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有机硫化合物

有机硫化合物是指含有硫原子的有机化合物。这些化合物在自然界中广泛存在,在医药、农药和材料科学等领域有着重要的应用。有机硫化合物因其化学性质独特,在药物设计、合成化学以及材料制备方面扮演着重要角色。

1. 结构与分类

有机硫化合物可以按硫的连接方式分为饱和和不饱和类,如二硫化物、噻吩衍生物、砜等。常见的结构类型有:

  • 二硫化物:含-S-S-键的化合物。
  • 硫醚(Thiols):含有-R-S-H或-R-S-R 基团的化合物。
  • 磺酸酯(Sulfonates)与磺酸盐(Sulfonates):带有-SO3H基团的化合物,广泛应用于合成和制药领域。
  • 噻吩及其衍生物:具有环状结构的有机硫化物。
2. 生物学活性

许多有机硫化合物在生物学上有重要功能或应用潜力。例如:

  • 某些硫醚类药物被用于抗真菌、抗菌以及抗癌治疗。
  • 硫代葡萄糖苷(Glycosinolate)是十字花科植物中的一种天然存在物质,具有生物活性。
3. 合成方法

有机硫化合物可通过多种途径合成:

  • 亲核取代反应:使用含硫试剂与卤化物进行反应。
  • 自由基加成法:采用氧化剂引发自由基形成,通过烯烃与H2S、R-S-H等反应制备。
  • 金属催化转化:利用钯、铜等催化剂促进特定硫化过程。
4. 应用领域

有机硫化合物的应用广泛:

  • 医药领域:用于开发抗菌剂、抗病毒药物及抗癌药物等。
  • 农学研究:某些有机硫化合物作为生物农药的有效成分,能够抑制病害的发生。
  • 材料科学与技术:在导电聚合物和塑料添加剂中有重要应用。
5. 环境与安全性

