CN1252075C - Complex ML(DCA) of copper(II), gallium(III) and rare earth ion(Ln**) containing non-methyl canthridic acid radical - Google Patents

Complex ML(DCA) of copper(II), gallium(III) and rare earth ion(Ln**) containing non-methyl canthridic acid radical Download PDF

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CN1252075C
CN1252075C CN 02148843 CN02148843A CN1252075C CN 1252075 C CN1252075 C CN 1252075C CN 02148843 CN02148843 CN 02148843 CN 02148843 A CN02148843 A CN 02148843A CN 1252075 C CN1252075 C CN 1252075C
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dca
compound
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CN1500789A (en
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李荣昌
尹富玲
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Peking University
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Abstract

The present invention relates to a new compound. The general formula of the compound is shown by the following formula: ML(DCA)(I), wherein M is selected from Cu<2+>, Ga<3+> and rare earth ions of La<3+>, Ce<3+>, Lu<3+>, Yb<3+> or Y<3+>; L is selected from bidentate ligands comprising nitrogen or oxygen; or under the condition that M is Ga<3+> and rare earth ions Ln<3+>, L can not exist; DCA is DCA which is methyl removing cantharis acid radicals; the general formula (I) comprises coordinated water, polynucleation bridged ligand coordination compounds, salt thereof (especially sodium salt) and crystal hydrate. The present invention also relates to the purposes of the compound for preparing antitumor medicines and anti-inflammation medicines.

