1322757-73-2

Upstream product

• 882278-95-7 C₁₇H₁₆ClNO₂S₂ 
• 2881-63-2 ethyl (4-chlorobenzoyl)acetate 
• 1322757-53-8 ethyl 3-(4-chlorophenyl)-4-cyano-5-(isopropylsulfonyl)thiophene-2-carboxylate 
• 1322757-80-1 ethyl 5-azido-3-(4-chlorophenyl)-4-cyanothiophene-2-carboxylate 

Downstream Products

• 1322757-82-3 ethyl 3-(4-chlorophenyl)-4-cyano-5-(1H-pyrrol-1-yl)thiophene-2-carboxylate 
• 1322758-01-9 5-amino-3-(4-chlorophenyl)-4-cyanothiophene-2-carboxylic acid 
• 1322758-08-6 3-(4-chlorophenyl)-4-cyano-5-(diethylamino)thiophene-2-carboxylic acid 
• 1322758-14-4 3-(4-chlorophenyl)-4-cyano-5-(1H-pyrrol-1-yl)thiophene-2-carboxylic acid 
• 1322757-78-7 ethyl 3-(4-chlorophenyl)-4-cyano-5-(diethylamino)thiophene-2-carboxylate 

Relevant academic research and scientific papers

Highly improved antiparasitic activity after introduction of an N -benzylimidazole moiety on protein farnesyltransferase inhibitors

In our search for new protein farnesyltransferase inhibitors with improved antiparasitic activities, we modified our previously developed 3-arylthiophene series of inhibitors by replacing the thioisopropyl group by different substituted imidazolylmethanamino moieties. Twenty four new derivatives were synthesized and evaluated against human and parasite farnesyltransferases, and their anti-parasitic activity was determined against Plasmodium falciparum, Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani. Introduction of a N-p-substituted-benzylimidazole led to significantly increase the inhibition of parasite proliferation in the submicromolar range. The structure of the best inhibitors was parasite dependent. Three compounds possess IC50 values at the same range as the reference miltefosine against L. donovani proliferation and other new derivatives display high level of anti-trypanosomal activity against T. cruzi, higher or in the same order of magnitude as the reference compounds benznidazole and nifurtimox.

SNAr and palladium-catalyzed reactions of deactivated thiophene: Application to the synthesis of protein farnesyltransferase inhibitors

To investigate the influence of the 5-thioether moiety of our previously identified hit thiophene compound upon protein farnesyltransferase inhibition, we synthesized a new library of 3-(4-chlorophenyl)-4-cyanothiophene-2-carboxylic derivatives through the application of aromatic nucleophilic substitutions benefiting from a sulfone-based leaving group and by direct palladium-catalyzed reactions on a thioalkylthiophene. This small library of ester derivatives and their corresponding acids was then evaluated for protein farnesyltransferase inhibitory activity; some library members exhibited promising submicromolar activities. Copyright