CN107652330B - A kind of half sandwich structure complex of iridium with anticancer activity and preparation method thereof, application - Google Patents
A kind of half sandwich structure complex of iridium with anticancer activity and preparation method thereof, application Download PDFInfo
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Abstract
The present invention relates to metal complexs, and in particular to a kind of half sandwich structure complex of iridium with anticancer activity and preparation method thereof, application belong to chemical pharmacy field, the molecular structural formula of the complex of iridium is as follows:.The anion ligand that the present invention selects P^O to chelate as two teeth, the complex of iridium of synthesis are half sandwich structure, have high anti-cancer activity, and Small side effects are high to the inhibiting rate of cervical cancer cell (HeLa) growth；Preparation method simple process provided by the invention, the advantages that low in cost, chemical constituent is easily controllable, reproducible and yield is high；The introducing of [P, O] neutral ligand of the invention makes this complex have high anti-cancer activity, provides a kind of new Research Thinking for the study on the synthesis of subsequent anticancer drug ligand.
Description
Technical field
The present invention relates to metal complexs, and in particular to a kind of half sandwich structure complex of iridium with anticancer activity and
Preparation method belongs to chemical pharmacy field.
Background technique
The nineteen sixty-five breakthrough cis-platinum that synthesized revolutionizes the status for only carrying out treating cancer by chemotherapy, and many cis-platinums spread out
Biology has also been carried out biological evaluation.However, only had approved in global range three kinds of platinum class anticarcinogens (cis-platinum, carboplatin and
Oxaliplatin), and be the whole world uniquely anticarcinogen used in clinic based on metal.Metal complex is for all swollen
About 50% treatment of tumor, but their use is often with toxic side effect, such as renal toxicity, it is main about platinum-containing anticancer drug
A restrictive condition be by cellule molecule (especially glutathione) inactivate and cell can be flowed out.Overcome these cis-platinums
Limitation is a really challenge in pharmacy research, and the strategy for opening up new channel is sought more and more using other than platinum
Metal complex.Based on the chemical differences between metal, the spectrum action of molecular mechanism and potential indication can be significantly
Expand, thus the problem of maximizing the influence to cancer cell and minimizing it adverse side effect.Therefore, research transition is golden extensively
Drug is belonged to become current development trend to anti-malignant tumor.
Liu Zhe, Peter J. Saler etc. have found pentamethylcyclopentadiene base IrIIIOrganometallic complex is as novel anti-
The active complex of cancer can be used as potential anticancer drug (Acc. Chem. Res.2014,47,1174 1185).Mesh
Preceding synthesized pentamethylcyclopentadiene base IrIIIOrganometallic complex is mostly the complex of iridium of N^N, C^C or C^N ligand.
In the prior art, P^O ligand is chiefly used in synthesizing metallic catalyst and apply as the significant unsymmetric ligand of a trans-effect
In catalysis organic reaction and polymerization.It is expected that chemically therapy obtains preferably development in terms for the treatment of tumour, this just needs to continue
The novel metal anticancer drug with different role mechanism is studied, to improve or supplement the performance of existing platinum medicine.
Summary of the invention
In view of the problems of the existing technology, the present invention provides a kind of, and the half sandwich structure iridium with anticancer activity is matched
Object is closed, the complex anticancer activity is high.
The preparation method of the present invention also provides a kind of half sandwich structure complex of iridium with anticancer activity, this method
Simple process, low in cost, yield height.
The present invention also provides a kind of application of half sandwich structure complex of iridium in anticancer drug.
The present invention to achieve the goals above used by technical solution are as follows:
The present invention provides a kind of half sandwich structure complex of iridium with anticancer activity, the molecule knot of the complex of iridium
Structure formula is as shown in the formula (I):
The R1Selected from hydrogen, aryl, alkyl, naphthenic base, halogen or halogenated alkyl, halogenated cycloalkyl, halogenated aryl；R2、R3
It is independently from each other C7~C30Substituted aryl, X be selected from phenyl or naphthyl；
When the X is phenyl, the molecular structural formula of the complex of iridium are as follows:
When the X is naphthalene, the molecular structural formula of the complex of iridium are as follows:
。
Further, in the formula (I), the substituent group in substituted aryl on aryl is C1~C12Alkoxy.
