CN110467555B - Axial chiral aryl indole compound and synthesis method thereof - Google Patents
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Abstract
The invention discloses an axial chiral aryl indoleThe chemical structural formula of the compound is shown as formula 3 or formula 5; taking a compound of formula 1 or a compound of formula 4 and a compound of formula 2 as reaction raw materials, taking dichloromethane as a solvent, adding
The molecular sieve is stirred to react under the action of a chiral phosphoric acid catalyst, TLC tracks the reaction to be complete, and the molecular sieve is prepared by filtering, concentrating and purifying; the compound is subjected to biological activity test, and the result shows that the compound has certain cytotoxic activity on MCF-7 breast cancer cells. The synthetic method disclosed by the invention is simple and convenient to operate, mild in reaction conditions, economic and easily available in raw materials, and the prepared axial chiral indole-naphthalene and indole-benzene compounds are high in optical purity and have wide application in the field of medicine research and development.
Description
Technical Field
The invention belongs to the field of organic synthetic chemistry, and particularly relates to an axial chiral aryl indole compound and a synthetic method thereof.
Background
Axial chiral indole-naphthalene, indole-benzene compounds possess a variety of biological activities, for example: the document j.med.chem.2015,58,6607 reports that such compounds may act as glucocorticoid receptor antagonists; document bioorg.med.chem.lett.2011,21,5336 reports that the compounds can be used as HCV NS5B polymerase inhibitors; the document res, chem, intermedia, 2017,43,2387 reports that the compounds have antioxidant and antibacterial activities.
The axial chiral indole-naphthalene and indole-benzene compounds have wide application prospects in the field of life science, and meanwhile, as the drug molecules play a role in biological activity and are usually an enantiomer in a racemate, an optically pure chiral catalyst is also needed for catalytic reaction in asymmetric catalysis, so that people urgently need to develop a method for efficiently synthesizing the axial chiral indole-naphthalene and indole-benzene compounds. However, the methods for synthesizing the axial chiral indole-naphthalene and indole-benzene compounds reported in the literature are very limited, and mainly produce an axial chiral skeleton through the coupling reaction of an indole ring and a naphthalene ring or a benzene ring. For example, Angew. chem. int. Ed.2017,56,116 reports the use of chiral phosphoric acid to catalyze the coupling reaction of 2-indolylmethanol with 2-naphthol or phenol to construct an axial chiral indole-naphthalene, indole-benzene backbone; document nat. chem.2018,10,58 reports the construction of an axially chiral indole-naphthalene skeleton using a chiral phosphate catalyzed coupling reaction of a 2-substituted indole with an azonaphthalene. Despite these approaches, there are still very limited, and there is a strong need to develop new methods and strategies for synthesizing axially chiral indole-naphthalene, indole-benzene compounds. At present, the dynamic kinetic resolution of racemic compounds becomes a simple and efficient method for synthesizing axial chiral compounds, and the research for synthesizing the axial chiral indole-naphthalene and indole-benzene compounds by using the method is a blank at home and abroad. Therefore, the synthesis of axial chiral indole-naphthalene and indole-benzene compounds with novel structures and the development of efficient asymmetric catalytic synthesis methods thereof are very necessary for the discovery of pharmaceutical lead compounds with important biological activity and the development of chiral catalysts with efficient catalytic activity.
Disclosure of Invention
One of the purposes of the invention is to provide an axial chiral aryl indole compound to fill the blank of the prior art and meet the requirements of the related fields.
The invention also aims to provide the synthesis method of the axial chiral aryl indole compound, which has the advantages of mild reaction conditions, low cost, high yield and high enantioselectivity.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows: an axial chiral aryl indole compound comprises an axial chiral indole-naphthalene compound and an axial chiral indole-benzene compound, and the chemical structural formulas of the axial chiral indole-naphthalene compound and the axial chiral indole-benzene compound are respectively shown in formula 3 or formula 5:
wherein R is selected from one of hydrogen, methyl (Me), ethyl (Et), isopropyl (i-Pr), phenyl (Ph), p-toluenesulfonyl (Ts), trifluoromethanesulfonyl (Tf), methanesulfonyl (Ms), benzenesulfonyl or substituted benzenesulfonyl; r1Selected from hydrogen, methyl, methoxy (MeO), ethoxy (EtO),One of halogen, ester group and trifluoromethyl; r2One selected from hydrogen, methyl, ethyl, methoxy, ethoxy, halogen, phenyl and substituted phenyl; r3One selected from hydrogen, methyl, ethyl, isopropyl, phenyl and benzyl (Bn); r6One selected from hydrogen, methyl, ethyl, methoxy, ethoxy and halogen.
