CN101863925B - Aryl ruthenium (11) composition and preparation method and application thereof - Google Patents
Aryl ruthenium (11) composition and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an aryl ruthenium (II) composition and preparation method and application thereof. In the structural formula (I) of the aryl ruthenium (II) composition, R is chosen from H, C1 to C6 alkyl or alkyl substituent, phenyl or phenyl substituent, pyridyl or pyridyl substituent, furyl or furyl substituent, pyrrolyl or pyrrolyl substituent and thiazole or thiazole substituent. R1, R2, R3, R4, R5 and R6 are independently chosen from H, C2 to C6 alkenyl, C2 to C6 alkynyl, oxhydryl C1 to C6 alkyl, amido C1 to C6 alkyl, halogen, CO2R7, CONR8R9, COR10, SO3H, SO2R11R12, aryloxy, C1 to C6 alkoxy, C1 to C6 alkylthio, -N=NR13,NR14R15, aryl or aralkyl. The aryl ruthenium(II) composition can be used to prepare tumor medicine, has good inhibitory action particularly on lung adenocarcinoma and has potential great value in terms of tumor disease clinical treatment application. The formula (I).
Description
Technical field
The present invention relates to the preparation field of ruthenium complexe, be specifically related to a kind of ruthenium (II) title complex.
Background technology
Ruthenium complexe becomes one of hot research fields such as pharmaceutical chemistry research in recent years, chemicobiology, bio-inorganic chemistry as the research of antitumor drug.For example, people such as Clarke have summarized the antitumour activity of ruthenium complex, particularly antimetastatic activity (Chem.Rev., 1999,99,2511); Sava " Metal Compoundsin Cancer Therapy (metallic compound in the cancer therapy) " (Chapman and Hall work, S P Fricker edits, London, 1994, summarized the antimetastatic activity of ruthenium complexe in 65-91).
People such as Guo have reported some other ruthenium (II) and ruthenium (III) complex compound, particularly trans-[RuCl that shows anti-tumor activity
2(DMSO)
4], trans-[RuCl
4(imidazoles)
2]
-And trans [RuCl
4(indoles)
2]
-(Inorg.Chim.Acta, 1998,273,1); People (J.Med.Chem., 2001,44,3616) such as Chen (J.Am.Chem.Soc., 2002,124,3046) and Morris have described ruthenium complexe and the guanine base coordination compound that has two amine ligands; People such as Bennet disclose some and have had ruthenium (II) complex compound (Can.J.Chem., 2001,79,655) of acetylacetonate compound part; People such as Kramer disclose half sandwich complex compound (Chem EurJ., 1996,2,1518) of ruthenium and amino ester.
WO01/30790 discloses ruthenium (II) compound and as the application of carcinostatic agent.These compounds have neutral N-donor part, and the gained ruthenium complex has positive charge usually;
US4980473 discloses 1 of the ruthenium (II) that allegedly can be used for treating tumour cell in the individuality, 10-phenanthroline complex compound; WO02/02572 discloses has the active ruthenium of anticancer clone (II) compound.People such as Oro have described and have contained η
6The ruthenium of-p-isopropyl methane and acetylacetonate part (II) complex compound (JChem Soc, Dalton Trans, 1990,1463); People such as Dale have described the metronidazole complex compound ［ η of ruthenium (II)
6-C
6H
6RuCl
2(metronidazole)] and to the influence (Anti-Cancer DrugDesign, 1992,7,3) of E.coli growth velocity.
Summary of the invention
The objective of the invention is to research, a kind of anticancer aryl ruthenium (II) title complex that can be used for is provided according to existing ruthenium (II) title complex.
Another purpose of the present invention is to provide the preparation method of above-mentioned ruthenium (II) title complex.
A further object of the invention is to provide the application of above-mentioned ruthenium (II) title complex.
