CN108530337A - A kind of alternative indole amides class compound for inhibiting stomach cancer cell - Google Patents
A kind of alternative indole amides class compound for inhibiting stomach cancer cell Download PDFInfo
- Publication number
- CN108530337A CN108530337A CN201810660487.4A CN201810660487A CN108530337A CN 108530337 A CN108530337 A CN 108530337A CN 201810660487 A CN201810660487 A CN 201810660487A CN 108530337 A CN108530337 A CN 108530337A
- Authority
- CN
- China
- Prior art keywords
- compound
- pharmaceutically acceptable
- hours
- formula
- acceptable salt
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- 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 kind of alternative indole amides class compounds for inhibiting stomach cancer cell, being capable of selective depression stomach cancer cell, especially selective depression MGC 803 (gastric carcinoma cells) cell strain.Therefore, it is possible to be used as the drug of selective therapy gastric cancer, there is good development prospect.
Description
Technical field
The present invention relates to medicinal chemistry arts, and in particular to a series of indole amides class compounds, preparation method and its
Purposes.
Background technology
Gastric cancer is to be happened at the malignant tumour of Weishang skin tissue, and in China, its incidence occupies the first place of all kinds of tumours.In stomach
Apoptosis regulating system gets muddled in carcinogenesis and the multi-step conversion process of differentiation, is that cells show goes out malignant phenotype
One of the major reasons.
Benzazole compounds are a kind of important heterocyclic compounds, have extensive bioactivity.In brassicaceous vegetable
And it is widely present indoles secondary metabolite in a large amount of marine organisms and actinomyces.In recent years, in the work of anticancer aspect
Property causes the common concern of people.Currently, SU11248 (trade names：Sutent), vincaleukoblastinum (VLB, Vinblastine),
Vincristine (VCR, Vincristine), eldisine (VDS, Vindesine), vinorelbine (VBR, Vinorelbine),
The features such as kind containing indole structure has been listed and come into operation indigo red etc. on a small quantity, and toxic side effect is small and selectivity is strong shows especially out
Special-effect (progress of the flat indoles anticancer compound of Liu little Yu, Ou Yanggui, the fining of indoles anticancer compound
Work intermediate, the 5th 1-8 pages of phase of volume 40 in October, 2010).Li Xuelin etc.（CN103214472A）Report a kind of acrylic acid Yin
Diindyl amides compound, the compound is for lung cancer, breast cancer, osteosarcoma, cervical carcinoma
There is inhibitory activity etc. a variety of cancer cells.Song Jun, etc.（《Central China University of Science and Technology's journal（Medicine）》, 2004, volume 33, the 6th
Phase, the 720-723 pages）Reporting the U.S. good fortune of indoles can induce apoptosis in gastric cancer, but its mechanism is indefinite.
With the development of modern medicine, it is that new drug development personnel are more next to carry out selectivity and/or targeted therapy for disease
The direction more paid close attention to.Because, it is alternatively that property and/or targeted drug can be directed to specific illness, pathogenic site carries out
Effect, and then side effect is reduced, save drug cost.Although reporting a series of Yin that can be used for treating gastric cancer in the prior art
Diindyl class compound, but the compound is usually inhibited for a variety of cancer cells simultaneously, it is less that there is selectivity suppression
The drug of gastric cancer processed.Based on drawbacks described above in the prior art, exploitation can be used for the drug of selective depression stomach cancer cell, for
Selective therapy gastric cancer is of great significance.
Invention content
The technical problem to be solved by the present invention is to：Provide a kind of indole amides class compound, alternative treatment
Gastric cancer, the especially strain of selective depression gastric cancer cell line MGC-803 have preferable development prospect.
The first aspect of the invention is to provide a kind of compound of Formula I and its pharmaceutically acceptable salt, shown chemical combination
Object alternative inhibits the growth of stomach cancer cell.
Wherein：R is each independently selected from halogen ,-NO2 ,-CN, C1-C8 alkyl, C1-C8 alkoxyl, C1-C8 alkyl halides
Base；
N is selected from 1,2,3 or 4.