The invention also provides a synthesis method of the axial chiral indole-naphthalene and indole-benzene compounds, which comprises the following steps:
taking a compound of a formula 1 or a compound of a formula 4 and a compound of a formula 2 as reaction raw materials, taking dichloromethane as a reaction solvent, adding
The molecular sieve is stirred to react under the action of a chiral phosphoric acid catalyst, TLC tracks the reaction to be complete, and the compound shown in the formula 3 is prepared after filtration, concentration and purification; wherein the reaction molar ratio of the compound shown in the formula 1 to the compound shown in the formula 2 is 1:1 to 1: 3; the reaction temperature is 20 to 30 ℃.
Wherein the structural formula of the compound shown in the formula 1 is shown in the specification
Wherein R is selected from one of hydrogen, methyl (Me), ethyl (Et), isopropyl (i-Pr), phenyl (Ph), p-toluenesulfonyl (Ts), trifluoromethanesulfonyl (Tf), methanesulfonyl (Ms), benzenesulfonyl or substituted benzenesulfonyl; r1One selected from hydrogen, methyl, methoxy (MeO), ethoxy (EtO), halogen, ester group and trifluoromethyl; r2One selected from hydrogen, methyl, ethyl, methoxy, ethoxy, halogen, phenyl and substituted phenyl.
The structural formula of the compound of the formula 4 is
Wherein R is selected from one of hydrogen, methyl (Me), ethyl (Et), isopropyl (i-Pr), phenyl (Ph), p-toluenesulfonyl (Ts), trifluoromethanesulfonyl (Tf), methanesulfonyl (Ms), benzenesulfonyl or substituted benzenesulfonyl; r1Is selected fromOne of hydrogen, methyl, methoxy (MeO), ethoxy (EtO), halogen, ester group and trifluoromethyl; r6One selected from hydrogen, methyl, ethyl, methoxy, ethoxy and halogen.
The structural formula of the compound of the formula 2 is
In the formula, R3One selected from hydrogen, methyl, ethyl, isopropyl, phenyl and benzyl (Bn).
The reaction route is as follows:
preferably, the chiral phosphoric acid catalyst is selected from one or two of binaphthyl skeleton derivatives, octahydrobinaphthyl skeleton and spiro skeleton derivatives; the structural formula of the binaphthyl skeleton derivative is shown in the specification
Wherein G is selected from 9-anthryl, 9-phenanthryl, 2,4, 6-triisopropyl, 2-naphthyl or 1-naphthyl; the structural formula of the octahydrobinaphthyl skeleton derivative is shown in the specification
Wherein G' is selected from 9-anthryl, 9-phenanthryl, 2,4, 6-triisopropyl, 2-naphthyl or 1-naphthyl; the structural formula of the spiro skeleton derivative is shown in the specification
Wherein G' is selected from 9-anthryl, 9-phenanthryl, 2,4, 6-triisopropyl, 2-naphthyl or 1-naphthyl.
More preferably, the chiral phosphoric acid catalyst is a compound of formula 61, and the structural formula of the compound of formula 61 is
Wherein G is selected from 2,4, 6-triisopropyl.
Preferably, the reaction molar ratio of the compound of formula 1 to the compound of formula 2 is 1:3, and the reaction molar ratio of the compound of formula 4 to the compound of formula 2 is 1: 3.
Preferably, the reaction temperature is 25 ℃.
Preferably, the purification is silica gel column chromatography, and the eluent is petroleum ether/ethyl acetate mixed liquor with the volume ratio of 10: 1.
Compared with the prior art, the invention has the following beneficial effects: in the process of synthesizing the axial chiral aryl indole compound, chiral phosphoric acid is used as a catalyst, so that the enantioselectivity of the reaction is well controlled; the reaction condition is conventional, mild reaction condition is realized, the method is more suitable for industrial mass production, and the application range of the method is widened; adopts more kinds of substrates as reactants to obtain products with structural diversity and complexity and high yield. The biological activity test result shows that the compound has certain cytotoxic activity on MCF-7 breast cancer cells, and the synthesized axial chiral aryl indole compound is expected to be applied to the field of medicines.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
In the examples described below, unless otherwise indicated, the experimental procedures described are generally carried out according to conventional conditions or conditions recommended by the manufacturer.
