.

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Gauvin, Régis M, Haim Rozenberg, Linda J W. Shimon, Yehoshoa Ben-David, and David Milstein. "Osmium-Mediated CH and CC Bond Cleavage of a Phenolic Substrate:p-Quinone Methide and Methylene Arenium Pincer Complexes." Chemistry - A European Journal 13, no. 5 (2007): 1382–93. http://dx.doi.org/10.1002/chem.200601385.

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