Above-mentioned purpose of the present invention is achieved through following technical scheme:
A kind of aryl ruthenium (II) title complex, its structural formula is suc as formula shown in (I):
Formula (I);
Wherein, said R is selected from H, C
1～C
6Alkyl or substituted alkyl, phenyl or substituted-phenyl, pyridyl or substituted pyridinyl, furyl or substituted furan base, pyrryl or substituted azole base, thiazole or substituted thiazolyl; Said R
1, R
2, R
3, R
4, R
5, R
6Independently be selected from H, C
2～C
6Alkenyl, C
2～C
6Alkynyl group, hydroxyl (C
1～C
6) alkyl, amino (C
1～C
6) alkyl, halogen, CO
2R
7, CONR
8R
9, COR
10, SO
3H, SO
2R
11R
12, aryloxy, C
1～C
6Alkoxyl group, C
1～C
6Alkylthio ,-N=NR
13, NR
14R
15, aryl or aralkyl; Said X is neutral or has O-, N-or the S-donor part or the halogen of negative charge; Said m is-1,0 or 1; Said R
7, R
8, R
9, R
10, R
11, R
12, R
13, R
14, R
15Independently be selected from H, C
1～C
6Alkyl, aryl or aralkyl.
As a kind of preferred version, the substituting group of said phenyl, pyridyl, furyl, thiazole is selected from hydroxyl, nitro, halogen, amino, carboxyl, cyanic acid, sulfydryl, C respectively
3～C
8Naphthenic base, SO
3H, C
1～C
6Alkyl, C
2～C
6Alkenyl, C
2～C
6Alkynyl group, hydroxyl (C
1-C
6) alkyl, amino (C
1-C
6) alkyl, CO
2R ', CONR ' R ', COR ', SO
2R ' R ', C
1～C
6Alkoxyl group, C
1～C
6Alkylthio ,-N=NR ', NR ' R ' or trifluoro (C
1-C
6) alkyl; Wherein, to be selected from H, carbonatoms be 1～6 alkyl or phenyl to said R '.
As a kind of preferred version, said R
1, R
2, R
3, R
4, R
5, R
6When independently being selected from aryl or aralkyl, optional on the aromatic ring by one or more C that independently are selected from
1～C
6Alkyl, C
2～C
6Alkenyl, C
2～C
6Alkynyl group, hydroxyl (C
1-C
6) alkyl, amino (C
1-C
6) alkyl, halogen, CO
2R
7a, CONR
8aR
9a, COR
10a, SO
3H, SO
2R
11aR
12a, aryloxy, C
1～C
6Alkoxyl group, C
1～C
6Alkylthio ,-N=N-R
13a, NR
14aR
15aGroup replace; Wherein, said R
7a, R
8a, R
9a, R
10a, R
Ua, R
12a, R
13a, R
14a, R
15aIndependently be selected from H, C
1～C
6Alkyl, aryl or aralkyl.
As a kind of preferred version, said R
1, R
2The ring that is connected is represented to contain to reach together has 3～8 yuan of carbon rings or saturated or unsaturated carbon ring of heterocyclic or heterocyclic group, wherein each carbon ring or heterocycle can with one or more other carbon rings or heterocycle thick with, and wherein each ring can choose wantonly by C
1～C
6Alkyl, C
2～C
6Alkenyl, C
2～C
6Alkynyl group, hydroxyl (C
1～C
6) alkyl, amino (C
1～C
6) alkyl, halogen, CO
2R
7b, CONR
8bR
9b, COR
10b, SO
3H, SO
2R
11bR
12b, aryloxy, C
1～C
6Alkoxyl group, C
1～C
6Alkylthio ,-N=N-R
13b, NR
14bR
15bGroup replace; Wherein, said R
7b, R
8b, R
9b, R
10b, R
11b, R
12b, R
13b, R
14b, R
15bIndependently be selected from H, C
1～C
6Alkyl, aryl or aralkyl.
As a kind of preferred version, said X is a halogen, most preferably is chlorine.
As a kind of preferred version, when said m was-1 or 1, said aryl ruthenium (II) title complex comprised counter ion, promptly in negatively charged ion or cationoid polymerisation, was respectively positive ion or negative ion.