The compound of formula 1 and the compound of formula 4 can be prepared by adopting a method reported in documents adv.synth.catal.2017,359, 1552; the compound of formula 2 and the chiral phosphoric acid catalyst and other reagents are commercially available.
The synthetic route of the axial chiral indole-naphthalene compound 3 is as follows:
the synthetic route for the axial chiral indole-benzene compound 5 is as follows:
in the two reactions, the catalyst chiral phosphoric acid is a compound of formula 61, and the structural formula is as follows:
example 1: to 1 ml of dichloromethane were added 0.1 mmol of the compound of formula 1c and 0.3 mmol of the compound of formula 2b as reactants, 100 mg
Molecular sieve as additive, 0.01 mmol chiral phosphoric acid (i.e. compound of formula 61) as catalyst, reacting at 25 deg.C for 48 hr, TLC tracking reaction to completion, filtering to remove
Molecular sieve, washing the filter cake with ethyl acetate, concentrating the obtained filtrate, and separating by silica gel column chromatography (the eluent is a mixed solution of petroleum ether and ethyl acetate with the volume ratio of 10: 1) to obtain the axial chiral indole-naphthalene 3cb, which is a white solid.
The structural characterization data for product 3cb in example 1 is as follows:
m.p.86.6-87.6℃；[α]D 20＝-44.7(c 0.81,acetone)；1H NMR(400MHz,DMSO-d6)11.48(s,1H),10.05(s,1H),8.15(d,J＝9.1Hz,1H),8.08(d,J＝8.2Hz,1H),7.62–7.55(m,2H),7.54–7.38(m,3H),7.36–7.09(m,10H),6.99(d,J＝8.1Hz,1H),6.63(s,1H),5.25–4.74(m,4H),2.22(s,3H)；13C NMR(100MHz,DMSO-d6)156.5,154.4,146.1,136.5,136.1,133.8,132.7,131.8,130.5,128.7,128.6,128.5,128.4,128.2,128.0,127.7,127.5,127.2,120.1,119.8,118.8,116.6,112.1,68.0,66.6,21.6；IR(KBr):3413,1732,1636,1420,1138,1062,938,611cm-1；ESI FTMS exact mass calcd for(C36H28F3N3O7S-H)-requires m/z 702.1522, found m/z 702.1516; ratio of enantiomersThe value was 96:4, HPLC (Daicel Chiralpak AD-H, n-hexane/isopropanol 70/30, flow rate 1.0mL/min, T30 ℃,254nm) TR＝9.943min(minor),tR＝13.750min(major).
The reaction schemes for examples 1-17 are shown below:
the reaction raw materials, reaction conditions and yields are shown in table 1:
TABLE 1
*0.1 mmol of the compound of formula 1 and 0.3 mmol of the compound of formula 2b as reactants, 0.0l of the compound of formula 4 as catalyst and 1 ml of dichloromethane as solvent.
Example 18: to 4 ml of dichloromethane were added 0.1 mmol of the compound of formula 1a and 0.12 mmol of the compound of formula 2a as reactants, 100 mg
Molecular sieve as additive, 0.01 mmol chiral phosphoric acid (i.e. compound of formula 61) as catalyst, reacting at 25 deg.C for 5 hr, TLC tracking reaction to completion, filtering to remove
Molecular sieve, washing the filter cake with ethyl acetate, concentrating the obtained filtrate, and separating by silica gel column chromatography (the eluent is a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 10: 1) to obtain the axial chiral indole-naphthalene 3aa, white solid.
The structural characterization data for product 3aa in example 18 is as follows:
m.p.85.1-85.8℃；[α]D 20＝-13.7(c 1.85,acetone)；1H NMR(400MHz,CDCl3)1H NMR(400MHz,CDCl3)9.36(s,1H),7.93(d,J＝9.0Hz,1H),7.87(d,J＝7.7Hz,1H),7.72–7.55(m,2H),7.50(d,J＝8.0Hz,1H),7.42(d,J＝9.1Hz,1H),7.39–7.28(m,3H),7.18(d,J＝7.2Hz,1H),7.12–7.05(m,1H),4.36–4.20(m,2H),3.84(s,3H),3.83–3.58(m,2H),1.30(s,3H),0.62(s,3H)；13C NMR(100MHz,CDCl3)157.7,155.3,155.1,134.2,133.3,132.8,129.6,128.0,127.3,126.5,126.2,123.9,123.0,120.7,120.1,116.3,114.6,111.7,105.9,63.2,62.7,57.4,14.5,13.6；IR(KBr):3308,3055,1716,1622,1507,1322,1058,1019,905,809,741cm-1；ESI FTMS exact mass calcd for(C25H25N3O5-H)-requires m/z 446.1716, found m/z 446.1725; enantiomeric ratio 92:8, HPLC (Daicel Chiralpak AD-H, n-hexane/isopropanol 70/30, flow rate 1.0mL/min, T30 ℃,254nm): TR＝7.333min(minor),tR＝9.937min(major).
