Synthesis and biological evaluation of pyrazolo[1,5-a]pyrimidine-3-carboxamide as antimicrobial agents

Hassan, Ashraf S.; Masoud, Doaa M.; Sroor, Farid M.; Askar, Ahmed

doi:10.1007/s00044-017-1990-y

Cited by 61 publications

(39 citation statements)

References 14 publications

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“…Many of drugs containing thiazole moiety in their structure used in wide rang in the pharmaceutical market such as fanetinole, combendazole, niridazole, tiazofuren, bleomycine and sulfathiazole (Figure ). Encouraged by the interesting bioactivity of diarylurea derivatives and in conjunction to our interest in preparation of bioactive molecules, a new series of diarylurea incorporating sulfamethoxazole and thiazole moieties were synthesized and screened for anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis, Structural Activity Relationship, Molecular Modeling and In Vitro Biological Evaluation of New Urea Derivatives with Incorporated Isoxazole and Thiazole Moieties as Anticancer Agents

2019

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A new series of isoxazolyl and thiazolyl urea derivatives was synthesized, fully characterized and evaluated in vitro as anticancer agents. The chemistry involves a facile protocol for the preparation of urea derivatives 12–22 through the reaction of isocyanates (p‐tolylsulfonyl isocyanate, p‐tolyl isocyanate, benzoyl isocyanate and ethylisocyanate) 8–11 with the corresponding aminoisoxazoles and aminothiazoles 2, 3, 6 and 7. The cytotoxicity of the synthesized compounds 12–22 were evaluated using human lung adenocarcinoma cell line (A549), cervical cancer cell line (HeLa), and breast cancer cell line (MCF7). All novel compounds (except compounds 12, 17, and 18) were potential cytotoxic against lung cancer as it displayed IC50s less than the reference drug (5‐Fluro uracil (5FU)). All tested compounds (except 15 and 19) showed strong inhibition of breast cancer cell line even much better than the 5FU. The tested compounds were less cytotoxic against cervical cancer except compounds 16, 19, 20, and 21. The molecular docking studies of the synthesized compounds against the three different proteins Janus kinase 2 (JAK2), cyclin dependent kinase‐2 (CDK2), and B‐cell lymphoma‐2 (BCL2) that are major proteins involved in pathogenesis of cancer were discussed. The molecular‐docking analyses revealed that compounds 13, 14 and 20 were the best docked ligand compared to reference docked ligands against the tested targeted proteins. In conclusion, the urea derivatives 13 and 14 were the most promising compounds with lowest IC50s against the tested cancer cell lines, and they displayed the lowest binding energies, critical hydrogen bonds and hydrophobic interactions with the molecular targets compared to other tested compounds.

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Section: Introductionmentioning

confidence: 99%

Facile Synthesis, Structural Activity Relationship, Molecular Modeling and In Vitro Biological Evaluation of New Urea Derivatives with Incorporated Isoxazole and Thiazole Moieties as Anticancer Agents

2019

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“…In addition, compound C showed antitumor activity by inhibition of cyclindependent kinases (CDK) [3] (Figure 1). Furthermore, pyrazole compounds used as intermediates in the synthesis of various bioactive compounds such as pyrazolopyrimidines, pyrazolotriazines, pyrazoloquinazolines and Schiff bases [4][5][6][7][8][9]. A recent review of 5-aminopyrazoles described the miscellaneous synthetic methods [10] as the condensation of β-ketonitriles [11] or malononitrile derivatives [12] with hydrazine hydrate.…”

Section: Introductionmentioning

confidence: 99%

“…13 C NMR (DMSO-d 6 , δ ppm) 55.6 (-OCH 3 ), 86.2 (C 4 , pyrazole), 114.6 (2C, aromatic), 117.4 (2C, aromatic), 137.0 (C, aromatic), 148.2 (C 5 , pyrazole), 152.2 (C 3 , pyrazole), 152.8 (C, aromatic), 167.2 (C=O, amide). MS (m/z): 247 (M + ) [18].5-Amino-3-[(4-methoxyphenyl)amino]-N-phenyl-1H-pyrazole-4-carboxamide(6). White crystals, m.p.…”

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confidence: 99%

V2O5/SiO2 as an efficient catalyst in the synthesis of 5-amino- pyrazole derivatives under solvent free condition

Khatab¹,

Hassan²,

Hafez³

2019

Bull. Chem. Soc. Eth.

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“…Pyrazolopyrimidines occupy an important place in medical chemistry due to their biological activities [1][2][3][4][5][6][7][8][9][10] and their structural resemblance to purines. Pyrazolopyrimidines occupy an important place in medical chemistry due to their biological activities [1][2][3][4][5][6][7][8][9][10] and their structural resemblance to purines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some novel pyrazolopyrimidotriazepine, pyrazolotriazolopyrimidine, and pyrazolopyrimidotetrazine derivatives

Hassan

Abdel‐Aziem

Hussain

2019

Journal of Heterocyclic Chem

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Reaction of ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate with thiocarbohydrazide yielded 5-amino-6-hydrazinyl-1-phenyl-1H-pyrazolo [3,4-d] pyrimidine-4-(5H)one (1), which used as precursor to synthesize pyrazolopyrimidotriazepine 2, pyrazolopyrimidotriazines 5-7, pyrazolotriazolopyrimidines 8-14, pyrazolopyrimidotetrazines 17. The structures of the newly synthesized compounds were confirmed by spectral data (IR, NMR, elemental analysis, and mass spectra).

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Synthesis and biological evaluation of pyrazolo[1,5-a]pyrimidine-3-carboxamide as antimicrobial agents

Cited by 61 publications

References 14 publications

Facile Synthesis, Structural Activity Relationship, Molecular Modeling and In Vitro Biological Evaluation of New Urea Derivatives with Incorporated Isoxazole and Thiazole Moieties as Anticancer Agents

Facile Synthesis, Structural Activity Relationship, Molecular Modeling and In Vitro Biological Evaluation of New Urea Derivatives with Incorporated Isoxazole and Thiazole Moieties as Anticancer Agents

V2O5/SiO2 as an efficient catalyst in the synthesis of 5-amino- pyrazole derivatives under solvent free condition

Synthesis of some novel pyrazolopyrimidotriazepine, pyrazolotriazolopyrimidine, and pyrazolopyrimidotetrazine derivatives

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