CN115181112B - Synthesis and anti-tumor application of 6-bromo-cycloicaritin chromane 3, 4-diketone derivative - Google Patents

Synthesis and anti-tumor application of 6-bromo-cycloicaritin chromane 3, 4-diketone derivative Download PDF

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CN115181112B
CN115181112B CN202211001247.6A CN202211001247A CN115181112B CN 115181112 B CN115181112 B CN 115181112B CN 202211001247 A CN202211001247 A CN 202211001247A CN 115181112 B CN115181112 B CN 115181112B
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赵长阔
崔晗琦
王先恒
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Zunyi Medical University
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Abstract

The application discloses a 6-bromo-cycloicaritin chromane 3, 4-diketone derivative with a structural formula shown as a formula I,
Figure ZY_1
wherein R is selected from alkenyl, alkynyl, alicyclic and substituted or unsubstituted benzyl, the 6-bromo-cycloicaritin chromane 3, 4-diketone derivative shown as I is prepared by taking cycloicaritin as a starting material, reacting with various proper alcohols under the action of a proper brominating reagent at a proper reaction temperature for a certain time and synthesizing in a medium yield, wherein the structure is prepared by 1 H NMR、 13 C NMR, HRMS confirmation. The synthesis method has mild conditions and is easy to implement and operate. The 6-bromo-cycloicaritin chroman 3, 4-dione derivatives synthesized by the invention show good anticancer activity on HepG2 and MCF-7 cell lines in vitro.

Description

Synthesis and anti-tumor application of 6-bromo-cycloicaritin chromane 3, 4-diketone derivative
Technical Field
The invention belongs to the field of new drug design and synthesis, and in particular relates to synthesis and antitumor application of 6-bromo-cycloicaritin chromane 3, 4-dione derivatives.
Background
Icariin is one of flavonoid compounds, and has various pharmacological and biological activities such as neuroprotection, promotion of osteogenic differentiation, inhibition of osteoclast differentiation, and antitumor activity.
Figure BDA0003807452630000011
Halogenation is a classical organic chemical reaction, and halogen groups are used as good pharmacophores, so that the lipophilicity of drug molecules can be effectively changed, and the drug activity can be increased. For the reasons stated above, the applicant devised: halogen groups are introduced into the C-6 position of icaritin by utilizing bromination reaction so as to improve the lipophilicity of the icaritin. Accordingly, a series of novel 6-bromo-icaritin chromane 3, 4-diketone derivatives are prepared by synthesis.
Disclosure of Invention
Aiming at the defects of the prior art, the invention researches and designs a series of novel 6-bromo-icaritin chromane 3, 4-diketone derivatives, and the activity research shows that the novel derivatives have better inhibition effect on liver cancer and breast cancer.
The invention aims to provide a 6-bromo-cycloicaritin chromane 3, 4-diketone derivative, the structural formula of which is shown as a formula I,
Figure BDA0003807452630000012
wherein R is selected from saturated alkyl or substituted alkyl.
Preferably, the 6-bromocycloicaritin chroman 3, 4-diketone derivative I and R are selected from saturated alkyl or benzyl of C1-C5.
On the other hand, the invention provides a synthesis method of the 6-bromo-cycloicaritin chromane 3, 4-diketone derivative I, which comprises the following synthesis route:
Figure BDA0003807452630000021
the method comprises the following steps: the method is characterized in that the cycloicaritin is used as a raw material, and reacts with a brominating reagent under proper alcohol reagent and under proper conditions to obtain the 6-bromo cycloicaritin chroman 3, 4-diketone derivative I.
The synthesis method of the 6-bromo-cycloicaritin chromane 3, 4-diketone derivative I comprises the steps of selecting a brominating reagent from N-bromo-succinimide (NBS) and liquid bromine (Br) 2 ) Hydrobromic acid (HBr), naBr/H 2 O 2 NBS/AIBN or alpha, beta-dibromocinnamic acid; preferably NBS.
The synthetic method of I as described above, wherein the suitable alcohol is selected from saturated alkyl alcohols or substituted alkyl alcohols; preferably, C1-C5 saturated alkyl or benzyl alcohols.