Further, in the formula (I), R1For methyl, R2、R3For cyclohexyl, X is phenyl, concrete structure formula such as formula 1
It is shown；In the formula (I), R1For phenyl, R2、R3For cyclohexyl, X is phenyl, and concrete structure formula is as shown in Equation 2；The formula
(I) in, R1For xenyl, R2、R3For cyclohexyl, X is phenyl, and concrete structure formula is as shown in Equation 3；In the formula (I), R1
For methyl, R2、R3For cyclohexyl, X is naphthalene, and concrete structure formula is as shown in Equation 4.
。
The preparation method of the present invention also provides a kind of half sandwich structure complex of iridium with anticancer activity, including with
Lower step: by iridium dimer shown in formula (III), formula (IV) and Na2CO3It is placed in container, makees solvent with methylene chloride, at room temperature
For 24 hours, filtering, filtrate is threaded to 1-2mL with Rotary Evaporators for stirring, and recrystallization purification obtains complex shown in formula (I)；It is specific to close
It is as follows at route；
(1) iridium dimer shown in formula (III) reacts to obtain complex shown in formula (I) with formula (IV):
When the X is phenyl, the structural formula of formula (IV) are as follows:
；
When the X is naphthalene, the structural formula of formula (IV) are as follows:
。
Further, it when the complex is formula 1, is prepared by the following method: by 48.0mg iridium dimer (formula
(III) R1=methyl), 42.5mg 2-(dicyclohexyl phosphino-) benzene sulfonic acid and 25.4mg Na2CO3It is placed in 50mL round-bottomed flask,
The analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate is threaded to 1-2mL with Rotary Evaporators, is transferred to reagent
In bottle, it is slowly added to 10mL n-hexane along bottle wall, makes to be layered, be recrystallized with diffusion method, obtain yellow crystals.
Further, it when the complex is formula 2, is prepared by the following method: by 46.0mg iridium dimer (formula
(III) R1=phenyl), 35.4 mg 2-(dicyclohexyl phosphino-s) benzene sulfonic acid and 21.2mg Na2CO3It is placed in 50mL round-bottomed flask,
The analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate is threaded to 1-2mL with Rotary Evaporators, is transferred to reagent
In bottle, it is slowly added to 10mL n-hexane along bottle wall, makes to be layered, be recrystallized with diffusion method, obtains Chinese red crystal.
Further, it when the complex is formula 3, is prepared by the following method: by 34.9mg iridium dimer (formula
(III) R1=xenyl), 23.1mg 2-(dicyclohexyl phosphino-) benzene sulfonic acid and 13.8mg Na2CO3It is placed in 50mL round-bottomed flask
In, the analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate is threaded to 1-2mL with Rotary Evaporators, is transferred to
In reagent bottle, it is slowly added to 10mL n-hexane along bottle wall, makes to be layered, be recrystallized with diffusion method, obtain orange crystals.
Further, it when the complex is formula 4, is prepared by the following method: by 48.0mg iridium dimer (formula
(III) R1=methyl), 48.5mg 2-(dicyclohexyl phosphino-) naphthalene -1- sulfonic acid and 25.4mg Na2CO3It is placed in 50mL round-bottomed flask
In, the analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate is threaded to 1-2mL with Rotary Evaporators, is transferred to
In reagent bottle, it is slowly added to 10mL n-hexane along bottle wall, makes to be layered, be recrystallized with diffusion method, obtain yellow solid.
The present invention also provides a kind of half sandwich structure complex of iridium prepared by the above method in anticancer drug
Application.
The invention has the benefit that
(1) anion ligand that the present invention selects P^O to chelate as two teeth, the complex of iridium of synthesis are half sandwich knot
Structure, has high anti-cancer activity, and Small side effects are high to the inhibiting rate of cervical cancer cell (HeLa) growth.
