CN116102562A - Naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative and preparation method thereof - Google Patents
Naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a naphtho [2,1-b ]]Indolo [2,3-d ]]The chemical structural formula of the cyclooctalactone derivative is shown as formula 1; the preparation method comprises the following steps: adding a compound of formula 2 and a compound of formula 3 as reaction raw materials into an organic solvent, and catalyzing scandium triflate, 4-dimethylaminopyridine, the compound of formula 4 and an oxidant formula 5 and a dehydrating agentStirring and reacting at 20-25deg.C for 72-75h in the presence of molecular sieve, performing TLC tracking reaction to completion, filtering, concentrating, and separating by column chromatography to obtain naphtho [2,1-b ] compound of formula 1]Indolo [2,3-d ]]Cyclooctalactone derivatives. The derivative has good sensitivity and cytotoxic activity to human kidney cancer cells Ketr-3; the method has simple process flow and mild reaction condition, and can realize one-step high-efficiency conversion.
Description
Technical Field
The invention relates to the technical field of synthesis of organic compounds, in particular to a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative and a preparation method thereof.
Background
Cyclic lactones are an important class of organic compounds that have a broad spectrum of physiological and pharmacological activities. For example, cyclooctalactone, octaactalin a, has activity against mouse melanoma and colon tumors. Indole compounds are important nitrogenous organic heterocyclic compounds and have important biological activity (modern chemical industry, 2022,51 (3), 718-722). The active group splicing method is utilized to synthesize the cyclooctalactone compound containing indole fragments, which has very important significance for the development and research of new drugs.
There is a report on a method for preparing a cyclooctalactone derivative: under the action of boron trifluoride diethyl etherate and 2,4, 6-trimethylpyridine, the cyclization reaction of 2-methoxyl tetrahydropyran and substituted siloxyalkyne is carried out to generate a cyclooctalactone derivative, and the reaction formula is shown as follows:
the method is only suitable for synthesizing cyclooctalactone compounds with simple substitution forms, and is difficult to splice heterocycle or aromatic ring with important pharmacological activity such as indole into cyclooctalactone skeleton.
Therefore, the cyclooctalactone compound containing heterocyclic ring or aromatic ring segments such as indole is synthesized by a simple and efficient active group splicing method, and has great significance for development and research of new drugs.
Disclosure of Invention
The invention aims to provide a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative and a preparation method thereof, wherein the derivative has good sensitivity and cytotoxic activity to human kidney cancer cells Ketr-3; the method has simple process flow and mild reaction condition, and can realize one-step high-efficiency conversion.
In order to achieve the above purpose, the invention provides a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative, the chemical structural formula of which is shown as formula 1:
in formula 1, R 1 Selected from hydrogen, halogenOne of C1-C2 alkyl and methyl ester groups substituted by elements; r is R 2 Selected from hydrogen or halogen.
The invention also provides a preparation method of the naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative, which comprises the following steps:
the compound 1- (1H-indol-2-yl) naphthalene-2-phenol derivative of formula 2 and 3-phenyl-alkynylaldehyde derivative of formula 3 are taken as reaction raw materials and added into an organic solvent, and scandium triflate, 4-dimethylaminopyridine and the compound (5 aS,10 bR) -2-phenyl-2, 5a,6,10 b-tetrahydro-4H-indeno [2, 1-b) of formula 4 are prepared][1,2,4]Triazolo [4,3-d ]][1,4]Oxazinyl-11-onium tetrafluoroborate and in the presence of the oxidizing agent compound 3,3', 5' -tetra-tert-butyl- [1,1' -bis (cyclohexadiene) of formula 5]-2,2', 5' -tetraene-4, 4' -dione and dehydrating agentStirring and reacting at 20-25deg.C for 72-75h in the presence of molecular sieve, performing TLC tracking reaction to completion, filtering, concentrating, and separating by column chromatography to obtain naphtho [2,1-b ] compound of formula 1]Indolo [2,3-d ]]A cyclooctalactone derivative;
