Addition–cyclization reactions of furan-2-carbonyl isothiocyanate with nitrogen nucleophiles as a synthetic route to novel azines and azoles of potential biological activity

Hamid, Atef M. Abdel

doi:10.1007/s13738-019-01659-6

Cited by 6 publications

(3 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, some fluorescent compounds are utilized in studying the environmental pollution . Thus, in the light of these reports and in continuation of our studies on the synthesis and properties of furan‐tagged condensed pyrimidines, we report herein a synthetic approach for a highly fluorescent series of these compounds.…”

Section: Introductionmentioning

confidence: 97%

Synthesis and fluorescent properties of some Furan‐tagged Thieno[2,3‐d]pyrimidines and Thieno[2,3‐d:4,5‐d']dipyrimidines

Hamid

Hamed

2020

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

Intermolecular cyclization of pyrimidinethiol 1 with ethyl chloroacetate and chloroacetonitrile furnished thieno[2,3-d]pyrimidines 2a,b. Hydrazinolysis of o-aminoester 2a gave acid hydrazide 3, which was cyclized with various electrophilic reagents including formic acid, triethyl orthoformate, acetic anhydride, p-chlorobenzaldehyde then triethyl orthoformate, carbon disulfide, and acetylacetone affording thienopyrimidine derivatives 4 to 10. Another thienopyrimidine series could be obtained via treatment of o-aminocarbonitrile 2b with a variety of reagents giving derivatives 11 to 17. The fluorescent measurements for a group of the synthesized compounds at room temperature demonstrated high fluorescent properties.

show abstract

Section: Introductionmentioning

confidence: 97%

Synthesis and fluorescent properties of some Furan‐tagged Thieno[2,3‐d]pyrimidines and Thieno[2,3‐d:4,5‐d']dipyrimidines

Hamid

Hamed

2020

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

show abstract

“…Functional moieties such as carbonyl, thiocarbonyl, and amines are building blocks of many drugs. These groups frequently perform a structural role, linking other functionalities and aiding in the optimal orientation for interaction with the drug’s target [ 18 , 19 ]. The chemical reactivity of carbonyl functional groups can also allow these groups to come into close contact with the target, generating hydrogen bonds and other intermolecular interactions.…”

Section: Introductionmentioning

confidence: 99%

In Vitro Anti-Microbial Activity and Anti-Cancer Potential of Novel Synthesized Carbamothioyl-Furan-2-Carboxamide Derivatives

2023

View full text Add to dashboard Cite

A series of carbamothioyl-furan-2-carboxamide derivatives were synthesized using a one-pot strategy. Compounds were obtained in moderate to excellent yields (56–85%). Synthesized derivatives were evaluated for their anti-cancer (HepG2, Huh-7, and MCF-7 human cancer cell lines) and anti-microbial potential. Compound p-tolylcarbamothioyl)furan-2-carboxamide showed the highest anti-cancer activity at a concentration of 20 μg/mL against hepatocellular carcinoma, with a cell viability of 33.29%. All compounds showed significant anti-cancer activity against HepG2, Huh-7, and MCF-7, while indazole and 2,4-dinitrophenyl containing carboxamide derivatives were found to be less potent against all tested cell lines. Results were compared with the standard drug doxorubicin. Carboxamide derivatives possessing 2,4-dinitrophenyl showed significant inhibition against all bacterial and fungal strains with inhibition zones (I.Z) in the range of 9–17 and MICs were found to be 150.7–295 μg/mL. All carboxamide derivatives showed significant anti-fungal activity against all tested fungal strains. Gentamicin was used as the standard drug. The results showed that carbamothioyl-furan-2-carboxamide derivatives could be a potential source of anti-cancer and anti-microbial agents.

show abstract

“…Several methods were reported for the synthesis of triazinethione analogs. One of the most popular methods involved the reaction of a carboximidamide [16], or urea [17] with isothiocyanates. The C=S bond in the latter is highly polar, with the carbon atom always positive and therefore being susceptible to nucleophilic attack.…”

Section: Introductionmentioning

confidence: 99%

One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions

Kang¹,

Zhang²

2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

A catalyst-free one-pot synthetic methodology was developed for the preparation of 1,3,5-triazine-2,4-dithione derivatives through three-component reactions of arylaldehydes, thiourea, and orthoformates. The procedure tolerated a diverse range of arylaldehydes and orthoformates and provided a rapid entry to a variety of 4-aryl-6-(alkylthio)-3,4-dihydro-1,3,5-triazine-2(1H)-thiones (29 examples). The synthetic strategy relies on the dual role of thiourea in the cyclization with the aldehydes and the alkylation via an intermediate imidate formation. The structures of 1,3,5-triazine-2,4-dithione derivatives were characterized by spectroscopic techniques as well as by single crystal X-ray diffraction.

show abstract

Addition–cyclization reactions of furan-2-carbonyl isothiocyanate with nitrogen nucleophiles as a synthetic route to novel azines and azoles of potential biological activity

Cited by 6 publications

References 19 publications

Synthesis and fluorescent properties of some Furan‐tagged Thieno[2,3‐d]pyrimidines and Thieno[2,3‐d:4,5‐d']dipyrimidines

Synthesis and fluorescent properties of some Furan‐tagged Thieno[2,3‐d]pyrimidines and Thieno[2,3‐d:4,5‐d']dipyrimidines

In Vitro Anti-Microbial Activity and Anti-Cancer Potential of Novel Synthesized Carbamothioyl-Furan-2-Carboxamide Derivatives

One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions

Contact Info

Product

Resources

About