769970-74-3

Upstream product

• 51-35-4 4R-4-hydroxyproline 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 769970-66-3 (2S,4R) methyl 1-[(E)-3-(3,4-dimethoxyphenyl)-2-propenoyl]-4-[(methylsulfonyl)oxy]-2-pyrrolidinecarboxylate 
• 769970-64-1 (2S,4R) methyl 1-[(E)-3-(3,4-dimethoxyphenyl)-2-propenoyl]-4-hydroxy-2-pyrrolidinecarboxylate 
• 769970-73-2 (2S,4S)-methyl 4-azido-1-((E)-3-(3,4-dimethoxyphenyl)acryloyl)pyrrolidine-2-carboxylate 
• 39856-08-1 (E)-3,4-dimethoxycinnamic chloride 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 331-39-5 caffeic acid 

Downstream Products

• 769970-83-4 (2S,4S) methyl 1-[(E)-3-(3,4-dimethoxyphenyl)-2-propenoyl]-4-[(E)-3-(4-methoxyphenyl)-2-propenoyl]amide-2-pyrrolidinecarboxylate 
• 769970-75-4 (2S,4S)-1-[(E)-3-(3,4-Dimethoxy-phenyl)-acryloyl]-4-propionylamino-pyrrolidine-2-carboxylic acid methyl ester 
• 769970-82-3 (2S,4S) methyl 1-[(E)-3-(3,4-dimethoxyphenyl)-2-propenoyl]-4-[(2-phenylpropanoyl)amide]-2-pyrrolidinecarboxylate 
• 769970-81-2 (2S,4S) methyl 1-[(E)-3-(3,4-dimethoxyphenyl)-2-propenoyl]-4-[(2-phenylethanoyl)amide]-2-pyrrolidinecarboxylate 
• 769970-79-8 (2S,4S) methyl 1-[(E)-3-(3,4-dimethoxyphenyl)-2-propenoyl]-4-[(4-methylphenyl)sulfonyl]amide-2-pyrrolidinecarboxylate 
• 769970-77-6 (2S,4S) methyl 1-[(E)-3-(3,4-dimethoxyphenyl)-2-propenoyl]-4-[(3-pyridinylcarbonyl)amid]-2-pyrrolidinecarboxylate 

Relevant academic research and scientific papers

Design, synthesis and preliminary evaluation of novel pyrrolidine derivatives as matrix metalloproteinase inhibitors

A series of novel pyrrolidine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. The hydroxamates 8a-c were equally or more potent MMP-2 inhibitors than the positive control LY52. The binding mode of the most potent compound 8a with MMP-2 was proposed. Structure-activity relationships were also briefly discussed.

Design, synthesis, and activity of caffeoyl pyrrolidine derivatives as potential gelatinase inhibitors

A group of caffeoyl pyrrolidine derivatives has been developed to act as potential gelatinase inhibitors. The synthesis and biological evaluation of caffonyl pyrrolidine derivatives as MMPs inhibitors are reported in this paper. Inhibiting activities of synthesized compounds on gelatinase (MMP-2 and -9) were tested by using succinylated gelatin as substrate. Structure-activity relationship results from these tested compounds demonstrated that longer and more flexible side chain linked to the pyrrolidine ring at C4 produced higher activity at gelatinase. Furthermore, aromatic heterocycle and sulfamide in the same position could enhance the activities. Compounds with free phenol hydroxyl group showed higher activity compared to methylated derivatives (or counterparts), which confirms the importance of phenol hydroxyl functionality in the interaction with gelatinase. The anti-metastasis model of mice bearing H22 tumor cell was used to evaluate their in vivo inhibiting activities. All tested compounds were orally administered at a dose of 50 or 100 mg/kg, 6 days/week for two weeks. The test results demonstrated that most of these inhibitors showed significant anti-cancer activities (inhibitory rate > 35%) and were devoid of toxic effects. Compound 29 showed the highest inhibitory rate at 69.25%, indicating that it might be a promising lead compound.