The synthesis method of I as described above, wherein the appropriate conditions include a reaction time of 1 to 48 hours, a reaction temperature of 0℃to a reflux temperature of the alcohol reagent used; preferably, the reaction time is 2 to 6 hours and the reaction temperature is 0 ℃ to room temperature.
The synthesis method of I as described above, wherein the appropriate conditions further comprise reacting cycloicaritin: the mole ratio of the brominating reagent is 1:1-1:8, and the cycloicaritin: the molar ratio of the alcohol reagent is 1:1-1: 100.
furthermore, the invention also provides the application of the 6-bromo-cycloicaritin chromane 3, 4-dione derivative in preparing antitumor drugs. Preferably, the application of the composition in preparing two antitumor drugs of human liver cancer and human breast cancer is specific.
The invention has the beneficial effects that: raw materials, reagents and solvents adopted in the synthesis method are cheap and easy to obtain; the synthesis method has mild conditions and is easy to implement and operate. The 6-bromo-icaritin chroman 3, 4-dione derivative synthesized by the invention has a good inhibition effect on HepG2 and MCF-7 tumor cells.
Detailed Description
The following is a further detailed description of the embodiments:
in the examples below, unless otherwise indicated, the test methods described are generally carried out under conventional conditions or conditions recommended by the manufacturer; the raw materials and reagents shown are all commercially available.
EXAMPLE 1 preparation of Compounds Ia-j
(1) Preparation of 6-bromo-icaritin chromane 3, 4-dione (Ia)
Figure BDA0003807452630000031
To a round bottom flask was added cycloicaritin (50 mg,0.135 mmol) and methanol (2 mL) under nitrogen. The mixture was then cooled to 0 ℃ and NBS (48 mg,2 eq.) was added in portions. The reaction mixture was then warmed to room temperature and stirred for 4 hours. After disappearance of starting material, the reaction solvent was concentrated under reduced pressure as detected by TLC. The remainder is added with CH 2 Cl 2 (10 mL) and water (2 mL) to dilute the mixture. The organic phase was separated by extraction and dried over magnesium sulfate. Petroleum ether was used: ethyl acetate = 6: the residue was purified by chromatography on a column with an eluent to give the title compound Ia in 65% yield as a pale yellow solid. M.p.149.5-150.2 ℃, R f =0.34 (petroleum ether: ethyl acetate=2:1). 1 H NMR(400MHz,CDCl 3 )δ＝11.30(s,1H),7.67(dd,J＝18.7,8.7Hz,2H),6.98(dd,J＝14.6,8.8Hz,2H),4.71(d,J＝49.1Hz,1H),3.84(dd,J＝4.3,1.4Hz,3H),3.06(s,1H),3.01(s,3H),2.89–2.77(m,1H),2.71–2.63(m,1H),1.87(q,J＝6.9Hz,2H),1.42(s,6H)。 13 C NMR(100MHz,CDCl 3 ) Delta: 192.33,160.39,160.10,157.44,154.08,129.97,129.76,125.16,113.80,113.31,106.12,102.97,99.77,92.87,55.26,50.51,50.11,31.59,27.27,26.36,16.41.HRMS-ESI (m/z) of formula C 22 H 21 BrO 7 Na，[M+Na] + Calculate value 499.0363 and measure value 499.0362.
(2) Preparation of Compound Ib
Figure BDA0003807452630000032
Referring to the above synthesis, ethanol was used as the reagent and solvent to give compound Ib in 67% yield as a pale yellow solid. M.p.153.5-154 ℃, R f =0.45 (petroleum ether: ethyl acetate=2:1), 1 H NMR(400MHz,CDCl 3 )δ＝11.31(s,1H),7.68(dd,J＝18.4,8.8Hz,2H),7.02–6.90(m,2H),3.84(d,J＝5.2Hz,3H),3.43–3.32(m,1H),3.24–3.10(m,1H),3.01(s,1H),2.81(ddt,J＝16.8,8.2,6.4Hz,1H),2.63(dq,J＝17.4,6.1Hz,1H),1.87(dt,J＝13.3,6.5Hz,1H),1.46–1.34(m,6H),0.97(dt,J＝11.6,7.1Hz,3H)。 13 C NMR(100MHz,CDCl 3 ) δ= 191.47,160.77,160.14,157.58,154.25,129.82,124.71,113.70,106.37,102.93,99.64,91.93,89.76,59.72,55.34,31.56,27.24,26.31,16.46,14.98.HRMS-ESI (m/z) of formula C 23 H 23 BrO 7 Na，[M+Na] + Calculate value 513.0519 and measure value 513.0519.