Description

The copper (II), gallium (III) and the rare earth ion (Ln that contain demethyl Chinese blister beetle acid group (DCA) 3+) mixed ligand coordination compound ML (DCA)
Invention field
The present invention relates to contain copper (II), gallium (III) and the rare earth ion (Ln of demethyl Chinese blister beetle acid group (DCA) 3+) mixed ligand coordination compound ML (DCA), and preparation method thereof and the purposes in antitumor, the anti-inflammatory drug of preparation.
Background technology
Tumour has become one of human major causes of death.Therefore, the medicine for new treatment tumour exists continuous demand.
Summary of the invention
The purpose of this invention is to provide a kind of novel cpd, the general formula of this compound is as follows:
ML(DCA) (I)
Wherein M is selected from Cu 2+, Ga 3+And rare earth ion La 3+, Ce 3+, Gd 3+, Lu 3+, Yb 3+Or Y 3+
L is selected from nitrogenous or oxygen containing bitooth ligand, for example comprises:
1,10-phenanthroline (being abbreviated as phen)
Figure C0214884300041
2,2 '-dipyridyl (being abbreviated as bipy)
Figure C0214884300042
Oxine (being abbreviated as oxine)
Figure C0214884300043
2,2 '-bisglyoxaline
Sulphosalicylic acid (root)
Figure C0214884300051
Selenite radical
Schiff base
Figure C0214884300053
Wherein DCA is a demethyl Chinese blister beetle acid group:
And contain coordinated water, multinuclear bridge ligand title complex and sodium salt thereof and crystallization hydrate;
For Ga 3+With rare earth ion Ln 3+, L can not exist, and for example comprises Ga (DCA) 2, Ga (DCA) 3, Ln (DCA) 2, Ln (DCA) 3And contain H 2The title complex of O, multinuclear bridge ligand title complex be sodium salt extremely.
Second purpose of the present invention provides the preparation method of above-claimed cpd, comprising:
(A) with copper (II), gallium (III) and rare earth ion (Ln 3+) compound and the reaction of the precursor compound of nitrogenous or oxygen containing bitooth ligand, generate copper (II), gallium (III) and rare earth ion (Ln 3+) title complex;
(B) allow gained title complex and demethyl Cantharidic acid or its salt or ester react, generate mixed ligand coordination compound.
Wherein copper (II), gallium (III) and rare earth ion (Ln 3+) compound and the mol ratio of the precursor compound of nitrogenous or oxygen containing bitooth ligand usually at 1-3: in the scope of 1-3, mol ratio such as preferred.The mol ratio of gained title complex and demethyl Cantharidic acid or its salt or ester is normally at 1-3 in the step (B): in the scope of 1-3, and mol ratio such as preferred.
Perhaps this method comprises:
Compound and demethyl Cantharidic acid or its salt or ester direct reaction with Ga (III) or rare earth ion.
Mol ratios the such as wherein mol ratio of the compound of Ga (III) or rare earth ion and demethyl Cantharidic acid or its salt or ester is in the scope of 1-3: 1-3, and is preferred.
Copper (II), gallium (III) and rare earth ion (Ln 3+) compound comprise their halogenide, oxide compound, oxyhydroxide or inorganic acid salt (as vitriol, nitrate, carbonate, muriate etc.As ventilation breather, cupric chloride, cupric nitrate, gallium hydroxide, gallium oxide, samarium sesquioxide, Lanthanum trichloride, lanthanum nitrate, cerous sulfate etc.).
Described compound can synthesize in the non-aqueous solution at the aqueous solution, or synthetic with solid state reaction.
The temperature of reaction is not special restriction, in the aqueous solution or non-aqueous solution under the synthetic situation ,-as at 30-120 ℃, in preferred 60-100 ℃ the scope, more preferably in 80-100 ℃ the scope.Under the situation of solid state reaction, usually under 200-500 ℃ temperature.
Of the present invention also-individual purpose provides that above-claimed cpd is antitumor in preparation, the purposes in the anti-inflammatory drug.
Embodiment
Below in conjunction with embodiment the present invention is described.Should be noted that these embodiment only are used for explanation, do not constitute limitation of the scope of the invention.
Embodiment 1
Cu (phen) is nH (DCA) 2O's (n=0～4) is synthetic
At first use thermal chlorination copper liquor and equimolar 1,10-phenanthroline prepared in reaction dichloro (1, the 10-phenanthroline) closes copper (II) title complex solid.Take by weighing a certain amount of dichloro (1, the 10-phenanthroline) and close copper (II) and be dissolved in an amount of hot water, add equimolar demethylate disodium cantharidinate, stirred for several hour, blue green solid.Recrystallization is got this an amount of solid and is dissolved in appropriate solvent cultivation monocrystalline.
Embodiment 2
Cu (bipy) is nH (DCA) 2O's (n=0～4) is synthetic
With the copper chloride solution of heat and equimolar 2,2 '-the dipyridyl reaction, cooling can get dichloro (2,2 '-dipyridyl) and close copper (II) solid.Take by weighing a certain amount of dichloro (2,2 '-dipyridyl) and close copper (II) and be dissolved in an amount of hot water, add equimolar demethylate disodium cantharidinate, stirred for several hour, De Lanse solid.Recrystallization.Wash used solvent and mode difference, contain the number difference of crystal water.Get this an amount of solid and be dissolved in appropriate solvent cultivation monocrystalline.
Embodiment 3
Na[La (DCA) 2] synthetic
Get a certain amount of LaCl 3Solid adds the hot water dissolving, and adds a certain amount of demethylate disodium cantharidinate solid, and stirring reaction dissolves it fully.Transfer pH to acid, heating concentrates, and places crystallization.
The composition and the structure determination of embodiment 4 title complexs
The composition of title complex and structure have been used ultimate analysis, and be infrared, and ultraviolet-visible spectrum, nucleus magnetic resonance, electricity are led and method such as X-ray diffraction is measured.Above the measurement result Lie Gebiao as follows of three routine title complexs:
The results of elemental analyses of table 1 title complex