The reaction schemes for examples 18-24 are as follows:
the reaction raw materials, reaction conditions and yields are shown in table 2:
TABLE 2
*0.1 mmol of the compound of formula 1 and 0.12 mmol of the compound of formula 2 as reactants, 0.0l of chiral phosphoric acid 4 as catalyst and 1 ml of dichloromethane as solvent.
Example 25: to 1 ml of dichloromethane were added 0.1 mmol of the compound of formula 4u and 0.3 mmol of the compound of formula 2b as reactants, 100 mg
Molecular sieve as additive, 0.01 mmol chiral phosphoric acid (i.e. compound of formula 61) as catalyst, reacting at 25 deg.C for 48 hr, TLC tracking reaction to completion, filtering to remove
Molecular sieve, washing the filter cake with ethyl acetate, concentrating the obtained filtrate, and separating by silica gel column chromatography (the eluent is a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 10: 1) to obtain the axial chiral indole-naphthalene 5ub, white solid, and the yield is 86%.
The structural characterization data for product 5ub in example 25 is as follows:
m.p.113.2-113.8℃；[α]D 20＝-5.1(c 0.71,acetone)；1H NMR(400MHz,DMSO-d6)11.48(s,1H),10.16(s,1H),7.46(d,J＝8.1Hz,1H),7.40–7.20(m,10H),7.19–7.09(m,2H),6.98(d,J＝4.9Hz,2H),5.37–4.92(m,4H),2.45(s,3H),1.99(s,3H)；13C NMR(100MHz,DMSO-d6)156.6,154.5,146.9,139.7,137.6,136.5,136.2,134.3,133.4,128.8,128.7,128.5,128.4,128.2,127.7,126.5,123.8,122.4,121.2,120.1,119.7,116.9,116.5,112.3,68.2,66.9,20.9,18.9；IR(KBr):3364,3277,1747,1715,1511,1426,1141,832,739,613cm-1；ESI FTMS exact mass calcd for(C33H27ClF3N3O7S-H)-requires m/z 700.1132, found m/z 700.1150; enantiomeric ratio 95:5, HPLC (Daicel Chiralpak IB, hexane/isopopanol 70/30, flow rate 1.0mL/min, T30 ℃,254nm): TR＝4.827min(major),tR＝5.820min(minor).
The reaction scheme and yield of example 25 are shown below:
as can be seen from tables 1 and 2, the method of the present invention can not only realize the synthesis of the axial chiral indole-naphthalene and indole-benzene compounds in one step, obtain high enantioselectivity and excellent yield, and has the advantages of high atom economy, environmental friendliness, wide application range, easily available raw materials, simple and safe operation, mild reaction conditions, short reaction time, simple post-treatment, and diversified product structures, thereby having great implementation value and potential social and economic benefits.
The axial chiral indole-naphthalene and indole-benzene compounds of the invention are tested for the cytotoxic activity of a part of the compounds on MCF-7 breast cancer cells by a CCK8 method, and the results are shown in Table 3. The result shows that the compound synthesized by the invention has certain cytotoxic activity on MCF-7 breast cancer cells. Among them, the most active compound is compound 3aa, which shows the most inhibitory effect (IC) on MCF-7 breast cancer cells50＝4.44μg/mL)。
TABLE 3 cytotoxic Activity of the Compounds of the present invention
The axial chiral aryl indole compound prepared by the invention has the potential application as a bioactive molecular skeleton. In addition, the compound is subjected to biological activity test, and the result shows that the compound has certain cytotoxic activity on MCF-7 breast cancer cells.
The method for preparing the axial chiral aryl indole compound is an asymmetric addition reaction under the catalysis of small organic molecules, and the axial chiral indole-naphthalene and indole-benzene structures are constructed in one step from racemized raw materials, so that the method is simple and convenient to operate, mild in reaction conditions, economical and easily available in raw materials, and the prepared axial chiral indole-naphthalene and indole-benzene compounds are high in optical purity (the er value is as high as 98: 2). The axial chiral aryl indole compound prepared by the invention is expected to be widely applied in the field of medicine research and development.
