CN1478786A - Platinum (II) compound using chiral diamine as ligand - Google Patents
Platinum (II) compound using chiral diamine as ligand Download PDFInfo
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- CN1478786A CN1478786A CNA03132181XA CN03132181A CN1478786A CN 1478786 A CN1478786 A CN 1478786A CN A03132181X A CNA03132181X A CN A03132181XA CN 03132181 A CN03132181 A CN 03132181A CN 1478786 A CN1478786 A CN 1478786A
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- platinum
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- trimethylammonium
- diamines
- compound
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- 150000004985 diamines Chemical class 0.000 title claims description 9
- -1 Platinum (II) compound Chemical class 0.000 title claims description 7
- 239000003446 ligand Substances 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 13
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 47
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims description 33
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052697 platinum Inorganic materials 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001457 metallic cations Chemical class 0.000 claims description 2
- 238000010850 salt effect Methods 0.000 claims description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 abstract description 2
- 125000002091 cationic group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 2
- 229960001756 oxaliplatin Drugs 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WEZYFYMYMKUAHY-UHFFFAOYSA-N tert-butyl 2,4-dibenzylpiperazine-1-carboxylate Chemical compound C1C(CC=2C=CC=CC=2)N(C(=O)OC(C)(C)C)CCN1CC1=CC=CC=C1 WEZYFYMYMKUAHY-UHFFFAOYSA-N 0.000 description 2
- IRMVJTGZFWHOKC-UHFFFAOYSA-N 2-methoxyacetic acid silver Chemical compound [Ag].COCC(=O)O IRMVJTGZFWHOKC-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical class N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
- 238000000119 electrospray ionisation mass spectrum Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NFOHLBHARAZXFQ-UHFFFAOYSA-N platinum(2+);dihydrate Chemical compound O.O.[Pt+2] NFOHLBHARAZXFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A Pt(II) counterpart and its preparing process are disclosed. It features that the chiral 1R, 3S-1,2,2,-trimethyl-1,3-cyclopentadiamine is used to coordinate with 2-valence Pt ions to obtain cationic ligand, which then acts on different carboxylic derivatives to obtain Pt(II) counterpart.
Description
One. technical field
The present invention relates to a class and contain novel platinum (II) title complex of chiral diamine ligands and preparation method thereof.
Two. background technology
Because cis-platinum in use can produce chemical sproof tumour cell, it is very necessary therefore seeking the platinum complex that can overcome with cis-platinum generation cross resistance.After chiral diamine formed title complex as part and metal platinum (II) ion, the difference on its three-dimensional and space often can be improved the character and the curative effect of medicine.The chiral diamine that has obtained clinical use have in the oxaliplatin (Oxaliplatin) (1R, 2R)-1, the trans cyclohexanediamine of 2-and Song's platinum (Sunpla, in SKI-2053R) (4R, 5R)-4,5-two (aminomethyl)-2-sec.-propyl-1,3-dioxolane.In addition, document has reported that also the chiral diamine of other kind is applied in the preparation of divalence platinum complex as part, is used to research and develop new antitumor platinum (II) class medicine.
Three. summary of the invention
The objective of the invention is to use the carboxylate radical part of different structure feature, regulate itself and chiral diamine and close the water-soluble and fat-soluble of cis-platinum (II) class title complex that platinum (II) complex cation generates, make it have low toxicity, good aqueous solubility and fat-soluble and effective antitumour is active, be used for the treatment of human tumor.The present invention discloses the novel platinum of a class (II) coordination compound, it is characterized in that being to use chirality 1R, 3S-1,2,2-trimethylammonium-1,3-ring pentamethylene diamine and the coordination of divalence platinum ion form complex cation, then with different carboxylic acid derivative effect generation platinum (II) title complexs.The composition of this compounds is represented by following formula (1), (2) and (3):
1R wherein, 3S-1,2,2-trimethylammonium-1, the chiral carbon atom of 3-ring pentamethylene diamine is used
*Number the expression.R group in the formula (1) is identical, is C
1-6Alkyl.R ' shown in the formula (2) is hydrogen atom or methyl; When R ' was methyl, lactate can be racemic isomer, R-configuration or S-configuration optically active isomer.Platinum complex of the present invention comprises all steric isomers shown in the above-mentioned chemical formula and composition thereof.
