950766-51-5

Upstream product

• 932-82-1 4,5-dibromo-1H-pyrrole-2-carbaldehyde 
• 950766-38-8 2-(N-t-butyoxycarbonylamino)histamine 
• 33694-80-3 4,5-dibromo-1-methyl-1H-pyrrol-2-carbaldehyde 
• 950766-38-8 tert-butyl 4-(2-aminoethyl)-1H-imidazol-2-ylcarbamate 
• 917919-51-8 2-(N-tert-butoxycarbonylamino)imidazol-4-carbaldehyde 
• 950766-47-9 C₁₆H₂₁Br₂N₅O₂ 

Relevant academic research and scientific papers

Synthesis and matrix metalloproteinase (MMP)-12 inhibitory activity of ageladine A and its analogs

Ageladine A (1) and its analogs 2-10 were expeditiously synthesized by featuring the biosynthetic route proposed for 1 (for 1-10) and by employing 2-(N-t-butoxycarbonylamino)imidazol-4-carbaldehyde as the starting material (for 1-8). From MMP-12 inhibitory activity assay, it appeared evident that the two bromine atoms and the three NH groups (1-NH, 14-NH, and 15-NH2) were indispensable for 1 to exhibit excellent activity.

Synthesis and matrix metalloproteinase-12 inhibitory activity of ageladine A analogs

Synthesis of the 37 ageladine A analogs was accomplished by employing the total synthetic route of natural ageladine A previously explored by us. From the matrix metalloproteinase-12 (MMP-12) inhibitory activity assay carried out using the novel analogs, it appeared evident that the halogen atom at the 2-position of pyrrole ring was essential for the inhibitory activity and that the introduction of a bromine atom into the 4-position of pyrrole ring is very effective for producing potent activity. In addition, exchange of the pyrrole ring to an imidazole ring was extremely effective in increasing activity, and the analog 29 thus obtained was found to show approximately 4 times more potent activity than natural ageladine A.