Chemical formula C H N
Cu(phen)(DCA)H 2O (CuC 20H 18N 2O 6) Cu(bipy)(DCA)2H 2O (CuC 18H 20N 2O 7) Na[La(DCA) 2] NaLaC 16H 16O 10 53.28(53，87) 48.93(49.15) 36.04(36.25) 3.73(4.07) 4.02(4.58) 3.32(3.04) 5.89(6.28) 6.15(6.37)
Annotate: data are calculated value in the bracket
The diffuse reflectance infrared spectroscopy of table 2 title complex absorbs (cm -1)
Compound The γ of aromatic ring-C=C-γ-C=N- Carboxyl γ-C=O γ-C-O δ=the C-H of aromatic ring Cyclic ethers oxygen δ-C-O-C-among the DCA
Cu(phen)(DCA)H 2O Cu(bipy)(DCA)2H 2O Na[La(DCA) 2] 1574.45 1428.08 1447.29 1624.78 1392.85 1623.25 1392.24 1654.99 1583.44 852.93 725.39 776.12 985.39 984.75 986.09
Ir data shows, contains the COO of part demethyl Chinese blister beetle acid group DCA in institute's synthetic title complex -With the charateristic avsorption band of cyclic ethers oxygen-C-O-C-, and and Na 2Tangible displacement has taken place in the peak position of comparing DCA, and COO is described -Participate in coordination with the oxygen of-C-O-C-.At (DCA) H of Cu (phen) 2Exist among the O phen-C=C-and-the C=N-stretching vibration peak, and peak position is compared with free ligand and is subjected to displacement; At (DCA) 2H of Cu (bipy) 2The characteristic absorbance of existence-C=N-and peak position are compared with bipy and are subjected to displacement among the O, illustrate that the N on the aromatic ring participates in coordination among phen and the bipy.These title complexs are at 3400cm -1About strong and wide absorption band is all arranged, illustrate to have crystal water or H 2O participates in coordination.
The ultraviolet-visible charateristic avsorption band of table 3 title complex
Title complex Ultraviolet region (nm) Visible region (nm)
Cu(phen)(DCA)H 2O Cu(bipy)(DCA)2H 2O Na[La(DCA) 2] 272.50，223.00，203.50 310.00，299.50，244.50， 207.50 207.00 654.00 642.00
The characteristic absorbance in ultraviolet-visible district has also proved phen, and bipy and DCA participate in coordination, because compare with free ligand, and its π → π *, n → π *Transition, and Cu (H 2O) 6 2+The aqueous solution 2Eg → 2T 2gThe peak position of transition is obviously displacement all.
The electric conductance determination result of table 4 title complex (29 ℃)
Title complex Specific conductivity/(scmmol -1)
Cu(phen)(DCA)H 2O Cu(bipy)(DCA)2H 2O Na[La(DCA) 2] 4.0 29.0 119.O
From the electric conductance determination result as can be seen, (DCA) H of Cu (phen) 2O and Cu (bipy) be 2H (DCA) 2O is the electric neutrality material, and its structure can be speculated as [Cu (phen) (DCA)] H 2O and [Cu (bipy) is (H2O) (DCA)] H 2O, and Na[La (DCA) 2] be 1-1 type ionogen, this molecular formula is correct.
Na[La (DCA) 2] 3The HNMR stave is bright, in the title complex among the DCA δ of the H on 7,5 C by former H 2The triplet of DCA becomes bimodal, and shifts to low; The δ (bimodal) that prosposition C goes up H also shifts to low, has confirmed COO among the DCA -And cyclic ethers oxygen and La 3+Coordination.
[Cu (phen) (DCA)] H 2O is with [Cu (bipy) is (H (DCA) 2O)] H 2The ray crystalline diffraction measurement result of O:
By in the crystalline structure as can be seen: phen is with the Sauerstoffatom and the Cu of two carboxyls of two N and DCA 2+Coordination forms the equator ligating atom, and the carboxyl oxygen atom coordination of the cyclic ethers Sauerstoffatom of DCA and another DCA forms axial coordination atom so Cu 2+Formed distored octahedra title complex, and a carboxyl among the DCA As bridged ligands simultaneously and two Cu with two Sauerstoffatoms 2+Coordination.With the carboxyl is bridge, has formed
Figure C0214884300082
Chain structure, chain and interchain pass through H 2The hydrogen bond that O forms connects.
From crystalline structure as can be seen, Cu 2+With bipy, DCA and H 2O has formed distorted octahedron title complex, Cu 1 2+With two N and the cyclic ethers oxygen of DCA and the carboxyl oxygen atom coordination of this DCA of bipy, another carboxyl oxygen of this DCA and another Cu 2 2+Coordination, Cu 2+Except with bipy, outside the DCA coordination, H 2O also participates in coordination, has therefore formed bridging coordination double-core copper (II) title complex, and its molecular formula should be: [(bipy) Cu-DCA-Cu (bipy) (H 2O)] 3H 2O
The outer antitumor cell experiment of embodiment 5 matching objects
The anticancer experiment in vitro of title complex is finished at Department Of Medicine, Peking University's natural drug and bionical medicine National Key Laboratory pharmacology group.Measured title complex to four kinds of representational JEG-3 with mtt assay (be tetramethyl-azo azoles blue analytical method) and srb assay (being sulphonyl rhodamine B analytical method): the HL-60 human leukemia cell, the BGC-823 gastric carcinoma cells, the inhibiting rate of Bel-7420 human liver cancer cell and Hela human cervical carcinoma cell, for relatively, measured demethylate disodium cantharidinate (Na simultaneously 2DCA has certain curative effect to primary hepatocarcinoma) to the inhibiting rate of these cancer cells.
Table 5 title complex is to the inhibiting rate (%) of four kinds of JEG-3
Title complex Cancer cells Method The inhibiting rate of different concns
0.1μm 1μm 10μm
Na 2DCA HL-60 BGC-823 Bel-7420 Hela cervical cancer MTT SRB SRB SRB -2.7 -3.05 -4.04 -12.89 -7.58 2.69 -1.02 -14.68 -5.44 12.93 13.62 10.84
Cu(phen)(DCA) HL-60 BGC-823 Bel-7420 Hela cervical cancer MTT SRB SRB SRB 3.03 5.42 -6.78 -9.96 8.48 8.83 1.64 1.46 86.63 92.32 97.82 98.83
Cu 2(bipy) 2(DCA) 2H 2O HL-60 BGC-823 Bel-7420 Hela cervical cancer MTT SRB SRB SRB 0.41 4.70 20.24 -7.77 2.55 7.29 21.65 -4.68 15.36 23.44 24.43 -8.66
Na[La(DCA) 2] HL-60 BGC-823 Bel-7420 Hela cervical cancer MTT SRB SRB SRB 4.86 -15.55 7.05 2.68 2.84 -14.52 1.15 4.93 10.91 8.96 16.61 -2.28
As can be seen from Table 5, with demethyl spot acid sodium Na 2DCA compares, and the antitumour activity of institute's synthetic anticancer complex all increases, and (DCA) H of Cu (phen) 2O has showed high antitumour activity.