(2) preparation method simple process provided by the invention, low in cost, chemical constituent is easily controllable, it is reproducible simultaneously
The advantages that yield is high.
(3) introducing of [P, O] neutral ligand of the invention makes this complex have high anti-cancer activity, matches for subsequent anticancer drug
The study on the synthesis of body provides a kind of new Research Thinking.
Detailed description of the invention
Fig. 1 is the mono-crystalline structures of complex prepared by embodiment 1.
Fig. 2 is the nucleus magnetic hydrogen spectrum of complex prepared by embodiment 1.
Fig. 3 is the nuclear-magnetism phosphorus spectrum of complex prepared by embodiment 1.
Fig. 4 is the nuclear-magnetism carbon spectrum of complex prepared by embodiment 1.
Fig. 5 is the mass spectrum of complex prepared by embodiment 1.
Fig. 6 is the mono-crystalline structures of complex prepared by embodiment 2.
Fig. 7 is the nucleus magnetic hydrogen spectrum of complex prepared by embodiment 2.
Fig. 8 is the nuclear-magnetism phosphorus spectrum of complex prepared by embodiment 2.
Fig. 9 is the nuclear-magnetism carbon spectrum of complex prepared by embodiment 2.
Figure 10 is the mass spectrum of complex prepared by embodiment 2.
Figure 11 is the mono-crystalline structures of complex prepared by embodiment 3.
Figure 12 is the nucleus magnetic hydrogen spectrum of complex prepared by embodiment 3.
Figure 13 is the nuclear-magnetism phosphorus spectrum of complex prepared by embodiment 3.
Figure 14 is the nuclear-magnetism carbon spectrum of complex prepared by embodiment 3.
Figure 15 is the mass spectrum of complex prepared by embodiment 3.
Figure 16 is the nucleus magnetic hydrogen spectrum of complex prepared by embodiment 4.
Figure 17 is the mass spectrum of complex prepared by embodiment 4.
Specific embodiment
The present invention is further described by the embodiment of following some representative compounds, but these explanations are not intended to limit
The present invention.
Initial compounds used are commercial prods or can prepare from known synthetic method, institute in the synthesis of compound
Having the preparation method of organic compound can obtain from document, and these methods are basic and aobvious and easy to synthesis chemist
See.Therefore, the description of following synthetic method is regarded as detailed and specific.
Embodiment 1
By 48.0mg iridium dimer (formula (III) R1=methyl), 42.5mg 2-(dicyclohexyl phosphino-) benzene sulfonic acid and
25.4mg Na2CO3It is placed in 50mL round-bottomed flask, the analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate
It is threaded to 1-2mL with Rotary Evaporators, is transferred in reagent bottle, 10mL n-hexane is slowly added to along bottle wall, makes to be layered, use diffusion method
Recrystallization, obtains yellow crystals, yield 73.0mg (84.9%), and the mono-crystalline structures of the complex are as shown in Figure 1.
Spectrogram is as Figure 2-Figure 5: nuclear-magnetism characterization are as follows:1H NMR (500 MHz, CDCl3): δ 8.18 (dd, J =
7.6,2.8 Hz, 1H, aryl-H), 7.49 (dt, J=22.7,7.4 Hz, 2H, aryl-H), 7.38 (t, J
=7.5 Hz, 1H, aryl-H), 3.06 (s, 1H, Cy-CH), 2.46 – 2.38 (m, 1H, Cy-CH), 2.33
(s, 1H, Cy-CH2), 2.23 – 1.57 (m, 4H, Cy-CH2; 15H, -CH3), 1.56 – 1.04 (m, 15H,
Cy-CH2). 31P NMR (202 MHz, CDCl3): δ 0.88.13C NMR (151 MHz, CDCl3): δ 130.83,
130.29, 129.16, 91.66, 65.96, 36.50, 31.69, 29.18, 27.84, 27.77, 27.68,
27.58, 27.49, 27.43, 27.34, 26.21, 26.07, 15.39, 9.32, 0.11. ESI-MS (m/z):
C28H41ClIrO3PS: theoretical value: 681.214, actually measured 681.215, [M].