尽管有机硫化合物具有许多潜在益处,但其生产和使用也可能对环境造成影响。因此,在设计和合成这些化合物时需要考虑可持续性和环保性因素。

以上是对有机硫化合物的简单介绍,包括它们的结构、生物学活性、合成方法及其应用领域等基本信息。

中文名称 英文名称 CAS号 化学式 结构式图片
—— N-methyl-N-[(2-methylsulfanylpyrimidin-5-yl)methyl]-2-pyridin-4-ylethanamine —— C14H18N4S
N-methyl-N-[(2-methylsulfanylpyrimidin-5-yl)methyl]-2-pyridin-4-ylethanamine
—— (3R,7R,8aS)-3-methyl-2-[(5-pyrimidin-2-ylsulfanylfuran-2-yl)methyl]-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-7-ol —— C17H22N4O2S
(3R,7R,8aS)-3-methyl-2-[(5-pyrimidin-2-ylsulfanylfuran-2-yl)methyl]-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-7-ol
—— (3R,8aR)-3-methyl-2-[(5-pyrimidin-2-ylsulfanylfuran-2-yl)methyl]-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine —— C17H22N4OS
(3R,8aR)-3-methyl-2-[(5-pyrimidin-2-ylsulfanylfuran-2-yl)methyl]-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine
—— (2S)-2-methyl-1-[(2S)-2-(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)pyrrolidin-1-yl]-3-(3,4,5-trimethylpyrazol-1-yl)propan-1-one —— C18H28N6OS
(2S)-2-methyl-1-[(2S)-2-(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)pyrrolidin-1-yl]-3-(3,4,5-trimethylpyrazol-1-yl)propan-1-one
—— N-methyl-1-(4-methylsulfanylphenyl)methanimine oxide —— C9H11NOS
N-methyl-1-(4-methylsulfanylphenyl)methanimine oxide
—— 4-[(3R)-1-[(2-ethylsulfanylpyrimidin-5-yl)methyl]piperidin-3-yl]-2-thiophen-2-yl-1H-pyrimidin-6-one —— C20H23N5OS2
4-[(3R)-1-[(2-ethylsulfanylpyrimidin-5-yl)methyl]piperidin-3-yl]-2-thiophen-2-yl-1H-pyrimidin-6-one
—— (2S)-3-(4-chloropyrazol-1-yl)-2-methyl-1-[(2R)-2-(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)pyrrolidin-1-yl]propan-1-one —— C15H21ClN6OS
(2S)-3-(4-chloropyrazol-1-yl)-2-methyl-1-[(2R)-2-(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)pyrrolidin-1-yl]propan-1-one
—— 2-[[5-(3,5-dimethylphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-[(R)-(4-fluorophenyl)-thiophen-2-ylmethyl]acetamide —— C23H20FN3O2S2
2-[[5-(3,5-dimethylphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-[(R)-(4-fluorophenyl)-thiophen-2-ylmethyl]acetamide
—— (2R)-1-[(2-chloro-4-fluorophenyl)methyl]-3-[(2-methylphenyl)methyl]-2-(4-methylsulfanylphenyl)-1,3-diazinane —— C26H28ClFN2S
(2R)-1-[(2-chloro-4-fluorophenyl)methyl]-3-[(2-methylphenyl)methyl]-2-(4-methylsulfanylphenyl)-1,3-diazinane
—— (2S)-1-[(4-fluorophenyl)methyl]-3-[(3-methylphenyl)methyl]-2-(4-methylsulfanylphenyl)-1,3-diazinane —— C26H29FN2S
(2S)-1-[(4-fluorophenyl)methyl]-3-[(3-methylphenyl)methyl]-2-(4-methylsulfanylphenyl)-1,3-diazinane
—— 2-[[4-methyl-5-[(2R)-1-[(2-morpholin-4-ylpyrimidin-4-yl)methyl]pyrrolidin-2-yl]-1,2,4-triazol-3-yl]sulfanyl]ethanol —— C18H27N7O2S
2-[[4-methyl-5-[(2R)-1-[(2-morpholin-4-ylpyrimidin-4-yl)methyl]pyrrolidin-2-yl]-1,2,4-triazol-3-yl]sulfanyl]ethanol
—— N-[(Z)-1-(4-hydroxyphenyl)ethylideneamino]-2-[[5-[(4-methylphenyl)methylsulfanyl]-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide —— C20H20N4O2S3
N-[(Z)-1-(4-hydroxyphenyl)ethylideneamino]-2-[[5-[(4-methylphenyl)methylsulfanyl]-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
—— (5E)-2-(5-chloro-2-methylphenyl)imino-5-[[5-(4-chlorophenyl)sulfanylfuran-2-yl]methylidene]-1,3-thiazolidin-4-one —— C21H14Cl2N2O2S2
(5E)-2-(5-chloro-2-methylphenyl)imino-5-[[5-(4-chlorophenyl)sulfanylfuran-2-yl]methylidene]-1,3-thiazolidin-4-one
—— (2E)-3-{4-bromo-5-[(4-chlorophenyl)sulfanyl]furan-2-yl}-2-cyano-N-(4-methylphenyl)prop-2-enamide —— C21H14BrClN2O2S
(2E)-3-{4-bromo-5-[(4-chlorophenyl)sulfanyl]furan-2-yl}-2-cyano-N-(4-methylphenyl)prop-2-enamide
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]-5-[(4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]triazole-4-carboxamide —— C17H17N11O3S
1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]-5-[(4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]triazole-4-carboxamide
