Cyclodehydration of Acylated alpha-Amino Acid Amides. II. Unsaturated Amides.

Unexpected Hydrolytic Instability of N-Acylated Amino Acid Amides and Peptides

Remote amide bonds in simple N-acyl amino acid amide or peptide derivatives 1 can be surprisingly unstable hydrolytically, affording, in solution, variable amounts of 3 under mild acidic conditions, such as trifluoroacetic acid/water mixtures at room temperature. This observation has important implications for the synthesis of this class of compounds, which includes N-terminal-acylated peptides...

Iodoarene-catalyzed cyclizations of unsaturated amides.

The cyclization of N-alkenylamides catalyzed by iodoarenes under oxidative conditions is presented. Five-, six-, and seven-membered rings with a range of substitutions can be prepared by this route. Preliminary data from the use of chiral iodoarenes as precatalysts show that enantiocontrol is feasible.

Microsomal synthesis of fatty acid amides.

A microsomal system is described which catalyzes the formation of fatty acid amides of ethanolamine and of several pharmacologically active amines. Although the system has no dependance on external energy sources and has a high K, for the amine substrate, it has several characteristics which differ markedly from an amide hydrolytic system in the microsomes. A possible mechanism for the formatio...

Steroid acid amides of diamino diphenyl sulfone.

For the past several years, I synthesized various new steroid compounds and steroid derivatives for chemotherapeutic purposes. The series of the steroid acid amides of diamino diphenyl sulfone included 4-cholylamino4’-amino diphenyl sulfone (B 110) and 4-desoxycholylamino 4’-amino diphenyl sulfone (Bill) which were chosen among representative members cf this group for more detailed study. A bri...

Cytotoxic fatty acid amides from Xenorhabdus.