Synthesis, DFT Study, and Antitumor Activity of Some New Heterocyclic Compounds Incorporating Isoxazole Moiety

Hamama, Wafaa S.; Ibrahim, Mona E.; Zoorob, Hanafi H.

doi:10.1002/jccs.201700064

Cited by 9 publications

(2 citation statements)

References 41 publications

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“…Fortunately, a single product, N ‐(4‐anisyl)‐5‐imino‐6‐methyl‐3‐oxo‐3,5‐dihydro‐2 H ‐thiazolo[3,2‐ a ]thieno‐[2,3‐ d ]pyrimidine‐7‐carboxamide ( 18 ), has been produced (Scheme 3). We expect the reaction to proceed via nucleophilic substituting the chlorine atom from compound 3 , followed by intramolecular cyclization of the thiocyanate intermediate and Dimroth‐like rearrangements [33, 34] to generate the 2‐(thienylimino)thiazolidin‐4‐one intermediate 17 . The unexpected ring closure of the intermediate 17 through nucleophilic addition of the imino group (=NH‐) on the nitrile group resulted in the formation of thiazolo[3,2‐ a ]thiazolo[2,3‐ d ]pyrimidine ring system 18 .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and anticancer activity of some thiophene, thienyl‐thiazole, and thienyl‐benzofuran analogues

El-Rayyes

Almatari

Ghani

et al. 2023

Journal of Heterocyclic Chem

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N‐(Anisyl)‐5‐(2‐chloroacetamido)‐4‐cyano‐3‐methylthiophene‐2‐carboxamide (3) was synthesized and reacted with several nucleophilic reagents. The reactions with sulfur nucleophiles (namely, mercaptoacetic acid, ethyl 2‐mercaptoacetate, 5‐(phenylamino)‐1,3,4‐thiadiazole‐2‐thiol, 2‐mercapto‐4,6‐dimethyl‐nicotinonitrile, 4‐anilino‐3‐arylazo‐4‐mercapto‐butenones, ethyl 3‐anilino‐2‐arylazo‐3‐mercapto‐acrylates, and ammonium thiocyanate) yielded the corresponding sulfide, thiophene, or thiazolin‐4‐one derivatives, respectively. The reaction with salicylaldehyde (an example of oxygen nucleophile) furnished the targeting benzofuran compound 21. The reactions with nitrogen nucleophiles (namely, piperidine and aniline) yielded the corresponding thiophene‐carboxamide derivatives 23 and 25, respectively. IR, 1H NMR, and 13C NMR were used to deduce the structures of the target thiophene containing compounds. The effect of the synthesized thiophenes on the viability of HepG2, A2780, and A2780CP was determined. The most effective drug was shown by the thienopyridine‐carboxamide compound 11, against liver cancer cell lines (HepG2) and ovarian cancer cell lines (A2780CP and A2780), whose IC50 values were remarkably near those of Sorafenib, the antitumor drug.

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Section: Resultsmentioning

confidence: 99%

“…Four (18), has been produced (Scheme 3). We expect the reaction to proceed via nucleophilic substituting the chlorine atom from compound 3, followed by intramolecular cyclization of the thiocyanate intermediate and Dimroth-like rearrangements [33,34]…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and anticancer activity of some thiophene, thienyl‐thiazole, and thienyl‐benzofuran analogues

El-Rayyes

Almatari

Ghani

et al. 2023

Journal of Heterocyclic Chem

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Selective Hydro‐ and Deuterodechlorination of Trichloroacetamides under Controlled Electrochemical Conditions To Prepare Mono‐, Di‐, and Deuterochloroacetamides

Bandyopadhyay,

Bera,

Pathak

et al. 2024

Adv Synth Catal

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Mono and dichloro acetamides were prepared via hydrodechlorination reaction of trichloroacetamides under controlled electrochemical conditions. The reactions were carried out in an undivided cell with constant current flow using n‐Bu4NI as supporting electrolyte and methanol as solvent and proton source. Deuterodechlorination of trichloroacetamide was also successful using methanol‐d4 as solvent under identical electrochemical conditions.

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A versatile precursor for one‐pot synthesis of novel azo‐thiazole and thiazole scaffolds as prospective antimicrobial and antioxidant agents

Alamshany,

Tashkandi,

Othman

2024

J Chinese Chemical Soc

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In this study, we present a simple method for preparing a new series of thiazoles with excellent isolated yields. To synthesize the target thiazole scaffolds, a straightforward one‐pot procedure was developed including an amine‐mediated reaction of isoxazolethiazolidin‐4‐one derivative, thiosemicarbazide, and appropriate hydrazonyl chlorides. The reaction conditions for this one‐pot protocol were optimized by experimenting with different solvents and amines. The best results were achieved by conducting the reaction in dioxane with triethylamine at 100°C for 5 h. The structures of the desired products were proved by different elemental analyses and spectral data. Additionally, the antimicrobial efficacy of all target derivatives was assessed against various types of microorganisms. The results observed indicated that the antimicrobial activity of the thiosemicarbazone derivative 2 was the strongest activity among the new series, with MIC values ranging from 0.03 ± 0.01 to 0.98 ± 0.15 μg/mL. Moreover, antioxidant evaluations were conducted on all the desired targets, using ascorbic acid as a reference drug. Significantly, derivatives 2 and 10 demonstrated the most promising antioxidant inhibitory effects. Additionally, further toxicity studies were performed on the most active novel compounds, revealing their best drug‐like properties and varying toxicity risks in humans.

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Synthesis, DFT Study, and Antitumor Activity of Some New Heterocyclic Compounds Incorporating Isoxazole Moiety

Cited by 9 publications

References 41 publications

Synthesis and anticancer activity of some thiophene, thienyl‐thiazole, and thienyl‐benzofuran analogues

Synthesis and anticancer activity of some thiophene, thienyl‐thiazole, and thienyl‐benzofuran analogues

Selective Hydro‐ and Deuterodechlorination of Trichloroacetamides under Controlled Electrochemical Conditions To Prepare Mono‐, Di‐, and Deuterochloroacetamides

A versatile precursor for one‐pot synthesis of novel azo‐thiazole and thiazole scaffolds as prospective antimicrobial and antioxidant agents

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