Synthesis and Reactions of Novel 2,5-Disubstituted 1,3,4-Thiadiazoles

Mahmoud, Mahmoud R.; Shiba, S. A.; El‐Ziaty, Ahmed K.; El‐Azm, Fatma S. M. Abu; Ismail, Mahmoud F.

doi:10.1080/00397911.2013.846381

Cited by 30 publications

(22 citation statements)

References 12 publications

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“…The nicotinonitriles were obtained by two different ways, from the reaction of chalcone with ethylcyanoacetate, ammonium acetate and drops of piperidine as a base and from one pot four components reaction of methylketone, aldehyde, ethylcyanoacetate, ammonium acetate and drops of piperidine as a base [15]. In prolongation of our work in the synthesis of heterocyclic compounds and evaluation of their medicinal importance [16,17,18,19,20,21,22,23,24,25,26,27] and based on the literature survey about the pharmacological and medicinal importance of pyrazoles and nicotinonitriles, we have devoted our efforts to design and synthesize novel heterocyclic compounds containing pyrazol and nicotine-nitrile moieties, 4-(3-(4-fluorophenyl)-1-phenyl-1 H -pyrazol-4-yl)-2-hydroxy-6-(naphthalen-1-yl)-nicotinenitrile 8 has been obtained by reacting of 1-acetylnaphthalene ( A ), 3-(4-fluorophenyl)-1-phenyl-1 H -pyrazole-4-carbaldehyde ( B ), ethyl 2-cyanoacetate, ammonium acetate and piperidine (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Effects of Newly Synthesized Heterocyclic Candidates Containing Nicotinonitrile and Pyrazole Moieties on Hepatocellular and Cervical Carcinomas

et al. 2019

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In this study, a series of newly synthesized substituted pyridine 9, 11–18, naphthpyridine derivative 10 and substituted pyrazolopyridines 19–23 by using cycnopyridone 8 as a starting material. Some of the synthesized candidates are evaluated as anticancer agents against different cancer cell lines. In vitro cytotoxic activities against hepatocellular and cervical carcinoma cell lines were evaluated using standard MTT assay. Different synthesized compounds exhibited potential in vitro cytotoxic activities against both HepG2 and HeLa cell lines. Furthermore, compared to standard positive control drugs, compounds 13 and 19 showed the most potent cytotoxic effect with IC50 values of 8.78 ± 0.7, 5.16 ± 0.4 μg/mL, and 15.32 ± 1.2 and 4.26 ± 0.3 μg/mL for HepG2 and HeLa cells, respectively.

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Section: Resultsmentioning

confidence: 99%

Cytotoxic Effects of Newly Synthesized Heterocyclic Candidates Containing Nicotinonitrile and Pyrazole Moieties on Hepatocellular and Cervical Carcinomas

et al. 2019

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“…In our previous work [17,18], when β-ketonitrile was refluxed with p-nitrobenzaldehyde in boiling ethanol in the presence of piperidine, the corresponding condensation product 9 was afforded (Scheme 5). Meanwhile, in this study, the diarylidene hydrazine derivative 4 was obtained instead.…”

Section: Chemistrymentioning

confidence: 99%

“…From synthetic aspect, since cyanoacetohydrazide derivatives possess both electrophilic and nucleophilic properties [16]. They have been used to design diverse heterocyclic moieties such as pyrazole, 1,3-dithiolane, thiadiazole, 1,3-thiazolidinone, iminocoumarin, and pyridazine derivatives [17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in-vitro antioxidant and antitumor evaluation of novel pyrazole-based heterocycles

Ismail

El‐Sayed

2018

J IRAN CHEM SOC

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Hydrazide-hydrazone, namely, N′-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)-2-cyanoacetohydrazide 3, was utilized as a key starting material for the construction of a variety of novel heterocyclic moieties. The newly synthesized compounds were characterized by elemental analyses and spectral data (IR, 1 H-NMR, and mass spectra). Some of the newly synthesized compounds were screened for their antitumor and antioxidant activities. The results showed clearly that compounds 6, 11, 13, 22, and 29 displayed promising in-vitro antitumor activity against two cell lines (HepG2 and MCF-7). Among these compounds, compounds 13 and 29 exhibited the highest activity as antitumor agents. On the other hand, compounds 13, 22, and 29 exhibited the highest inhibitory antioxidant activity using ABTS method. While, in case of erythrocytes hemolysis, compounds 4, 13, and 29 proved to exhibit potent antioxidative activity as vitamin C. Meanwhile, compounds 6, 11, 16, 21, and 22 showed a remarkable promising activity. In light of the highest potency of our novel compounds in targeting both antitumor and antioxidant activities, compounds 13 and 29 warrant persistent preclinical development as antitumor and antioxidant agents.

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“…31 Over the past decades, significant efforts have been devoted to develop the synthesis of pyrimidinethione derivatives, 32,33 as they are considered versatile synthons for the construction of many heterocycles of synthetic and biological importance. [34][35][36][37] Thus, in view of the above facts and in continuation of our efforts to construct heterocyclic compounds from pyran derivatives, and to study their biological potency, [38][39][40][41][42][43][44][45] it was of interest to synthesize a ring system combine both the pyrazole and the pyran moieties which might have good biological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Bioactive Heterocycles from 6-amino-4-(2-chloro-5-nitrophenyl)-3-methyl-1,4-dihydropyrano[2,3-c] pyrazole-5-carbonitrile

El‐Ziaty

Bassioni²,

Hassan³

et al. 2018

ECB

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Enaminonitrile derivative, 6-amino-4-(2-chloro-5-nitrophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (1) was synthesized. This compound was utilized as a building block for the synthesis of new 3-methylpyrazolopyran moiety incorporated with different heterocycles involving pyrimidinone, oxazinone, and iminopyrimidine, in addition to novel derivatives including diacetyl derivative (5), benzoyl derivative (6), carbamodithioic acid (10) and urea derivative (13). Spectral techniques, FT-IR, 1 H-NMR and mass spectroscopy and elemental analysis were used to characterize the synthesized compounds. Screening and evaluation of these products as antimicrobial agents showed that the derivatives 5, 6, 10, and 13 possess a potent activity.

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Synthesis and Reactions of Novel 2,5-Disubstituted 1,3,4-Thiadiazoles

Cited by 30 publications

References 12 publications

Cytotoxic Effects of Newly Synthesized Heterocyclic Candidates Containing Nicotinonitrile and Pyrazole Moieties on Hepatocellular and Cervical Carcinomas

Cytotoxic Effects of Newly Synthesized Heterocyclic Candidates Containing Nicotinonitrile and Pyrazole Moieties on Hepatocellular and Cervical Carcinomas

Synthesis and in-vitro antioxidant and antitumor evaluation of novel pyrazole-based heterocycles

Synthesis of Bioactive Heterocycles from 6-amino-4-(2-chloro-5-nitrophenyl)-3-methyl-1,4-dihydropyrano[2,3-c] pyrazole-5-carbonitrile

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