Embodiment 2
By 46.0mg iridium dimer (formula (III) R1=phenyl), 35.4 mg 2-(dicyclohexyl phosphino-s) benzene sulfonic acid and
21.2mg Na2CO3It is placed in 50mL round-bottomed flask, the analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate
It is threaded to 1-2mL with Rotary Evaporators, is transferred in reagent bottle, 10mL n-hexane is slowly added to along bottle wall, makes to be layered, use diffusion method
Recrystallization, obtain Chinese red crystal, yield: 66.1mg (85.0%), the mono-crystalline structures of the complex are as shown in Figure 6.
Spectrogram is as shown in Fig. 7-Figure 10: nuclear-magnetism characterization are as follows:1H NMR (500 MHz, CDCl3): δ 8.18 (dd,J =
7.6,3.2 Hz, 1H, aryl-H), 7.61 (dd, J=6.5,3.0 Hz, 2H, aryl-H), 7.54 (t, J
=7.6 Hz, 1H, aryl-H), 7.45 (dd, J=13.3,5.7 Hz, 1H, aryl-H), 7.42 – 7.29
(m, 4H, aryl-H), 2.90 (s, 1H, Cy-CH), 2.37 (d, J = 27.0 Hz, 1H, Cy-CH), 2.22
(s, 1H, Cy-CH2), 1.88 – 1.72 (m, 10H, Cy-CH2), 1.58 (s, 12H, -CH3), 1.33 –
0.94 (m, 9H, Cy-CH2).31P NMR (202 MHz, CDCl3):δ 4.81. 13C NMR (151 MHz, CDCl3):
δ 131.14, 131.07, 130.54, 130.14, 129.01, 128.75, 128.48, 104.70, 104.66,
27.65, 27.56, 27.38, 27.34, 27.30, 27.25, 25.84, 25.77, 11.71, 9.64, 9.16,
0.11. ESI-MS (m/z): C33H43ClIrO3PS: theoretical value: 743.230, actually measured 743.230, [M].
Embodiment 3
By 34.9mg iridium dimer (formula (III) R1=xenyl), 23.1mg 2-(dicyclohexyl phosphino-) benzene sulfonic acid and
13.8mg Na2CO3It is placed in 50mL round-bottomed flask, the analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate
It is threaded to 1-2mL with Rotary Evaporators, is transferred in reagent bottle, 10mL n-hexane is slowly added to along bottle wall, makes to be layered, use diffusion method
Recrystallization, obtains orange crystals, yield 44.5mg (80.2%), and the mono-crystalline structures of the complex are as shown in figure 11.
Spectrogram is as shown in Figure 12-Figure 15: nuclear-magnetism characterization are as follows:1H NMR (500 MHz, CDCl3): δ 8.19 (dd,J =
7.8,3.0 Hz, 1H, aryl-H), 7.69 (d, J=8.2 Hz, 2H, aryl-H), 7.66 – 7.57 (m,
4H, aryl-H), 7.54 (t, J=7.6 Hz, 1H, aryl-H), 7.46 (t, J=7.6 Hz, 3H, aryl-H), 7.42-7.34 (m, 2H, aryl-H), 2.91 (s, 1H, Cy-CH), 2.37 (s, 1H, Cy-CH),
2.23 (s, 1H, Cy-CH2), 1.98 – 1.48 (m, 12H, Cy-CH2；12H, -CH3), 1.24 – 0.95 (m,
7H, Cy-CH2).31P NMR (202 MHz, CDCl3):δ 4.87.13C NMR (151 MHz, CDCl3):δ 141.22,
140.55, 131.08, 130.55, 130.20, 129.05, 127.76, 127.40, 127.09, 104.79,
104.75, 65.97, 53.57, 35.88, 28.98, 27.65, 27.56, 27.36, 27.34, 27.29, 27.25,
25.85, 25.73, 15.40, 11.79, 11.76, 9.75, 9.18, 0.11. ESI-MS (m/z):
C39H47ClIrO3PS: theoretical value: 819.261, actually measured 818.578, [M].
