CN113980077A - on-DNA的邻苯酚亚硫亚胺类化合物的合成方法及其应用 - Google Patents
on-DNA的邻苯酚亚硫亚胺类化合物的合成方法及其应用 Download PDFInfo
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- CN113980077A CN113980077A CN202111591626.0A CN202111591626A CN113980077A CN 113980077 A CN113980077 A CN 113980077A CN 202111591626 A CN202111591626 A CN 202111591626A CN 113980077 A CN113980077 A CN 113980077A
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- 108020004414 DNA Proteins 0.000 title claims abstract description 33
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- 238000001308 synthesis method Methods 0.000 title claims abstract description 8
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- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 125000003118 aryl group Chemical group 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 31
- 239000002904 solvent Substances 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 24
- 239000007853 buffer solution Substances 0.000 claims abstract description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000003729 nucleotide group Chemical group 0.000 claims abstract description 6
- 238000010189 synthetic method Methods 0.000 claims abstract description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 30
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- 238000003786 synthesis reaction Methods 0.000 claims description 16
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
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- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
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- 150000002148 esters Chemical class 0.000 claims description 7
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
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- 150000001408 amides Chemical class 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
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- 238000001514 detection method Methods 0.000 description 4
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- GLBQVJGBPFPMMV-UHFFFAOYSA-N sulfilimine Chemical group S=N GLBQVJGBPFPMMV-UHFFFAOYSA-N 0.000 description 4
- 125000005555 sulfoximide group Chemical group 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229940113088 dimethylacetamide Drugs 0.000 description 3
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
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- 238000002156 mixing Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 238000012917 library technology Methods 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
- C07H21/04—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids with deoxyribosyl as saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B40/00—Libraries per se, e.g. arrays, mixtures
- C40B40/04—Libraries containing only organic compounds
- C40B40/06—Libraries containing nucleotides or polynucleotides, or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B50/00—Methods of creating libraries, e.g. combinatorial synthesis
- C40B50/08—Liquid phase synthesis, i.e. wherein all library building blocks are in liquid phase or in solution during library creation; Particular methods of cleavage from the liquid support
- C40B50/10—Liquid phase synthesis, i.e. wherein all library building blocks are in liquid phase or in solution during library creation; Particular methods of cleavage from the liquid support involving encoding steps
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Structural Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
编号 | 化合物(6)或(7)的结构式 | 转化率 | 理论分子量 | 实验分子量 |
6a | 46% | 8509.63 | 8509.8 | |
6b | 41% | 8467.58 | 8467.5 | |
6c | 59% | 8487.52 | 8487.5 | |
6d | 61% | 8531.47 | 8532.6 | |
7a | 79% | 8477.6 | 8477.2 | |
7b | 72% | 8497.54 | 8497.7 | |
7c | 69% | 8541.49 | 8542.5 | |
7d | 93% | 8539.61 | 8539.3 | |
7e | 85% | 8513.60 | 8512.8 | |
7f | 62% | 8389.57 | 8391.2 |
Claims (10)
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CN202111591626.0A CN113980077B (zh) | 2021-12-23 | 2021-12-23 | on-DNA的邻苯酚亚硫亚胺类化合物的合成方法及其应用 |
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CN113980077A true CN113980077A (zh) | 2022-01-28 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114920790A (zh) * | 2022-04-28 | 2022-08-19 | 康龙化成(宁波)科技发展有限公司 | 一种寡聚核酸-二酰亚胺化合物的合成方法 |
CN114920791A (zh) * | 2022-04-28 | 2022-08-19 | 康龙化成(宁波)科技发展有限公司 | 一种寡聚核酸-琥珀酰亚胺化合物的合成方法 |
CN115340581A (zh) * | 2022-10-18 | 2022-11-15 | 深圳市小分子新药创新中心有限公司 | 邻苯酚亚硫亚胺类on-DNA化合物的合成方法及其应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109456368A (zh) * | 2018-10-11 | 2019-03-12 | 上海药明康德新药开发有限公司 | 用于dna编码化合物库构建中的碱性缓冲液及其应用 |
-
2021
- 2021-12-23 CN CN202111591626.0A patent/CN113980077B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109456368A (zh) * | 2018-10-11 | 2019-03-12 | 上海药明康德新药开发有限公司 | 用于dna编码化合物库构建中的碱性缓冲液及其应用 |
Non-Patent Citations (3)
Title |
---|
FENG XIONG ET AL.: "A bioinspired and biocompatible ortho-sulfiliminyl phenol synthesis", 《NATURE COMMUNICATIONS》 * |
YINGYING ZUO ET AL.: "An internal oxidant-directing strategy enabling transition metal-free C-S bond ligation", 《TETRAHEDRON》 * |
熊峰: "氧乙酰基胺导向的邻位硫亚胺基苯酚", 《中国博士学位论文全文数据库》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114920790A (zh) * | 2022-04-28 | 2022-08-19 | 康龙化成(宁波)科技发展有限公司 | 一种寡聚核酸-二酰亚胺化合物的合成方法 |
CN114920791A (zh) * | 2022-04-28 | 2022-08-19 | 康龙化成(宁波)科技发展有限公司 | 一种寡聚核酸-琥珀酰亚胺化合物的合成方法 |
CN115340581A (zh) * | 2022-10-18 | 2022-11-15 | 深圳市小分子新药创新中心有限公司 | 邻苯酚亚硫亚胺类on-DNA化合物的合成方法及其应用 |
CN115340581B (zh) * | 2022-10-18 | 2023-02-03 | 深圳市小分子新药创新中心有限公司 | 邻苯酚亚硫亚胺类on-DNA化合物的合成方法及其应用 |
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