(3) Preparation of Compound Ic
Figure BDA0003807452630000041
Referring to the above synthesis, propanol was used as the reagent and solvent to give compound Ic in 61% yield as pale yellow solid, M.p.163-164 ℃, R f =0.5 (petroleum ether: ethyl acetate=2:1). 1 H NMR(400MHz,CDCl 3 )δ11.31(s,1H),7.69(d,J＝8.7Hz,2H),6.98(d,J＝8.6Hz,2H),3.84(s,3H),3.31(dt,J＝9.3,6.6Hz,1H),3.06(dt,J＝9.3,6.8Hz,1H),2.78(q,J＝3.6,2.9Hz,1H),2.70–2.61(m,1H),1.89–1.79(m,2H),1.41(d,J＝2.5Hz,6H),1.36(qd,J＝6.8,2.0Hz,2H),0.63(t,J＝7.4Hz,3H)。 13 C NMR(100MHz,CDCl 3 ) Delta 191.48,160.77,160.12,157.57,154.25,129.89,124.57,113.69,106.14,103.00,99.65,91.90,89.80,65.56,55.34,31.57,27.18,26.33,22.55,16.50,10.45.HRMS-ESI (m/z) of formula C 24 H 25 BrO 7 K[M+K] + Calculate value 543.0415 and measure value 543.0821.
(4) Preparation of Compound Id
Figure BDA0003807452630000042
Referring to the above synthesis method, isopropanol is used as a reaction reagent and a solvent to obtain a compound Id with a yield of 54%, a pale yellow solid, M.p.186.5-188 ℃, R f =0.34 (petroleum ether: ethyl acetate=2:1). 1 H NMR(400MHz,CDCl 3 )δ＝11.28(s,1H),7.79(d,J＝8.8Hz,2H),6.98(d,J＝8.9Hz,2H),3.85(s,3H),3.82(d,J＝4.6Hz,1H),2.87–2.80(m,1H),2.72–2.65(m,1H),1.90–1.85(m,1H),1.81(d,J＝7.3Hz,1H),1.41(d,J＝11.8Hz,6H),1.02(d,J＝6.2Hz,3H),0.75(d,J＝6.2Hz,3H). 13 C NMR(100MHz,CDCl 3 ) Delta = 160.91,160.29,157.67,154.86,130.40,125.46,106.83,102.84,99.54,91.84,90.01,26.97,26.76,23.86,22.94,16.99.hrms-ESI (m/z): molecular formula C 24 H 25 BrO 7 Na，[M+Na] + Calculate value 527.0676 and measure value 527.0675.
(5) Preparation of Compound Ie
Figure BDA0003807452630000043
Referring to the above synthesis method, n-butyl alcohol is used as a reaction reagent and a solvent to obtain a compound Ie with a yield of 60%, a pale yellow solid, M.p.158.5-160 ℃, R f =0.36 (petroleum ether: ethyl acetate=2:1). 1 H NMR(400MHz,CDCl 3 )δ11.31(s,1H),7.70(d,J＝8.5Hz,2H),6.99(d,J＝8.5Hz,2H),3.84(d,J＝8.6Hz,3H),3.34(dd,J＝9.5,6.6Hz,1H),3.16–3.10(m,1H),2.84–2.77(m,1H),2.68–2.63(m,1H),1.86(q,J＝6.8,6.4Hz,1H),1.83–1.77(m,1H),1.41(s,6H),1.35–1.29(m,2H),1.12–1.03(m,2H),0.70(t,J＝7.4Hz,3H)。 13 C NMR(100MHz,CDCl 3 ) Delta 191.45,160.79,160.12,157.57,154.23,129.87,128.91,124.54,113.98,113.71,106.16,102.96,99.63,91.90,89.79,63.61,55.34,31.59,31.27,27.13,26.37,19.02,16.51,13.60.HRMS-ESI (m/z) of formula C 25 H 27 BrO 7 Na，[M+Na] + Calculate value 541.0832 and measure value 541.0832.