The preparation method of aryl ruthenium according to the invention (II) title complex comprises the steps: [π-C
6H
6Rucl
2]
2Under room temperature, add methylene dichloride with part, ultrasonic back stirring reaction under argon shield, be transferred to revolve in the round-bottomed flask dried; Adding the filtration of zero(ppm) water ultrasonic dissolution; Remove with Rotary Evaporators once more afterwards and desolvate,, promptly get product end product recrystallization in methyl alcohol.Reaction is suc as formula shown in (II):
Formula (II).
The amount of said adding tetrachloromethane is preferably 40ml, and the add-on of zero(ppm) water is preferably 40ml, and the ultransonic time is preferably 0.5h, and the time of stirring reaction is preferably 4h.
Concrete steps are stated the file record as follows: R.A.Zelonka, M.C.Baird, Can.J. Chem.1972,50,3063; M.A.Bennett, A.K.Smith, J. Chem.Soc., Dalton Trans.1974,233; M.A.Bennett, T.-N.Huang, T.W.Matheson, A.K.Smith, Inorg.Synth., 1982,21,74; J.Liu, W.J.Mei, L.J.Lin, K.C.Zheng, H.Chao, F.C.Yun, L.N.Ji, Inorg.Chim.Acta, 2004,357,285; B.P.Sullivan, D.J.Salmon, T.J.Meyer, Inorg.Chem., 1978,17,3334; W.J.Mei, Y.Z.Ma, J.Liu, J.C.Chen, K.C.Zheng, L.N.Ji, J.H.Yao, Trans.Met.Chem., 2006,31,277-285; J.C.Lydia, K.Brelot, G.Suss-Fink, J. Organometa.Chem., 2005,690,3202.
Aryl ruthenium of the present invention (II) title complex shows the cytotoxic activity of anticancer clone, therefore can expect to can be used for preparing the medicine that prevents or treat cancer, kill tumor cell in external or body by the demonstration antitumour activity.
Compared with prior art, the present invention has following beneficial effect:
Aryl ruthenium of the present invention (II) title complex all shows good inhibition activity to A549 human lung adenocarcinoma cell, SMMC-7721 human liver cancer cell and SW620 human large intestine cancer clone; Especially the most obvious to the inhibition of A549 human lung adenocarcinoma cell; Therefore aryl ruthenium of the present invention (II) title complex can be used for preparing the medicine of prevention or treatment tumor disease, in the clinical treatment of tumor disease is used, has the potential immense value.
Embodiment
Come further to explain the present invention below in conjunction with embodiment, but embodiment does not do any type of qualification to the present invention.
Abbreviation submeter among the following embodiment is represented following chemical formula:
O-FPIP:2-(2-trifluoromethyl) imidazoles [4,5-f] [1,10] phenanthroline;
2-HO-4-MeOPIP:2-(2-hydroxyl-4-methoxyphenyl) imidazoles [4,5-f] [1,10] phenanthroline;
P-NPIP:2-(4-nitre phenyl) imidazoles [4,5-f] [1,10] phenanthroline;
P-CPIP:2-(4-carboxyl phenyl) imidazoles [4,5-f] [1,10] phenanthroline;
Phdt: phenanthroline 5,6-diketone;
P-ClPIP:2-(4-chloro-phenyl-) imidazoles [4,5-f] [1,10] phenanthroline;
P-HPIP:2-(4-hydroxy phenyl) imidazoles [4,5-f] [1,10] phenanthroline;
P-Me2NPIP:2-(4-dimethylamino phenyl) imidazoles [4,5-f] [1,10] phenanthroline;
M-NPIP:2-(3-nitre phenyl) imidazoles [4,5-f] [1,10] phenanthroline;
O-ClPIP:2-(2-chloro-phenyl-) imidazoles [4,5-f] [1,10] phenanthroline.
Embodiment 1 [(η 6-C6H6) Ru (o-FPIP) Cl]
+Synthetic
Initial ruthenium complex [π-C
6H
6RuCl
2]
2The method preparation that can adopt people (J.Chem.Soc., Dalton Trans., 1974,233) such as people (J.Chem.1972,50,3063) such as people such as M.A.Bennett (Inorg.Synth.1982,21,74) and R.A.Zelonka and T.-N.Huang to describe is implemented.
