A new method for the synthesis of chalcone derivatives promoted by PPh<sub>3</sub>/I<sub>2</sub>under non-alkaline conditions

Xue, Kangsheng; Sun, Guangmin; Zhang, Yanzhi; Chen, Xubing; Yang, Zhihui; Hou, Jinjun; Long, Huali; Zhang, Zijia; Lei, Min; Wu, Wanying

doi:10.1080/00397911.2020.1847295

Cited by 5 publications

(7 citation statements)

References 60 publications

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“…1 (11). 53 Following the general method A, using 4-chlorobenzaldehyde 3 and acetophenone 5, compound 11 was obtained as a white solid in 82% yield. R f = 0.76 (PE/AcOEt 9:1) 1 H NMR (400 MHz, DMSO): δ 8.16 (d, 2H, J = 6.9 Hz), 7.99−7.93 (m, 3H), 7.75−7.65 (m, 2H), 7.60−7.52 (m, 4H).…”

Section: General Methods For the Synthesis Of Chalcones 9− 14 Amentioning

confidence: 99%

“…1 (13). 53 Following the general method A, using benzaldehyde 1 and 4-hydroxyacetophenone 6, compound 13 was obtained as a white solid in 20% yield. R f = 0.25 (PE/AcOEt 9:1).…”

Section: (E)-3-(4-fluorophenyl)-1-phenylprop-2-en-1-one (12)mentioning

confidence: 99%

“…R f = 0.29 (CH 2 Cl 2 /MeOH 9.9:0.1). 1 (53). Following the general method H using thiazole 48, thiazolyl thiourea 53 was obtained as a white solid in 90% yield.…”

Section: 1 5 N ′ -( ( 1 E 2 E ) -3 -( -C H L O R O P H E N Y L ) ...mentioning

confidence: 99%

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Exploration of Thiourea-Based Scaffolds for the Construction of Bacterial Ureases Inhibitors

Tabor,

Katsogiannou,

Karta

et al. 2023

ACS Omega

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A series of 32 thiourea-based urease inhibitors were synthesized and evaluated against native bacterial enzyme and whole cells of Sporosarcina pasteurii and Proteus mirabilis strains. The proposed inhibitors represented structurally diverse thiosemicarbazones and thiocarbohydrazones, benzyl-substituted thiazolyl thioureas, 1H-pyrazole-1-carbothioamides, and dihydropirimidine-2(1H)-thiones. Kinetic characteristics with purified S. pasteurii enzyme determined low micromolar inhibitors within each structural group. (E)-2-(1-Phenylethylidene)hydrazine-1-carbothioamide 19 (K i = 0.39 ± 0.01 μM), (E)-2-(4-methylbenzylidene)hydrazine-1-carbothioamide 16 (K i = 0.99 ± 0.04 μM), and N′-((1E,2E)-1,3-diphenylallylidene)hydrazinecarbothiohydrazide 29 (K i = 2.23 ± 0.19 μM) were used in modeling studies that revealed sulfur ion coordination of the active site nickel ion and hydrogen bonds between the amide group and the side chain of Asp363 and Ala366 carbonyl moiety. Whole-cell studies proved the activity of compounds in Gram-positive and Gram-negative microorganisms. Ureolysis control observed in P. mirabilis PCM 543 (e.g., IC 50 = 304 ± 14 μM for 1-benzyl-3-(4-(4-hydroxyphenyl)thiazol-2-yl)thiourea 52) is a valuable achievement, as urease is recognized as a major virulence factor of this urinary tract pathogen.

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Section: General Methods For the Synthesis Of Chalcones 9− 14 Amentioning

confidence: 99%

“…1 (13). 53 Following the general method A, using benzaldehyde 1 and 4-hydroxyacetophenone 6, compound 13 was obtained as a white solid in 20% yield. R f = 0.25 (PE/AcOEt 9:1).…”

Section: (E)-3-(4-fluorophenyl)-1-phenylprop-2-en-1-one (12)mentioning

confidence: 99%

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Exploration of Thiourea-Based Scaffolds for the Construction of Bacterial Ureases Inhibitors

Tabor,

Katsogiannou,

Karta

et al. 2023

ACS Omega

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“…A yellow precipitate formed during the course of the reaction was filtered and washed with chilled ethanol, dried, and recrystallized from ethanol to afford pure product [42]. All the chalcones were reported earlier [43–45].…”

Section: Methodsmentioning

confidence: 99%

Biological evaluation of novel side chain containing CQTrICh-analogs as antimalarials and their development as PfCDPK1 kinase inhibitors

