CN108623511A - A kind of indole amides class compound can be used for treating cancer - Google Patents
A kind of indole amides class compound can be used for treating cancer Download PDFInfo
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Abstract
The invention discloses a kind of indole amides class compounds having antitumor activity, and it can be used to treat a plurality of types of cancers.Therefore, it is possible to be used as the lead compound of antitumor drug, 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
Medically, cancer（cancer）Refer to the malignant tumour originating from epithelial tissue, is most common in malignant tumour
It is a kind of.Cancer has cell differentiation and proliferative disorder, the growth biological properties such as out of hand, wellability and metastatic, hair
Life is a multiple-factor, the complex process of multi-step, is divided into three carcinogenic, rush cancer, evolution processes, sudden and violent with smoking, infection, occupation
Dew, environmental pollution, unreasonable diet, inherent cause are closely related.The cause of disease of malignant tumour is not fully understood.It is more bright at present
True factor related with cancer can be divided into exogenous and endogenous two major classes.Gastric cancer, liver cancer, breast cancer, lung carcinoma cell and palace
Neck cancer is the higher a few class cancers of China's incidence.It is also directed to above-mentioned a few class cancers mostly in current new drug development.
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.
Therefore, the compound that R and D have extensive active anticancer still has significance.
Invention content
The technical problem to be solved by the present invention is to：A kind of indole amides class compound is provided, can widely be pressed down
Kinds cancer processed.
The first aspect of the invention is to provide a kind of compound of Formula I and its pharmaceutically acceptable salt：
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.
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 has the following structure：
R14 R16
R17 R19
R20 R21 。
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 definition of R and n is as described in claim 1；
Specific reaction step is as follows：
Step 1：4- methylanilines and hydrochloric acid are added in the reaction vessel, sodium nitrite solution is added drop-wise in solution.Reaction 1
Hour filters, and in filtrate added drop-wise to sodium sulfite solution, 80 DEG C are reacted 1-3 hours, then concentrated hydrochloric acid is added dropwise, and 95 DEG C of reaction 1-3 are small
When be placed on ambient temperature overnight, 4- hydrazinobenzoic acid hydrochloride solids are precipitated；
Step 2：Sequentially add 4- hydrazinobenzoic acid hydrochlorides in the reaction vessel, the chloro- 1- hydroxy-butans sodium sulfonates of 4-, ethyl alcohol,
Water, then solution PH is adjusted to 6-7,75 DEG C are reacted 5-7 hours；Vacuum distillation removes ethyl alcohol and part water, and surplus solution is first with two
Chloromethanes washs, then adjusts PH to 8-10, then uses chloroform, is placed in 4 DEG C of refrigerator cool overnights, precipitation 5-methyltryptamine hydrochloric acid
Salt solid；
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 1-3 hours；Add 5-methyltryptamine hydrochloric acid obtained by step 2
Salt, Anhydrous potassium carbonate, stirring at normal temperature is to the reaction was complete；Column chromatography purifies, and obtains compound shown in Formulas I.
Preferably, the molar ratio of the 4- methylanilines, sodium nitrite and sodium sulfite of step 1 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 4- hydrazinobenzoic acid hydrochlorides and 4- of step 2 is 1:1-1.5, preferably
It is 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 5-methyltryptamine 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
It can be used for cancer；In particular for treatment gastric cancer, liver cancer, breast cancer, lung carcinoma cell and cervical carcinoma；It is especially used to inhibit people's stomach
Cancer cell MGC-803, human liver cancer cell HepG2, human breast cancer cell line Bcap-37, human lung cancer cell A549 and human cervical carcinoma cell
HELA cell strains.
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）The indole amides class compound with active anticancer that the present invention provides a new class of, has widened existing anti-cancer compounds
The range of object can be used as lead compound and continue to optimize.
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- (5- Methyl-1H-indole -3- bases) ethyl) -2-Hydroxylbenzamide (compound R 14)
Step 1：4- methylanilines are added in 200ml round-bottomed flasks（10.7g 0.1mol）And dilute hydrochloric acid, contained with 30 ml
（7.3g, 0.105 mol）Sodium nitrite solution is added dropwise in solution.Reaction filters out supernatant liquid in 1 hour or so and is added dropwise to
70ml contains（37.8g, 0.3 mol）In sodium sulfite solution, 80 DEG C are reacted about 1.5 hours, then about 25ml are added dropwise（0.3mol）It is dense
Hydrochloric acid, 95 DEG C of reactions are placed on ambient temperature overnight for 2.5 hours or so, and 12.9 g of 4- hydrazinobenzoic acid hydrochlorides solid is precipitated.Yield：
90.0%.
