CN110305061B - Potential antitumor drug compound structure - Google Patents
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- 150000001875 compounds Chemical group 0.000 title claims abstract description 24
- 239000002246 antineoplastic agent Substances 0.000 title claims abstract description 13
- 229940041181 antineoplastic drug Drugs 0.000 title claims abstract description 13
- -1 7-chloro-1-cyclopropyl-6-fluoro-3- (2,4, 6-trimethylbenzenesulfenyl) quinolin-4 (1H) -one Chemical compound 0.000 claims abstract description 8
- 238000012360 testing method Methods 0.000 abstract description 8
- 230000004071 biological effect Effects 0.000 abstract description 6
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 210000004881 tumor cell Anatomy 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 239000003814 drug Substances 0.000 description 9
- 229940079593 drug Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 6
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 6
- 150000007660 quinolones Chemical class 0.000 description 6
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 101000600434 Homo sapiens Putative uncharacterized protein encoded by MIR7-3HG Proteins 0.000 description 3
- 102100037401 Putative uncharacterized protein encoded by MIR7-3HG Human genes 0.000 description 3
- 239000006285 cell suspension Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 230000001766 physiological effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- AOMJIUUKFCINIG-UHFFFAOYSA-N 1,3,5-trimethyl-2-[(2,4,6-trimethylphenyl)disulfanyl]benzene Chemical compound CC1=CC(C)=CC(C)=C1SSC1=C(C)C=C(C)C=C1C AOMJIUUKFCINIG-UHFFFAOYSA-N 0.000 description 2
- HETSDWRDICBRSQ-UHFFFAOYSA-N 3h-quinolin-4-one Chemical class C1=CC=C2C(=O)CC=NC2=C1 HETSDWRDICBRSQ-UHFFFAOYSA-N 0.000 description 2
- ISPVACVJFUIDPD-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ISPVACVJFUIDPD-UHFFFAOYSA-N 0.000 description 2
- KRKGBMZLNKHPNL-UHFFFAOYSA-N 7-chloro-1-ethyl-6-fluoro-3-(4-methylphenyl)sulfanylquinolin-4-one Chemical group ClC1=C(C=C2C(C(=CN(C2=C1)CC)SC1=CC=C(C=C1)C)=O)F KRKGBMZLNKHPNL-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 241000224016 Plasmodium Species 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- WIKQEUJFZPCFNJ-UHFFFAOYSA-N carbonic acid;silver Chemical compound [Ag].[Ag].OC(O)=O WIKQEUJFZPCFNJ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 2
- KQTXIZHBFFWWFW-UHFFFAOYSA-L silver(I) carbonate Inorganic materials [Ag]OC(=O)O[Ag] KQTXIZHBFFWWFW-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- AQTQHPDCURKLKT-JKDPCDLQSA-N vincristine sulfate Chemical compound OS(O)(=O)=O.C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 AQTQHPDCURKLKT-JKDPCDLQSA-N 0.000 description 2
- 229960002110 vincristine sulfate Drugs 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- 102000003915 DNA Topoisomerases Human genes 0.000 description 1
- 108090000323 DNA Topoisomerases Proteins 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N acetic acid;palladium Chemical compound [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 229940033495 antimalarials Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940072132 quinolone antibacterials Drugs 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a novel compound structure of a potential antitumor drug. The potential antitumor drug compound is 7-chloro-1-cyclopropyl-6-fluoro-3- (2,4, 6-trimethylbenzenesulfenyl) quinolin-4 (1H) -one, and the structural formula is shown in a formula 5. The invention has simple and feasible synthetic route and easily obtained raw materials, and can be applied to the synthesis of similar compounds; the results of preliminary biological activity tests show that the novel compound shows excellent tumor cell inhibitory activity, is a potential antitumor drug and has great significance for developing new antitumor drugs.
Description
Technical Field
The invention belongs to the technical field of organic synthesis and chemical medicine preparation, and relates to a novel structure of a potential antitumor drug compound, in particular to a novel compound 7-chloro-1-cyclopropyl-6-fluoro-3- (2,4, 6-trimethylbenzenesulfenyl) quinolin-4 (1H) -one.
Technical Field
The document reports that the quinolone compounds break through the traditional antibacterial concept and have new progress in the aspects of plasmodium resistance, inflammation resistance, tumor resistance and the like. Vandekerckhove et al reported that halogenated 4-quinolones and derivatives thereof have excellent anti-plasmodium activity in 2014, and the structures of the halogenated 4-quinolones and the derivatives are shown as the following formulas:
formula 1 halo 4-quinolones and derivatives thereof
Nilsen et al reported that 4(1H) -quinolone-3-alkyl derivatives are an excellent class of antimalarials.
