Ca. Merlic et al., STRUCTURE DETERMINATION AND SYNTHESIS OF FLUORO-NISSL-GREEN - AN RNA-BINDING FLUOROCHROME, Journal of organic chemistry, 60(11), 1995, pp. 3365-3369
The isolation, structure determination, and total synthesis of Fluoro
Nissl Green, a novel RNA-binding fluorochrome, are reported. Initially
obtained: in only one part per 10(5), via a microwave-induced synthes
is from m-phenylenediamine, the structure was determined by spectrosco
pic methods to be 3,8-diamino-10H-quindoline. The proposed structure w
as confirmed by a rational synthesis starting from m-phenylene diamine
:and 2,4-dinitrobenzaldehyde. The key step employed a Friedlander reac
tion to construct the quindoline ring system from 1-acetyl-6-(acetylam
ino)-3-indolinone and 2-amino-4-(acetylamino)benzaldehyde. Histochemic
al studies with synthetic Fluoro Nissl Green demonstrate selective sta
ining of neuronal perikarya and nucleoli.