wherein the molar ratio between the compound of formula 2,1- (1H-indol-2-yl) naphthalene-2-ol derivative, the compound of formula 3, 3-phenylalkynylaldehyde derivative, 4-dimethylaminopyridine, scandium triflate, the compound of formula 4, (5 as,10 br) -2-phenyl-2, 5a,6,10 b-tetrahydro-4H-indeno [2,1-b ] [1,2,4] triazolo [4,3-d ] [1,4] oxazinyl-11-ium tetrafluoroborate and the compound of formula 5, 3', 5' -tetra-tert-butyl- [1,1 '-bis (cyclohexadiene) ] -2,2',5 '-tetraene-4, 4' -dione is 1.0:3.5:1:0.2:0.15:3, a step of;
the structural formula of the compound 1- (1H-indol-2-yl) naphthalene-2-phenol derivative shown in the formula 2 is
the structural formula of the 3-phenylalkynylaldehyde derivative of the compound shown in the formula 3 isIn formula 3, R 2 Selected from hydrogen or halogen;
the compound of formula 4 (5 aS,10 bR) -2-phenyl-2, 5a,6,10 b-tetrahydro-4H-indeno [2,1-b][1,2,4]Triazolo [4,3-d ]][1,4]Oxazinyl-11-onium tetrafluoroborate has the structural formula
The compound of formula 5 3,3', 5' -tetra-tert-butyl- [1,1' -bis (cyclohexadiene)]-2,2', 5' -tetraene-4, 4' -dione of formula
Preferably, the compound of formula 2,1- (1H-indol-2-yl) naphthalene-2-ol derivative, is selected from one of 1- (5- (trifluoromethyl) -1H-indol-2-yl) naphthalene-2-ol, 1- (5-fluoro-1H-indol-2-yl) naphthalene-2-ol, 1- (5-bromo-1H-indol-2-yl) naphthalene-2-ol, 1- (5- (methyl formate) -1H-indol-2-yl) naphthalene-2-ol.
Preferably, the 3-phenylalkynylaldehyde derivative of the compound of formula 3 is selected from one of 3-phenylalkynylaldehyde and 3- (3-bromophenyl) propynylaldehyde.
Preferably, the organic solvent is tetrahydrofuran.
Preferably, the method comprises the steps of,the molecular sieve is added in an amount of 0.5-1.5g/mmol of the compound of formula 2.
Preferably, the amount of organic solvent is 20-30ml/mmol of compound of formula 2.
Compared with the prior art, the invention has the following beneficial effects:
the method has simple process flow, can realize the efficient construction of the naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone skeleton through a one-step efficient conversion process, and has high synthesis efficiency and step economy; the preparation method is simple and convenient to operate, the reaction condition is mild, the metal catalyst and inert gas protection are not required, and the preparation can be smoothly carried out under the conditions of air and room temperature; the functional groups such as fluorine, bromine, ester groups and the like in the target product can be subjected to further conversion and functionalization reaction, so that the target product is convenient to carry out diversified structural modification, and the target product of the preparation process has good anti-tumor activity and can be applied to anti-tumor drugs.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a target compound I synthesized in example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the target compound II synthesized in example 2 of the present invention;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of the target compound III synthesized in example 3 of the present invention;
FIG. 4 is a chart showing the hydrogen nuclear magnetic resonance spectrum of the target compound IV synthesized in example 4 of the present invention;
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of the target compound V synthesized in example 5 of the present invention;
FIG. 6 is a graph showing comparison of cytotoxicity inhibition ratio of Ketr-3 by the target compound I synthesized in example 1 of the present invention;
FIG. 7 is a graph showing comparison of cytotoxicity inhibition ratio of Ketr-3 against the target compound II synthesized in example 2 of the present invention;
FIG. 8 is a graph showing comparison of cytotoxicity inhibition ratio of Ketr-3 against the target compound III synthesized in example 3 of the present invention;
FIG. 9 is a graph showing comparison of cytotoxicity inhibition ratio of Ketr-3 by the target compound IV synthesized in example 4 of the present invention;
FIG. 10 is a graph showing comparison of cytotoxicity inhibition ratios of Ketr-3 against the target compound V synthesized in example 5 of the present invention.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
In the examples below, unless otherwise indicated, the experimental methods described are generally carried out under conventional conditions or conditions recommended by the manufacturer; the raw materials and the reagents can be obtained in a commercially available mode.
