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Sci. Pharm. 2009, 77(4), 755-774; doi:10.3797/scipharm.0904-17

Synthesis of Tetrahydrobenzothieno[ 2,3-d]pyrimidine and Tetrahydrobenzothieno[3,2-e]- [1,2,4]triazolo[4,3-c]pyrimidine Derivatives as Potential Antimicrobial Agents

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Alexandria, Alexandria, Egypt
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Author to whom correspondence should be addressed.
Received: 1 August 2009 / Accepted: 17 August 2009 / Published: 18 August 2009
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Abstract

Five series of tetrahydrobenzothieno[2,3-d]pyrimidine and tetrahydrobenzothienotriazolopyrimidine derivatives have been synthesized namely: 4-(substituted amino)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidines 4a–d, 4-substituted (methylidenehydrazino)-5,6,7,8-tetrahydro[1]benzothieno- [2,3-d]pyrimidines 6a–c, 4-(3,5-disubstituted pyrazol-1-yl)-5,6,7,8-tetrahydro- [1]benzothieno[2,3-d]pyrimidines 7a,b, 3-substituted-8,9,10,11-tetrahydro- [1]benzothieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidines 8a,b, N-(phenyl or 4-substituted phenyl)-2-(8,9,10,11-tetrahydro[1]benzothieno[3,2-e][1,2,4]- triazolo[4,3-c]pyrimidin-3-ylsulfanyl)acetamides 10a–c. Preliminary antimicrobial testing revealed that compounds 4a and 10b were the most active among the tested compounds against C. albicans showing IZ = 22 mm and MIC = MBC = 31.25 μg/ml, with no significant antibacterial activity. Compounds 6b and 6c showed the highest antibacterial activity against S. aureus (IZ = 21 mm, MIC = 62.5 μg/ml, MBC = 125 μg/ml for 6b; IZ = 21 mm, MIC = MBC = 125 μg/ml for 6c). Compounds 4c and 6c showed the highest antibacterial potency against P. aeruginosa among the tested compounds (IZ = 19–20 mm, MIC = MBC = 62.5 μg/ml). None of the tested compounds showed significant antibacterial activity against E. coli.
Keywords: Tetrahydrobenzothieno[2,3-d]pyrimidine; Triazolotetrahydrobenzothienopyrimidine; Pyrazole; Synthesis; Antimicrobial activity Tetrahydrobenzothieno[2,3-d]pyrimidine; Triazolotetrahydrobenzothienopyrimidine; Pyrazole; Synthesis; Antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

SOLIMAN, R.; HABIB, N.S.; EL-TOMBARY, A.A.; EL-HAWASH, S.A.M.; SHAABAN, O.G. Synthesis of Tetrahydrobenzothieno[ 2,3-d]pyrimidine and Tetrahydrobenzothieno[3,2-e]- [1,2,4]triazolo[4,3-c]pyrimidine Derivatives as Potential Antimicrobial Agents. Sci. Pharm. 2009, 77, 755-774.

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