Preferably, R is each independently selected from halogen, C1-C4 alkyl, C1-C4 alkoxies, C1-C4 halogenated alkyls；
It is highly preferred that R is each independently selected from fluorine, chlorine, bromine, methyl, ethyl, methoxyl group, ethyoxyl, trifluoromethyl；
Most preferably, R is each independently selected from methyl, chlorine, bromine.
Preferably, n is selected from 1 or 2；
It is highly preferred that n is 1.
Preferably, the compounds of this invention is selected from compound R 2, R3, R4, R5 or R6, is respectively provided with such as lower structure：
R2
R3 R4
R5 R6
Another aspect of the present invention provides a kind of the method for preparing compound of formula I, and synthetic route is as follows：
；
Wherein, the range of choice of R and n is as previously described.
Specific reaction step is as follows：
Step 1：Aniline and hydrochloric acid are added in the reaction vessel, sodium nitrite solution is added drop-wise in solution.Reaction is taken out for 1 hour
It filters, in filtrate added drop-wise to sodium sulfite solution, 80 DEG C are reacted 2 hours, then concentrated hydrochloric acid is added dropwise, and 95 DEG C of reactions are placed on often for 2 hours
Overnight, hydrazinobenzene hydrochloride salt solid is precipitated in temperature.
Step 2：Sequentially add hydrazinobenzene hydrochloride salt in the reaction vessel, the chloro- 1- hydroxy-butans sodium sulfonates of 4-, ethyl alcohol, water,
Solution PH is adjusted again to 6-7, and 75 DEG C are reacted 6 hours；Vacuum distillation removes ethyl alcohol and part water, surplus solution first use dichloromethane
Washing, then adjusts PH to 8-10, then uses chloroform, is placed in 4 DEG C of refrigerator cool overnights, precipitation tryptamine hydrochloride solid.
Step 3：Salicyclic acid derivatives, 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne are sequentially added in the reaction vessel
Diimmonium salt hydrochlorate, I-hydroxybenzotriazole, acetone, stirring at normal temperature 2 hours；Add tryptamine hydrochloride obtained by step 2, nothing
Aqueous carbonate potassium, stirring at normal temperature is to the reaction was complete；Column chromatography purifies, and obtains compound shown in Formulas I.
Wherein, the molar ratio of the aniline, sodium nitrite and sodium sulfite of step 1 is 1: 1-1.5 :2-4.5, preferably
It is 1: 1.05 : 3；
The molar ratio of the chloro- 1- hydroxy-butans sodium sulfonate of hydrazinobenzene hydrochloride salt and 4- of step 2 is 1:1-1.5 preferably 1:
1-1.2；
Salicyclic acid derivatives, 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate, the 1- hydroxy benzos of step 3
Triazole and the molar ratio of tryptamine hydrochloride are 1: 1-2 : 1-2 : 0.5-1.5；Preferably 1: 1-1.5 : 1-1.5 :
0.8-1.2。
Another aspect of the present invention provides a kind of pharmaceutical composition, it includes Formulas I compound represented or its pharmaceutically may be used
Salt and pharmaceutically acceptable carrier, the excipient of receiving.
Another aspect of the present invention is related to a kind of purposes of compound of formula I in medicine preparation, it is characterised in that the drug
Alternative treatment gastric cancer；Preferably, the drug alternative inhibits gastric cancer cell line MGC-803 strain.
