Synthesis, stereochemistry, and biological properties of the depigmenting agents, melanostatin, feldamycin and analogs.

Catalyst- and solvent-free regioselective ring opening of aziridines with amines: application in the gram-scale synthesis of the α,β-diamino propionic derivative, aspergillomarasmine A

“…As shown in Fig. 1, β-[( p -hydroxyphenyl)amino]alanine and melanostatin have been found to inhibit melanotic melanoma 1 and melanin bio-synthesis, 2 respectively. Anap, a useful genetically encoded fluorescent probe, has been applied to investigate the structure and function of proteins, such as ion channel regulation and protein–protein interactions.…”

Asymmetric Syntheses with Aziridinecarboxylate and Aziridinephosphonate Building Blocks

“…FR900490 (264; Scheme 3.96), a new immunomodulator, has been prepared from aziridine-2-carboxylic ester 261 [146,147]. This aziridine reacts with (S)-histidine (262) in the presence of 1 n sodium hydroxide, giving 263 in 31-44 % yield after removal of the tosyl group with sodium in liquid ammonia.…”

“…Feldamycin (265), an inhibitor of melanin synthesis in the growing cells of S. bikiniensis and B16 melanoma, was also prepared from aziridine 261. On the other hand, melanostatin (268; Scheme 3.97) has been synthesized in a manner similar to 266 via 267 [147].…”

Síntese de um fragmento precursor do fármaco Indinavir

“…Para efeito de comparação, é necessário mencionar que, na literatura, existem dois métodos para a síntese de aziridinas enantiomericamente puras, do tipo mostrado acima (20) (Beresford, 2006;Baldwin, 1993;Nakagawa, 1972;Imae, 1991; Esquema 10). Destes métodos, o primeiro (método 1; Beresford, 2006;Baldwin, 1993) apresenta rendimento de 50%, após uma longa série de reações, enquanto o segundo (método 2; Nakagawa, 1972;Imae, 1991) …”