Synthesis of 2-[4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio]-N-(thiazole-2-yl)acetamide derivatives and their anticancer activities

Duran, Murat; Demirayak, Şeref

doi:10.1007/s00044-012-0411-5

Cited by 16 publications

(8 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Our scope was extended to study the effect of various five‐membered rings fused to the purine nucleus and encouraged by the fact that various reports stated potent anticancer activities for imidazole rings . So compound 1 was reacted with different reagents: cyanamide and thioacetamide to produce imidazo[1,5,4‐ gh ]purin‐5‐amine 8 and 5‐methylimidazo[1,5,4‐ gh ]purine 9 , respectively.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Anticancer Activity of Novel Fused Purine Analogues

Hassan

Sarg

Bayoumi

et al. 2017

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

6‐Mercaptopurine has been utilized for the synthesis of various fused purine analogues through different chemical reactions to yield [1,4]thiazino[4,3,2‐gh]purines 2, 3, 10a,b, 14, (8‐oxo‐[1,4]thiazino[4,3,2‐gh]purin‐7(8H)‐ylidene) acetate 4, [1,4]thiazepino[4,3,2‐gh]purine 6, thiazolo[3,4,5‐gh]purine 7, imidazo[1,5,4‐gh]purin‐5‐amine 8, 5‐methylimidazo[1,5,4‐gh]purine 9, [1,2,4]triazino[4,3‐i]purines 16, 18, 21, [1,2,4]triazino[4,5,6‐gh]purine 20, 5‐methyl‐2‐(7H‐purin‐6‐yl)‐1H‐pyrazol‐3(2H)‐one 22, [1,2,4]triazolo[4,3‐i]purine 23, [1,2,5]triazepino[5,4,3‐gh]purine 24, and ethyl 6‐(2‐(ethoxycarbonyl)hydrazinyl)‐9H‐purine‐9‐carboxylate 26. Seventeen of the newly synthesized compounds were selected by the NCI, Maryland, USA, and were tested for their anticancer activity in an initial single high dose in the full NCI 60 cell line panel among which [1,4]thiazino[4,3,2‐gh]purine‐7,8‐dione 2, 7‐benzyl‐[1,4]thiazino[4,3,2‐gh]purine 10b, and 3‐(2,4‐dimethoxyphenyl)‐7H‐[1,2,4]triazolo[4,3‐i]purine 23 were found to possess very potent anticancer activity against most of the cancer cell lines.

show abstract

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Anticancer Activity of Novel Fused Purine Analogues

Hassan

Sarg

Bayoumi

et al. 2017

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…The studied acetamide derivatives were synthesized according to the methods described in our previous work [31]. The buffer solutions used were prepared from: (a) HCl-KCl, pH = 1.0; (b) KH 2 PO 4 -NaOH, pH = 7.0; (c) borax-HCl, pH = 8.0 to 9.0; (d) borax-NaOH, pH = 9.3 to 10.7.…”

Section: Methodsmentioning

confidence: 99%

“…Imidazole and thiazole represent an interesting class of heterocyclic compounds. Phenyl thiazole and imidazole-2-thione were observed to play important roles in biological functions, such as antimicrobial, antidiabetic, antiviral, anti-inflammatory, antituberculosis, and anticancer activities [23][24][25][26][27][28][29][30][31]. In particular, 2-amino-4-phenyl-1,3-thiazole has pharmaceutical characteristics and it is used in industrial applications [32][33][34].…”

Section: Introductionmentioning

confidence: 99%

Bazi İmi̇dazol Ve Ti̇yazol Bağli Asetami̇t Bi̇leşi̇kleri̇ni̇n Asi̇tli̇k Sabi̇tleri̇ni̇n İncelenmesi̇ Ve Değerlendi̇ri̇lmesi̇

Tay¹,

Duran²,

İspir³

et al. 2016

AUBTD-A

Self Cite

View full text Add to dashboard Cite

In this work, the effect of substituents on the acidity constants of some acetamide derivatives was investigated. The acidity constants of nine acetamide derivatives were determined at 25 °C using a UV spectrophotometric method. When the molecules possessed different substituents the values of the acidity constants changed from 6.01 to 8.22 for the first protonation and from 3.07 to 4.73 for the second protonation. The first protonation under these circumstances was observed to occur on the nitrogen atom of the 2-mercaptoimidazole ring. The second protonation was observed to occur on the nitrogen atom of the thiazole ring.

show abstract

“…15 Also, recent research has indicated that some acetamides could successfully be applied as melatonin analogs 16 , lidocaine analogs 17 , positive allosteric modulators of sigma-1 receptor 18 and potential acetylholinesterase inhibitors. 19 Besides all the above mentioned application, the pharmacological tests are mostly directed to the discovery of derivatives with antitumor activity 20,21 and HIV inhibitory properties. 22 The recognition of bioactive substances is closely related to the knowledge about the relationship between the structure, the physicochemical characteristics, and the potential activities that the new molecule may exhibit in the biological medium.…”

Section: Introductionmentioning

confidence: 99%

Thin-Layer Chromatography on Reversed Phase in the Characterization of Retention Behaviour, Lipophilicity, and Pharmacokinetics of Cyanoacetamide Derivatives

Apostolov

Vastag

Matijević

et al. 2020

J. Chil. Chem. Soc.

View full text Add to dashboard Cite

Biological activity of a molecule is closely related to its lipophilicity. This significant parameter was determined for a group of potentially bioactive N-(4-phenylmonosubstituted)-2-cyanoacetamides applying thin-layer chromatography on reversed phase (RP-TLC) in mixtures of water and two organic modifiers separately, i-propanol and dioxane. The effect of the chemical structure of derivatives and the influence of the applied organic modifier on their retention were studied. The determined chromatographic retention constants, RM 0 , and the chromatographic parameter, m, of compounds were correlated with software calculated partition coefficients, log P as the standard measure of lipophilicity and with different pharmacokinetic predictors applying classical linear and multiple regression analysis. By classical linear regression analysis in both water-modifier systems only RM 0-log P and m-log P correlations were established (average r, 0.909 and 0.826). All studied relationships were enhanced by molecular descriptors that fulfilled the modified Lipinski's rule of five. Thereby, the performed multiple regression analysis gave better correlations (for RM 0-log P and m-log P average r 2 , 0.994 and 0.993; for RM 0-pharmacokinetic parameters and m-pharmacokinetic parameters average r 2 0.978 and 0.980). The obtained results indicate that the chromatographic parameters, RM 0 and m determined by RP-TLC at given conditions could be used successfully for the description of lipophilicity and the evaluation of pharmacokinetic properties of N-(4-phenylmonosubstituted)-2-cyanoacetamides as potential bioactive molecules.

show abstract

Synthesis of 2-[4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio]-N-(thiazole-2-yl)acetamide derivatives and their anticancer activities

Cited by 16 publications

References 28 publications

Design, Synthesis, and Anticancer Activity of Novel Fused Purine Analogues

Design, Synthesis, and Anticancer Activity of Novel Fused Purine Analogues

Bazi İmi̇dazol Ve Ti̇yazol Bağli Asetami̇t Bi̇leşi̇kleri̇ni̇n Asi̇tli̇k Sabi̇tleri̇ni̇n İncelenmesi̇ Ve Değerlendi̇ri̇lmesi̇

Thin-Layer Chromatography on Reversed Phase in the Characterization of Retention Behaviour, Lipophilicity, and Pharmacokinetics of Cyanoacetamide Derivatives

Contact Info

Product

Resources

About