Another object of the present invention provides the method for platinum (II) title complex shown in preparation formula (1), formula (2) and the formula (3).In the preparation of above-mentioned divalence platinum complex, at first close sour potassium of platinum (II) and 1R by tetrachloro, 3S-1,2,2-trimethylammonium-1, (slightly: diamines) effect obtains two halogen ion diamines and closes platinum (II) title complex 3-ring pentamethylene diamine, is represented by formula (4).Then under the logical condition of nitrogen gas of lucifuge, by method A: use the carboxylic acid silver salt directly to close platinum (II) and act on and obtain described compound with the dihalo-diamines; Or by method B: use silver ions to remove the halide-ions that the dihalo-diamines closes platinum (II), the carboxylate salt effect of gained intermediate and monovalent base metallic cation obtains described compound.
Hal in the formula (4) represents Cl
-, Br
-And I
-Ion.
The representational compound of the present invention comprises:
Suitable-two (methoxyacetic acid roots) (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1) close platinum (II); Suitable-two (ethoxyacetic acid roots) (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1) close platinum (II); Suitable-two (butoxy acetic acid roots) (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1) close platinum (II); Suitable-lactate (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1) closes platinum (II); Suitable-the ethanol acid group (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1) closes platinum (II); Platinum (II) dihydrate is closed in suitable-(1, the 1-cyclobutane dicarboxylic acid radical) (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1).
1R, 3S-1,2,2-trimethylammonium-1,3-ring pentamethylene diamine part press literature method prepare (Z.-H.Yang, L.-X.Wang, Z.-H.Zhou, Tetrahedron:Asymmetry, 2001,12,1579-1582).Structure by the prepared compound of the present invention is confirmed by different analytical procedures such as ultimate analysis, infrared spectra, proton magnetic resonance (PMR) spectrum and positively charged ion electrospray ionization mass spectrum.All compounds have been determined their decomposition temperature and whether have been contained recrystallisation solvent or adsorption solvent through thermogravimetric analysis.
The present invention is further set forth by the embodiment of more following representative compounds, but these explanations are not restriction the present invention.Embodiment 1: usefulness method A synthesizes suitable-two (methoxyacetic acid roots) (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1) and closes platinum (II)
Suitable-diiodo-(1R, 3S-1,2,2-trimethylammonium-1,3-encircles pentamethylene diamine) close methoxyacetic acid silver (0.79 gram of platinum (II) (1.18 grams, 2 mmoles) and new system, 4 mmoles) adding water (100 milliliters) mixes, 40 ℃ of logical nitrogen of following lucifuge reacted 12 hours, used the diatomite aided filter then, and filtrate is concentrated, separate out yellow solid, filter, 60 ℃ of following vacuum-dryings get product 0.77 gram (75%).IR (KBr): 3446m (br), 3268m, 3198s, 3122s, 2965s, 2942s, 2826m, 1671s, 1636vs (br), 1457m, 1420m, 1389vs, 1353s, 1336s, 1304s, 1269s, 1194s, 1122vs, 1046w, 1019w, 942m
1H-NMR (D
2O/TMS): δ 0.76-0.77 (m, 3H), 1.02-1.16 (m, 6H), 1.84-1.93 (m, 2H), 2.04-2.13 (m, 2H), 2.48-2.52 (m, 1H), 3.21-3.25 (m, 6H), 3.80-3.87 (m, 4H) ESI-MS (H
2O solution): [M+Na]
+=538 (20%), [M-CH
3OCH
2COO
-+ H
2O]
+=444 (100%) TGA: compound does not contain crystal water or planar water, and decomposition temperature is 207.6 ℃.Embodiment 2: usefulness method A synthesizes suitable-two (ethoxyacetic acid roots) (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1) and closes platinum (II)
Suitable-diiodo-(1R, 3S-1,2,2-trimethylammonium-1,3-encircles pentamethylene diamine) close ethoxyacetic acid silver (0.84 gram of platinum (II) (1.18 grams, 2 mmoles) and new system, 4 mmoles) adding water (100 milliliters) mixes, 50 ℃ of logical nitrogen of following lucifuge reacted 18 hours, used the diatomite aided filter then, and filtrate is concentrated, separate out yellow solid, filter, 60 ℃ of following vacuum-dryings get product 0.51 gram (47%).IR (KBr): 3444m (br), 3207m, 3123m, 2974m, 2936w, 2878w, 1604s (br), 1384s, 1335m, 1299m, 1261w, 1175w, 1115s, 1041w
