Synthesis and Bioactivities of β-Amino Ketones Containing Sulfadiazine Moiety

doi:10.11944/j.issn.1000-0518.2015.11.150070

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (11): 1231-1239.DOI: 10.11944/j.issn.1000-0518.2015.11.150070

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Synthesis and Bioactivities of β-Amino Ketones Containing Sulfadiazine Moiety

TANG Xuemei^a,FAN Li^b,ZHAO Qin^b,YANG Dacheng^b^*()

^aSchool of Life Science
^bSchool of Chemistry and Chemical Engineering,Southwest University,Chongqing 400715,China

Received:2015-02-20 Accepted:2015-08-17 Published:2015-11-02 Online:2015-11-02
Contact: YANG Dacheng
Supported by:
Supported by Fundamental Research Funds for the Central Universities(No.XDJK2015C128), the Natural Science Foundation of Chongqing(No.2005BB5095)

Abstract

Abstract:

Sixteen new β-amino ketones containing sulfadiazine moiety have been directly synthesized through atom-economic Mannich reaction of sulfadiazine with 1-acetonaphthone and some aromatic aldehydes. The chemical structures of these obtained compounds were identified by ¹H NMR, ¹³C NMR, and HRMS. The biological assay results show that all obtained compounds in the concentration range of 17.04~19.69 nmol/L possess very weak α-glucosidase inhibitory activities, while some compounds can activate peroxisome proliferator-activated receptor response element(PPRE) moderately, of which one exhibits the strongest activity(52%).

Key words: diabetes mellitus, peroxisome proliferator-activated receptor response element(PPRE), α-glucosidase, Mannich reaction, β-amino ketones, sulfadiazine

TANG Xuemei, FAN Li, ZHAO Qin, YANG Dacheng. Synthesis and Bioactivities of β-Amino Ketones Containing Sulfadiazine Moiety[J]. Chinese Journal of Applied Chemistry, 2015, 32(11): 1231-1239.

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Synthesis and Bioactivities of β-Amino Ketones Containing Sulfadiazine Moiety

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