Definition：
" alkyl " refers to only being made of carbon and hydrogen atom, does not contain degree of unsaturation, can be C1-6 alkyl.In some embodiments
In, alkyl has 1 to 6 or 1 to 4 carbon atom.Representative straight chain saturated alkyl include but not limited to-methyl ,-ethyl ,-positive third
Base ,-normal-butyl ,-n-pentyl and-n-hexyl；And be saturated branched alkyl include but not limited to-isopropyl ,-sec-butyl ,-isobutyl
Base ,-tertiary butyl ,-isopentyl, 2- methyl butyls, 3- methyl butyls, 2- Methyl pentyls, 3- methyl amyls, 4- methyl amyls, 2-
Methylhexyl, 3- methylhexyls, 4- methylhexyls, 5- methylhexyls, 2,3- dimethyl-butyls etc..Alkyl is connected by singly-bound
In parent molecule.Unless in addition statement in the description, otherwise alkyl includes optionally independently below take by one or more
Replace for base：Acyl group, alkyl, alkenyl, alkynyl, alkoxy, alkylaryl, naphthenic base.In a non-limiting embodiments, take
The alkyl in generation can be selected from methyl fluoride, difluoromethyl, trifluoromethyl, 2- fluoro ethyls, 3- fluoropropyls, hydroxymethyl, 2- hydroxyethyls,
3- hydroxypropyls, benzyl and phenethyl.
" alkoxy " refers to that " alkyl " is connected by oxygen atom with parent molecule, is determined as described above wherein " alkyl " has
Justice.
" halogenated alkyl " refers to wherein all hydrogen moieties or all by selected from fluoro base, chloro base, bromo base and iodine
The alkyl of the halogen displacement of Dai Ji.In some embodiments, all hydrogen atoms are all respectively replaced by fluoro base.In some implementations
In scheme, all hydrogen atoms are all respectively replaced by chloro base.The example of halogenated alkyl include-CF3 ,-CF2CF3 ,-
CF2CF2CF3 ,-CFCl2 ,-CF2Cl etc..
In certain embodiments, pharmaceutically acceptable form is pharmaceutically acceptable salt, pharmaceutically acceptable
Salt is well known in the art.The example of pharmaceutically acceptable salt is such as hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, high chlorine
Acid, acetic acid, oxalic acid, maleic acid, tartaric acid, citric acid, succinic acid or malonic acid, acetic acid, propionic acid, glycolic, pyruvic acid,
Oxalic acid, lactic acid, trifluoroacetic acid, Loprazolam, ethane sulfonic acid, p-methyl benzenesulfonic acid, salicylic acid etc..
" pharmaceutically acceptable carrier " or " pharmaceutically acceptable excipient " includes any and all solvents, dispersion Jie
Matter, covering, antibacterial agent and antifungal agent, isotonic agent and absorption delaying agent etc..Pharmaceutically acceptable carrier or excipient
The pharmacological activity of disclosed compound is not destroyed, and is nothing when to be enough to deliver the dosage application of the compound of therapeutic dose
Poison.The use of the medium and reagent of pharmaceutically active substance is well known in the art.
Compared with prior art, the beneficial effects of the invention are as follows：
（1）There is the active indole amides class compound of anti-gastric cancer the present invention provides a new class of, widened existing anti-gastric cancer
The range of compound can be used as lead compound and continue to optimize；
（2）The compounds of this invention has the activity of selective depression stomach cancer cell, can be used as selectivity and/or targeted drug, has
There is good development prospect.
Specific implementation mode
Present disclosure is illustrated below by embodiment.In the present invention, following embodiment is in order to more preferable
Ground illustrates the present invention, is not for limiting the scope of the invention.
Embodiment 1
N- (2- (1H- indol-3-yls) ethyl) -2- hydroxy-3-methyls benzamide (compound R 2)
Step 1：Aniline is added in 200ml round-bottomed flasks（9.3g, 0.1mol）And dilute hydrochloric acid, contained with 30 ml（7.3g, 0.105
mol）Sodium nitrite solution is added dropwise in solution.Reaction, which filters out supernatant liquid in 1 hour and is added dropwise to 70ml, to be contained（37.8g 0.3
mol）In sodium sulfite solution, 80 DEG C are reacted 2 hours, then about 25ml are added dropwise（0.3mol）Concentrated hydrochloric acid, after 95 DEG C are reacted 2 hours
It is placed in ambient temperature overnight, 12.6 g of hydrazinobenzene hydrochloride salt solid is precipitated.Yield：87.1%.