Carbostyril-3-alkyl derivatives of formula 2
The Chern and Harris research groups reported that 3-heteroaromatic quinolones can inhibit topoisomerase I and tyrosine kinase, respectively, and have potential antitumor activity.
Formula 33-heteroaromatic carbostyril derivatives
Rajput team studies found that compounds of the formula have anti-inflammatory activity.
Novel quinolone structural derivatives of formula 4
The novel quinolone derivative has the advantages that the novel quinolone derivative is structurally creative with the original quinolone antibacterial drugs, other alkyl, aryl, aromatic heterocyclic rings and other structures are mainly introduced to the 3-position to replace the traditional carboxyl structure, great breakthrough is made in the aspect of biological activity, multiple functions of resisting tumors, inflammation, plasmodium and acetylcholine can be achieved, and a good foundation is laid for the research and development of new drugs.
However, the new quinolone derivative has not yet achieved the effect expected by researchers, and is not much superior to the drugs commonly used on the market in terms of biological activity, and the research and development of the drugs with higher activity is the trend of new drug development at present and is also the technical difficulty to be solved. Subject groups such as Caucasian J.2016 (11, 360-366) further studied and developed a series of novel quinolone derivatives, the most active compound in HepG2 (human hepatoma cell) activity test is 7-chloro-1-ethyl-6-fluoro-3- (4-methylphenylsulfanyl) quinolin-4 (1H) -one, and the half-inhibitory rate IC of the quinolone derivatives50The value was 3.05 uM.
In order to overcome the defect of low biological activity of the existing drugs, the invention prepares the target product 7-chloro-1-cyclopropyl-6-fluoro-3- (2,4, 6-trimethylthiophenyl) quinoline-4 (1H) -ketone in one step by taking quinolone-3-carboxylic acid as a raw material and carrying out decarboxylation coupling with disulfide under the action of a catalyst on the basis of researching a novel quinolone structure and a novel application thereof and the action of thioether bonds in drug molecule construction. HepG2 (human liver cancer cell) half-inhibition rate IC of common anticancer drug vincristine sulfate on the market50The value was 48.53 uM. HepG2 (human liver cancer cell) half-inhibition rate IC of novel compound50The value is 0.65uM, which is 2 orders of magnitude better than vincristine sulfate. The new compound guides the new direction of research of quinolone compounds and has important significance on the research of synthetic new antitumor drugs.
Disclosure of Invention
The invention aims to overcome the defect of low biological activity of the existing medicines and provides a new structure of a potential antitumor medicine compound.
The potential antitumor drug compound is 7-chloro-1-cyclopropyl-6-fluoro-3- (2,4, 6-trimethylbenzenesulfenyl) quinolin-4 (1H) -one, and the structural formula is as follows:
formula 57-chloro-1-cyclopropyl-6-fluoro-3- (2,4, 6-trimethylphenylthio) quinolin-4 (1H) -one
The preparation method of the novel compound can be prepared by the following steps:
7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylic acid and bis (2,4, 6-trimethylphenyl) disulfide in the solvent DMSO in Ag2CO3、Pd(OAc)2And PPh3The new compound 7-chloro-1-cyclopropyl-6-fluoro-3- (2,4, 6-trimethylbenzenesulfenyl) quinoline-4 (1H) -ketone is prepared by decarboxylation coupling one-step reaction under catalysis. The reaction formula is as follows:
has the advantages that: 1. the invention has simple and feasible synthetic route and easily obtained raw materials, and can be applied to the synthesis of similar compounds; 2. the results of preliminary biological activity tests show that the novel compound shows excellent tumor cell inhibitory activity, is a potential antitumor drug and has great significance for developing new antitumor drugs.
Detailed Description
The invention is further illustrated, but not limited, by the following examples.
Example 1:
7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylic acid (281.5mg, 1mmol), Ag2CO3(275mg,1mmol)，Pd(OAc)2(22.4mg,0.1mmol), bis (2,4, 6-trimethylphenyl) disulfide (453mg,1.5mmol), PPh3(52.4mg,0.2mmol), dissolved in DMSO (8mL), and then the reaction temperature was raised to 130 ℃ for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, and then 25mL of CH was added to the reaction system2Cl2Adding 20mL of water, extracting by layers, and adding 20mL of CH2Cl2The aqueous phase was extracted twice, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was separated by means of a chromatography column (PE/EA,10:1to 2:1) to give the desired product 7-chloro-1-cyclopropyl-6-fluoro-3- (2,4, 6-trimethylbenzenethio) quinolin-4 (1H) -one in 88% yield.
