Synthesis of anthradipyridone derivatives

Identification of 3H-Naphtho[1,2,3-de]quinoline-2,7-diones as Inhibitors of Apoptosis Signal-Regulating Kinase 1 (ASK1)

“…Compounds 2 , 3 , and 5 were prepared from 3-methylanthrapyridone-1-sulfonic acid sodium salt ( 16 ) that was synthesized accordingly to the original report …”

“…Compound 10 was prepared from 1-(cyclohexylamino)-3-methyl-3 H -naphtho[1,2,3- de ]quinoline-2,7-dione ( 17 ) that was synthesized by the method previously described . Bromine (240 mg, 1.5 mmol) in acetic acid (5 mL) was added dropwise over 10 min to a solution of 17 (537 mg, 1.5 mmol) in acetic acid (5 mL).…”

“…Compound 10 was prepared from 1-(cyclohexylamino)-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7dione ( 17) that was synthesized by the method previously described. 18 Bromine (240 mg, 1.5 mmol) in acetic acid (5 mL) was added dropwise over 10 min to a solution of 17 (537 mg, 1.5 mmol) in acetic acid (5 mL). After 1 h, the volatiles were removed under reduced pressure and the residual solid was recrystallized from ethanol to give 10 (466 mg, 1.06 mmol, 71%).…”

“…Methyl-1-(methylamino)-3H-naphtho[1,2,3-de]quinoline-2,7-dione (2), 3-Methyl-1-(ethylamino)-3H-naphtho[1,2,3de]quinoline-2,7-dione (3), and 1-[(2-Hydroxyethyl)amino]-3methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione (5). Compounds 2, 3, and 5 were prepared from 3-methylanthrapyridone-1sulfonic acid sodium salt (16) that was synthesized accordingly to the original report 18. …”

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

“…Related work by Tokita et al showed that, when a tertiary diamine analogous to 32.5 was subjected to cyclization in AlCl 3 –NaCl, the nonquinoidal product 32.8 was obtained (for related pyrenoid systems, see Scheme , section ). To date, the only known fully conjugated nonfused 3,9-diazaperylene is 32.10 , first reported in 1983 by Tatke and Seshadri. , However, a range of bis-lactams of the general structure 32.9 has been reported by several research groups − (for a structurally related triaza system, see ref ).…”