68172-39-4

Upstream product

• 51-35-4 4R-4-hydroxyproline 
• 100-51-6 benzyl alcohol 

Downstream Products

• 1375570-98-1 (2S,4R)-4-(acetoxy)-2-(2-[p-biphenyl]-2-oxoethyl)-1-(2-phenylacetyl)pyrrolidine 
• 1375570-96-9 (2R,4R)-4-(acetoxy)-2-(2-[p-biphenyl]-2-oxoethyl)-1-(2-phenylacetyl)pyrrolidine 
• 1375570-94-7 (2S,4R)-4-(acetoxy)-2-(2-[4-bromophenyl]-2-oxoethyl)-1-(2-phenylacetyl)pyrrolidine 
• 1375570-92-5 (2R,4R)-4-(acetoxy)-2-(2-[4-bromophenyl]-2-oxoethyl)-1-(2-phenylacetyl)pyrrolidine 
• 1034128-46-5 (3R,5S)-5-(2-(4-methoxyphenyl)-2-oxoethyl)-1-(2-phenylacetyl)pyrrolidin-3-yl acetate 
• 1034128-52-3 (3R,5R)-5-(2-(4-methoxyphenyl)-2-oxoethyl)-1-(2-phenylacetyl)pyrrolidin-3-yl acetate 
• 1375571-24-6 (2S,4R)-4-(hydroxy)-2-(2-[p-biphenyl]-2-oxoethyl)-1-(2-phenylacetyl)pyrrolidine 
• 1375571-22-4 (2R,4R)-4-(hydroxy)-2-(2-[p-biphenyl]-2-oxoethyl)-1-(2-phenylacetyl)pyrrolidine 

Relevant academic research and scientific papers

Synthesis and evaluation of constrained phosphoramidate inhibitors of prostate-specific membrane antigen

Abstract Prostate-specific membrane antigen (PSMA) is a cell-surface enzyme-biomarker that is actively pursued for targeted delivery of imaging and therapeutic agents for prostate cancer. Our lab has developed PSMA inhibitors based on a phosphoramidate scaffold, which has shown both high selectivity for PSMA-positive tumors and rapid clearance in vivo when radiolabeled with 18F. However, this scaffold exhibits hydrolytic instability under low pH and high temperature conditions, barring the use of other imaging or therapeutic radionuclides such as 68Ga or 177Lu. Previous studies in our lab have shown a trend in increasing acid stability as the distance between the phosphoramidate core and the α-carboxylate of the P1 residue is increased. Therefore, a new generation of phosphoramidate inhibitors was developed based on trans-4-hydroxyproline as the P1 residue to restrict the interaction of the α-carboxylate to the phosphoramidate core. These hydroxyproline inhibitors demonstrated comparable IC50 values to earlier generations as well as enhanced thermal and acid stability.

Simplification of antitumoral phenanthroindolizidine alkaloids: Short synthesis of cytotoxic indolizidinone and pyrrolidine analogs

Hydroxylated seco-analogs of cytotoxic phenanthroindolizidine alkaloids were prepared in good yields from inexpensive 4-hydroxyproline derivatives, in just two steps. Thus, a sequential oxidative radical scission - oxidation was used for the direct conversion of the proline derivative into a 2-(2-aryl-oxoethyl) pyrrolidine with a variety of aryl and heteroaryl groups. The 4R-stereogenic center allowed ready isomer separation, and stereocontrol in the introduction of new chains (interestingly, the 2,4-cis isomers predominated). In the second step, a cyclization reaction afforded alkaloid analogs with an indolizidinone core; a partial isomerization took place but the isomers were readily purifi ed. Then the cytotoxic activity of the bicyclic indolizidinones and the simpler pyrrolidine derivatives was compared against tumorogenic human neuronal SHSY-5Y and breast cancer MCF7 cells. All the biphenyl derivatives displayed a potent activity (one derivative caused >80% cell death in both tumor lines at micromolar dosis), being comparable in the pyrrolidine and indolizidinone series.

Antibiotic oxazolidinone derivatives

The invention concerns a compound of the formula (I): wherein, for example:T is of the formula (IA), (IB), or (IC); R1 is of the formula —NHC(=O)Rb wherein Rb is (1-4C)alkyl;R2 and R3 are hydrogen or