Embodiment 4
By 48.0mg iridium dimer (formula (III) R1=methyl), 48.5mg 2-(dicyclohexyl phosphino-) naphthalene -1- sulfonic acid and
25.4mg Na2CO3It is placed in 50mL round-bottomed flask, the analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate
It is threaded to 1-2mL with Rotary Evaporators, is transferred in reagent bottle, 10mL n-hexane is slowly added to along bottle wall, makes to be layered, use diffusion method
Recrystallization, obtains yellow solid, yield 56.9mg (61.8%).
Spectrogram is as shown in Figure 16-Figure 17: nuclear-magnetism characterization are as follows:1H NMR (500 MHz, CDCl3): δ 9.14 (d,J =
8.7 Hz, 1H, aryl-H), 7.92 (d, J=8.8 Hz, 1H, aryl-H), 7.80 (d, J=8.1 Hz, 1H,
Aryl-H), 7.66-7.58 (m, 1H, aryl-H), 7.54 (t, J=7.4 Hz, 1H, aryl-H), 7.49 –
7.42 (m, 1H, aryl-H), 3.15 (s, 1H, Cy-CH2), 2.39 (s, 2H, Cy-CH), 2.10 (s, 2H, Cy-
CH2), 1.93 (s, 2H, Cy-CH2), 1.86-1.23 (m, 15H ,-CH3; 14H, Cy-CH2), 1.15 (s,
1H, Cy-CH2). ESI-MS (m/z): C32H43ClIrO3PS: theoretical value: 731.230, actually measured 731.231,
[M].
Effect example
The proliferation inhibition activity of 1 ~ 4 pair of tumor cell line of complex with anticancer activity is tested:
(1) preparation of untested compound:
Solid complexes 1 ~ 4 are dissolved in DMSO respectively, are made into certain density stock solution, with cell culture fluid into one
Step dilution stock solution is until reaching working concentration, and culture is for 24 hours；
(2) cell growth inhibition test (mtt assay):
1) 5000 cervical cancer cells (HeLa) are taken, cell suspension is configured to, is inoculated in 96 well culture plates；
2) with no medicine culture medium pre-cultured cell, 5%CO2, 310K be incubated for 24 hours, prepared test compounds are added
Object cultivates 24 h；
3) the MTT solution of 15 μ L, 5 mg/mL is added in every hole, continues culture 4 hours, forms purple crystal substance first a ceremonial jade-ladle, used in libation；
4) culture is terminated, culture solution in hole is carefully sucked, the DMSO that 100 μ L are added in every hole sufficiently dissolves first a ceremonial jade-ladle, used in libation precipitating, vibration
After swinging device mixing, the microplate reader OD value that wavelength is that 570nm measures each hole；
5) each to test in triplicate, IC50 =average value ± SEM
Complex 1 ~ 4, iridium dimer, 2-(dicyclohexyl phosphino-) benzene sulfonic acid and cis-platinum be raw to cervical cancer cell (HeLa)
Long inhibiting rate is shown in Table 1.
Table 1
From table 1 it follows that ligand i C50> 100 μM of value, show activity, complex 1 ~ 4 do not show extraordinary anti-
Cancer activity, in addition to the anticancer activity of complex 1 maintains an equal level with commercialized cis-platinum anticarcinogen substantially, other complexs are superior to suitable
Platinum, the activity of especially complex 4 are cis-platinums more than 6 times.In addition, anticancer activity also changes with the change of substituent group,
Work as R1From methyl become phenyl again to xenyl when, anticancer activity increases；When by R2、R3When the cyclohexyl of position changes into phenyl,
Anticancer activity increases；When the phenyl connecting with phosphorus, sulphur atom is changed to naphthalene, anticancer activity also increases.This illustrates substituent group
Modification anticancer activity can be produced a very large impact.
