Selective disulfidation reagent using nitrogen-containing compound and method for producing disulfide-containing compound

A nitrogen-containing compound represented by Chemical Formula 1 below or a salt thereof:

• wherein
• W, together with other ring member atoms, forms a nitrogen-containing heterocycle selected from the group consisting of a pyridine ring, a pyrazine ring, an imidazole ring, an oxazole ring, a thiazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a phenanthroline ring, a pteridine ring, and an azocine ring,
• X is —O— or —NH—,
• Y is selected from the group consisting of:
• a substituted or unsubstituted alkyl group selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, 1,2-dimethylpropyl, n-hexyl, 1,3-dimethylbutyl, 1-isopropylpropyl, 1,2-dimethylbutyl, n-heptyl, 1,4-dimethylpentyl, 2-methyl-1-isopropylpropyl, 1-ethyl-3-methylbutyl, n-octyl, 2-ethylhexyl, 3-methyl-1-isopropylbutyl, 2-methyl-1-isopropyl, 1-tert-butyl-2-methylpropyl, n-nonyl, and 3,5,5-trimethylhexyl;
• a substituted or unsubstituted alkenyl group selected from the group consisting of vinyl, allyl, isopropenyl, 1-butenyl, 2-butenyl, 2-methyl-2-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, a pentenyl, 1-hexenyl, and 3,3-dimethyl-1-butenyl;
• a substituted or unsubstituted alkynyl group selected from the group consisting of ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 3-methyl-1-propynyl, 2-methyl-3-propynyl, pentynyl, 1-hexynyl, 3-methyl-1-butynyl, and 3,3-dimethyl-1-butynyl;
• a substituted or unsubstituted cycloalkyl group selected from the group consisting of cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl;
• a substituted or unsubstituted cycloalkenyl group selected from the group consisting of cyclobutenyl, cyclopentenyl, and cyclohexenyl;
• a substituted or unsubstituted aryl group selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, and 9-anthracenyl;
• a substituted or unsubstituted heteroaryl group selected from the group consisting of 2-thienyl, 4-pyridyl, 3-pyridyl, 2-pyridyl, 1-pyridyl, 2-furyl, 2-pyrimidinyl, 2-benzothiazolyl, 1-imidazolyl, 1-pyrazolyl, benzotriazol-1-yl, and 7-azabenzotriazol-1-yl;
• and a a substituted or unsubstituted group selected from the group consisting of phthalimidyl, glutarimidyl, bornane-2,3-dicarboximidyl, morpholinyl, succinimidyl, maleimidyl, 5-norbornene-2,3-dicarboximidyl, 3-hydantoinyl, and piperidinyl;
• Z represents a hydrogen atom or an electron-withdrawing substituent selected from the group consisting of nitro, trifluoromethyl, fluorine, chlorine, bromine, iodine, acetyl, methanesulfonyl, trifluoroacetyl, trifluoromethane sulfonyl, and cyano, present on the nitrogen-containing heterocycle,
• p, q, and r are each independently 0 or 1,
• s represents an integer of 0 to 10,
• L0 and L1 each independently represent a linker selected from the group consisting of C1-C6 alkylene, polyoxyalkylene having a molecular weight of 100 to 1000, and linkers represented by Chemical Formula (a),
• wherein Ra represents substituted or unsubstituted C1-C8 alkylene;
• Aa and Ab are each independently a group selected from the group consisting of —CH═CH—, —C≡C—, —C(═O)—, —C(═O)—O—, —O—C(═O), —O—, oxyalkylene group, alkyleneoxy group, —C(═O)—NH—, —NH—C(═O)—, —NH—C(═O)—NH—, hydrazine, triazole, sulfone, sulfoxide, sulfonic acid ester, sulfonamide, sulfinic acid ester, sulfinamide, piperidine, and dioxane, and
• R is a hydrogen atom, a substituted or unsubstituted alkyl group selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, 1,2-dimethylpropyl, n-hexyl, 1,3-dimethylbutyl, 1-isopropylpropyl, 1,2-dimethylbutyl, n-heptyl, 1,4-dimethylpentyl, 2-methyl-1-isopropylpropyl, 1-ethyl-3-methylbutyl, n-octyl, 2-ethylhexyl, 3-methyl-1-isopropylbutyl, 2-methyl-1-isopropyl, 1-tert-butyl-2-methylpropyl, n-nonyl, and 3,5,5-trimethylhexyl;
• a substituted or unsubstituted alkenyl group selected from the group consisting of vinyl, allyl, isopropenyl, 1-butenyl, 2-butenyl, 2-methyl-2-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, pentenyl, 1-hexenyl, and 3,3-dimethyl-1-butenyl;
• a substituted or unsubstituted alkynyl group selected from the group consisting of ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 3-methyl-1-propynyl, 2-methyl-3-propynyl, pentynyl, 1-hexynyl, 3-methyl-1-butynyl, and 3,3-dimethyl-1-butynyl;
• a substituted or unsubstituted cycloalkyl group selected from the group consisting of cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl;
• a substituted or unsubstituted cycloalkenyl group selected from the group consisting of cyclobutenyl, cyclopentenyl, and cyclohexenyl;
• a substituted or unsubstituted aryl group selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, and 9-anthracenyl;
• a substituted or unsubstituted heteroaryl group selected from the group consisting of 2-thienyl, 4-pyridyl, 3-pyridyl, 2-pyridyl, 1-pyridyl, 2-furyl, 2-pyrimidinyl, 2-benzothiazolyl, 1-imidazolyl, 1-pyrazolyl, benzotriazol-1-yl, and 7-azabenzotriazol-1-yl;
• an amino group a hydroxy group or a polymer carrier;
• provided that the following compounds (A) to (H) are excluded:
• (A) 3-nitro-2-pyridine sulfinic acid methyl,
• (B) 3-nitro-2-pyridine sulfinic acid ethyl,
• (C) 3-nitro-2-pyridine sulfinic acid N,N-diethylaminoethyl,
• (D) N-(3′-nitro-T-pyridinesulfenyloxy)-5-norbornene-2,3-dicarboximide,
• (E) (S)-((tert-butoxycarbonyl)amino)-3-(((3-nitropyridin-2-yl)thio)oxy)propanoic acid,
• (F) (2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-(((3-nitropyridin-2-yl)thio)oxy)butanoic acid,
• (G) 4-((((3-nitropyridin-2-yl)thio)oxy)methyl)benzoic acid, and
• (H) (S)-2-(((3-nitropyridin-2-yl)thio)oxy)-3-phenylpropanoic acid.