Anticancer, neuroprotective activities and computational studies of 2-amino-1,3,4-thiadiazole based compound

Rzeski, Wojciech; Matysiak, Joanna; Kandefer‐Szerszeń, Martyna

doi:10.1016/j.bmc.2007.02.041

Cited by 153 publications

(82 citation statements)

References 38 publications

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“…They have demonstrated significant biological activities, e. g., antimicrobial [1], antitumour and antiviral activities [2][3][4]. The title crystal structure is built up only by the Schiff base molecules, within which all bond lengths and bond angles are in normalranges [5].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-[(2-bromophenylimino)methyl]-4-chlorophenol, C13H9BrClNO

Fei-wen¹,

Zhang²

2012

Zeitschrift Für Kristallographie - New Crystal Structures

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C 13 H 9 BrClNO, orthorhombic, Pbca (no. 61), a =7.102(1) Å, b =13.082(2) Å, c =25.333(5) Å, V =2353.6 Å 3 , Z =8,Source of material 5-Chlorosalicylaldehyde(0.5 mmol) and an equimolar quantity of 2-bromoaniline were dissolved in methanol (50 mL). The reaction mixture was stirred at room temperature for 30 min and allowedtostand in air. Yellow crystals were formedafter 5days. They were filtered andw ashedw iths mall amountso fc ooled methanol, and finally recrystallized from methanol in good yield (76.8 %). configuration about the C=N. The whole molecule is nearly coplanar with the dihedral angle between two phenyl rings of 9.59°, which is interpreted by conjugation effect and the stabilization of rings from intramolecular hydrogen bond. In the structure, the bromine atom at the phenyl ring is slightly twisted out of the ring with the torsion angle Br1-C1-C2-C3 =-179.9(1)°and the hydroxylgroup nearly oriented out of the phenyl ring, as indicated by the torsion angle Experimental details

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-[(2-bromophenylimino)methyl]-4-chlorophenol, C13H9BrClNO

Fei-wen¹,

Zhang²

2012

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Schiff bases are new important organic ligands forming metal complexes and they have in general been reported to possess antimicrobial [1,2] and antitumour activities [3][4][5]. The title crystal structure is built up by only the Schiff base molecules, within which all bond lengths and bond angles are in normalranges [6].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-bromo-4-chloro-6-[(4-bromophenylimino) methyl]phenol, C13H8Br2ClNO

Zhang¹,

Guo²

2011

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of material 3-Bromo-5-chlorosalicylaldehyde (23.5 mg, 0.1 mmol) dissolved in methanol (10 mL) was addedt o4 -bromoaniline (17.2 mg, 0.1 mmol) in methanol (10 mL). The reaction mixture was heated to 313 Kfor 2hand then cooled to room temperature followed by concentrating the resulting mixture to give an orange product. The product was filtered off, washed with cold methanol, and finally dried in vacuum (yield 75.7%). Experimental detailsAllHatoms on carbon atoms were generated geometrically and Discussion

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“…These different actions result from how the 1,3,4-thiadiazole ring is modified in the various derivatives thus arising [2][3][4]. Indeed, previous studies by our group have described the synthesis of compounds belonging to the 2-amino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole set [5][6][7] that exhibit in vitro anticancer and neuro-protective activity thereby suggesting a possible role in the future drug treatment of cancer and nervous system disease.…”

Section: Introductionmentioning

confidence: 99%

A simple HPLC method for determining 2-(3-chlorophenyloamino)-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole in brain and plasma of animals: Application to a pharmacokinetic study

Raszewski

Juszczak²,

Lemieszek³

et al. 2014

Acta Chromatographica

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Summary. The development, optimization, and validation of a new high-performance liquid chromatography ultraviolet (HPLC-UV) method is presented for determining 2-(3-chlorophenyloamino)-5-(2,4-dihydroxy-phenyl)-1,3,4-thiadiazole (ClABT) in biological samples of rat plasma and brain tissue. ClABT was extracted directly from a plasma supernatant fraction following protein precipitation with acetonitrile and high speed centrifugation. Reverse phase HPLC separation was performed using an ODS-2 Hypersil column with the mobile phase consisting of 0.05 M triethylammonium phosphate buffer solution in acetonitrile and methanol (120:280:600, v/v/v), at room temperature, 1.2 mL min −1 flow rate, and UV-diode-array detection (DAD), at 335 nm. A linear response was obtained between 12.5 and 2000 ng mL −1 at analytically acceptable levels of precision (intra/inter-day) and accuracy. Mean recoveries ranged from 92.7% to 107.9%. It was concluded that the method was specific and precise and thus suitable for quantitative analysis in clinical pharmacokinetic studies of ClABT.

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Anticancer, neuroprotective activities and computational studies of 2-amino-1,3,4-thiadiazole based compound

Cited by 153 publications

References 38 publications

Crystal structure of 2-[(2-bromophenylimino)methyl]-4-chlorophenol, C13H9BrClNO

Crystal structure of 2-[(2-bromophenylimino)methyl]-4-chlorophenol, C13H9BrClNO

Crystal structure of 2-bromo-4-chloro-6-[(4-bromophenylimino) methyl]phenol, C13H8Br2ClNO

A simple HPLC method for determining 2-(3-chlorophenyloamino)-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole in brain and plasma of animals: Application to a pharmacokinetic study

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