Step 2：Gained in step 1 is sequentially added in 200ml round-bottomed flasks（12.9g, about 0.09mol）4- methylbenzenes
Hydrazine hydrochloride,（22.7g 0.108mol）The chloro- 1- hydroxy-butans sodium sulfonates of 4-, 45ml ethyl alcohol, 45ml water, then with phosphoric acid hydrogen two
Sodium solution adjusts solution PH to 6-7,75 DEG C of condensing refluxes 5 hours or so；Ethyl alcohol and a small amount of water are removed with Rotary Evaporators rotation, is remained
Remaining solution is first washed with dichloromethane, then adjusts PH to 8-10, then with chloroform with sodium carbonate liquor, and it is cold to be placed in 4 DEG C of refrigerators
But overnight, 11.5 g of 5-methyltryptamine HCl, solid is precipitated.Yield：60.6%.
Step 3：It is sequentially added in 50ml round-bottomed flasks（0.83g, 6 mmol）Salicylic acid,（1.15g, 9 mmol）
EDCI（1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate）,（1.215g 9 mmol）HOBT（1- hydroxy benzenes
And triazole）, 15ml acetone, stirring at normal temperature 2.5 hours；Add (1.16g, 5.5 mmol) 5-methyltryptamine salt obtained by step 2
Hydrochlorate, Anhydrous potassium carbonate, stirring at normal temperature about 20 hours；Column chromatography purifies, and eluant, eluent is molten for the mixing of ethyl acetate and petroleum ether
Agent.Obtain 1.35g compound Rs 14（Yield：83.6%）, it is brown solid, fusing point is：156-158℃.1H NMR (400
MHz, Acetone) δ 12.78 (s, 1H), 9.74 (s, 1H), 8.11 (s, 1H), 7.58 (d, J = 8.0
Hz, 1H), 7.26 (s, 1H), 7.23 (s, 1H), 7.12 (d, J = 8.2 Hz, 1H), 7.02 (s, 1H),
6.81 – 6.76 (m, 1H), 6.75 (s, 1H), 6.68 (t, J = 7.6 Hz, 1H), 3.58 (dd, J =
13.5, 6.7 Hz, 2H), 2.92 (t, J = 7.2 Hz, 2H), 2.23 (s, 3H)。
Embodiment 2-6
With reference to the method for embodiment 1, following compound is prepared, corresponding data are as follows：
| Compound | R（n=1） | Fusing point/DEG C | 1H NMR |
| R16 | 3-CH3 | 145-148 | 1H NMR (400 MHz, DMSO) δ 12.75 (s, 1H), 10.67(s, 1H), 8.88 (t, J = 5.6 Hz, 1H), 7.74 (d, J = 8.0 Hz, 1H), 7.35 (s, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.13 (d, J = 2.2 Hz, 1H), 6.85 (dd,J = 8.3, 1.3 Hz, 1H), 6.71 (d, J = 6.1 Hz, 1H), 6.70 (s, 1H), 3.55 (dd, J = 13.3, 7.2 Hz, 2H), 2.94 (t, J = 7.4 Hz, 2H), 2.36 (s, 3H), 2.28 (s, 3H) |
| R17 | 4-CH3 | 142-144 | 1H NMR (400 MHz, DMSO) δ 12.73 (s, 1H), 10.69 (s, 1H), 8.86 (t, J = 5.6 Hz, 1H), 7.73 (d, J = 8.0 Hz, 1H), 7.34 (s, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.13 (d, J = 2.2 Hz, 1H), 6.89 (dd,J = 8.3, 1.3 Hz, 1H), 6.71 (d, J = 6.1 Hz, 1H), 6.70 (s, 1H), 3.55 (dd, J = 13.3, 7.2 Hz, 2H), 2.94 (t, J = 7.4 Hz, 2H), 2.36 (s, 3H), 2.28 (s, 3H) |
| R19 | 4-Cl | 145-147 | 1H NMR (400 MHz, Acetone) δ 13.27 (s, 1H), 9.90 (s, 1H), 8.34 (s, 1H), 7.75 (d, J = 8.5 Hz, 1H), 7.40 (s, 1H), 7.28 (d, J = 8.2 Hz, 1H), 7.17 (s, 1H), 6.96 (s, 1H), 6.94 (s, 1H), 6.87 (d, J = 8.5 Hz, 1H), 3.73 (q, J = 6.5 Hz, 2H), 3.07 (t, J = 7.2 Hz, 2H), 2.39 (s, 3H) |
| R20 | 5-Cl | 145-148 | 1H NMR (400 MHz, Acetone) δ 12.93 (s, 1H), 9.91 (s, 1H), 8.38 (s, 1H), 7.78 (s, 1H), 7.42 (s, 1H), 7.40 (s, 1H), 7.28 (d, J = 8.2 Hz, 1H), 7.18 (s, 1H), 6.95 (d, J = 3.8 Hz, 1H), 6.93 (s, 1H), 3.74 (q, J = 6.5 Hz, 2H), 3.08 (t, J = 7.2 Hz, 2H), 2.39 (s, 3H) |
| R21 | 5-Br | 161-163 | 1H NMR (400 MHz, Acetone) δ 12.97 (s, 1H), 9.91 (s, 1H), 8.40 (s, 1H), 7.90 (s, 1H), 7.54 (d, J = 8.8 Hz, 1H), 7.40 (s, 1H), 7.28 (d, J = 8.3 Hz, 1H), 7.17 (s, 1H), 6.95 (d, J = 8.2 Hz, 1H), 6.89 (d, J = 8.8 Hz, 1H), 3.74 (q, J = 6.5 Hz, 2H), 3.08 (t, J = 7.1 Hz, 2H), 2.39 (s, 3H) |
Comparative example 1