Example 1
A preparation method of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative I comprises the following specific steps:
1- (5-fluoro-1H-indol-2-yl) naphthalene-2-ol (0.3 mmol), 3', 5' -tetra-tert-butyl- [1,1' -bis (cyclohexadiene) are introduced into a reaction tube]-2,2', 5' -tetraene-4, 4' -dione (0.9 mmol), 4-dimethylaminopyridine (0.3 mmol), and,Molecular sieves (300 mg), scandium triflate (0.06 mmol), (5 aS,10 bR) -2-phenyl-2, 5a,6,10 b-tetrahydro-4H-indeno [2, 1-b)][1,2,4]Triazolo [4,3-d ]][1,4]Oxazinyl-11-onium tetrafluoroborate (0.045 mmol), tetrahydrofuran (7.5 mL) and 3-phenylalkynylaldehyde (1.05 mmol) were reacted at 20℃for 3 days, after the completion of the reaction, the solvent was removed, and the naphtho [2,1-b ] was isolated by column chromatography]Indolo [2,3-d ]]Pure cyclooctalactone derivative I: 3-phenyl-naphtho [2,1-b]-5-fluoro-indolo [2,3-d ]]-cyclooctalactone of the formula:
yield: 51%; yellow solid;
as shown in FIG. 1, the nuclear magnetic resonance hydrogen spectrum (CDCl) of the target compound I 3 ,400MHz)(δ,ppm):9.06(s,1H),7.92–7.86(m,1H),7.56–7.50(m,1H),7.39–7.26(m,4H),7.26–7.21(m,3H),6.99–6.90(m,1H),6.52(d,J=9.2Hz,1H),6.42(s,1H)。
Example 2
A preparation method of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative II comprises the following specific steps:
1- (5-bromo-1H-indol-2-yl) naphthalene-2-ol (0.3 mmol), 3', 5' -tetra-tert-butyl- [1,1' -bis (cyclohexadiene) are introduced into a reaction tube]-2,2', 5' -tetraene-4, 4' -dione (0.9 mmol), 4-dimethylaminopyridine (0.3 mmol),Molecular sieve (300 mg), scandium triflate (0.0)6 mmol), (5 aS,10 bR) -2-phenyl-2, 5a,6,10 b-tetrahydro-4H-indeno [2,1-b][1,2,4]Triazolo [4,3-d ]][1,4]Oxazinyl-11-onium tetrafluoroborate (0.045 mmol), tetrahydrofuran (7.5 mL) and 3-phenylalkynylaldehyde (1.05 mmol) were reacted at 20℃for 3 days, after the completion of the reaction, the solvent was removed, and the naphtho [2,1-b ] was isolated by column chromatography]Indolo [2,3-d ]]Pure cyclooctalactone derivative II: 3-phenyl-5-bromonaphtho [2,1-b]Indolo [2,3-d ]]Cyclooctalactone, the reaction formula is as follows:
yield: 48%; yellow solid;
as shown in FIG. 2, the nuclear magnetic resonance hydrogen spectrum (CDCl) of the target compound II 3 ,400MHz)(δ,ppm):8.97(s,1H),7.90(d,J=8.4Hz,2H),7.84(d,J=8.8Hz,1H),7.56–7.51(m,2H),7.33–7.27(m,5H),7.26–7.20(m,3H),7.02(s,1H),6.44(s,1H)。
Example 3
A preparation method of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative III comprises the following specific steps:
1- (5- (trifluoromethyl) -1H-indol-2-yl) naphthalene-2-ol (0.3 mmol), 3', 5' -tetra-tert-butyl- [1,1' -bis (cyclohexadiene) are introduced into a reaction tube]-2,2', 5' -tetraene-4, 4' -dione (0.9 mmol), 4-dimethylaminopyridine (0.3 mmol), and,Molecular sieves (300 mg), scandium triflate (0.06 mmol), (5 aS,10 bR) -2-phenyl-2, 5a,6,10 b-tetrahydro-4H-indeno [2, 1-b)][1,2,4]Triazolo [4,3-d ]][1,4]Oxazinyl-11-onium tetrafluoroborate (0.045 mmol), tetrahydrofuran (7.5 mL) and 3-phenylalkynylaldehyde (1.05 mmol) were reacted at 20℃for 3 days, after the completion of the reaction, the solvent was removed, and the naphtho [2,1-b ] was isolated by column chromatography]Indolo [2,3-d ]]Pure product III of cyclooctalactone derivative: 3-phenyl-5-trifluoromethylnaphtho [2,1-b ]]Indolo [2,3-d ]]Cyclooctalactone, the reaction formula is as follows:
yield: 74%; yellow solid;