Claims (7)
1. a kind of half sandwich structure complex of iridium with anticancer activity, which is characterized in that the molecular structure of the complex of iridium
Formula is as shown in the formula (I):
In the formula (I), R1For methyl, R2、R3For cyclohexyl, X is phenyl, and concrete structure formula is as shown in Equation 1；The formula
(I) in, R1For phenyl, R2、R3For cyclohexyl, X is phenyl, and concrete structure formula is as shown in Equation 2；In the formula (I), R1For
Xenyl, R2、R3For cyclohexyl, X is phenyl, and concrete structure formula is as shown in Equation 3；In the formula (I), R1For methyl, R2、R3
For cyclohexyl, X is naphthalene, and concrete structure formula is as shown in Equation 4；
。
2. a kind of preparation method of half sandwich structure complex of iridium as described in claim 1, which is characterized in that including following
Step: by iridium dimer shown in formula (III), formula (IV) and Na2CO3It is placed in container, makees solvent with methylene chloride, stir at room temperature
It mixes for 24 hours, filtering, filtrate is threaded to 1-2mL with Rotary Evaporators, and recrystallization purification obtains complex shown in formula (I), specific to synthesize
Route is as follows:
(1) iridium dimer shown in formula (III) reacts to obtain complex shown in formula (I) with formula (IV):
(III) (IV) (I)
When the X is phenyl, the structural formula of formula (IV) are as follows:
；
When the X is naphthalene, the structural formula of formula (IV) are as follows:
。
3. preparation method according to claim 2, which is characterized in that when the complex is formula 1, make by the following method
It is standby to form: by 48.0mg formula (III) R1The iridium dimer of=methyl, 42.5mg 2-(dicyclohexyl phosphino-) benzene sulfonic acid and 25.4mg
Na2CO3It is placed in 50mL round-bottomed flask, the analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate rotation
Evaporimeter is threaded to 1-2mL, is transferred in reagent bottle, is slowly added to 10mL n-hexane along bottle wall, makes to be layered, and is tied again with diffusion method
Crystalline substance obtains yellow crystals.
4. preparation method according to claim 2, which is characterized in that when the complex is formula 2, make by the following method
It is standby to form: by 46.0mg formula (III) R1The iridium dimer of=phenyl, 35.4 mg 2-(dicyclohexyl phosphino-s) benzene sulfonic acid and
21.2mg Na2CO3It is placed in 50mL round-bottomed flask, the analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate
It is threaded to 1-2mL with Rotary Evaporators, is transferred in reagent bottle, 10mL n-hexane is slowly added to along bottle wall, makes to be layered, use diffusion method
Recrystallization, obtains Chinese red crystal.
5. preparation method according to claim 2, which is characterized in that when the complex is formula 3, make by the following method
It is standby to form: by 34.9mg formula (III) R1The iridium dimer of=xenyl, 23.1mg 2-(dicyclohexyl phosphino-) benzene sulfonic acid and
13.8mg Na2CO3It is placed in 50mL round-bottomed flask, the analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate
It is threaded to 1-2mL with Rotary Evaporators, is transferred in reagent bottle, 10mL n-hexane is slowly added to along bottle wall, makes to be layered, use diffusion method
Recrystallization, obtains orange crystals.
6. preparation method according to claim 2, which is characterized in that when the complex is formula 4, make by the following method
It is standby to form: by 48.0mg formula (III) R1=methyl iridium dimer, 48.5mg 2-(dicyclohexyl phosphino-) naphthalene -1- sulfonic acid and
25.4mg Na2CO3It is placed in 50mL round-bottomed flask, the analytically pure CH of 15mL is added2Cl2, stir at room temperature for 24 hours, filtering, filtrate
It is threaded to 1-2mL with Rotary Evaporators, is transferred in reagent bottle, 10mL n-hexane is slowly added to along bottle wall, makes to be layered, use diffusion method
Recrystallization, obtains yellow solid.
7. a kind of half sandwich structure complex of iridium by any one of claim 2-6 preparation is preparing answering in anticancer drug
With.
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