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• Shen, Y
• Sun, Y
• Sang, Z
• Sun, C
• Dai, Y
• Deng, Y
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• Shen, Y
• Sun, Y
• Sang, Z
• Sun, C
• Dai, Y
• Deng, Y
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• Sun, Y
• Sang, Z
• Sun, C
• Dai, Y
• Deng, Y

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Molecules 2012, 17(7), 8661-8673; doi:10.3390/molecules17078661

Article

Synthesis, Characterization, Antibacterial and Antifungal Evaluation of Novel Monosaccharide Esters

Yi Shen ^1,2 , Yufeng Sun ² , Zhipei Sang ³ , Chengjun Sun ¹ , Ya Dai ^2,*  and Yong Deng ^3,*

¹ West China School of Public Health, Sichuan University, Chengdu 610041, China ² Harmful Components and Tar Reduction in Cigarette, Sichuan Key Laboratory. No. 56, Section 1, Chenglong Road, Chengdu 610066, China ³ Key Laboratory of Drug Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China

* Authors to whom correspondence should be addressed.

Received: 13 April 2012; in revised form: 5 July 2012 / Accepted: 16 July 2012 / Published: 23 July 2012

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Abstract: A novel series of 3-(2-furyl)acrylate monosaccharide esters Ia–f and menthyloxycarbonyl monosaccharide esters IIa–f were designed and synthesized. The chemical structures of the target compounds were confirmed by IR, ¹H- and ¹³C-NMR and ESI-MS, and the target compounds were investigated for their in vitro antibacterial and antifungal activities. The antibacterial screening results showed that the 3-(2-furyl)acrylate monosaccharide ester derivatives Ia–f were either inactive or only weakly active against the three Gram-positive bacterial strains tested, whereas the menthyloxycarbonyl monosaccharide ester derivatives IIa–f exhibited higher levels of activity, with compound IIe being especially potent. The results of the antifungal screening revealed that compounds Ib, Ie, IIb and IIc displayed potent in vitro activities, whereas If and IIf showed promising activities against all of the microorganisms tested, with If exhibiting levels of activity deserving of further investigation.

Keywords: carbohydrate-acetonides; 3-(2-furyl)acrylate monosaccharide esters; menthyloxycarbonyl monosaccharide esters; antibacterial activities; antifungal activities

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