Synthesis
GENERAL METHOD: To a solution of 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl, 1 eq.) in acetonitrile (0.1 M) was added benzylamine (1.1 eq.) followed by triethylamine (2 eq.). The reaction mixture was stirred at reflux for 16 hours under nitrogen protection. Upon completion of the reaction, the solvent was removed by rotary evaporator under reduced pressure. The residue was redissolved in ethyl acetate, washed sequentially with 1 M hydrochloric acid, water and saturated saline, the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography with gradient elution using ethyl acetate/hexane mixed solvent.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 370 - 374
[2] Journal fuer Praktische Chemie (Leipzig), 1985, vol. 327, # 3, p. 487 - 504
[3] Journal of Medicinal Chemistry, 1968, vol. 11, # 2, p. 305 - 311
[4] R. A. KENNER A. A A. New fluorescent probe for protein and nucleoprotein conformation. Binding of 7-(p-methoxybenzylamino)-4-nitrobenzoxadiazole to bovine trypsinogen and bacterial ribosomes[J]. Biochemistry Biochemistry, 1971, 10 24: 4433-4440. DOI:
10.1021/bi00800a013[5] SARAH A. STEVENSON G. J B. Dynamics of 4-Benzylamino-7-nitrobenzofurazan in the 1-Propanol/Water Binary Solvent System. Evidence for Composition-Dependent Solvent Organization[J]. The Journal of Physical Chemistry A, 2006, 110 10: 3426-3431. DOI:
10.1021/jp057039g[6] Y MATSUSHITA I M M Takahashi. Binding of fluorescent 7-amino-4-nitrobenzoxadiazole derivatives to bovine serum albumin.[J]. Chemical & pharmaceutical bulletin, 1986, 34 1: 333-339. DOI:
10.1248/cpb.34.333
