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Antitumor platinum (II) compound using camphor acid radical as ligand

A technology of camphoric acid and complexes, applied in the field of new platinum complexes, can solve the problems of compound inactivity and increased toxicity of compounds

Inactive Publication Date: 2005-05-25
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compounds become more toxic if labile leaving groups are used; compounds are generally inactive if inert leaving groups are used

Method used

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  • Antitumor platinum (II) compound using camphor acid radical as ligand
  • Antitumor platinum (II) compound using camphor acid radical as ligand
  • Antitumor platinum (II) compound using camphor acid radical as ligand

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Embodiment 1: Synthesis of cis-(DL-camphorate) diammine platinum (II)

[0032] cis-diiododiammine platinum (II) (0.97 g, 2 mmol) and silver nitrate (0.68 g, 4 mmol) were mixed and added to water (50 ml), and reacted at 60° C. for 24 hours in the dark and nitrogen. Diatomaceous earth assisted filtration, the aqueous solution of DL-camphoric acid (0.40 g, 4 mmol) and sodium hydroxide (0.16 g, 4 mmol) was added to the filtrate, and the reaction was carried out under nitrogen at 60 ° C for 16 hours in the dark, and the solution was concentrated , a large amount of white solid was precipitated. Filter, wash repeatedly with water, ethanol and ether, and dry under vacuum at 60°C to obtain 0.41 g (48%) of the product.

[0033] IR(KBr): 3424vs(br), 3266vs(br), 2967m, 2881w, 1594vs, 1544vs, 1460m, 1384vs, 1355vs

[0034] 1 H-NMR (D 2 O / TMS): δ0.47-0.67(m, 3H), 0.91-1.08(m, 6H), 1.24-1.31(s, 1H), 1.60(s, 1H), 1.74-1.75(s, 1H), 2.08(m, 1H), 2.55-2.56(s, 1H)

[0035] ESI-MS: [...

Embodiment 2

[0036] Example 2: Synthesis of cis-(DL-camphorate) two (isopropylamine) platinum (II)

[0037] cis-diiodo·bis(isopropylamine)platinum(II) (1.13 g, 2 mmol), silver nitrate (0.68 g, 4 mmol) were mixed and added to water (50 ml), and reacted in the dark at 60°C under nitrogen gas After 24 hours, diatomaceous earth was assisted to filter, and the aqueous solution of DL-camphoric acid (0.40 g, 4 mmol) and sodium hydroxide (0.16 g, 4 mmol) was added to the filtrate, and it was reacted in the dark at 60° C. for 16 hours, The solution was concentrated and a large amount of white solid precipitated out. It was filtered, washed repeatedly with water, ethanol and ether, and dried under vacuum at 60°C to obtain 0.39 g (38%) of the product.

[0038] IR(KBr): 3430s(br), 3217s(sh,br), 2971vs, 2880w, 1595vs(br), 1462m, 1383vs, 1351vs, 1164w, 1118w

[0039] 1 H-NMR (DMSO-d 6 / TMS): δ0.70-0.85 (m, 3H), 0.97-1.26 (m, 18H), 1.44-2.36 (br, 4H), 2.64-2.70 (br, 1H, CH), 2.96-3.18 (m, 2H), 5.85-...

Embodiment 3

[0041] Example 3: Synthesis of cis-(D-camphorate)·[(1R,2R)-1,2-trans-cyclohexanediamine] platinum(II)

[0042]Cis-dichloro[(1R, 2R)-1,2-trans-cyclohexanediamine] platinum (II) (0.76 g, 2 mmol), silver nitrate (0.68 g, 4 mmol) were mixed and added to water ( 50 milliliters), under 60 ℃, shielded from light and reacted with nitrogen for 24 hours, diatomaceous earth assisted filtration, added the aqueous solution of D-camphoric acid (0.40 gram, 4 mmol) and sodium hydroxide (0.16 gram, 4 mmol) in the filtrate , React at 60°C for 16 hours in the dark and pass through nitrogen, the solution is concentrated, and a large amount of white solid is precipitated. Filter, wash repeatedly with water, ethanol and ether, and dry under vacuum at 60°C to obtain 0.65 g (64%) of the product.

[0043] IR(KBr): 3424vs(br), 3226s(sh,br), 2939s, 2872w, 1598vs(br), 1457m, 1381vs, 1350s, 1169w, 1126w, 1063w

[0044] 1 H-NMR (DMSO-d 6 / TMS): δ0.84-0.91(m, 3H), 1.09-1.20(m, 6H), 1.28(m, 4H), 1.48(m, ...

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Abstract

The invention discloses a type of platinum (II) coordination compound with effective anti-cancer activity, which is characterized by using camphorate as a complex anion and a new platinum (II) coordination compound formed by reacting with a platinum amine complex cation, and its preparation method is disclosed. and the in vitro inhibitory effects of typical compounds on human leukemia cells, ovarian cancer cells, liver cancer cells, and lung cancer cells. The composition of this type of compound is represented by the following formula: ∴∴∴The camphorate radical in formula (1), formula (2) and formula (3) can be its DL racemate and D-type optical isomer [(1R , 3S)-(+)-camphorate] or L-type optical isomer [(1S, 3R)-(-)-camphorate]. The R groups in formula (1) are the same, which are hydrogen atoms and C 1-5 Alkyl or C 1-8 Oxaalkyl; cyclohexanediamine in formula (2) is 1,2-trans-cyclohexanediamine, two chiral carbon atoms (marked with * The absolute configuration of No.) is R configuration or S configuration; 4,5-di(aminomethyl)-2-alkyl-1,3-dioxolane in formula (3) represents R 1 and R 2 Same or different, respectively hydrogen atom or C 1-5 Alkyl group, or can be linked to one carbon atom to form a cycloalkyl group, two chiral carbon atoms (marked with * The absolute configuration of No.) is R configuration or S configuration. The platinum complex of the present invention includes all stereoisomers represented by the above chemical formula and mixtures thereof.

Description

technical field [0001] The present invention relates to novel platinum(II) complexes having potent antitumor activity, processes for their preparation and in vitro antitumor properties of typical compounds of said platinum(II) complexes. Background technique [0002] In the research of cisplatin anticancer drugs, the characteristics of the anion as the leaving group have a great influence on the activity of the drug. If an unstable leaving group is used, the toxicity of the compound will increase; if an inert leaving group is used, the compound is generally inactive. Since the successful development of carboplatin containing cyclosuccinate, dicarboxylic acids have been playing an important role in the research and development of anti-tumor platinum (II) complex drugs. Such as oxalic acid, malonic acid and norcantharidic acid have been practically used. Therefore, it is an important way to design and synthesize cisplatin compounds with low toxicity and good water solubility...

Claims

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Application Information

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IPC IPC(8): C07C61/06C07C211/65C07D317/28
CPCC07C61/06C07C211/65C07D317/28A61P35/00
Inventor 苟少华王联红
Owner NANJING UNIV
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