10.1039/c39900000874
The research focuses on the synthesis and reactivity of a novel oxazolo[2,3-c][1,4]benzodiazepine (OBD) ring system, which has potential DNA recognition capabilities and could be a new class of anthramycins, a type of antitumor antibiotics. The purpose of the study was to create a compound that could selectively bind to GC-rich regions of DNA, which are associated with some oncogenes, and to compare its properties with the pyrrolo[2,1-c][1,4]benzodiazepine (PBD) system found in DNA-binding anthramycin antitumor antibiotics. The researchers synthesized the OBD ring system through a novel route involving the formation of oxazolidine (C)-ring and attachment of the A-ring fragment via N-benzoylation, followed by steps leading to ring closure.
10.1016/S0040-4039(00)96916-8
The research focuses on the attachment of the anthramycin acrylamide side chain to the pyrrolo(1,4)benzodiazepine structure via a palladium-catalyzed coupling reaction of a vinyl triflate. Anthramycin, an antitumor antibiotic, has a complex synthesis process. The study explores a more efficient route by converting the 2-keto group in the pyrrolo ring to a vinyl triflate and then coupling it with various reagents. Key chemicals involved include N-methyl isatoic anhydride, L-hydroxyproline, triflic anhydride, pyridine, tributylvinylstannane, ethyl acrylate, and palladium catalysts such as (Ph3P)2Pd and PdCl2. The methodology provides a convenient procedure for constructing anthramycin derivatives, offering a rapid entry into the pyrrolo(1,4)benzodiazepine structure with the desired side chain.