Claims (6)
1. An axial chiral aryl indole compound is characterized by comprising an axial chiral indole-naphthalene compound and an axial chiral indole-benzene compound, wherein the chemical structures of the axial chiral indole-naphthalene compound and the axial chiral indole-benzene compound are respectively shown as a formula 3 or a formula 5:
wherein R is selected from one of hydrogen, methyl, ethyl, isopropyl, phenyl, p-toluenesulfonyl, trifluoromethanesulfonyl, methylsulfonyl and phenylsulfonyl; r1One selected from hydrogen, methyl, methoxy, ethoxy, halogen and trifluoromethyl; r2One selected from hydrogen, methyl, ethyl, methoxy, ethoxy, halogen and phenyl; r3One selected from hydrogen, methyl, ethyl, isopropyl, phenyl and benzyl; r6One selected from hydrogen, methyl, ethyl, methoxy, ethoxy and halogen.
2. A method for synthesizing the axial chiral aryl indole compound of claim 1, which comprises the following steps:
taking a compound of a formula 1 or a compound of a formula 4 and a compound of a formula 2 as reaction raw materials, taking dichloromethane as a reaction solvent, adding
Stirring the molecular sieve to react under the action of a chiral phosphoric acid catalyst, tracking the TLC to react completely, filtering, concentrating and purifying to obtain a compound of a formula 3 or a compound of a formula 5; wherein the reaction molar ratio of the compound shown in the formula 1 to the compound shown in the formula 2 is 1:1 to 1: 3; the reaction molar ratio of the compound of formula 4 to the compound of formula 2 is 1:1 to 1: 3; the reaction temperature is 20 to 30 ℃;
the structural formula of the compound of the formula 1 is
Wherein R is selected from hydrogen, methyl, ethyl, isopropyl, phenyl, p-toluenesulfonyl, trifluoromethanesulfonyl, methylsulfonyl and benzeneOne of sulfonyl groups; r1One selected from hydrogen, methyl, methoxy, ethoxy, halogen and trifluoromethyl; r2One selected from hydrogen, methyl, ethyl, methoxy, ethoxy, halogen and phenyl;
the structural formula of the compound of the formula 4 is
Wherein R is selected from one of hydrogen, methyl, ethyl, isopropyl, phenyl, p-toluenesulfonyl, trifluoromethanesulfonyl, methylsulfonyl and phenylsulfonyl; r1One selected from hydrogen, methyl, methoxy, ethoxy, halogen and trifluoromethyl; r6One selected from hydrogen, methyl, ethyl, methoxy, ethoxy and halogen;
the structural formula of the compound of the formula 2 is
In the formula, R3One selected from hydrogen, methyl, ethyl, isopropyl, phenyl and benzyl;
the chiral phosphoric acid catalyst is selected from one or two of binaphthyl skeleton derivatives, octahydrobinaphthyl skeleton derivatives and spiro skeleton derivatives; the structural formula of the binaphthyl skeleton derivative is shown in the specification
Wherein G is selected from 9-anthryl, 9-phenanthryl, 2,4, 6-triisopropylphenyl, 2-naphthyl or 1-naphthyl; the structural formula of the octahydrobinaphthyl skeleton derivative is shown in the specification
Wherein G' is selected from 9-anthryl, 9-phenanthryl, 2-naphthyl or 1-naphthyl; the structural formula of the spiro skeleton derivative is shown in the specification
Wherein G' is selected from 9-anthryl, 9-phenanthryl, 2-naphthyl or 1-naphthyl.
3. The method for synthesizing axial chiral aryl indole compound according to claim 2, wherein the chiral phosphoric acid catalyst is a compound of formula 61, and the structural formula of the compound of formula 61 is
Wherein G is selected from 2,4, 6-triisopropylphenyl.
4. The method for synthesizing axial chiral arylindole compound according to claim 2, wherein the reaction molar ratio of the compound of formula 1 to the compound of formula 2 is 1:3, and the reaction molar ratio of the compound of formula 4 to the compound of formula 2 is 1: 3.
5. The method for synthesizing an axial chiral arylindole compound according to claim 2, wherein the reaction temperature is 25 ℃.
6. The method for synthesizing the axial chiral arylindole compound according to claim 2, wherein the purification is performed by silica gel column chromatography, and the eluent is a petroleum ether/ethyl acetate mixed solution with a volume ratio of 10: 1.
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