1H NMR(500MHz,CDCl3)：8.13–8.06(m,1H),8.02(s,1H),7.98(d,J＝5.9 Hz,1H),6.71(s,5H),3.48–3.39(m,1H),2.21(s,9H),1.31–1.27(m,2H),1.08(q,J ＝6.7Hz,2H).13C NMR(126MHz,CDCl3)174.38,156.07,154.08,148.64,143.18, 137.82,136.95,136.21,128.97,128.35,126.23,118.76,113.41,34.31,23.68,20.01, 8.32.HRMS(ESI+):Calculated for C21H19ClFNOS:[M+H]+388.0939,Found 388.0955.
Example 2 physiological Activity assay
Cell culture:
human hepatoma cell line: huh7, HepG2 was provided by shanghai institute of cell biology, china academy of sciences.
The cells were grown in RPMI-1640 medium + 10% fetal calf serum at 37 deg.C (5% CO)2-95% air) growth in incubator.
Sample preparation: the compound 7-chloro-1-cyclopropyl-6-fluoro-3- (2,4, 6-trimethylbenzenethio) quinolin-4 (1H) -one obtained in example 1 was dissolved in DMSO to prepare a stock solution having a concentration of 5mM, and further diluted to a concentration of 1.0,10,100, and 500. mu.M, respectively, so that the DMSO concentration in the solution used in the experiment was less than 0.1% (v/v) in order to avoid the toxicity of DMSO.
Detecting cell proliferation by MTT method:
(1) taking a bottle of cell strains which are in good growth state and in logarithmic phase, and blowing and beating the cell strains into cell suspension by using a culture solution after conventional pancreatin digestion.
(2) After counting by the cell counting plate, the cell density was adjusted to 4-5X 104 cells/ml of cell suspension. The cell suspension (100. mu.l) and the culture medium (100. mu.l) were added to each well of the 96-well plate, and 200. mu.l of the culture medium was added to each well of the plate. Placing at 37 deg.C and saturated humidity with 5% CO2Culturing in an incubator.
(3) After cell attachment, experimental groups were dosed with a range of concentrations of different compounds. The blank control group was added with the same amount of culture medium without drug and the zero setting wells were set. Each group is provided with 5 multiple holes.
(4) At 37 deg.C, saturated humidity, 5% CO2After 72 hours of incubation in the incubator, 10. mu.l of freshly prepared MTT solution at a concentration of 5mg/ml was added to each well.
(5) After further culturing for 4 hours, the plate was taken out, the supernatant in the plate was carefully and slowly aspirated (without aspiration of the purple crystals at the bottom), 150. mu.l of DMSO was added, and after the purple crystals were completely dissolved, the absorbance (OD value) of each well was measured at 490nm with a microplate reader, and the cell inhibition was calculated according to the following formula: the cell inhibition ratio (%) × (control well OD value-administration well OD value)/(control well OD value-blank well OD value) × 100%.
Half-inhibitory IC of the Compound 7-chloro-1-cyclopropyl-6-fluoro-3- (2,4, 6-trimethylbenzenethio) quinolin-4 (1H) -one in the Huh7 cell Activity test group50The value was 3.45 uM; in the HepG2 cell activity test group, the half-inhibition rate IC is higher than that of the HepG2 cell activity test group50The value was 0.65uM, and excellent tumor cell inhibitory activity was exhibited.
Comparative example 1 physiological Activity test
Experimental procedure As in example 2, the compound was changed to 7-chloro-1-ethyl-6-fluoro-3- (4-methylphenylsulfanyl) quinolin-4 (1H) -one, whose half-inhibitory rate IC of Huh7 cells (human hepatoma cells)50A value of 17.57 uM; HepG2 (human hepatoma cell) half-inhibition rate IC50The value was 3.05 uM.
Comparative example 2 physiological Activity test
Experimental procedure As in example 2, the compound was changed to 7-chloro-1-cyclopropyl-6-fluoro-3-thiophenyl-quinolin-4 (1H) -one, and its half-inhibitory rate IC of Huh7 cells (human hepatoma cells)50A value of 66.25 uM; HepG2 (human hepatoma cell) half-inhibition rate IC50The value was 44.58 uM.
Claims (1)
1. An antitumor drug compound, which is characterized in that the compound is 7-chloro-1-cyclopropyl-6-fluoro-3- (2,4, 6-trimethylbenzenesulfenyl) quinolin-4 (1H) -one, and the structural formula is as follows:
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