Irfan¹,

Uddin

Jain

et al. 2022

Preprint

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To combat the emergence of drug resistance against the existing antimalarials, novel side chain containing 7-chloroquinoline-indole-chalcones tethered with a triazole (CQTrICh-analogs 7 (a-s) and 9) were designed and synthesized by reacting substituted 1-phenyl-3-(1-(prop-2-yn-1-yl)-1H-indol-3-yl) prop-2-en-1-one and 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde with 4-azido-7-chloroquinoline, respectively via a click reaction. The selected CQTrICh-analogs: 7l and 7r inhibited chloroquine-sensitive (3D7) and resistant (RKL-9) strains of Plasmodium falciparum, with IC50 values of 2.4 μM & 1.8 μM (7l), and 3.5 μM & 2.7 μM (7r), respectively, and showed insignificant hemolysis and cytotoxicity in mammalian cells. Intra-erythrocytic progression studies revealed that the active hybrids: 7l and 7r are effective against the mature stages of the parasite. Given the importance of Calcium-Dependent Protein Kinase 1 (PfCDPK1) in the parasite biology, notably during late schizogony and subsequent invasion of merozoites into host RBCs, we identified this protein as a possible molecular target of these active hybrids. In silico interaction analysis indicated that 7l and 7r stably interact with the catalytically active ATP-binding pocket of PfCDPK1, by the formation of energetically favorable H-bonds. Furthermore, in vitro Microscale Thermophoresis and kinase assays with recombinant PfCDPK1 demonstrated that the active hybrids interact with and inhibit the kinase activity, thus presumably responsible for the parasite growth inhibition. Interestingly, 7l and 7r showed no inhibitory effect on the human kinases, indicating that they are selective for the parasite kinase. Conceivably, we report the antiplasmodial potential of novel kinase targeting bio-conjugates, a step towards developing pan-kinase inhibitors, which is a prerequisite for cross-stage anti-malarial protection.

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“…Reactive hydrogens from the basic structure of chalcones determine the possibility of these compounds being structurally modified in order to obtain a large number of derivatives [ 89 ]. Chalcones are precursors for many heterocyclic compounds such as cyanopyridines, 2-pyrazolines, pyrazoles, isoxazoles, pyrimidine-2-ones, flavanones and flavones and so forth [ 90 , 91 ]. Data from literature indicate that molecules with a 1,3-diaryl-2-propen-1-one residue have numerous biological activities and, for this reason, are of particular pharmacological importance [ 92 , 93 ].…”

Section: Flavonoidsmentioning

confidence: 99%

Two Important Anticancer Mechanisms of Natural and Synthetic Chalcones

Constantinescu

Mihis

2022

IJMS

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ATP-binding cassette subfamily G and tubulin pharmacological mechanisms decrease the effectiveness of anticancer drugs by modulating drug absorption and by creating tubulin assembly through polymerization. A series of natural and synthetic chalcones have been reported to have very good anticancer activity, with a half-maximal inhibitory concentration lower than 1 µM. By modulation, it is observed in case of the first mechanism that methoxy substituents on the aromatic cycle of acetophenone residue and substitution of phenyl nucleus by a heterocycle and by methoxy or hydroxyl groups have a positive impact. To inhibit tubulin, compounds bind to colchicine binding site. Presence of methoxy groups, amino groups or heterocyclic substituents increase activity.

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A new method for the synthesis of chalcone derivatives promoted by PPh₃/I₂under non-alkaline conditions

Cited by 5 publications

References 60 publications

Exploration of Thiourea-Based Scaffolds for the Construction of Bacterial Ureases Inhibitors

Exploration of Thiourea-Based Scaffolds for the Construction of Bacterial Ureases Inhibitors

Biological evaluation of novel side chain containing CQTrICh-analogs as antimalarials and their development as PfCDPK1 kinase inhibitors

Two Important Anticancer Mechanisms of Natural and Synthetic Chalcones

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A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions

Cited by 5 publications

References 60 publications

Exploration of Thiourea-Based Scaffolds for the Construction of Bacterial Ureases Inhibitors

Exploration of Thiourea-Based Scaffolds for the Construction of Bacterial Ureases Inhibitors

Biological evaluation of novel side chain containing CQTrICh-analogs as antimalarials and their development as PfCDPK1 kinase inhibitors

Two Important Anticancer Mechanisms of Natural and Synthetic Chalcones

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A new method for the synthesis of chalcone derivatives promoted by PPh₃/I₂under non-alkaline conditions