1H-NMR (D
2O/TMS): δ 0.76-0.79 (m, 3H), 0.98-1.21 (m, 12H), 1.84-1.93 (m, 2H), 2.04-2.12 (m, 2H), 2.39-2.62 (m, 1H), 3.39-3.53 (m, 4H), 3.86-3.97 (m, 4H) ESI-MS (H
2O solution): [M+Na]
+=566 (100%), [M-CH
3CH
2OCH
2COO
-+ H
2O]
+=458 (94%) TGA: compound does not contain crystal water or planar water, and decomposition temperature is 210.3 ℃.Embodiment 3: usefulness method A synthesizes suitable-two (butoxy acetic acid roots) (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1) and closes platinum (II)
Suitable-diiodo-(1R, 3S-1,2,2-trimethylammonium-1,3-encircles pentamethylene diamine) close butoxy acetic acid silver (0.96 gram of platinum (II) (1.18 grams, 2 mmoles) and new system, 4 mmoles) adding water (100 milliliters) mixes, 60 ℃ of logical nitrogen of following lucifuge reacted 48 hours, used the diatomite aided filter then, and filtrate is concentrated, separate out yellow solid, filter, 60 ℃ of following vacuum-dryings get product 0.74 gram (62%).IR (KBr): 3444m (br), 3211m, 3083m, 2958m, 2934w, 2872m, 1640s (br), 1462m, 1385s, 1303m, 1265m, 1111s, 1043w, 1027w
1H-NMR (D
2O/TMS): δ 0.75-0.79 (m, 9H), 1.01-1.03 (m, 2H), 1.11 (m, 1H), 1.14-1.16 (m, 2H), 1.19-1.24 (m, 4H), 1.42-1.47 (m, 4H), 1.84-1.87 (m, 2H), 2.03-2.12 (m, 2H), 2.48-2.62 (m, 1H), 3.35-3.43 (m, 4H), 3.83-3.93 (m, 4H) ESI-MS (H
2O solution): [M+Na]
+=622 (100%), [M-CH
3CH
2OCH
2COO
-+ H
2O]
+=486 (95%) TGA: compound does not contain crystal water or planar water, and decomposition temperature is 209.0 ℃.Embodiment 4: usefulness method B synthetic suitable-lactate (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1) closes platinum (II)
Suitable-diiodo-(1R, 3S-1,2,2-trimethylammonium-1,3-encircles pentamethylene diamine) close platinum (II) (1.18 grams, 2 mmoles), Silver Nitrate (0.68 gram, 4 mmoles) mixing adds entry (50 milliliters), and 50 ℃ of logical nitrogen of following lucifuges reacted the diatomite aided filter 24 hours, the aqueous solution that adds lactic acid (0.18 gram, 2 mmoles) and sodium hydroxide (0.08 gram, 2 mmoles) in the filtrate, transfer pH to neutral, 50 ℃ of logical nitrogen of following lucifuge reacted 16 hours, with solution concentration, separated out a large amount of white solids.Filter, water, ethanol, ether repetitive scrubbing, 60 ℃ of following vacuum-dryings get product 0.5 gram (59%).IR (KBr): 3422s (br), 3218s, 3130s, 2972m, 2879w, 1606vs (br), 1459m, 1379s, 1293w, 1176w, 1115m, 1044m
1H-NMR (D
2O/TMS): δ 0.77 (s, 3H), 1.05-1.34 (m, 9H), 1.85 (m, 2H), 2.04-2.14 (m, 2H), 2.64-2.71 (m, 1H), 3.99-4.09 (m, 1H) ESI-MS (H
2O solution): [M+Na]
+=448 (100%), [M+H
2O+H]
+=444 (90%), [M+H]
+=426 (50%) TGA: the easy moisture absorption of compound, contain planar water, decomposition temperature is 216.7 ℃.Embodiment 5: usefulness method B synthetic suitable-ethanol acid group (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1) closes platinum (II)
Suitable-diiodo-(1R, 3S-1,2,2-trimethylammonium-1,3-encircles pentamethylene diamine) close platinum (II) (1.18 grams, 2 mmoles), Silver Nitrate (0.68 gram, 4 mmoles) mixing adds entry (50 milliliters), and 60 ℃ of logical nitrogen of following lucifuges reacted the diatomite aided filter 12 hours, the aqueous solution that adds lactic acid (0.15 gram, 2 mmoles) and sodium hydroxide (0.08 gram, 2 mmoles) in the filtrate, transfer pH to neutral, 60 ℃ of logical nitrogen of following lucifuge reacted 10 hours, with solution concentration, separated out a large amount of white solids.Filter, water, ethanol, ether repetitive scrubbing, 60 ℃ of following vacuum-dryings get product 0.56 gram (68%).IR (KBr): 3419s (br), 3206s, 3119s, 2970m, 2879w, 1613vs (br), 1461m, 1431w, 1382s, 1262w, 1175w, 1132w, 1073m
1H-NMR (D
2O/TMS): δ 0.77 (s, 3H), 1.01-1.22 (m, 6H), 1.84-1.86 (m, 2H), 2.02-2.14 (m, 2H), 2.61-2.69 (m, 1H), 3.83-3.99 (m, 2H) ESI-MS (H
2O solution): [M+H
2O+H]