The synthetic of part o-FPIP can be with reference to the described preparation method of following file: J.Liu, W.J.Mei, L.J.Lin, K.C.Zheng, H.Chao, F.C.Yun, L.N.Ji, Inorg.Chim.Acta (2004,357,285); B.P.Sullivan, D.J.Salmon, T.J.Meyer, Inorg.Chem., (1978,17,3334); W.J.Mei, Y.Z.Ma, J.Liu, J.C.Chen, K.C.Zheng, L.N.Ji, J.H.Yao, Trans.Met.Chem. (2006,31,277).
With [π-C
6H
6Rucl
2]
2(0.15mmol, 75mg) with part o-FPIP (0.3mmol, 105mg) under the room temperature methylene dichloride (40ml) after ultrasonic half a hour under argon shield stirring reaction 4 hours; Be transferred to revolve in the round-bottomed flask dried; Adding the filtration of 40ml zero(ppm) water ultrasonic dissolution, removing with Rotary Evaporators once more afterwards and desolvate, end product recrystallization in methyl alcohol; Promptly get product 150mg, productive rate 86%.ESI-MS(in?MeOH，m/z)：578.50。
1H-NMR(in?DMSO-d6，δ/ppm)：6.3(s，6H，C6H6)，10.0(m，2H，phen-H)，9.7(m，2H，phen-H)，9.3(m，2H，phen-H)，8.4(dd，2H，Ar-H)，7.5(d，2H，Ar-H)
Embodiment 2 [(η
6-C
6H
6) Ru (2-HO-4-MeOPIP) Cl]
+Synthetic
Experimental technique is with embodiment 1, with part o-FPIP (0.3mmol, 105mg) change into 2-HO-4-MeOPIP (0.3mmol, 98mg), productive rate: 84%.ESI-MS(in?MeOH，m/z)：557.20。
1H-NMR(in?DMSO-d6，δ/ppm)：6.3(s，6H，C6H6)，9.9(d，2H，phen-H)，9.7(m，2H，phen-H)，8.2(d，2H，Ar-H)，8.1(m，1H，Ar-H)，7.9(m，1H，Ar-H)，7.0(d，1H，Ar-H)，4.0(s，3H，CH3)。
Embodiment 3 [(η
6-C
6H
6) Ru (p-NPIP) Cl]
+Synthetic
Experimental technique is with embodiment 1, with part o-FPIP (0.3mmol, 105mg) change into p-NPIP (0.3mmol, 102mg), productive rate: 86%.ESI-MS(in?MeOH，m/z)：556.10。
1H-NMR(in?DMSO-d6，δ/ppm)：6.3(s，6H，C6H6)，9.9(m，2H，phen-H)，9.2(m，2H，phen-H)，8.7(m，2H，phen-H)，8.4(m，2H，Ar-H)，8.1(m，2H，Ar-H)
Embodiment 4 [(η
6-C
6H
6) Ru (p-CPIP) Cl]
+Synthetic
Experimental technique is with embodiment 1, with part o-FPIP (0.3mmol, 105mg) change into p-CPIP (0.3mmol, 107mg), productive rate: 79%.ESI-MS(in?MeOH，m/z)：555.13。
1H-NMR(in?DMSO-d6，δ/ppm)：6.3(s，6H，C6H6)，9.8(m，2H，phen-H)，9.3(m，2H，phen-H)，8.4(m，2H，phen-H)，8.1(m，2H，Ar-H)，7.1(m，2H，Ar-H)。
Embodiment 5 [(η
6-C
6H
6) Ru (phdt) Cl]
+Synthetic
Experimental technique is with embodiment 1, with part part o-FPIP (0.3mmol, 105mg) change into phdt (0.3mmol, 63mg), productive rate: 85%.ESI-MS(in?MeOH，m/z)：425.20。
1H-NMR(in?DMSO-d6，δ/ppm)：6.2(s，6H，C6H6)，9.7(m，2H，phen-H)，9.5(m，2H，phen-H)，8.4(m，2H，phen-H)。
Embodiment 6 [(η
6-C
6H
6) Ru (p-ClPIP) Cl]
+Synthetic
Experimental technique is with embodiment 1, with part o-FPIP (0.3mmol, 105mg) change into p-ClPIP (0.3mmol, 66mg), productive rate: 84%.ESI-MS(in?MeOH，m/z)：435.07。
1H-NMR(in?DMSO-d6，δ/ppm)：6.3(s，6H，C6H6)，10.0(d，2H，phen-H)，9.6(d，2H，phen-H)，8.7(d，2H，phen-H)，7.7(d，1H，imidazo-H)。
Embodiment 7 [(η
6-C
6H
6) Ru (p-MeOPIP) Cl]
+Synthetic