—— 1-(2,3-dimethylphenyl)-3-[(Z)-(4-methylsulfanylphenyl)methylideneamino]thiourea —— C17H19N3S2
1-(2,3-dimethylphenyl)-3-[(Z)-(4-methylsulfanylphenyl)methylideneamino]thiourea
—— (E)-3-amino-2-[2-(1-oxidopyridin-1-ium-2-yl)sulfanylacetyl]but-2-enenitrile —— C11H11N3O2S
(E)-3-amino-2-[2-(1-oxidopyridin-1-ium-2-yl)sulfanylacetyl]but-2-enenitrile
—— 2-[(5-methyl-1,3,4-oxadiazol-2-yl)sulfanyl]-N-[1-[[1-(4-methylphenyl)cyclopropyl]methyl]piperidin-4-yl]acetamide —— C21H28N4O2S
2-[(5-methyl-1,3,4-oxadiazol-2-yl)sulfanyl]-N-[1-[[1-(4-methylphenyl)cyclopropyl]methyl]piperidin-4-yl]acetamide
—— N-(6-amino-1-butyl-2,4-dioxopyrimidin-5-yl)-2-(3-cyano-4,5,6-trimethylpyridin-2-yl)sulfanyl-N-ethylacetamide —— C21H28N6O3S
N-(6-amino-1-butyl-2,4-dioxopyrimidin-5-yl)-2-(3-cyano-4,5,6-trimethylpyridin-2-yl)sulfanyl-N-ethylacetamide
—— N-[(Z)-(2-bromophenyl)methylideneamino]-2-phenylsulfanylacetamide —— C15H13BrN2OS
N-[(Z)-(2-bromophenyl)methylideneamino]-2-phenylsulfanylacetamide
—— N-[(Z)-benzylideneamino]-2-(4-methyl-6-morpholin-4-ylpyrimidin-2-yl)sulfanylacetamide —— C18H21N5O2S
N-[(Z)-benzylideneamino]-2-(4-methyl-6-morpholin-4-ylpyrimidin-2-yl)sulfanylacetamide
—— [(Z)-[4-(4-chlorophenyl)sulfanyl-3-nitrophenyl]methylideneamino]thiourea —— C14H11ClN4O2S2
[(Z)-[4-(4-chlorophenyl)sulfanyl-3-nitrophenyl]methylideneamino]thiourea
—— 2-[(Z)-(4-bromophenyl)methylideneamino]oxy-N'-[(E)-(3-oxo-1-benzothiophen-2-ylidene)methyl]propanehydrazide —— C19H16BrN3O3S
2-[(Z)-(4-bromophenyl)methylideneamino]oxy-N'-[(E)-(3-oxo-1-benzothiophen-2-ylidene)methyl]propanehydrazide
—— N-[(R)-(4-fluorophenyl)-thiophen-2-ylmethyl]-2-[(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetamide —— C16H14FN3OS4
N-[(R)-(4-fluorophenyl)-thiophen-2-ylmethyl]-2-[(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetamide
—— 3-[2-[[5-(3,4-dimethylphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]ethyl]-4-methyl-1,3-thiazol-2-one —— C16H17N3O2S2
3-[2-[[5-(3,4-dimethylphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]ethyl]-4-methyl-1,3-thiazol-2-one
—— N-[(2R)-heptan-2-yl]-2-[[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide —— C18H25N3O2S
N-[(2R)-heptan-2-yl]-2-[[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]acetamide
—— 2-[[5-[4-(diethylamino)phenyl]-1,3,4-oxadiazol-2-yl]sulfanyl]-N-[(2R)-heptan-2-yl]acetamide —— C21H32N4O2S
2-[[5-[4-(diethylamino)phenyl]-1,3,4-oxadiazol-2-yl]sulfanyl]-N-[(2R)-heptan-2-yl]acetamide
—— 2-(2-Bromophenyl)-5-[(5-phenyl-1,2-oxazol-3-yl)methylsulfanyl]-1,3,4-oxadiazole —— C18H12BrN3O2S
2-(2-Bromophenyl)-5-[(5-phenyl-1,2-oxazol-3-yl)methylsulfanyl]-1,3,4-oxadiazole
—— 2-[[4-amino-5-(2-methylfuran-3-yl)-1,2,4-triazol-3-yl]sulfanyl]-N-[(R)-(4-fluorophenyl)-thiophen-2-ylmethyl]acetamide —— C20H18FN5O2S2
2-[[4-amino-5-(2-methylfuran-3-yl)-1,2,4-triazol-3-yl]sulfanyl]-N-[(R)-(4-fluorophenyl)-thiophen-2-ylmethyl]acetamide
—— 5-(2-Anilinovinyl)-3-[(2-chloro-6-fluorobenzyl)sulfanyl]-4-isothiazolecarbonitrile —— C19H13ClFN3S2
5-(2-Anilinovinyl)-3-[(2-chloro-6-fluorobenzyl)sulfanyl]-4-isothiazolecarbonitrile
—— (2R)-N-(2-phenylsulfanylphenyl)-2-[(2-pyrrol-2-ylidene-3H-1,3,4-oxadiazol-5-yl)sulfanyl]propanamide —— C21H18N4O2S2
(2R)-N-(2-phenylsulfanylphenyl)-2-[(2-pyrrol-2-ylidene-3H-1,3,4-oxadiazol-5-yl)sulfanyl]propanamide
—— (2R)-N-ethyl-2-[(2-pyrrol-2-ylidene-3H-1,3,4-oxadiazol-5-yl)sulfanyl]propanamide —— C11H14N4O2S
(2R)-N-ethyl-2-[(2-pyrrol-2-ylidene-3H-1,3,4-oxadiazol-5-yl)sulfanyl]propanamide
—— (2S)-2-[[5-(2,4-dimethoxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-(2-phenylsulfanylphenyl)propanamide —— C25H23N3O4S2
(2S)-2-[[5-(2,4-dimethoxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-(2-phenylsulfanylphenyl)propanamide