(6) Preparation of Compound If
Figure BDA0003807452630000051
Referring to the above synthesis method, n-amyl alcohol is used as a reaction reagent and a solvent to obtain a compound If, the yield is 50 percent, the compound is a pale yellow solid, M.p.121-123 ℃, R f =0.48 (petroleum ether: ethyl acetate=2:1), 1 H NMR(400MHz,CDCl 3 )δ11.31(s,1H),7.68(d,J＝8.8Hz,2H),6.98(d,J＝8.9Hz,2H),3.84(s,3H),3.33(dd,J＝9.5,6.4Hz,1H),3.11(dt,J＝9.4,6.8Hz,1H),2.83–2.76(m,1H),2.69–2.62(m,1H),1.90–1.77(m,2H),1.41(s,6H),1.37–1.31(m,2H),1.07(ddd,J＝13.0,7.9,5.0Hz,2H),1.03–0.96(m,2H),0.71(t,J＝7.1Hz,3H). 13 C NMR(100MHz,CDCl 3 ) Delta = 191.65,160.70,160.09,157.55,154.25,129.89,124.57,113.64,106.17,103.03,99.70,91.88,89.88,78.07,63.78,55.32,31.58,28.89,28.02,27.12,26.42,22.15,16.51,13.94.hrms-ESI (m/z) molecular formula C 26 H 29 BrO 7 Na，[M+Na] + Calculate value 555.0989 and measure value 555.0988.
(7) Preparation of Compound Ig
Figure BDA0003807452630000052
Referring to the above synthesis method, 3-methyl-1-butanol is used as a reaction reagent and a solvent to obtain a compound Ig with a yield of 55%, a pale yellow solid, M.p.108-110 ℃, R f =0.56 (petroleum ether: ethyl acetate=2:1). 1 H NMR(400MHz,CDCl 3 )δ11.30(s,1H),7.68(d,J＝8.5Hz,2H),6.98(d,J＝8.6Hz,2H),3.84(s,3H),3.37–3.30(m,1H),3.20–3.13(m,1H),2.86–2.77(m,2H),2.69–2.61(m,1H),1.90–1.84(m,1H),1.83–1.76(m,1H),1.40(s,6H),1.22(d,J＝7.4Hz,2H),0.69(d,J＝6.6Hz,3H),0.61(d,J＝6.6Hz,3H). 13 C NMR(100MHz,CDCl 3 ) Delta 191.52,160.76,160.11,157.56,154.22,129.86,124.54,113.70,106.18,102.95,99.63,91.90,89.81,62.19,55.34,38.00,31.59,27.05,26.89,26.44,24.68,22.49,22.04,16.53.HRMS-ESI (m/z) of formula C 26 H 29 BrO 7 Na，[M+Na] + Calculate value 555.0989 and measure value 555.0988.
(3) Preparation of Compound Ih
Figure BDA0003807452630000061
Referring to the above synthesis method, benzyl alcohol is used as a reaction reagent and a solvent to obtain a compound Ih with a yield of 35%, a pale yellow solid, M.p.98-100deg.C, R f =0.38 (petroleum ether: ethyl acetate=2:1). 1 H NMR(400MHz,CDCl 3 )δ＝11.32(s,1H),7.78(d,J＝8.9Hz,2H),7.17(dd,J＝4.9,1.8Hz,3H),7.02(d,J＝8.9Hz,2H),6.97(q,J＝2.9,2.3Hz,2H),4.46(d,J＝12.1Hz,1H),4.24(d,J＝12.2Hz,1H),3.86(d,J＝5.3Hz,3H),2.73(ddd,J＝14.9,8.6,6.3Hz,2H),2.53–2.46(m,1H),1.83–1.77(m,1H),1.36(d,J＝3.5Hz,6H). 13 C NMR(100MHz,CDCl 3 ) Delta: 160.35,157.75,128.37,127.72,114.03,103.21,31.61,29.84,16.53.HRMS-ESI (m/z) of formula C 28 H 25 BrO 7 Na，[M+Na] + Calculate value 575.0676 and measure value 575.0675.
