1429503-68-3

Upstream product

• 680227-80-9 [(S)-2-((S)-2-Cyano-pyrrolidin-1-yl)-1-(4-iodo-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 1429504-06-2 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-1-oxo-3-[4-(1-phenethyl-1H-1,2,3-triazol-4-yl)phenyl]propan-2-yl}carbamate 
• 1429503-90-1 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-1-oxo-3-[4-(1-(pyridin-4-ylmethyl)-1H-1,2,3-triazol-4-yl)phenyl]propan-2-yl}carbamate 
• 1429503-91-2 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-1-oxo-3-[4-(1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl)phenyl]propan-2-yl}carbamate 
• 1429503-99-0 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-3-[4-(1-(2-fluorobenzyl)-1H-1,2,3-triazol-4-yl)phenyl]-1-oxopropan-2-yl}carbamate 
• 1429503-94-5 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-3-[4-(1-(3-fluorobenzyl)-1H-1,2,3-triazol-4-yl)phenyl]-1-oxopropan-2-yl}carbamate 
• 1429503-82-1 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-3-[4-(1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)phenyl]-1-oxopropan-2-yl}carbamate 
• 1429504-00-6 tert-butyl {(S)-3-[4-(1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl)phenyl]-1-[(S)-2-cyanopyrrolidin-1-yl]-1-oxopropan-2-yl}carbamate 
• 1429503-95-6 tert-butyl {(S)-3-[4-(1-(3-chlorobenzyl)-1H-1,2,3-triazol-4-yl)phenyl]-1-[(S)-2-cyanopyrrolidin-1-yl]-1-oxopropan-2-yl}carbamate 
• 1429503-83-2 tert-butyl {(S)-3-[4-(1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)phenyl]-1-[(S)-2-cyanopyrrolidin-1-yl]-1-oxopropan-2-yl}carbamate 
• 1429504-02-8 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-3-[4-(1-(2-methoxybenzyl)-1H-1,2,3-triazol-4-yl)phenyl]-1-oxopropan-2-yl}carbamate 
• 1429503-97-8 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-3-[4-(1-(3-methoxybenzyl)-1H-1,2,3-triazol-4-yl)phenyl]-1-oxopropan-2-yl}carbamate 
• 1429503-85-4 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-3-[4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)phenyl]-1-oxopropan-2-yl}carbamate 
• 1429503-88-7 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-3-[4-(1-(3,4-difluorobenzyl)-1H-1,2,3-triazol-4-yl)phenyl]-1-oxopropan-2-yl}carbamate 
• 1429503-93-4 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-3-[4-(1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)phenyl]-1-oxopropan-2-yl}carbamate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel benzyl-substituted (S)-phenylalanine derivatives as potent dipeptidyl peptidase 4 inhibitors

A series of novel benzyl-substituted (S)-phenylalanine derivatives were synthesized and evaluated for their dipeptidyl peptidase 4 (DPP-4) inhibitory activity and selectivity. It was found that most synthesized target compounds were potent DPP-4 inhibitors with IC50 values in 3.79-25.52 nM, which were significantly superior to that of the marketed drug sitagliptin. Furthermore, the 4-fluorobenzyl substituted phenylalanine derivative 6g not only displayed the potent DPP-4 inhibition with an IC50 value of 3.79 nM, but also showed better selectivity against DPP-4 over other related enzymes including DPP-7, DPP-8, and DPP-9. In an oral glucose tolerance test (OGTT) in normal Sprague Dawley rats, compound 6g reduced blood glucose excursion in a dose-dependent manner.

Design, synthesis, biological evaluation, and docking studies of (S)-phenylalanine derivatives with a 2-cyanopyrrolidine moiety as potent dipeptidyl peptidase 4 inhibitors

A novel series of (S)-phenylalanine derivatives with a 2-cyanopyrrolidine moiety were designed and synthesized through a rational drug design strategy. Biological evaluation revealed that most tested compounds were potent dipeptidyl peptidase 4 (DPP-4) inhibitors; among them, the cyclopropyl-substituted phenylalanine derivative 11h displayed the most potent DPP-4 inhibitory activity with an IC50 value of 0.247 μm. In addition, molecular docking analysis of the representative compounds 11h, 11k, and 15a were performed, which not only revealed the impact of binding modes on DPP-4 inhibitory activity but also provided additional methodological values for design and optimization. A novel series of (S)-phenylalanine derivatives with a 2-cyanopyrrolidine moiety were designed and synthesized. It was found that the cyclopropyl-substituted phenylalanine derivative 11h displayed the most potent DPP-4 inhibitory activity with an IC50 value of 0.247 μm. Further docking analysis of the representative compounds 11h, 11k, and 15a not only revealed the impact of binding modes on DPP-4 inhibitory activity, but also provided additional methodological values for design and optimization.