Experimental technique is with embodiment 1, with part o-FPIP (0.3mmol, 105mg) change into p-MeOPIP (0.3mmol, 98mg), productive rate: 83%.ESI-MS(in?MeOH，m/z)：541.13。
1H-NMR(in?DMSO-d6，δ/ppm)：6.3(s，6H，C6H6)，9.8(d，2H，phen-H)，9.2(m，2H，phen-H)，8.4(m，2H，phen-H)，8.0(m，2H，Ar-H)，7.4(d，2H，Ar-H)。
Embodiment 8 [(η
6-C
6H
6) Ru (p-CFPIP) Cl]
+Synthetic
Experimental technique is with embodiment 1, with part o-FPIP (0.3mmol, 105mg) change into p-CFPIP (0.3mmol, 109mg), productive rate: 87%.ESI-MS(in?MeOH，m/z)：579.00。
1H-NMR(in?DMSO-d6，δ/ppm)：6.3(s，6H，C6H6)，9.8(d，2H，phen-H)，9.2(d，2H，phen-H)，8.6(d，2H，phen-H)，8.1(m，2H，Ar-H)，7.9(d，2H，Ar-H)。
Embodiment 9 [(η
6-C
6H
6) Ru (p-ClPIP) Cl]
+Synthetic
Experimental technique is with embodiment 1, with part o-FPIP (0.3mmol, 105mg) change into p-ClPIP (0.3mmol, 99mg), productive rate: 76%.ESI-MS(in?MeOH，m/z)545.10。
1H-NMR(in?DMSO-d6，δ/ppm)：6.3(s，6H，C6H6)，10.0(d，2H，phen-H)，8.4(m，2H，phen-H)，8.2(d，2H，phen-H)，7.7(dd，4H，Ar-H)。
Embodiment 10 [(η
6-C
6H
6) Ru (p-HPIP) Cl]
+Synthetic
Experimental technique is with embodiment 1, with part o-FPIP (0.3mmol, 105mg) change into p-HPIP (0.3mmol, 99mg), productive rate: 82%.ESI-MS(in?MeOH，m/z)：527.07。
1H-NMR(in?DMSO-d6，δ/ppm)：6.3(s，6H，C6H6)，9.9(m，2H，phen-H)，8.3(d，2H，phen-H)，8.1(d，2H，phen-H)，7.4(d，2H，Ar-H)，7.0(d，2H，Ar-H)。
Embodiment 11 [(η
6-C
6H
6) Ru (p-Me
2NPIP) Cl]
+Synthetic
Experimental technique is with embodiment 1, and (0.3mmol 105mg) changes p-Me into part o-FPIP
2NPIP (0.3mmol, 102mg), productive rate: 85%.ESI-MS(in?MeOH，m/z)：554.10。
1H-NMR(in?DMSO-d6，δ/ppm)：13.1(s，NH)，8.8(m，4H，phen-H)，8.5(dd，1H，phen-H)，8.3(dd，1H，phen-H)，7.6(m，2H，Ar-H)，7.3(m，2H，Ar-H)，2.7(s，3H，CH3)，2.5(s，3H，CH3)。
Embodiment 12 [(η
6-C
6H
6) Ru (m-NPIP) Cl]
+Synthetic
Experimental technique is with embodiment 1, with part o-FPIP (0.3mmol, 105mg) change into m-NPIP (0.3mmol, 102mg), productive rate: 86%.ESI-MS(in?MeOH，m/z)：556.20。
1H-NMR(in?DMSO-d6，δ/ppm)：6.3(s，6H，C6H6)，8.0(m，2H，phen-H)，7.7(m，2H，phen-H)，7.4(m，2H，phen-H)。
Embodiment 13 [(η
6-C
6H
6) Ru (o-ClPIP) Cl]
+Synthetic
Experimental technique is with embodiment 1, with part o-FPIP (0.3mmol, 105mg) change into o-ClPIP (0.3mmol, 98mg), productive rate: 81%.ESI-MS(in?MeOH，m/z)：547.00。
1H-NMR(in?DMSO-d6，δ/ppm)：6.3(s，6H，C6H6)，10.0(m，2H，phen-H)，9.3(m，2H，phen-H)，8.2(dd，2H，phen-H)，7.6(dd，4H，Ar-H)。
Embodiment 14 rutheniums (II) compound anti tumor activity in vitro
1.Ru the experimental program of compound
The compound anti tumor activity in vitro is evaluated with IC50 value (the needed concentration of 50% cell growth-inhibiting): cell is inoculated in 96 orifice plates of the RPMI1640 substratum (including an amount of green grass or young crops, Streptomycin sulphate and Stimulina) that contains 10% calf serum 5%CO by certain density