as shown in FIG. 3, the nuclear magnetic resonance hydrogen spectrum (CDCl) of the target compound 3 ,400MHz)(δ,ppm):9.29(s,1H),7.93–7.88(m,1H),7.86–7.82(m,1H),7.57–7.53(m,1H),7.50–7.36(m,3H),7.35–7.27(m,7H),7.26–7.22(m,1H),7.17(s,1H),6.48(s,1H)。
Example 4
A preparation method of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative IV comprises the following specific steps:
1- (5- (methyl formate) -1H-indol-2-yl) naphthalene-2-ol (0.3 mmol), 3', 5' -tetra-tert-butyl- [1,1' -bis (cyclohexadiene) are introduced into a reaction tube]-2,2', 5' -tetraene-4, 4' -dione (0.9 mmol), 4-dimethylaminopyridine (0.3 mmol), and,Molecular sieves (300 mg), scandium triflate (0.06 mmol), (5 aS,10 bR) -2-phenyl-2, 5a,6,10 b-tetrahydro-4H-indeno [2, 1-b)][1,2,4]Triazolo [4,3-d ]][1,4]Oxazinyl-11-onium tetrafluoroborate (0.045 mmol), tetrahydrofuran (7.5 mL) and 3-phenylalkynylaldehyde (1.05 mmol) were reacted at 20℃for 3 days, after the completion of the reaction, the solvent was removed, and the naphtho [2,1-b ] was isolated by column chromatography]Indolo [2,3-d ]]Pure cyclooctalactone derivative IV: 3-phenyl-5-carbomethoxy naphtho [2,1-b ]]Indolo [2,3-d ]]Cyclooctalactone, the reaction formula is as follows:
yield: 80%; yellow solid;
as shown in FIG. 4, the nuclear magnetic resonance hydrogen spectrum (CDCl) of the target compound 3 ,400MHz)(δ,ppm):9.53(s,1H),7.91–7.83(m,1H),7.63(s,1H),7.53–7.49(m,1H),7.43(d,J=8.8Hz,1H),7.32–7.26(m,5H),7.25–7.20(m,1H),6.48(s,1H),3.75(s,3H)。
Example 5
A preparation method of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative V comprises the following specific steps:
1- (1H-indol-2-yl) naphthalene-2-ol (0.3 mmol), 3', 5' -tetra-tert-butyl- [1,1' -bis (cyclohexadiene) are introduced into a reaction tube]-2,2', 5' -tetraene-4, 4' -dione (0.9 mmol), 4-dimethylaminopyridine (0.3 mmol), and,Molecular sieves (300 mg), scandium triflate (0.06 mmol), (5 aS,10 bR) -2-phenyl-2, 5a,6,10 b-tetrahydro-4H-indeno [2, 1-b)][1,2,4]Triazolo [4,3-d ]][1,4]Oxazinyl-11-onium tetrafluoroborate (0.045 mmol), tetrahydrofuran (7.5 mL) and 3- (3-bromophenyl) propynylaldehyde (1.05 mmol) were reacted at 20℃for 3 days, after the completion of the reaction, the solvent was removed, and the naphtho [2,1-b ] was isolated by column chromatography]Indolo [2,3-d ]]Pure product V of cyclooctalactone derivative: 3- (3-bromophenyl) -naphtho [2,1-b]Indolo [2,3-d ]]Cyclooctalactone, the reaction formula is as follows:
yield: 85%; yellow solid;
as shown in FIG. 5, the nuclear magnetic resonance hydrogen spectrum (CDCl) of the target compound 3 ,400MHz)(δ,ppm):8.95(s,1H),7.97–7.88(m,3H),7.57–7.47(m,4H),7.44(d,J=7.6Hz,1H),7.38(d,J=8.8Hz,1H),7.28(s,1H),7.18(d,J=7.6Hz,1H),7.13–7.07(m,1H),7.06–6.99(m,1H),6.93(d,J=8.0Hz,1H),6.42(s,1H)。
The growth inhibitory ability of the target compounds I-V prepared in examples 1-5 on Ketr-3 of human renal cancer cells was measured by the CCK8 method. The target compounds I-V were diluted with dimethylsulfoxide to three concentrations of 1, 10 and 100ng/mL, respectively, and after 24 hours of action, their cytotoxicity against Ketr-3 was measured, respectively. The results are shown in the following table 1 and fig. 6-10, and the analysis of the results in the table and the graph shows that the target compound naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone compound has good activity of inhibiting the growth of tumor cells, can be used for inhibiting the growth of tumor cells, and has important guiding significance and application prospect in discovering novel and efficient antitumor drugs.