Step 2：Gained in step 1 is sequentially added in 200ml round-bottomed flasks（12.6g, about 0.087mol）Phenylhydrazine salt
Hydrochlorate,（21.1g 0.10mol）The chloro- 1- hydroxy-butans sodium sulfonates of 4-, 40ml ethyl alcohol, 40ml water, then use disodium phosphate soln
Solution PH is adjusted to 6-7,75 DEG C of condensing refluxes 6 hours；Ethyl alcohol and a small amount of water, surplus solution is gone first to use with Rotary Evaporators rotation
Dichloromethane wash, then with sodium carbonate liquor adjust PH to 8-10, then use chloroform, be placed in 4 DEG C of refrigerator cool overnights, precipitation
10.3 g of tryptamine hydrochloride solid.Yield：60.3%.
Step 3：It is sequentially added in 50ml round-bottomed flasks（0.912g, 6 mmol）3- cresotinic acids,（1.15g 9
mmol）EDCI（1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate）,（1.215g 9 mmol）HOBT（1- hydroxyls
Base benzotriazole）, 15ml acetone, stirring at normal temperature 2 hours；Add (1.08g, 5.5 mmol) tryptamines hydrochloric acid obtained by step 2
Salt, Anhydrous potassium carbonate, stirring at normal temperature 24 hours；Column chromatography purifies, and eluant, eluent is：Ethyl acetate：Petroleum ether=1：2.
1.31g compound R 2（Yield：81.2%）, it is white solid, fusing point is：165-167℃.1H NMR (400 MHz,
CDCl3) δ 12.39 (s, 1H), 8.22 (s, 1H), 7.61 (s, 1H), 7.33 (d, J = 8.5 Hz, 1H),
7.29 (s, 1H), 7.20 (d, J = 7.9 Hz, 1H), 7.11 (s, 1H), 7.08 (d, J = 7.8 Hz,
1H), 6.82 (s, 1H), 6.62 (d, J = 7.3 Hz, 1H), 6.37 (s, 1H), 3.77 (d, J = 5.1
Hz, 2H), 3.07 (d, J = 5.9 Hz, 2H), 2.33 (s, 3H)。
Embodiment 2-5
With reference to the method for embodiment 1, compound R 3-R6 is prepared, corresponding data are as follows：
| Compound | R（n=1） | Fusing point/DEG C | 1H NMR |
| R3 | 4-CH3 | 165-167 | 1H NMR (400 MHz, CDCl3) δ 12.72 (s, 1H), 8.02 (s, 1H), 7.43 (s, 1H), 7.31 (d, J = 8.3 Hz, 1H), 7.29 (s, 1H), 7.25 (d, J = 7.2 Hz, 1H), 7.10 (s, 1H), 7.07 (s, 1H), 6.97 (d,J = 7.9 Hz, 1H), 6.67 (t, J = 7.6 Hz, 1H), 6.42 (s, 1H), 3.83 – 3.73 (m, 2H), 3.10 (t, J = 6.3 Hz, 2H), 2.46 (s, 3H) |
| R4 | 4-Cl | 158-160 | 1H NMR (400 MHz, CDCl3) δ 12.55 (s, 1H), 8.12 (s, 1H), 7.51 (s, 1H), 7.22 (d, J = 8.6 Hz, 1H), 7.18 (s, 1H), 7.16 (d, J = 7.3 Hz, 1H), 7.09 (d, J = 8.6 Hz, 1H), 7.01 (s, 1H), 6.94 (d, J = 7.9 Hz, 1H), 6.60 (t, J = 7.6 Hz, 1H), 6.32 (s, 1H), 3.67 (q, J = 6.0 Hz, 2H), 2.96 (t, J = 6.5 Hz, 2H) |
| R5 | 5-Cl | 170-173 | 1H NMR (400 MHz, CDCl3) δ 12.35 (s, 1H), 8.20 (s, 1H), 7.60 (s, 1H), 7.46 (d, J = 8.8 Hz, 1H), 7.33 (d, J = 8.6 Hz, 1H), 7.28 (s, 2H), 7.21 (d, J = 8.6 Hz, 1H), 7.12 (s, 1H), 6.90 (d, J = 8.8 Hz, 1H), 6.38 (s, 1H), 3.77 (q, J = 6.4 Hz, 2H), 3.07 (t, J = 6.6 Hz, 2H) |
| R6 | 5-Br | 174-177 | 1H NMR (400 MHz, CDCl3) δ 12.40 (s, 1H), 8.15 (s, 1H), 7.67 (d, J = 7.8 Hz, 1H), 7.46 (s, 1H), 7.44 (s, 1H), 7.27 (s, 1H), 7.23 (s, 1H), 7.20 (d, J = 7.4 Hz, 1H), 7.12 (s, 1H), 6.90 (d, J = 8.8 Hz, 1H), 6.36 (s, 1H), 3.92 – 3.68 (m, 2H), 3.13 (t, J = 6.5 Hz, 2H) |
