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Anti-tumor platinum (II) complex

A technology of complexes and coordination compounds, which can be used in antitumor drugs, active ingredients of heavy metal compounds, drug combinations, etc., can solve the problems of poor solubility of cisplatin, limited application, limited dose toxicity, etc.

Inactive Publication Date: 2005-01-26
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Cisplatin has been shown to be effective against various human tumors with broad-spectrum anticancer properties, but it has severe dose-limiting toxicities such as nephrotoxicity, bone marrow suppression, nausea and vomiting, and neurotoxicity
And the poor solubility of cisplatin in water also limits its application
Since the existing cisplatin drugs have not fully achieved the goals of good water solubility, low toxicity and effective anti-tumor activity, it is still necessary to design and synthesize low-toxicity and good water-soluble cisplatin compounds to improve anti-tumor preparations

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: Synthetic cis-bis(methoxy acetate) diammine platinum (II) with method B

[0018] Cis-diiododiammine platinum (II) (0.4 g, 0.84 mmol) was mixed with newly prepared silver methoxyacetate (0.33 g, 1.7 mmol), and water (40 ml) was added. Reacted for 24 hours, then assisted filtration with diatomaceous earth, concentrated the filtrate, precipitated an earthy white solid, filtered, and dried under vacuum at 60°C to obtain 0.12 g (35%) of the product.

[0019] IR(KBr): 3279s, 3222s, 3124s, 2989m, 2901m, 2827m, 1662vs, 1571vs, 1466m, 1423vs, 1393vs, 1335vs, 1284s, 1205s, 1117vs, 1015m, 989m

[0020] 1 H-NMR (D 2 O / TMS): δ3.34(m, 6H), 4.02(m, 4H)

[0021] ESI-MS: [M+Na] + =430(100%)

Embodiment 2

[0022] Embodiment 2: synthesizing cis-bis(methoxy acetate) diisopropylamine platinum (II) with method B

[0023] Cis-diiododiisopropylamine platinum (II) (1.13 g, 2 mmol) was mixed with newly prepared silver methoxyacetate (0.79 g, 4 mmol), and water (100 ml) was added, and exposed to light at 40°C. Nitrogen was reacted for 18 hours, assisted by diatomaceous earth filtration, the filtrate was concentrated, a white solid was precipitated, filtered, and vacuum-dried at 60°C to obtain 0.35 g (36%) of the product.

[0024] IR(KBr): 3451m, 3207s, 3106m, 1630s, 1449w, 1384vs, 1333m, 1298m, 1173m, 1119s, 1065m, 1031m

[0025] 1 H-NMR (DMSO-d 6 / TMS): δ1.25(m, 12H), 3.22(m, 6H), 3.36-3.85(m, 6H)

[0026] ESI-MS: [M+Na] + =514(100%)

Embodiment 3

[0027] Example 3: Synthesis of cis-bis(methoxyacetate)[(1R,2R)-1,2-trans-cyclohexanediamine]platinum(II) by method A

[0028] Cis-dichloro[(1R, 2R)-1,2-trans-cyclohexanediamine] platinum (II) (1.10 g, 2.9 mmol), silver nitrate (0.99 g, 5.8 mmol) were mixed and added to water ( 50 milliliters), 55 DEG C, shielded from light, reacted with nitrogen for 36 h, assisted filtration with diatomaceous earth, added an aqueous solution of methoxyacetic acid (0.52 g, 5.8 mmol) and sodium hydroxide (0.23 g, 5.8 mmol) to the filtrate, React at 30°C for 8 hours in the dark under nitrogen, then concentrate the solution, and a large amount of light yellow solid is precipitated. It was filtered, washed repeatedly with water, ethanol and ether, and dried under vacuum at 60°C to obtain 0.89 g (63%) of the product.

[0029] IR(KBr): 3449br, 3218s, 3111m, 2937m, 2861w, 2821w, 2362w, 2342w, 1633vs, 1449w, 1385s, 1338m, 1305m, 1120s, 1064w, 1035w

[0030] 1 H-NMR (D 2 O / TMS): δ1.08(m, 2H), 1.08(m...

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Abstract

The invention discloses a group of platinum (II) coordinated complex having effective anticancer activity, which is represented by the structural formula (1) disclosed in the specification, wherein R groups are the same, which are hydrogen atoms or C1-5 alkyl, the cyclohexane diamine is 1,2-trans-cyclohexane diamine, R3 and R4 in formula (3) can be identical or different, which are hydrogen atom or C1-5 alkyl, or can connect with a carbon atom to form a cycloalkyl.

Description

1. Technical field [0001] The present invention relates to a novel platinum(II) complex with good water solubility, low toxicity and effective antitumor activity, its preparation method and the in vitro antitumor properties of typical compounds in the above platinum(II) complexes. 2. Background technology [0002] Due to the clinical success of cisplatin and carboplatin, thousands of new platinum complexes have been synthesized and screened for anti-tumor activity, and about 30 compounds have entered human clinical trials. Nedaplatin was launched in Japan in 1995 [1] , Oxaliplatin was first launched in France in 1996, and has recently been launched in other countries in Europe and America [2] , Song Platinum (Sunpla, SKI-2053R) was launched in Korea in 1999 [3] . [0003] Cisplatin has been shown to be effective against various human tumors with broad-spectrum anticancer properties, but it has severe dose-limiting toxicities such as nephrotoxicity, myelosuppression, nause...

Claims

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Application Information

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IPC IPC(8): A61K31/28A61P35/00C07F15/00
Inventor 苟少华刘芸
Owner NANJING UNIV
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