TABLE 1 inhibition results of Ketr-3 by target compounds I-V at various concentrations
The method has simple process flow, can realize the efficient construction of the naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone skeleton by a one-step efficient conversion process, and has high synthesis efficiency and step economy. The preparation method is simple and convenient to operate, the reaction condition is mild, the metal catalyst and inert gas protection are not required, and the preparation method can be smoothly carried out under the conditions of air and room temperature. The functional groups such as fluorine, bromine, ester groups and the like in the target product can undergo further conversion and functionalization reaction, so that the target product is convenient to carry out diversified structural modification, has good anti-tumor activity, and can be applied to anti-tumor drugs.
Claims (9)
2. A process for the preparation of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative according to claim 1, characterized in that: the method comprises the following steps:
by the compound of formula 2 1- (1H-indol-2-yl) naphthalene-2-ol derivative and the compound of formula 3-phenyl-alkynylAldehyde derivative is added into organic solvent as reaction raw material, and is added into scandium triflate, 4-dimethylaminopyridine and compound (5 aS,10 bR) -2-phenyl-2, 5a,6,10 b-tetrahydro-4H-indeno [2, 1-b) of formula 4][1,2,4]Triazolo [4,3-d ]][1,4]Oxazinyl-11-onium tetrafluoroborate and in the presence of the oxidizing agent compound 3,3', 5' -tetra-tert-butyl- [1,1' -bis (cyclohexadiene) of formula 5]-2,2', 5' -tetraene-4, 4' -dione and dehydrating agentStirring and reacting at 20-25deg.C for 72-75h in the presence of molecular sieve, performing TLC tracking reaction to completion, filtering, concentrating, and separating by column chromatography to obtain naphtho [2,1-b ] compound of formula 1]Indolo [2,3-d ]]A cyclooctalactone derivative;
wherein the molar ratio between the compound of formula 2,1- (1H-indol-2-yl) naphthalene-2-ol derivative, the compound of formula 3, 3-phenylalkynylaldehyde derivative, 4-dimethylaminopyridine, scandium triflate, the compound of formula 4, (5 as,10 br) -2-phenyl-2, 5a,6,10 b-tetrahydro-4H-indeno [2,1-b ] [1,2,4] triazolo [4,3-d ] [1,4] oxazinyl-11-ium tetrafluoroborate and the compound of formula 5, 3', 5' -tetra-tert-butyl- [1,1 '-bis (cyclohexadiene) ] -2,2',5 '-tetraene-4, 4' -dione is 1.0:3.5:1:0.2:0.15:3, a step of;
the structural formula of the compound 1- (1H-indol-2-yl) naphthalene-2-phenol derivative shown in the formula 2 is
the structural formula of the 3-phenylalkynylaldehyde derivative of the compound shown in the formula 3 isIn formula 3, R 2 Selected from hydrogen or halogen; />
The compound of formula 4 (5 aS,10 bR) -2-phenyl-2, 5a,6,10 b-tetrahydro-4H-indeno [2,1-b][1,2,4]Triazolo [4,3-d ]][1,4]Junction of oxazinyl-11-onium tetrafluoroboratesThe structure is that
3. A process for the preparation of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative according to claim 2, characterized in that: the compound of formula 2,1- (1H-indol-2-yl) naphthalene-2-ol derivative, is selected from one of 1- (5- (trifluoromethyl) -1H-indol-2-yl) naphthalene-2-ol, 1- (5-fluoro-1H-indol-2-yl) naphthalene-2-ol, 1- (5-bromo-1H-indol-2-yl) naphthalene-2-ol, 1- (5- (methyl formate) -1H-indol-2-yl) naphthalene-2-ol.
4. A process for the preparation of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative according to claim 2, characterized in that: the 3-phenylalkynylaldehyde derivative of the compound shown in the formula 3 is one selected from 3-phenylalkynylaldehyde and 3- (3-bromophenyl) propynylaldehyde.
5. A process for the preparation of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative according to claim 2, characterized in that: the organic solvent is tetrahydrofuran.
7. A process for the preparation of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative according to claim 2, characterized in that: the organic solvent is used in an amount of 20-30ml/mmol of the compound of formula 2.
8. A process for the preparation of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative according to claim 2, characterized in that: the reaction was stirred at 20℃for 72h.
9. A process for the preparation of a naphtho [2,1-b ] indolo [2,3-d ] cyclooctalactone derivative according to claim 2, characterized in that: the volume ratio of the eluent used for the column chromatography is 20:1 and ethyl acetate.
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