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Microwave Assisted Synthesis and Bioactivity of Arylthiazolidin-4-ones

Author: BaiJie
Tutor: ChenHua；LiXiaoLiu
School: Hebei University
Course: Organic Chemistry
Keywords: arylthiazolidin-4-one microwave assisted antibacterial anti-virus anti-tumor
CLC: TQ453.2
Type: Master's thesis
Year: 2008
Downloads: 14
Quote: 1
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Abstract


4-Thiazolidinone is a type of broad pharmacodynamical group, which derivatives possess diverse biological activities of bactericidal, antivirus, anti-inflammatory, anti-tumor etc.. Microwave has been widely used because of many advantages of shorter reaction time, higher yield, less byproduct, ease of manipulation and cleaner reaction. Herein, a series of arylthiazolidin-4-ones were synthesized using a microwave-assisted method, and the biological activities were evaluated. The works as follows:1. A series of 3-naphthyl-2-[(un)substituted phenyl]-1,3-thiazolidin-4-ones were synthesized by the three-component one-pot cyclocondensation of naphthylamine, aromatic aldehyde and 2-mercaptoacetic acid using a microwave-assisted method. The antibacterial (Pseudomonas springae pv. lachrymans (Smith et Bryan) Young, Dye& Wilkie, Botrytis cinerea Pers., and Sphaerotheca fusca Blum.) and antivirus (human cytomegalovirus (HCMV) and varicella-zoster virus (VZV)) activities of the compounds were evaluated. Compounds 41,4m,61 and 6m showed notable selective inhibition against Sphaerotheca fusca Blum and HCMV.2. A series of thiazolidin-4-ones with different group on the position N-3 were synthesized by the three-component cyclocondensation of 2,6-dichlorophenyl aldehyde, amines and 2-mercaptoacetic acid under microwave sealed vessel or refluxing condition. Some corresponding thiazolidin-4-thiones were also prepared in the presence of Lawesson’s reagent. Antifungal (Sphaerotheca fusca Blum.) and anti-tumor activities of the compounds were evaluated, and some showed good biological activities.3.2-(2,6-dihalogenphenyl)-3-(4,6-dimethyl-5-substituted-prymidin-2-yl)thizalidin-4-one were designed to synthesized for the anti-HIV activity of 2,3-diaryl-4-thiazolidinones. The use of microwave-assisted method and DCC could highly accelerate the yields.

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