2, cultivate after 24 hours under 37 ℃ of conditions, use the fresh culture that different concns receives reagent thing (be mixed with 1 μ g/mL working fluid with PBS, dilute with substratum on demand during use) instead, continue to cultivate 48 hours; Every then hole adds 50 μ L precoolings, 50% trichoroacetic acid(TCA) (TCA, final concentration are 10%), leave standstill 5 minutes after, distilled water wash 5 times; Dry air adds 100 μ L MTT dye liquors, and 10min is handled in dyeing; 1% acetum washed cell 4 times is removed not combination dye, dry air; Add 150 μ L10mmol/L Tris solution at last, fully behind the mixing, ELIASA is measured the OD value under the 490nm wavelength.Each concentration parallel laboratory test of each sample 6 times is averaged.
2 results
Adopt above-mentioned experimental program; Select for use in A549 human lung adenocarcinoma, SMMC-7721 people's liver cancer, the SW620 human large intestine cancer clone and tested multiple compound of the present invention; The result shows that (like table 1) IC50 value of the present invention is lower than 150 μ M; Especially adenocarcinoma of lung A549 has been showed good anti-tumor activity, its IC50 less than 100 μ M, has the potential industrial application value basically in the clinical treatment of tumor disease.
Table 1 aryl ruthenium (II) title complex is to the effect of tumour cell
Claims (4)
1. an aryl ruthenium (II) title complex, its structural formula is suc as formula shown in (I):
Formula (I);
Wherein, said R is 2-trifluoromethyl, 2-hydroxyl-4-p-methoxy-phenyl, 4-chloro-phenyl-, 4-trifluoromethyl, 4-hydroxy phenyl, 4-(N, N-dimethylamino) phenyl, 3-nitrophenyl, 2-chloro-phenyl-; Said R
1, R
2, R
3, R
4, R
5, R
6Be H; Said X is Cl
-Said m is 1, and said aryl ruthenium (II) title complex comprises counter ion.
2. the preparation method of the said aryl ruthenium of claim 1 (II) title complex is characterized in that comprising the steps: [π-C
6H
6RuCl
2]
2Under room temperature, add methylene dichloride with part, ultrasonic back stirring reaction under argon shield, be transferred to revolve in the round-bottomed flask dried; Adding the filtration of zero(ppm) water ultrasonic dissolution; Remove with Rotary Evaporators once more afterwards and desolvate,, promptly get product end product recrystallization in methyl alcohol.
3. according to the preparation method of the said aryl ruthenium of claim 2 (II) title complex, it is characterized in that the said ultransonic time is 0.5h, the time of stirring reaction is 4h.
4. the application of the said aryl ruthenium of claim 1 (II) title complex in the medicine of preparation prevention or treatment cancer.
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| CN102898480B (en) * | 2012-09-13 | 2015-07-01 | 广东药学院 | Microwave-assisted synthesis method for ruthenium (II) arene compound |
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