Use of pyrroloquinoline compounds to kill clinically latent microorganisms
A compound, pyrrole technology, applied in the direction of active ingredients of heterocyclic compounds, biocides, plant growth regulators, etc.
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Embodiment 1
[1015] The compounds listed below are prepared by any one of the following three general methods. The crude compound is then purified by any of the purification methods described below.
[1016] Conventional method 1
[1017] Combine the relevant substituted 4-chloro-3-(2-chloroethyl)-2-methylquinoline (0.5 mmol; see Preparation 1 above) and the desired primary amine or aniline (1.0 mmol; see table of contents above 2) Heating to reflux in butanol for 48 hours. The solvent was distilled off, and the residue was purified.
[1018] Conventional method 2
[1019] The relevant substituted 4-chloro-3-(2-chloroethyl)-2-methylquinoline (0.2 mmol; see Preparation 1 above) and the desired primary amine or aniline (0.4 mmol; see table of contents above 2) Dissolve in ethanol or n-butanol and heat to 170° C. in a sealed tube for up to 48 hours to distill off the solvent and then purify the residue.
[1020] Conventional method 3
[1021] The relevant substituted 4-chloro-3-(2-chlor...
Embodiment 2
[1109] According to or analogously to the methods described in the text, the following compounds were prepared from appropriate intermediates (such as the compounds described earlier herein):
[1110] (i) 1-(4-methoxyphenyl)-4-methyl-8-phenoxy-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline trifluoroacetic acid Salt;
[1111] Prepared by conventional method 3 and purification method 1.
[1112] LCMS (Method B): Rt = 8.14 min, m / z = 383.11 [M+H] + ;C 25 h 22 N 2 o 2 , monoisotopic molecular weight = 382.17.
[1113] 1 H-NMR (400MHz, D 4 - Methanol): δ7.77 (d, J=9.2Hz, 1H), 7.59 (dd, J=9.2, 2.6Hz, 1H), 7.30 (m, 2H), 7.18 (m, 3H), 6.82 (m, 4H), 6.41(d, J=2.6Hz, 1H), 4.27(t, J=9.5Hz, 2H), 3.84(s, 3H), 3.33(t, J=9.5Hz, 2H), 2.58(s, 3H).
[1114] (ii) 4-methyl-1-(4-phenoxyphenyl)-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline hydrochloride;
[1115] Prepared by conventional method 2 and purification method 1. The product was then converted to the hydrochloride salt by addition of 1N hy...
Embodiment 3
[1135] According to or analogously to the methods described in the text, the following compounds were prepared from appropriate intermediates (such as the compounds described earlier herein):
[1136] (i) 6,8-dimethoxy-1-(4-hydroxyphenyl)-4-methyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline;
[1137] Prepared by conventional method 2 and purification method 3.
[1138] LCMS (method B): Rt = 6.43 min, m / z = 337.13 [M+H] + ;C 20 h 20 N 2 o 3 , monoisotopic molecular weight = 336.15.
[1139] 1 H-NMR (400MHz, D 6 -DMSO): δ9.50(s, br, 1H), 7.07(m, 2H), 6.81(m, 2H), 6.53(d, J=2.6Hz, 1H), 5.90(d, J=2.6Hz, 1H), 3.95(t, J=9.2Hz, 2H), 3.84(s, 3H), 3.32(s, 3H), 3.16(t, J=9.2Hz, 2H), 2.42(s, 3H).
[1140] (ii) 6,8-dimethoxy-1-(3-hydroxyphenyl)-4-methyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline formate ;
[1141]Prepared by conventional method 2 and purification method 2.
[1142] LCMS (Method B): Rt = 6.68 min, m / z = 337.09 [M+H] + ;C 20 h 20 N 2 o 3 , monoisotopic molecular wei...
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