Synthetic utility of bifunctional thiophene derivatives and antimicrobial evaluation of the newly synthesized agents

Abu‐Hashem, Ameen A.; Abu-Zied, Khadiga M.; Shehry, Mohamed F. El

doi:10.1007/s00706-011-0456-z

Cited by 37 publications

(53 citation statements)

References 16 publications

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“…On the other hand, compounds attached or fused to pyrimidine ring have been exhibited to possess antibacterial, antifungal, antimalarial, anticonvulsant, and antitumor activities. Furthermore, thienopyrimidines have anticipated biological activity . In the light of the previous biological importance and in our ongoing endeavor to create new pyrazole thienopyrimidine‐based hybrids, we have synthesized here a series of new heterocyclic compounds isoindole, pyrazole, and triazepine attached or fused to the pyrazolothienopyrimidine ring system.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, reactions, and spectral characterization of some new biologically active compounds derived from thieno[2,3‐c]pyrazole‐5‐carboxamide

Saber

Zaki

El‐Dean

et al. 2019

Journal of Heterocyclic Chem

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The starting compound 4-amino-3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazole-5-carboxamide (1), that has been previously synthesized according to the literature procedure, underwent a reaction with the anhydride of phthalic acid either in AcOH or DMF to give isoindolinylpyrazole-5-carboxamide 3 and pyrazolothienopyrimidoisoindoledione 4, respectively. Also, it was subjected to react with diethylmalonate followed by hydrazinolysis by hydrazine hydrate to yield the pyrazolothienopyrimidinyl acetohydrazide 5. The carbohydrazide derivative 5 was used as a key intermediate for the preparation of other new heterocyclic systems containing pyrazolylacetyl pyrazolothienopyrimidines and pyrazolothieno-pyrimidotriazepine compounds 6-11. The structures of these new heterocycles have been characterized by using analytical and spectroscopic analyses (IR, 1 H-NMR, 13 C-NMR and MS). Some derivatives of the synthesized compounds exhibited remarkable antibacterial and antifungal activities against many bacterial and fungal strains.

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Section: Introductionmentioning

confidence: 99%

Synthesis, reactions, and spectral characterization of some new biologically active compounds derived from thieno[2,3‐c]pyrazole‐5‐carboxamide

Saber

Zaki

El‐Dean

et al. 2019

Journal of Heterocyclic Chem

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“…The reaction mixture was heated at reflux for 4 h, then allowed to cool in an ice bath, and was poured into a suitable amount of ice. The formed precipitate was filtered off and washed several times with cold water, and diethyl ether afforded 9 as a yellow solid (3.22 General procedure for synthesis of 1-N-substituted-3trimethyl-6-pyridin-4-yl-10-(pyridin-4-ylmethylene)-7,8,9,10tetrahydro-6H-isothiochromeno [3,4-d]pyrimidine (10,11,12,13,14). First method.…”

Section: Synthesismentioning

confidence: 99%

“…In our research group, we are interested in exploring the reactivity ortho-aminocarbonitriles 1, easily formed by base-catalyzed intermolecular cyclization of malononitrile with α,β-unsaturated ketone in the presence of sulfur [9,10]. 3-Amino-4-cyano-isothiochromene derivatives 1 is considered a straightforward and convenient precursor for fused nitrogen heterocycles [11], which showed interesting biological activities [12][13][14][15][16][17]. These findings prompted us to build isothiochromene moiety fused with pyrimidine, pyridine, and other heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Direct Amination and Synthesis of Fused N‐Substituted Isothiochromene Derivatives

Abu‐Hashem

Zaki

2019

Journal of Heterocyclic Chem

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Isothiochromene[3,4‐d] pyrimidine derivatives 2, 3, and 4a,b were synthesized from the reaction of 3‐amino‐1‐(pyridin‐4‐yl)‐5‐(pyridin‐4‐ylmethylene)‐5,6,7,8‐tetrahydro‐1H‐isothiochromene‐4‐carbonitrile 1 with acetic anhydride, formamide, urea, or thiourea in appropriate experimental conditions. Combination of 1 with carbon acid derivatives afforded isothiochromene [3,4‐b]pyridine 6–8 in good yield. A simple approach for N‐substituted fused isothiochromene derivatives has been explored. A POCl3‐mediated direct amination of isothiochromene amide 2 with NH2‐heterocycles, secondary amines, and carbohydrazides is described and compared with classical method, yielding 10–14. The structures of the newly synthesized compounds were elucidated on the basis of elemental analysis, and spectral data.

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“…proton , and a lack of the amino proton signal detected for the parent 1 , Pyrazolopyrimidine derivatives 3 was obtained by refluxing 2 with hydrazine hydrate . The reaction sequence and mechanism are outlined in scheme 1 [12] .The 1 HNMR of 3 revealed two exchangeable broad singlet signals at δ 6.11 and 11.12 ppm for two amino groups, without the ester proton signals detected for the parent 2 .Compound 1 was diazotized hydrochloric acid and sodium nitrile .The desired diazonium chloride was then coupled with malononitrile to yield the corresponding azo derivatives 4 . 1 HNMR of 4 showed the absence of an amino signal and the presence of signals at δ 1.30 and 4.30 ppm for ethyl ester group and δ11.30 ppm for an exchangeable NH proton.…”

Section: Synthesis Procedures Of Ethyl-5-(2-(dicyano Methylene)-1-phenmentioning

confidence: 99%

Synthesis of New Pyrazolo[3,4-D]pyrimidine and Their Fused Heterocycles.

Hassan¹

2019

IJAR

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Novel pyrazolo[3,4-.]pyrimidine derivatives were synthesized via various synthetic pathways. Among which were different substituted pyrazole analogues that were synthesized , in addition to various fused dipyrazolo[1,5-c:4',3'-c]pyrimidine derivatives , imidazo[1,2b]pyrazole and imidazo[1',2':3,4]imidazo[1,2-b]pyrazole derivatives .Besides pyrazolo[5,1-b]quinazoline dervatives was also synthesized. The structure of the synthesized compounds were confirmed by IR, 1 H and 13 CNMR, elemental analysis and mass spectra data and all structures of synthesized compounds agree with spectral data and elemental analysis.

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Synthetic utility of bifunctional thiophene derivatives and antimicrobial evaluation of the newly synthesized agents

Cited by 37 publications

References 16 publications

Synthesis, reactions, and spectral characterization of some new biologically active compounds derived from thieno[2,3‐c]pyrazole‐5‐carboxamide

Synthesis, reactions, and spectral characterization of some new biologically active compounds derived from thieno[2,3‐c]pyrazole‐5‐carboxamide

Direct Amination and Synthesis of Fused N‐Substituted Isothiochromene Derivatives

Synthesis of New Pyrazolo[3,4-D]pyrimidine and Their Fused Heterocycles.

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