Synthesis of substituted thieno[2,3-d]pyrimidine-2,4-dithiones and their S-glycoside analogues as potential antiviral and antibacterial agents

Hafez, Hend N.; Hussein, Hoda A. R.; El‐Gazzar, A. B. A.

doi:10.1016/j.ejmech.2010.05.060

Cited by 71 publications

(48 citation statements)

References 27 publications

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“…The obtained solid was crystallized from ethanol as a pale-brown powder. (10). -A mixture of compound 9 (2.78 g, 10 mmol), and 4-benzylidene-2-phenyl-4H-oxazol-5-one (2.49 g, 10 mmol) in glacial acetic acid (20 mL) containing fused sodium acetate (2 g) was refl uxed for 5 h. The reaction mixture was cooled and then poured onto cold water, the solid obtained was crystallized from DMF as a white powder.…”

Section: -{mentioning

confidence: 99%

“…Thienopyrimidines occupy a special position among condensed heterocyclic compounds. They have been widely employed due to their activities as antitumor (3,4), antimetabolite (5), antiviral, anti-HIV-1 (6), antiproliferative (7), antimicrobial (10,11), analgesic and anti-infl ammatory (12,13) agents, as well as kinase (8) and phospho-diesterase IV inhibitors (9). Among these active compounds, thieno [3,2-d]pyrimidines have generated wide-spread interest due to their remarkable antitumor activities (3,4,14).…”

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Synthesis of thiophene and N-substituted thieno[3,2-d] pyrimidine derivatives as potent antitumor and antibacterial agents

2017

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A novel series of carbamothioylamino-benzene-sulfonamidethiophene-carboxylates 4a-c and thieno [3,2-d]pyrimidin-2-yl-amino-benzene-sulfonamides 5a-c were synthesized in a series of synthetic steps and were used as key intermediates for the synthesis of thienotriazolopyrimidine-benzene-sulfonamide derivatives 6a-c and 7a-c. Thieno[3,2-d]pyrimidinones (8 and 9) were also prepared. Compound 9 was used as an intermediate for the synthesis of imidazole/1,2,4-triazole and tetrazine functionalized thieno[3,2-d]pyrimidine derivatives (10-12). Pyrrole derivatives/pyrrolopyrimidine/pyrrolotriazolopyrimidine functionalized thiophenes (15-19) were also synthesized. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. Most of the newly synthesized compounds were evaluated for their in vitro activity against three human tumor cell lines, namely, liver cancer (HepG-2), colon cancer (HT-29) and lung cancer (NCI-H460), using doxorubicin as standard. , resp.) showed higher activity against all cell lines than doxorubicin. Most of the compounds were also screened for antibacterial activity using ciprofl oxacin as standard drug. Compounds 4b and 6b, both containing benzenesulfonamide linked to N-, 10 bearing imidazole moiety, and 15 and 19b,c with a thiophene-2-carboxylic acid chain, exhibited high activity against Gram-positive and Gram-negative bacteria.

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Synthesis of thiophene and N-substituted thieno[3,2-d] pyrimidine derivatives as potent antitumor and antibacterial agents

2017

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“…This scaffold shows a broad spectrum of biological activities. The thienopyrimidines were assessed as antitumour [6][7][8][9], medicine [10], enzyme [11][12][13][14], phosphodiesterase inhibitors [15], antioxidative [16,17], antimalarial drug [18,19], antibacterial drug [20], antiviral [21], antifungal [22,23], medication [24], antiplatelet [25] and medicament [26]. In view of these observations, the varied biological property of thienopyrimidine pharmacophore impelled to synthesize the title compounds.…”

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confidence: 99%

Synthesis and Antibacterial Activity of Thienopyrimidine Amide Derivatives

Tharikoppula¹,

Eppakayala²,

Chary³

et al. 2017

Asian J. Chem.

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Thienopyrimidine amide derivatives are important class of organic compounds and show wide range of biological activity. Hence the researchers are paying more attention towards the synthesis of these compounds. A series of thienopyrimidine amide derivatives (13a-m) were synthesized. The newly synthesized amide derivatives (13a-m) were characterized by 1 H NMR, 13C NMR, Mass and IR spectral data. Further these compounds were also evaluated for their antibacterial activity.

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“…locked nucleic acid (LNA) and peptide nucleic acid (PNA) or having different nucleobases like morpholine. 2 In medicine several nucleosides analogues are used as antiviral, 3 anticancer, 4 antibacterial 5 and antifungal 6 agents. Synthetic modified nucleosides designed to pair in unusual ways with natural or unnatural nucleobases have many potential applications in biology; biotechnology and medicine have been reported.…”

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confidence: 99%

Synthetic Studies and Antibacterial Activity of Nucleobases and their N- and S-Glucosidesfrom 2-Amino Benzoic Acid and its Benzamido Derivatives

Benhammadi¹,

Salimairaten²,

Othman³

2016

Orient. J. Chem

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A series of S-glucosides 11a-14a and their benzamido derivatives 11b-14b have been synthesized by reacting D-glucose with thiol groups of 5-(2'-aminophenylene)-1,3,4-oxadiazole-2-thioles 7(a,b), 5-(2'-aminophenylene)-1,3,4-thiadiazole-2-thiols 8(a,b), 5-(2'-aminophenylene)-1,2,4-triazole-3-thiols 9(a,b) and 5-(2'-aminophenylene)-4-N-amino-1,2,4-triazole-3-thiols 10(a,b). The thiols 7(a,b)-10(a,b) have been synthesized from hydrazides 3(a,b) which already been synthesized from 2-aminobenzoic acid and its benzamido derivative. All synthesized compounds were characterized by IR, UV, 1 H-and 13 C-NMR. Nucleobases and a representative of S-glycoside were tested in vitro against the following microorganisms: two Gram-positive bacteria Staphylococcus aureus and Bacillus cereusand two Gram-negative bacteria Escherichia coli, Pseudomonas aeruginosa and they exhibited significant effects. Amykacine was used as positive standard.

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Synthesis of substituted thieno[2,3-d]pyrimidine-2,4-dithiones and their S-glycoside analogues as potential antiviral and antibacterial agents

Cited by 71 publications

References 27 publications

Synthesis of thiophene and N-substituted thieno[3,2-d] pyrimidine derivatives as potent antitumor and antibacterial agents

Synthesis of thiophene and N-substituted thieno[3,2-d] pyrimidine derivatives as potent antitumor and antibacterial agents

Synthesis and Antibacterial Activity of Thienopyrimidine Amide Derivatives

Synthetic Studies and Antibacterial Activity of Nucleobases and their N- and S-Glucosidesfrom 2-Amino Benzoic Acid and its Benzamido Derivatives

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