6 external activity test of embodiment
Cell strain selects MGC-803 (gastric carcinoma cells), HepG2 (human liver cancer cell), MCF-7（Human breast cancer cell）, A549
（Human lung carcinoma cell）And HELA（Human cervical carcinoma cell）.
Culture solution is that DMEM+15% NBS+ are dual anti-
Sample liquid is prepared：After being dissolved with DMSO (Merck), a concentration of 33333.33 μm of ol/L
1. 96 orifice plates are added in cell suspension by plate in, per 100 μ l of hole（Cell content per hole is about 8000/hole）, it is placed in 37
DEG C, 5% CO2 incubators cultivate for 24 hours；
2. dosing prepares sample liquid gradient concentration with culture medium（256,128,64,32,16,8,4,2 μm of ol/L）, then discard 96
The culture medium of drug various concentration is added in original culture medium on orifice plate, and per 100 μ L of hole, each concentration does 5 secondary orifices.Remaining hole
It is compareed with the culture medium containing 3 ‰ DMSO, sets 37 DEG C, 5% incubator cultivation 48h；
96 orifice plates are taken out in the test of 3.MTT methods, and 10 μ LMTT (3- (4,5- dimethylthiazole -2- are added under the conditions of being protected from light per hole
Base) -2,5- diphenyltetrazoliumbromide father-in-law's bromides, 5mg/mL）Solution places into and places 4h in incubator；Culture is discarded after 4 hours
150 μ LDMSO dissolving concussions are added per hole, surveys 490nm OD values with the full-automatic microplate reader of MK-2, calculates half and inhibit dense for liquid
Spend IC50.
Test result is as follows：
It can be seen by upper table, the compound of the present invention being capable of selective depression stomach cancer cell, especially selective depression MGC-803
(gastric carcinoma cells) cell strain.Therefore, it is possible to be used as the drug of selective therapy gastric cancer, there is good development prospect.
Claims (10)
1. a kind of compound of Formula I or its pharmaceutically acceptable salt, have the following structure：
I
Wherein：R is each independently selected from halogen ,-NO2 ,-CN, C1-C8 alkyl, C1-C8 alkoxyl, C1-C8 halogenated alkyls；
N is selected from 1,2,3 or 4.
2. compound of formula I as described in claim 1 or its pharmaceutically acceptable salt, R are each independently selected from halogen, C1-
C4 alkyl, C1-C4 alkoxies, C1-C4 halogenated alkyls.
3. compound of formula I as claimed in claim 1 or 2 or its pharmaceutically acceptable salt, R be each independently selected from fluorine, chlorine,
Bromine, methyl, ethyl, methoxyl group, ethyoxyl, trifluoromethyl；N is selected from 1 or 2.
4. compound of formula I as claimed in claim 1 or 2 or its pharmaceutically acceptable salt, R be each independently selected from methyl,
Chlorine, bromine；N is 1.
