911301-34-3

Upstream product

• 136265-10-6 ethyl 4-fluorocinnamate 
• 637-81-0 ethyl-2-azidoacetate 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 191930-41-3 (±)-ethyl 2-amino-3-(4-fluorophenyl)propanoate 
• 1240982-71-1 ethyl 4-(4-fluorophenyl)pyrrolo[1,2-a]pyrazine-3-carboxylate 
• 348-37-8 6-fluoro-1H-indole-2-carboxylic acid ethyl ester 
• 1314185-41-5 4-(4-fluorophenyl)-1,3-diphenyl-1H-pyrazole-5-carboxylic acid ethyl ester 
• 1345509-69-4 ethyl 4-(4-fluorophenyl)-1,2-diphenyl-1H-imidazole-5-carboxylate 
• 1173094-34-2 ethyl 4-(4-fluorophenyl)-5-tosyl-1H-pyrrole-3-carboxylate 
• 1421932-99-1 ethyl 5-amino-4-cyano-2-(4-fluorophenyl)-1H-pyrrole-3-carboxylate 
• 1544452-21-2 ethyl 2-amino-4-(4-fluorophenyl)-1H-imidazole-5-carboxylate 
• 49759-55-9 ethyl N-benzyloxycarbonyl-4-fluorophenylalaninate 

Relevant academic research and scientific papers

Thermal and photochemical annulation of vinyl azides to 2-aminoimidazoles

2-Aminoimidazoles represent useful synthons for incorporation into medicinal compounds. They provide hydrogen bonding loci, water solubilizing properties and convenient handles for further synthetic elaboration. The rapid and facile generation of diverse

Synthesis of 2,3,4-trisubstituted pyrroles via a facile reaction of vinyl azides and tosylmethyl isocyanide

A facile synthesis of polysubstituted pyrroles from tosylmethyl isocyanide (TOSMIC) and readily synthesized vinyl azides was developed. The reaction proceeded under mild conditions in the presence of base. 2-Tosyl-substituted pyrroles were obtained in moderate to good isolated yields. Additionally, a base-initiated one-pot pyrrole synthesis also was developed using carboxaldehydes, ethyl 2-azidoacetate, and TOSMIC.

Indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors

Indoleamine 2,3-dioxygenase (IDO) is a heme dioxygenase which has been shown to be involved in the pathological immune escape of diseases such as cancer. The synthesis and structure-activity relationships (SAR) of a novel series of IDO inhibitors based on the indol-2-yl ethanone scaffold is described. In vitro and in vivo biological activities have been evaluated, leading to compounds with IC50 values in the micromolar range in both tests. Introduction of small substituents in the 5- and 6-positions of the indole ring, indole N-methylation and variations of the aromatic side chain are all well tolerated. An iron coordinating group on the linker is a prerequisite for biological activity, thus corroborating the virtual screening results.

Synthesis of phenylalanine analogs

A straight forward synthesis of phenylalanine analogs is described. Cerium ammonium nitrate (CAN) mediated addition of azide to cinnamicester, followed by reaction with sodium acetate aff orded the α-azidocinnamate in moderate yield. Hydrogenation of α-azidocinnamate, followed by BOC, CBZ or Fmoc protection gave phenylalanine analogs. A new approach for synthesizing racemic p-boronophenylalanine analog was also explored.