Synthesis and Properties of Diamino-Substituted Dipyrido [3,2-a: 2′,3′-c]phenazine

Abstract

A heteroaromatic compound 3,6-diaminodipyrido[3,2-a: 2′,3′-c]phenazine was synthesized with an improved method to convert 1,10-phenanthroline derivatives to the corresponding 5,6-diones. It was shown that the electron-donating effects of amino substituents were extended not only to pyridine rings but also to the phenazine ring.

Phenanthroline Derivatives with Improved Selectivity as DNA‐Targeting Anticancer or Antimicrobial Drugs

“…ESI MS spectra were recorded on a Finnigan AQA instrument equipped with an electrospray ionization (ESI) interface. The ligands phendione (1,10-phenanthroline-5,6-dione [20] ) and dppz (dipyrido[3,2-a:2',3'-c]phenazine [25] ) were synthesized according to published methods. Cisplatin was synthesized from K 2 -…”

“…Because the zones depend on diffusion, the activity decreases exponentially. Surprisingly, whereas dppz (L 2 ) did not produce clearance zones, indicative of very low or no antimicrobial activity, phendione (L 1 ) had a very strong inhibitory effect on the growth of all strains, giving zones of 16,20 ] showed some precipitation from solution, potentially reducing their effectiveness. Neither L 2 nor its platinum complex inhibited growth of E. coli at 200 mg mL À1 .…”

“…Several derivatives of phenanthroline have been described, with varying degrees of activity against eukaryotic cells. [12,18,19] To further analyze the possible use of phenanthroline derivatives as anticancer drugs, as well as to assess their antimicrobial activities, two derivatives were synthesized: 1,10-phenanthroline-5,6-dione (phendione, L 1 ) [20] and dipyrido[3,2-a:2',3'-c]phenazine (dppz, L 2 ). These ligands were selected for their subtle differences in aromaticity and coordination properties over the parent ligand (phenanthroline, L 3 ).…”

Synthesis and X-ray crystal structure of [Ag(phendio)2]ClO4 (phendio = 1,10-phenanthroline-5,6-dione) and its effects on fungal and mammalian cells

“…Phendio, which was essentially insoluble in water, was prepared in accordance with the literature method (Yamada et al 1992). Infrared spectra of solids (in a KBr matrix) were recorded in the region 4000-400 cm −1 on a Nicolet FT-IR Impact 400D infrared spectrometer.…”

cis,trans-Dicarbonyldichlorido(1,10-phenanthroline-5,6-dione-κ2N,N′)ruthenium(II)

“…The ligand 1,10-phenanthroline-5,6-dione (phendione) was prepared as described by Yamada et al (1992). It proved to be analytically and spectroscopically pure (IR and 1 H NMR data).…”