Thiazole-containing compounds as therapeutic targets for cancer therapy

Sharma, Prabodh Chander; Bansal, Kushal Kumar; Sharma, Archana; Sharma, Diksha; Deep, Aakash

doi:10.1016/j.ejmech.2019.112016

Cited by 242 publications

(151 citation statements)

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“…The antiproliferative activity of the morpholine-, thiazole-, and pyrrole-condensed derivatives and their precursors were evaluated initially against A2780 ovarian and WM35 melanoma cancer cell lines at 50 μM concentration by monitoring at 24 and 72 h ( Figures S262 and S263 ). While morpholine and pyrrole units are common structural elements in cytotoxic compounds of synthetic or natural origin [ 35 , 36 , 37 , 38 , 39 ], there are fewer reports available on cytotoxic condensed thiazole derivatives [ 40 , 41 ]. The N -chloroacetyl-3-amino-flavan-4-ol derivatives rac - 19a - g and 22a-g exhibited strong antiproliferative activity regardless the stereochemistry against both cell lines at 50 μM concentration, while the related N -acetyl derivatives rac-cis - 24a - e , g or rac-trans - 24a - g were inactive or they had much weaker activity.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones

et al. 2020

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Racemic chiral O,N-heterocycles containing 2-arylchroman or 2-aryl-2H-chromene subunit condensed with morpholine, thiazole, or pyrrole moieties at the C-3-C-4 bond were synthesized with various substitution patterns of the aryl group by the cyclization of cis- or trans-3-aminoflavanone analogues. The 3-aminoflavanone precursors were obtained in a Neber rearrangement of oxime tosylates of flavanones, which provided the trans diastereomer as the major product and enabled the isolation of both the cis- and trans-diastereomers. The cis- and trans-aminoflavanones were utilized to prepare three diastereomers of 5-aryl-chromeno[4,3-b][1,4]oxazines. Antiproliferative activity of the condensed heterocycles and precursors was evaluated against A2780 and WM35 cancer cell lines. For a 3-(N-chloroacetylamino)-flavan-4-ol derivative, showing structural analogy with acyclic acid ceramidase inhibitors, 0.15 μM, 3.50 μM, and 6.06 μM IC50 values were measured against A2780, WM35, and HaCat cell lines, and apoptotic mechanism was confirmed. Low micromolar IC50 values down to 2.14 μM were identified for the thiazole- and pyrrole-condensed 2H-chromene derivatives. Enantiomers of the condensed heterocycles were separated by HPLC using chiral stationary phase, HPLC-ECD spectra were recorded and TDDFT-ECD calculations were performed to determine the absolute configuration and solution conformation. Characteristic ECD transitions of the separated enantiomers were correlated with the absolute configuration and effect of substitution pattern on the HPLC elution order was determined.

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Section: Resultsmentioning

confidence: 99%

Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones

et al. 2020

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“…Various pyrazolinyl thiazoles have pharmacological and biological applications (Abdel-Wahab et al, 2017;Abd-Rabou et al, 2018;Saeed et al, 2017). In addition, heterocycles containing both pyrazole and thiazole moieties have been used as versatile intermediates in organic synthesis of biologically active compounds (Secrieru et al, 2019;Shaabani et al, 2019;Sharma et al, 2020). Recently, we have published the X-ray crystal structures for related heterocycles (El-Hiti, Abdel-Wahab, Alqahtani et al, 2019;El-Hiti, Abdel-Wahab, Yousif et al, 2019;El-Hiti et al, 2018).…”

Section: Structure Descriptionmentioning

confidence: 99%

2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-5-[(4-fluorophenyl)diazenyl]-4-methylthiazole

et al. 2020

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The molecule of the title compound, C25H18ClF2N5S, comprises almost co-planar fluorophenyl, methylthiazolyl, pyrazolyl and chlorophenyl rings with the second fluorophenyl ring almost perpendicular to this plane. One fluorophenyl group is disordered over two components of occupancy ratio 0.767 (10):0.233 (10) related by a 24.2 (8)° twist. In the crystal, two molecules related by inversion symmetry are linked by a pair of C—H...F contacts in an R(8)2 2 geometry.

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“…ring systems are versatile scaffolds in organic synthesis and medicinal chemistry due to their biological activities [8][9][10]. 1,2,3-Triazole connected to other heterocycles can be synthesized from reactions of 1,3-diketones, activated alkenes, and alkynes with nitrogen containing reagents [11].…”

Section: Commentmentioning

confidence: 99%

The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C₃₀H₂₅FN₁₀S⋅C₃H₇NO

Alotaibi

Abdel‐Wahab

Hegazy

et al. 2020

Zeitschrift Für Kristallographie - New Crystal Structures

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Thiazole-containing compounds as therapeutic targets for cancer therapy

Cited by 242 publications

References 216 publications

Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones

Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones

2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-5-[(4-fluorophenyl)diazenyl]-4-methylthiazole

The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C₃₀H₂₅FN₁₀S⋅C₃H₇NO

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Thiazole-containing compounds as therapeutic targets for cancer therapy

Cited by 242 publications

References 216 publications

Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones

Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones

2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-5-[(4-fluorophenyl)diazenyl]-4-methylthiazole

The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C30H25FN10S⋅C3H7NO

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The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C₃₀H₂₅FN₁₀S⋅C₃H₇NO