5. compound according to any one of claims 1-4 is selected from following compound：
R2
R3 R4
R5 R6 。
6. a kind of method preparing compound of formula I as described in claim 1, reaction route are as follows：
；
Wherein, the definition of R and n is as described in claim 1；
Specific reaction step is as follows：
Step 1：Aniline and hydrochloric acid are added in the reaction vessel, sodium nitrite solution is added drop-wise in solution；
Reaction filters for 1 hour, and in filtrate added drop-wise to sodium sulfite solution, 80 DEG C are reacted 2 hours, then concentrated hydrochloric acid is added dropwise, and 95 DEG C anti-
It answers and is placed within 2 hours ambient temperature overnight, hydrazinobenzene hydrochloride salt solid is precipitated；
Step 2：Hydrazinobenzene hydrochloride salt, the chloro- 1- hydroxy-butans sodium sulfonates of 4-, ethyl alcohol, water are sequentially added in the reaction vessel, then are adjusted
Solution PH is saved to 6-7,75 DEG C are reacted 6 hours；Vacuum distillation removes ethyl alcohol and part water, surplus solution are first washed with dichloromethane
It washs, then adjusts PH to 8-10, then with chloroform, be placed in 4 DEG C of refrigerator cool overnights, tryptamine hydrochloride solid is precipitated；
Step 3：Salicyclic acid derivatives are sequentially added in the reaction vessel, and 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne two is sub-
Amine hydrochlorate, I-hydroxybenzotriazole, acetone, stirring at normal temperature 2 hours；Add tryptamine hydrochloride obtained by step 2, anhydrous carbon
Sour potassium, stirring at normal temperature is to the reaction was complete；Column chromatography purifies, and obtains compound shown in Formulas I.
7. preparation method as claimed in claim 6, it is characterised in that：
The molar ratio of the aniline of step 1, sodium nitrite and sodium sulfite is 1: 1-1.5 :2-4.5 preferably 1: 1.05
: 3；
The molar ratio of the chloro- 1- hydroxy-butans sodium sulfonate of hydrazinobenzene hydrochloride salt and 4- of step 2 is 1:1-1.5 preferably 1:
1-1.2；
Salicyclic acid derivatives, 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate, the 1- hydroxy benzos of step 3
Triazole and the molar ratio of tryptamine hydrochloride are 1: 1-2 : 1-2 : 0.5-1.5；Preferably 1: 1-1.5 : 1-1.5 :
0.8-1.2。
8. a kind of pharmaceutical composition, it includes any one of claim 1-5 Formulas I compound represented or its is pharmaceutically acceptable
Salt and pharmaceutically acceptable carrier, excipient.
9. any one of the claim 1-5 compounds or pharmaceutical composition according to any one of claims 8 are in medicine preparation
Purposes, it is characterised in that the drug can be used for treating gastric cancer.
10. medicinal as claimed in claim 9, which is characterized in that the drug alternative inhibits gastric cancer cell line MGC-803 strain.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810660487.4A CN108530337B (en) | 2018-06-25 | 2018-06-25 | Indoleamide compound capable of selectively inhibiting gastric cancer cells |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810660487.4A CN108530337B (en) | 2018-06-25 | 2018-06-25 | Indoleamide compound capable of selectively inhibiting gastric cancer cells |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108530337A true CN108530337A (en) | 2018-09-14 |
| CN108530337B CN108530337B (en) | 2020-11-03 |
Family
ID=63486825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810660487.4A Expired - Fee Related CN108530337B (en) | 2018-06-25 | 2018-06-25 | Indoleamide compound capable of selectively inhibiting gastric cancer cells |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108530337B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108912035A (en) * | 2018-06-21 | 2018-11-30 | 雷可欣 | A kind of indole amides class compound having anti-tumor activity |
