853941-51-2Relevant academic research and scientific papers
Suzuki-Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies
Phakhodee, Wong,Toyoda, Mitsuko,Chou, Chun-Ming,Khunnawutmanotham, Nisachon,Isobe, Minoru
, p. 1150 - 1157 (2011/03/21)
Synthesis of coelenterazine analogs is in recent demand to supply more luminescent compounds with reasonable stability as substrate for the photoprotein manipulated in a living cells or particular organelle. There are limited methods for the synthesis of
Novel synthetic route of coelenterazines -2-:Synthesis of various dehydrocoelenterazine analogs
Kondo, Nobuhiro,Kuse, Masaki,Mutarapat, Thumnoon,Thasana, Nopporn,Isobe, Minoru
, p. 843 - 856 (2007/10/03)
The novel synthetic route to introduce varioussubstituents into 5-position of coelenteramine is described. Difficulties, however, are observed in the attempted synthesis of some analogs having labile functional groups. This is due to the strong acid conc. H2SO4 after Suzuki-Miyaura coupling, so that the route was limited only to the synthesis for aminopyrazines having acid-stable functional groups. In this report, we describe alternative success in the deprotection of N-tosyl-animopyrazine triflate before the cross coupling; thus, we obtained the aminopyrazine triflate in high yield. This compound enables us to synthesize various coelenterazine analogs. This triflate was proven to be so important intermediate that the versatile synthesis for coelenterazine and dehydrocoelenterazine analogs was established through Suzuki-Miyaura or Sonogashira coupling.
