CN110183467A - P-methoxyphenyl substituted chromone structure-containing spiro [ indazole-isoxazole ] derivative, and preparation method and application thereof - Google Patents
P-methoxyphenyl substituted chromone structure-containing spiro [ indazole-isoxazole ] derivative, and preparation method and application thereof Download PDFInfo
- Publication number
- CN110183467A CN110183467A CN201910530326.8A CN201910530326A CN110183467A CN 110183467 A CN110183467 A CN 110183467A CN 201910530326 A CN201910530326 A CN 201910530326A CN 110183467 A CN110183467 A CN 110183467A
- Authority
- CN
- China
- Prior art keywords
- indazole
- isoxazole
- derivative
- methoxyphenyl
- spiral shell
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical group C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 125000003003 spiro group Chemical group 0.000 title abstract 4
- GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical group COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 title description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims abstract description 23
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 229960004756 ethanol Drugs 0.000 claims description 12
- 235000019441 ethanol Nutrition 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 238000007259 addition reaction Methods 0.000 claims description 4
- 230000003993 interaction Effects 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000003851 azoles Chemical class 0.000 claims description 3
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 2
- 230000000259 anti-tumor effect Effects 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940041181 antineoplastic drug Drugs 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 150000004880 oxines Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 7
- -1 4-methoxybenzylidene Chemical group 0.000 abstract description 6
- 229940079593 drug Drugs 0.000 abstract description 4
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 abstract description 3
- 150000004777 chromones Chemical group 0.000 abstract description 3
- UZMOAUHZAQAFKX-UHFFFAOYSA-N 1,5-dihydroindazol-4-one Chemical compound O=C1CC=CC2=C1C=NN2 UZMOAUHZAQAFKX-UHFFFAOYSA-N 0.000 abstract description 2
- YWOYDSXGPUZKBI-UHFFFAOYSA-N 6-bromo-3-(hydroxyiminomethyl)chromen-4-one Chemical compound C1=C(Br)C=C2C(=O)C(C=NO)=COC2=C1 YWOYDSXGPUZKBI-UHFFFAOYSA-N 0.000 abstract 2
- CKVVOMLWWOIRIP-UHFFFAOYSA-N O1N=CC=C1.N1N=CC2=CC=CC=C12 Chemical compound O1N=CC=C1.N1N=CC2=CC=CC=C12 CKVVOMLWWOIRIP-UHFFFAOYSA-N 0.000 abstract 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 230000002401 inhibitory effect Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000004663 cell proliferation Effects 0.000 description 5
- 230000008859 change Effects 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- CDTIRJYYEPOPNF-UHFFFAOYSA-N 4h-chromene-3-carbaldehyde Chemical compound C1=CC=C2CC(C=O)=COC2=C1 CDTIRJYYEPOPNF-UHFFFAOYSA-N 0.000 description 2
- 206010009944 Colon cancer Diseases 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000013096 assay test Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000002508 compound effect Effects 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 230000001461 cytolytic effect Effects 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/424—Oxazoles condensed with heterocyclic ring systems, e.g. clavulanic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910530326.8A CN110183467B (en) | 2019-06-19 | 2019-06-19 | P-methoxyphenyl substituted chromone structure-containing spiro [ indazole-isoxazole ] derivative, and preparation method and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910530326.8A CN110183467B (en) | 2019-06-19 | 2019-06-19 | P-methoxyphenyl substituted chromone structure-containing spiro [ indazole-isoxazole ] derivative, and preparation method and application thereof |
Publications (2)
Publication Number | Publication Date |
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CN110183467A true CN110183467A (en) | 2019-08-30 |
CN110183467B CN110183467B (en) | 2020-12-08 |
Family
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Family Applications (1)
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CN201910530326.8A Active CN110183467B (en) | 2019-06-19 | 2019-06-19 | P-methoxyphenyl substituted chromone structure-containing spiro [ indazole-isoxazole ] derivative, and preparation method and application thereof |
Country Status (1)
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CN (1) | CN110183467B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114790213A (en) * | 2022-04-29 | 2022-07-26 | 徐诺药业(南京)有限公司 | Synthetic method of spiro [ indazole-isoxazole ] derivative applied to methoxyphenyl substituted chromone-containing structure |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103554135A (en) * | 2013-11-15 | 2014-02-05 | 绍兴文理学院 | Chromone structure containing isoxazole norcantharidin derivatives as well as preparation method and application thereof |
-
2019
- 2019-06-19 CN CN201910530326.8A patent/CN110183467B/en active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103554135A (en) * | 2013-11-15 | 2014-02-05 | 绍兴文理学院 | Chromone structure containing isoxazole norcantharidin derivatives as well as preparation method and application thereof |
Non-Patent Citations (2)
Title |
---|
NAIR, VIJAY,等: "1,3-Dipolar cycloaddition reactions of nitrile-N-oxides with o-benzoquinones", 《TETRAHEDRON》 * |
REN, DEMIN,等: "1,3-Dipolar cycloaddition of diphenylnitrilimine and 5-arylmethylidene-1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-ones to afford novel spiro[indazole-5,3"-pyrazole] derivatives", 《CHEMISTRY OF HETEROCYCLIC COMPOUNDS》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114790213A (en) * | 2022-04-29 | 2022-07-26 | 徐诺药业(南京)有限公司 | Synthetic method of spiro [ indazole-isoxazole ] derivative applied to methoxyphenyl substituted chromone-containing structure |
Also Published As
Publication number | Publication date |
---|---|
CN110183467B (en) | 2020-12-08 |
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GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20211118 Address after: 250000 1422, building n, Hengda City, No. 58, Gongye North Road, Licheng District, Jinan City, Shandong Province Patentee after: Jinan Weiyang Technology Co.,Ltd. Address before: 312000 No. 508 West Ring Road, Zhejiang, Shaoxing Patentee before: SHAOXING University |
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TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20220512 Address after: 211899 floor 3, building 02, life science and technology Island, No. 11, Yaogu Avenue, Jiangbei new area, Nanjing, Jiangsu Patentee after: Xunuo Pharmaceutical (Nanjing) Co.,Ltd. Address before: 250000 1422, building n, Hengda City, No. 58, Gongye North Road, Licheng District, Jinan City, Shandong Province Patentee before: Jinan Weiyang Technology Co.,Ltd. |
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TR01 | Transfer of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method and application of spiro [indazole isoxazole] derivatives with methoxyphenyl substituted chromone structure Granted publication date: 20201208 Pledgee: Bank of Nanjing Jiangbei District branch of Limited by Share Ltd. Pledgor: Xunuo Pharmaceutical (Nanjing) Co.,Ltd. Registration number: Y2024980022886 |