| CN111116449A (en) * | 2019-11-22 | 2020-05-08 | 兰州大学 | Novel tryptamine derivative and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101641093A (en) * | 2006-11-22 | 2010-02-03 | 因塞特公司 | Imidazotriazines and imidazopyrimidines as kinase inhibitors |
| WO2014053852A1 (en) * | 2012-10-05 | 2014-04-10 | Virttu Biologics Limited | Treatment of cancer |
| CN105646448A (en) * | 2016-02-03 | 2016-06-08 | 沈阳药科大学 | Pyridine compounds and application thereof |
-
2018
- 2018-06-25 CN CN201810660487.4A patent/CN108530337B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101641093A (en) * | 2006-11-22 | 2010-02-03 | 因塞特公司 | Imidazotriazines and imidazopyrimidines as kinase inhibitors |
| WO2014053852A1 (en) * | 2012-10-05 | 2014-04-10 | Virttu Biologics Limited | Treatment of cancer |
| CN105646448A (en) * | 2016-02-03 | 2016-06-08 | 沈阳药科大学 | Pyridine compounds and application thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108912035A (en) * | 2018-06-21 | 2018-11-30 | 雷可欣 | A kind of indole amides class compound having anti-tumor activity |
| CN108912035B (en) * | 2018-06-21 | 2020-09-29 | 雷可欣 | Indole amide compound with anti-tumor activity |
| CN111116449A (en) * | 2019-11-22 | 2020-05-08 | 兰州大学 | Novel tryptamine derivative and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108530337B (en) | 2020-11-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102153551B (en) | Indazole/azaindazole-based diarylcarbamide/thiocarbamide-structure antineoplastic drug | |
| US9187474B2 (en) | Raf inhibitor compounds | |
| CN105008355B (en) | It is used as the 7-azaindole derivatives of kinases inhibitor | |
| CN104059039B (en) | There is the fused ring compound of GPR40 function of receptors adjustment effects | |
| EA024824B1 (en) | Raf inhibitors compounds | |
| US10689361B2 (en) | Quinoline derivative and use thereof | |
| BG107212A (en) | Substituted benzoic acid amides and use thereof for the inhibition of angiogenesis | |
| CN107021937B (en) | Benzothiazole Carbox amide and its application | |
| CN107176932A (en) | Benzoxazine ketone derivatives and its production and use | |
| CN110627801A (en) | HDAC inhibitor and application thereof | |
| Shan et al. | Expanding the structural diversity of diarylureas as multi-target tyrosine kinase inhibitors | |
| Deng et al. | Novel complex crystal structure of prolyl hydroxylase domain-containing protein 2 (PHD2): 2, 8-Diazaspiro [4.5] decan-1-ones as potent, orally bioavailable PHD2 inhibitors | |
| CN108530337A (en) | A kind of alternative indole amides class compound for inhibiting stomach cancer cell | |
| CN108623511A (en) | A kind of indole amides class compound can be used for treating cancer | |
| CN108558732A (en) | A kind of indole amides class compound of alternative treatment gastric cancer and cervical carcinoma | |
| CN109456279A (en) | Thiazoleamino benzamide acetic ester derivative and application thereof | |
| CN111253339B (en) | Synthetic preparation method of curcumin derivatives and application of curcumin derivatives in cancer treatment | |
| CN108017633A (en) | N- [5- (pyrimidine -2- amino) -2,4- di-substituted-phenyls] -2- fluoropropenes amide derivatives and application | |
| Chen et al. | Design, synthesis and anticancer evaluation of 6, 7-disubstituted-4-phenoxyquinoline derivatives bearing 1, 8-naphthyridine-3-carboxamide moiety as novel multi-target TKIs | |
| CN106966986B (en) | N- benzyl heterocyclic nitro ketene semiamine analog derivative and synthetic method and antitumor application thereof | |
| CN114437113B (en) | Thiazolopyridine cyclotriazole compound, and preparation method and application thereof | |
| CN104163772A (en) | Substituted diaryl ester compound, and preparation method and application thereof | |
| WO2022111729A1 (en) | Salt form used as cdc7 inhibitor and crystal form thereof | |
| CN107163028A (en) | A kind of benzamides Hedgehog inhibitor and its preparation method and application | |
| JP7034430B2 (en) | Deuterated indoleamine 2,3-dioxygenase inhibitor and its use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20201103 Termination date: 20210625 |