+=430 (36%) TGA: the easy moisture absorption of compound, contain planar water, decomposition temperature is 208.7 ℃.Embodiment 6: usefulness method A is synthetic suitable-1, and 1-cyclobutane dicarboxylic acid radical (2,2-trimethylammonium-1,3-encircles pentamethylene diamine for 1R, 3S-1) closes platinum (II) 2H
2O
Suitable-diiodo-(1R, 3S-1,2,2-trimethylammonium-1,3-encircles pentamethylene diamine) close platinum (II) (1.18 grams, 2 mmoles) and 1 of new system, 1-cyclobutane dicarboxylic acid silver (0.72 gram, 2 mmoles), it is mixed to add water (100 milliliters), 60 ℃ of logical nitrogen of following lucifuge reacted 24 hours, used the diatomite aided filter then, and filtrate is concentrated, separate out white solid, filter, 60 ℃ of following vacuum-dryings get product 0.52 gram (52%).IR (KBr): 3476m (br), 3196s, 3127s, 2979m, 2952m, 2905m, 2879w, 1635s (br), 1463m, 1370s, 1261m, 1213w, 1173w, 1118m, 1045m, 950w, 903m
1H-NMR (D
2O/TMS): δ 0.77 (s, 3H), 1.00 (s, 3H), 1.15 (s, 3H), 1.74-1.86 (m, 4H), 1.99-2.06 (m, 2H), 2.22-2.57 (m, 1H), 2.65-2.68 (m, 2H), 2.86-2.89 (m, 2H) ESI-MS (H
2O solution): [M+H]
+=480 (100%) TGA: compound contains two crystal water (weightlessness 7.09% between 70-100 ℃), 287.4 ℃ of decomposition temperatures.Annotate: the coordination higher because of the Pt elemental abundance have
194Pt,
195Pt and
196Pt is so the mass spectral quasi-molecular ion peak of above-claimed cpd ESI-MS all has three isotopic peaks that abundance is higher.
Claims (2)
1, novel platinum (II) coordination compound of a class is characterized in that being to use chirality 1R, 3S-1,2,2-trimethylammonium-1,3-ring pentamethylene diamine are (slightly: diamines) form complex cation with the coordination of divalence platinum ion, then with different carboxylic acid derivative effect generation platinum (II) title complexs.The composition of this compounds is represented by following formula (1), (2) and (3):
1R wherein, 3S-1,2,2-trimethylammonium-1, the chiral carbon atom of 3-ring pentamethylene diamine is used
*Number the expression.R group in the formula (1) is identical, is C
1-6Alkyl.R ' shown in the formula (2) is hydrogen atom or methyl; When R ' was methyl, lactate can be racemic isomer, R-configuration or S-configuration optically active isomer.Platinum complex of the present invention comprises all steric isomers shown in the above-mentioned chemical formula and composition thereof.
2, according to the preparation method of the defined platinum of claim 1 (II) title complex, it is characterized in that the dihalo-diamines of formula (4) representative is closed platinum (II) under the logical condition of nitrogen gas of lucifuge, by method A: use the carboxylic acid silver salt directly to close platinum (II) and act on and obtain the defined compound of claim 1 with the dihalo-diamines; Or by method B: use silver ions to remove the halide-ions that the dihalo-diamines closes platinum (II), the carboxylate salt effect of gained intermediate and monovalent base metallic cation obtains the defined compound of claim 1.
Hal in the formula (4) represents Cl
-, Br
-And I
-Ion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN03132181.XA CN1203081C (en) | 2003-07-07 | 2003-07-07 | Platinum (II) compound using chiral diamine as ligand |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN03132181.XA CN1203081C (en) | 2003-07-07 | 2003-07-07 | Platinum (II) compound using chiral diamine as ligand |
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| Publication Number | Publication Date |
|---|---|
| CN1478786A true CN1478786A (en) | 2004-03-03 |
| CN1203081C CN1203081C (en) | 2005-05-25 |
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|---|---|---|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1312115C (en) * | 2004-08-20 | 2007-04-25 | 南京大学 | Chiral 1,4 diamidogen and its complex of platinum II |
-
2003
- 2003-07-07 CN CN03132181.XA patent/CN1203081C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1312115C (en) * | 2004-08-20 | 2007-04-25 | 南京大学 | Chiral 1,4 diamidogen and its complex of platinum II |
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| Publication number | Publication date |
|---|---|
| CN1203081C (en) | 2005-05-25 |
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