Aminonaphthoquinone compounds for treatment and/or prevention of fibrosis diseases
A fibrous, compound technology, applied in the field of aminonaphthoquinone compounds for the treatment and/or prevention of fibrotic diseases
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example 1
[0146] Example 1 4-(((3-chloro-1,4-dipentoxy-1,4-dihydronaphthalen-2-yl)amino)methyl)-N-hydroxybenzamide (1)
[0147]
[0148] A mixture of 97 (0.36g, 1.05mmol), EDC.HCl (0.30g, 1.58mmol), HOBt (0.17g, 1.26mmol), NMM (0.28ml, 2.52mmol) and DMF (2.5ml) was stirred for a while, Then o-(tetrahydro-2H-pyran-2-yl)hydroxylamine (0.15 g, 1.26 mmol) was added thereto at room temperature, and the mixture was stirred overnight. The residue was purified by flash column on silica gel (ethyl acetate:n-hexane=2:1, Rf=0.45) to obtain an oily product. The oily product was then dissolved in MeOH (3ml) and 10% TFA(aq) (3ml) was added at room temperature and the mixture was stirred overnight. Add H 2 O to react to produce a precipitate. The residue was filtered without further purification to afford 1 (0.24 g, 98.93%) as a red solid. 1 H-NMR (500MHZ, DMSO-d 6 ): δ4.98(s,2H),7.35(d,J=8.5Hz,2H),7.68(d,J=8.5Hz,2H),7.73(m,1H),7.81(m,1H),7.96 (m,2H), 8.03(s,1H).
example 2
[0149] Example 2 4-(((3-Chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)methyl)-N-(pyridin-2-yl)benzyl Amides (2)
[0150]
[0151] A mixture of 97 (0.25g, 0.73mmol), EDC.HCl (0.21g, 1.10mmol), HOBt (0.12g, 0.88mmol), NMM (0.19ml, 1.75mmol) and DMF (2.0ml) was stirred for a while, Then 2-aminopyridine (0.08 g, 0.88 mmol) was added thereto at room temperature, and the mixture was stirred overnight. The residue was purified by flash column on silica gel (dichloromethane:methanol=30:1, Rf=0.50) to give 2 (0.04 g, 13.11%) as a red solid. 1 H-NMR (300MHz, CDCl 3 ): δ5.15(d, J=6.6Hz, 2H), 6.33(s, 1H), 7.08-7.12(m, 1H), 7.49(d, J=8.4Hz, 2H), 7.67(m, 1H) ,7.77(m,2H),7.97(d,J=8.4Hz,2H),8.08(m,1H),8.18(m,1H),8.33(m,1H),8.40(d,J=8.4Hz, 1H), 8.59 (br, 1H).
example 3
[0152] Example 3 N-(2-aminophenyl)-4-(((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)methyl)benzene Formamide (3)
[0153]
[0154] A mixture of 97 (0.25g, 0.73mmol), EDC.HCl (0.21g, 1.10mmol), HOBt (0.12g, 0.88mmol), NMM (0.19ml, 1.75mmol) and DMF (2.0ml) was stirred for a while, Then o-phenylenediamine (0.08 g, 0.88 mmol) was added thereto at room temperature, and the mixture was stirred overnight. The residue was purified by flash column on silica gel (dichloromethane:methanol=30:1, Rf=0.50) to give 3 (0.06 g, 19.03%) as a red solid. 1 H-NMR (300MHz, DMSO-d 6): δ4.86(s, 2H), 5.03(s, 2H), 6.57(t, J=7.8Hz, 1H), 6.75(d, J=6.6Hz, 1H), 6.95(t, J=7.8Hz ,1H),7.14(d,J=6.6Hz,1H),7.42(d,J=7.8Hz,2H),7.74(t,J=7.2Hz,1H),7.82(t,J=7.2Hz,1H ), 7.95 (m, 4H), 8.10 (br, 1H), 9.59 (s, 1H).
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