With reference to the method for embodiment 1, comparative example compound R 1 is prepared, structure is as follows：
R1
R1 is faint yellow solid, and fusing point is 154-156 DEG C,1H NMR (400 MHz, CDCl3) δ 12.41 (s, 1H),
8.20 (s, 1H), 7.62 (s, 1H), 7.39 (t, J = 7.6 Hz, 1H), 7.33 (d, J = 8.5 Hz,
1H), 7.29 (s, 1H), 7.21 (s, 1H), 7.19 (s, 1H), 7.12 (s, 1H), 7.01 (d, J = 8.3
Hz, 1H), 6.81 (t, J = 7.3 Hz, 1H), 6.44 (s, 1H), 3.79 (d, J = 5.7 Hz, 2H),
3.08 (t, J = 6.2 Hz, 2H)。
7 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, after introducing methyl in the positions 5- of indole ring, compound anti-cancering activity significantly improves.With comparative example
Close object R1（5- unsubstituteds of indole ring）It compares, although hydrogen and methyl can be considered classical bioisostere, this
Application compound obviously has the effect of preferably inhibiting cancer have unexpected technique effect and significant progress.
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 0,1,2,3 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：
R14 R16
R17 R19
R20 R21 。
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 1：4- methylanilines and hydrochloric acid are added in the reaction vessel, sodium nitrite solution is added drop-wise in solution；Reaction 1
Hour filters, and in filtrate added drop-wise to sodium sulfite solution, 80 DEG C are reacted 1-3 hours, then concentrated hydrochloric acid is added dropwise, and 95 DEG C of reaction 1-3 are small
When be placed on ambient temperature overnight, 4- hydrazinobenzoic acid hydrochloride solids are precipitated；
Step 2：Sequentially add 4- hydrazinobenzoic acid hydrochlorides in the reaction vessel, the chloro- 1- hydroxy-butans sodium sulfonates of 4-, ethyl alcohol,
Water, then solution PH is adjusted to 6-7,75 DEG C are reacted 5-7 hours；Vacuum distillation removes ethyl alcohol and part water, and surplus solution is first with two
Chloromethanes washs, then adjusts PH to 8-10, then uses chloroform, is placed in 4 DEG C of refrigerator cool overnights, precipitation 5-methyltryptamine hydrochloric acid
Salt solid；
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 1-3 hours；Add 5-methyltryptamine hydrochloric acid obtained by step 2
Salt, Anhydrous potassium carbonate, 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 4- methylanilines 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 4- hydrazinobenzoic acid hydrochlorides and 4- of step 2 is 1:1-1.5, preferably
It is 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 5-methyltryptamine 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 compound shown in the Formulas I of any one of claim 1-5 or its is pharmaceutically acceptable
Salt and pharmaceutically acceptable carrier, excipient.
9. compound or pharmaceutical composition according to any one of claims 8 described in any one of claim 1-5 are in medicine preparation
Purposes, it is characterised in that the drug can be used for treating gastric cancer, liver cancer, breast cancer, lung carcinoma cell and cervical carcinoma.
10. medicinal as claimed in claim 9, which is characterized in that the drug alternative inhibition gastric carcinoma cells MGC-803,
Human liver cancer cell HepG2, human breast cancer cell line Bcap-37, human lung cancer cell A549 and human cervical carcinoma cell HELA.
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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 |
-
2018
- 2018-06-25 CN CN201810660068.0A patent/CN108623511A/en active Pending
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 |
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