—— 2-[(4-benzyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanyl]-N-[(2R)-heptan-2-yl]acetamide —— C22H28N4OS2
2-[(4-benzyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanyl]-N-[(2R)-heptan-2-yl]acetamide
—— 2-[[4-amino-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanyl]-N-cyclohexyl-N-propan-2-ylacetamide —— C14H22F3N5OS
2-[[4-amino-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanyl]-N-cyclohexyl-N-propan-2-ylacetamide
—— 2-(4-bromo-2,5-dimethylphenyl)sulfanyl-N-[(Z)-[(3Z)-3-[[2-(4-bromo-2,5-dimethylphenyl)sulfanylacetyl]hydrazinylidene]cyclohexylidene]amino]acetamide —— C26H30Br2N4O2S2
2-(4-bromo-2,5-dimethylphenyl)sulfanyl-N-[(Z)-[(3Z)-3-[[2-(4-bromo-2,5-dimethylphenyl)sulfanylacetyl]hydrazinylidene]cyclohexylidene]amino]acetamide
—— (2S)-2-(4-chlorophenyl)sulfanyl-N-[2-(2-methylphenyl)ethyl]propanamide —— C18H20ClNOS
(2S)-2-(4-chlorophenyl)sulfanyl-N-[2-(2-methylphenyl)ethyl]propanamide
—— 3-(Tert-butyl)-4-((5-nitro-2-(2-pyridylthio)phenyl)methylene)-1-phenyl-2-pyrazolin-5-one —— C25H22N4O3S
3-(Tert-butyl)-4-((5-nitro-2-(2-pyridylthio)phenyl)methylene)-1-phenyl-2-pyrazolin-5-one
—— 5-[(2Z)-2-benzylidenehydrazinyl]-3-methylsulfanyl-1,2-thiazole-4-carbonitrile —— C12H10N4S2
5-[(2Z)-2-benzylidenehydrazinyl]-3-methylsulfanyl-1,2-thiazole-4-carbonitrile
—— (2S)-1-(4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)-2-[[5-[(3S,5R)-3,5-dimethylpiperidin-1-yl]-4-(furan-2-ylmethyl)-1,2,4-triazol-3-yl]sulfanyl]propan-1-one —— C25H33N5O3S
(2S)-1-(4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)-2-[[5-[(3S,5R)-3,5-dimethylpiperidin-1-yl]-4-(furan-2-ylmethyl)-1,2,4-triazol-3-yl]sulfanyl]propan-1-one
—— N-[(Z)-benzylideneamino]-2-methylsulfanylpyrimidin-5-amine —— C12H12N4S
N-[(Z)-benzylideneamino]-2-methylsulfanylpyrimidin-5-amine
—— (2S)-2-(4-chlorophenyl)sulfanyl-N-[(1R)-1-thiophen-2-ylethyl]propanamide —— C15H16ClNOS2
(2S)-2-(4-chlorophenyl)sulfanyl-N-[(1R)-1-thiophen-2-ylethyl]propanamide
—— (7E)-2-methylsulfanyl-4-thiophen-2-yl-7-(thiophen-2-ylmethylidene)-5,6-dihydrocyclopenta[b]pyridine-3-carbonitrile —— C19H14N2S3
(7E)-2-methylsulfanyl-4-thiophen-2-yl-7-(thiophen-2-ylmethylidene)-5,6-dihydrocyclopenta[b]pyridine-3-carbonitrile
—— N-cyclopropyl-N-[(3S)-1,1-dioxothiolan-3-yl]-2-[[5-(3-methylanilino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide —— C18H22N4O3S3
N-cyclopropyl-N-[(3S)-1,1-dioxothiolan-3-yl]-2-[[5-(3-methylanilino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
—— [(1S)-1-(5-thiophen-2-yl-1,3,4-oxadiazol-2-yl)ethyl] 2-(2-cyanophenyl)sulfanylbenzoate —— C22H15N3O3S2
[(1S)-1-(5-thiophen-2-yl-1,3,4-oxadiazol-2-yl)ethyl] 2-(2-cyanophenyl)sulfanylbenzoate
—— [(1R)-1-(5-thiophen-2-yl-1,3,4-oxadiazol-2-yl)ethyl] 2-(2-cyanophenyl)sulfanylbenzoate —— C22H15N3O3S2
[(1R)-1-(5-thiophen-2-yl-1,3,4-oxadiazol-2-yl)ethyl] 2-(2-cyanophenyl)sulfanylbenzoate
—— (5Z)-5-[[4-(4-chlorophenyl)sulfanyl-3-nitrophenyl]methylidene]-3-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazolidine-2,4-dione —— C23H20ClN3O5S2
(5Z)-5-[[4-(4-chlorophenyl)sulfanyl-3-nitrophenyl]methylidene]-3-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazolidine-2,4-dione
—— 3,4,4-trimethyl-5-[(Z)-[4-(methylsulfanyl)benzylidene](oxido)-lambda~5~-azanyl]-1,3-thiazolidine-2-thione —— C14H18N2OS3
3,4,4-trimethyl-5-[(Z)-[4-(methylsulfanyl)benzylidene](oxido)-lambda~5~-azanyl]-1,3-thiazolidine-2-thione
—— N-[(Z)-[4-bromo-5-(4-chlorophenyl)sulfanylfuran-2-yl]methylideneamino]pyridine-2-carboxamide —— C17H11BrClN3O2S
N-[(Z)-[4-bromo-5-(4-chlorophenyl)sulfanylfuran-2-yl]methylideneamino]pyridine-2-carboxamide
—— (2S)-2-[4-[(2R)-4-oxo-3,1-benzoxathiin-2-yl]phenyl]-3,1-benzoxathiin-4-one —— C22H14O4S2
(2S)-2-[4-[(2R)-4-oxo-3,1-benzoxathiin-2-yl]phenyl]-3,1-benzoxathiin-4-one