Synthesis and Reactions of Some Tetrahydrobenzothieno[2,3- d ]Pyrimidine Derivatives with Biological Interest

El‐Sharief, A. M. Sh.; Micky, Jehane A.; Shmeiss, N. A. M. M.; El-Gharieb, G.

doi:10.1080/10426500307912

Cited by 18 publications

(7 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The starting compounds, 2-thioxo-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one (1a) and 2,4-dithioxo-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidine (1b) were prepared as reported in the literature 19 from the reaction of 2-amino-4,5,6,7-tetrahydrobenzo-thiophene-3-[carbo(thio)oxamide] with carbondisulfide. Ribosylation of 1a,b was achieved by refluxing in hexamethyldisilazane (HMDS) to give the silylated derivatives 2a,b.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Some New S-Nucleoside Derivatives of 2-Thioxo and (2,4-Dithioxo)-5,6,7,8-Tetrahydrobenzo-Thieno[2,3-d]Pyrimidin-4-(3H)Ones

Break

Shmiss

Mosselhi

2010

Phosphorus, Sulfur, and Silicon and the Related Elements

View full text Add to dashboard Cite

Ribosylation of 2-thioxo-5,6,7,8-tetrahydrobenzo thieno[2,3-d]pyrimidin-4(3H)-one 1a and 2,4-dithioxo-5,6,7,8-tetrahydrobenzo thieno[2,3-d]pyrimidine 1b with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 7 afforded the benzoylated S-nucleoside derivatives 3 and 4, respectively. Debenzoylation of 3 and 4 by using methanolic sodium methoxide yielded the corresponding free S-nucleosides 5 and 6, respectively. Furthermore, the reaction of potassium salt of 2-thioxo-5,6,7,8-tetrahydrobenzo thieno[2,3-d]pyrimidin-4(3H)-one 8 with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 9, afforded 10. Deacetylation of the latter by using methanolic sodium methoxide yielded the corresponding S-glycoside, 2-(2 ,3 ,4 ,6 -tetra-hydroxy-β-D-glucopyranosylthio)-5,6,7,8-tetrahydro-benzothieno [2,3-d]pyrimidin-4-one 11. The structural elucidation of the new nucleosides formed was reported.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of Some New S-Nucleoside Derivatives of 2-Thioxo and (2,4-Dithioxo)-5,6,7,8-Tetrahydrobenzo-Thieno[2,3-d]Pyrimidin-4-(3H)Ones

Break

Shmiss

Mosselhi

2010

Phosphorus, Sulfur, and Silicon and the Related Elements

View full text Add to dashboard Cite

show abstract

“…They are also known to inhibit CDC25BP phosphatase, [8] and 2-methylerythritol 2,4-cyclodiphosphate synthase (IspF) from Mycobacterium tuberculosis and Plasmodium falciparum, [9] while there are still two reports about the synthesis of thienopyrimidothiazine heterocycles. [10,11] On the other hand, 1,2,3-triazoles have occupied an important role not only in organic chemistry but also in medicinal chemistry due to their easy synthesis by click chemistry and attractive features as well as numerous biological activities. [12][13][14] By combining 1,2,3-triazole with other pharmacophores via click chemistry, a number of compounds with potent antitumor activity were synthesized.…”

Section: Introductionmentioning

confidence: 99%

A new route for the synthesis of pyrimido[2,1-b][1,3]thiazine ring system

Ameen

Ahmed

2015

Journal of Sulfur Chemistry

View full text Add to dashboard Cite

A simple and efficient pathway to conjugate monosaccharides to thienopyrimidines via click chemistry establishing a 1,2,3-triazole linker was reported. Potential pharmaceutical interest is envisaged for the expected target products. Starting from a 2-isothiocyanate-thiophene-3-carboxylate, an allylthiourea was obtained with allylamine, cyclized and S-propargylated to give a thienopyrimidine-alkyne core. Click reaction with tetraacetyl-1-azidoglucose was successful to give the target conjugate with one sugar unit. When propargylamine was used in the first step, the expected thiourea cyclized via the alkyne moiety leading to pyrimido[2,1-b][1,3]thiazine.

show abstract

“…Such medicines as sulfathiazole, phthalylsulfathiazole and related compounds are commonly used in medical practice as well [8]. Besides, the antimicrobial profile of condensed thiophenes, particularly, their thieno [2,3-d]pyrimidin-4-one analogues is also well categorized in the literature [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis and antimicrobial studies of novel bridgehead nitrogen heterocycles containing the thienopyrimidinone skeleton

Gaber

Moussa

2011

Eur. J. Chem.

View full text Add to dashboard Cite

KEYWORDSVersatile 2-(alkylthio)pyrimidine-type and 2-(phenacylamino)thiophene building blocks (4ad) and 16 were obtained based on an ortho functionalized thiophene derivative 1. A novel series of thieno[2,3-d]pyrimidin-4-one derivatives with annelated bridgehead nitrogen heterocycles was synthesized starting from precursors 4 and 16 through convenient methods. Cyclocondensation of 2-(phenacylthio)pyrimidinone derivative (4b) with sulfuric acid led to the tricyclic thiazole derivative 5. Initial hydrazinolysis of 3-(carbethoxymethyl)pyrimidinone derivative (4d) followed by nitrous acid deamination of the formed N-aminolactam (7) to obtain a N-protodeamino analogue 8a, which on further treatment with formaldehyde and piperidine yielded the respective Mannich-type base 8b. On the other hand, initial hydrazinolysis of 3-unsubstituted pyrimidinone derivative 4a and subsequent acetylation gave the condensed 3-methyltriazole derivative 12, whereas the condensed pyrrole derivative 19 was obtained by heterocyclization of 2-phenacylamine derivative 16 with malononitrile. All newly-obtained thienopyrimidinones with annelated bridgehead nitrogen were screened for their antimicrobial activity against strains of a representative panel of Gram-positive and Gram-negative bacteria as well as fungi together with reference drugs. The compounds under investigation displayed generally good in vitro antibacterial and antifungal activities, with compound 8b that has a N-piperidinylmethyl moiety showing essentially the highest inhibition in both assays. Despite promising antimicrobial activity of N-1-substituted imidazole derivative 8b, the corresponding N-1-unsubstituted analogue 8a displayed poor activity. The heteroannelation of a N-(piperidinylmethyl)imidazole or 3-methyltriazole moiety to the thienopyrimidinone scaffold could be considered as a potential strategy for the development of new therapeutic antimicrobial agents.Thienopyrimidinone Alkylation Cyclodehydration Hydrazinolysis Acetylation Antimicrobial activity

show abstract

Synthesis and Reactions of Some Tetrahydrobenzothieno[2,3- d ]Pyrimidine Derivatives with Biological Interest

Cited by 18 publications

References 6 publications

Synthesis of Some New S-Nucleoside Derivatives of 2-Thioxo and (2,4-Dithioxo)-5,6,7,8-Tetrahydrobenzo-Thieno[2,3-d]Pyrimidin-4-(3H)Ones

Synthesis of Some New S-Nucleoside Derivatives of 2-Thioxo and (2,4-Dithioxo)-5,6,7,8-Tetrahydrobenzo-Thieno[2,3-d]Pyrimidin-4-(3H)Ones

A new route for the synthesis of pyrimido[2,1-b][1,3]thiazine ring system

Regioselective synthesis and antimicrobial studies of novel bridgehead nitrogen heterocycles containing the thienopyrimidinone skeleton

Contact Info

Product

Resources

About