Claims (7)

1, a compounds, this compound is selected from: the compound shown in the following general formula (I):
ML(DCA) (I)
Wherein M is selected from Cu 2+Or rare earth ion Ln 3+, Ln wherein 3+Be La 3+, Ce 3+, Gd 3+, Lu 3+, Yb 3+Or Y 3+L is selected from nitrogenous or oxygen containing bitooth ligand, and bitooth ligand is selected from:
1, the 10-phenanthroline is abbreviated as phen
Figure C021488430002C1
2,2 '-dipyridyl, be abbreviated as bipy
Figure C021488430002C2
Oxine is abbreviated as oxine
Figure C021488430002C3
2,2 '-bisglyoxaline
Sulphosalicylic acid or its acid group
Figure C021488430002C5
Selenite radical
Figure C021488430002C6
Schiff base
Figure C021488430002C7
When M is rare earth ion Ln 3+The time, L can not exist;
DCA is a demethyl Chinese blister beetle acid group:
Figure C021488430003C1
Or the salt of the multinuclear bridge ligand coordination compound of the coordination compound that contains coordinated water of general formula (I) or general formula (I) or general formula (I) or its crystallization hydrate.
2, compound as claimed in claim 1 is characterized in that, this compound is selected from (DCA) nH of Cu (phen) 2O (n=0-4), wherein phen is 1, the 10-phenanthroline; Or (DCA) nH of Cu (bipy) 2O (n=0-4), wherein bipy be 2,2 '-dipyridyl; Or Ln (DCA) 2Contain water complex, multinuclear bridge ligand title complex or sodium salt; Or Ln (DCA) 3Contain water complex, multinuclear bridge ligand title complex or sodium salt.
3, compound as claimed in claim 2 is characterized in that, this compound is Na[La (DCA) 2] or its contain water complex or multinuclear bridge ligand title complex.
4, the preparation method of the compound of claim 1 comprises:
(A) with cupric ion Cu 2+Or rare earth ion Ln 3+Compound and nitrogenous or oxygen containing bitooth ligand reaction, generate cupric ion Cu 2+Or rare earth ion Ln 3+Title complex;
(B) allow gained title complex and demethyl Cantharidic acid or its salt or ester react, generate mixed ligand coordination compound;
Perhaps this method comprises:
Compound and demethyl Cantharidic acid or its salt or ester direct reaction with rare earth ion.
5, according to the method for claim 4, cupric ion Cu wherein 2+Or rare earth ion Ln 3+Compound be selected from their halogenide, oxide compound, oxyhydroxide or inorganic acid salt.
6, the purposes of the compound of claim 1 in the medicine of preparation treatment tumour.
7, the purposes of the compound of claim 1 in preparation treatment anti-inflammatory drug.
CN 02148843 2002-11-19 2002-11-19 Complex ML(DCA) of copper(II), gallium(III) and rare earth ion(Ln**) containing non-methyl canthridic acid radical Expired - Fee Related CN1252075C (en)

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