Example 2 6-test of antitumor Activity of bromocycloicaritin chromane 3, 4-dione
Cell lines and solvents were used: human hepatoma cell HepG2; human breast cancer cell MCF-7; tumor cells were cultured in DMEM medium containing 10% fetal bovine serum; the solvent is dimethyl sulfoxide (DMSO for short).
Embodiment of CCK-8 staining method for detection of cell anti-tumor Activity: cells in logarithmic growth phase were taken and tested. Cells were digested, counted, prepared into cell suspensions, seeded in 96-well plates (100. Mu.L/well), placed at 37℃in 5% CO 2 Culturing in an incubator for 24 hours; adding a test substance with corresponding concentration into each hole, and simultaneously setting a negative control group and a blank group, wherein each 5 holes are formed; after plates were placed in an incubator for 72 hours, the morphology of each group of cells was observed under a microscope, 10. Mu.L of CCK-8 solution was added to each well, incubation was continued in the incubator for 4 hours, absorbance was measured at 450nm, and the inhibition of cells was calculated. Setting concentration gradient to obtain IC 50 Values (. Mu.M) and experimental results are detailed in Table 1.
Table 16 inhibition ratio and IC of bromocycloicaritin chromane 3, 4-dione Ia-h on tumor cells 50 Value (mu M)
Figure BDA0003807452630000071
From the experimental results in Table 1, the 6-bromo-cycloicaritin chromane 3, 4-dione which is designed and synthesized by the invention and shown in the formula I has good anti-tumor effect on human liver cancer and human breast cancer. The novel derivatives of the compounds can be used for preparing antitumor drugs, in particular to the preparation of drugs for liver cancer and breast cancer.
The foregoing is merely exemplary embodiments of the present invention, and specific structures and features that are well known in the art are not described in detail herein. It should be noted that modifications and improvements can be made by those skilled in the art without departing from the structure of the present invention, and these should also be considered as the scope of the present invention, which does not affect the effect of the implementation of the present invention and the utility of the patent. The protection scope of the present application shall be subject to the content of the claims, and the description of the specific embodiments and the like in the specification can be used for explaining the content of the claims.

Claims (9)

  1. The 1, 6-bromo-cycloicaritin chromane 3, 4-diketone derivative is characterized in that the structural formula is shown in a formula I,
    Figure QLYQS_1
    ；
    wherein R is selected from saturated alkyl or benzyl of C1-C5.
  2. 2. The synthetic method of the 6-bromo-cycloicaritin chroman 3, 4-diketone derivative I according to claim 1, wherein the synthetic route is as follows:
    Figure QLYQS_2
    ；
    the method comprises the following steps: the method is characterized in that the cycloicaritin is used as a raw material, and reacts with a brominating reagent under proper alcohol reagent and under proper conditions to obtain the 6-bromo cycloicaritin chroman 3, 4-diketone derivative I.
  3. 3. The synthesis method according to claim 2, characterized in that: the brominating reagent is selected from NBS, br 2 、HBr、NaBr/H 2 O 2 NBS/AIBN or alpha, beta-dibromocinnamic acid.
  4. 4. The synthesis method according to claim 2, characterized in that: suitable conditions include a reaction time of 1 to 48 hours and a reaction temperature of 0℃to the reflux temperature of the alcohol reagent used.
  5. 5. The synthesis method according to claim 2, characterized in that: suitable conditions include in-reaction cycloicaritin: the mole ratio of the brominating reagent is 1:1-1:8, and the cycloicaritin: the molar ratio of the alcohol reagent is 1:1-1: 100.
  6. 6. the synthetic method according to any one of claims 2 to 5, wherein: the brominating reagent is selected from NBS.
  7. 7. The method of synthesis according to claim 6, wherein: suitable alcohols are selected from the group consisting of C1-C5 saturated alkyl alcohols and benzyl alcohols.
  8. 8. The method of synthesis according to claim 7, wherein: suitable conditions include a reaction time of 2 to 6 hours and a reaction temperature of 0℃to room temperature.
  9. 9. The use of the 6-bromo-cycloicaritin chromane 3, 4-dione derivative in preparation of antitumor drugs according to claim 1.
CN202211001247.6A 2022-08-19 2022-08-19 Synthesis and anti-tumor application of 6-bromo-cycloicaritin chromane 3, 4-diketone derivative Active CN115181112B (en)

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