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Beta-element nitrogenous derivative, and its preparing method and use

A derivative, the technology of elemene, which is applied in the application field of nitrogen-containing derivatives of β-elemene, can solve the problems of weak anticancer effect, poor stability, and ineffective curative effect, etc.

Inactive Publication Date: 2006-10-25
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

β-Elemene has high selectivity to tumor cells, no myelosuppressive effect, no obvious liver and kidney toxicity, and has the "double effect" of selectively inhibiting tumor cell proliferation and improving immune function. This kind of tumor has definite curative effect, showing broad-spectrum anti-tumor characteristics (Wang XW. Elemene [J]. Drugs Fut, 1998, 23 (3): 266-270. Qian Jun. New anticancer drug-Elemene's pharmacology and clinical .[J]. Chinese Oncology Clinic, 1996, 23(6): 453-455. Chen Jianqun, Wu Kejian. Effects of Injection on Peripheral Blood T Lymphocyte Subgroups of Patients with Malignant Tumors [J]. Chinese Oncology Clinic, 1996, 23 (4): 299-301.) At present, elemene milk is used as a second-line anticancer drug in clinical practice. Its anticancer effect is weaker than that of 5-fluorouracil and cisplatin, and its effect on some solid tumors is not obvious.
Moreover, elemene has poor water solubility, and the clinically used dosage form is only emulsion, which has poor stability. Intravenous administration has obvious vascular irritation, and it is difficult to reach the site of action, which limits its clinical application.

Method used

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  • Beta-element nitrogenous derivative, and its preparing method and use
  • Beta-element nitrogenous derivative, and its preparing method and use
  • Beta-element nitrogenous derivative, and its preparing method and use

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Embodiment 1 Chlorinated β-elemene intermediate and preparation of

[0026] Add 51.0g (0.25mol) of β-elemene and 35mL (0.61mol) of glacial acetic acid into a three-necked flask equipped with a mechanical stirrer, cool to about 5°C with an ice-water bath, and add 180mL (1.41mol) dropwise under stirring. / L, 0.254mol) sodium hypochlorite solution, the dropwise addition is completed in about 4 hours, and the reaction is continued for 1 hour. Then the reaction solution was transferred to a separatory funnel, extracted twice with 50 mL of petroleum ether (60-90° C.), the organic phases were combined, washed with water until neutral, dried over anhydrous sodium sulfate, and concentrated to obtain 52.5 g of light yellow-green oil. GC showed 41.4% of unreacted elemene and 44.5% of monochloro-elemene, a mixture of 13-chloro-β-elemene and 14-chloro-β-elemene. It was separated by silica gel column chromatography and eluted with petroleum ether.

Embodiment 2

[0027] General method for the preparation of embodiment 2 β-elemene nitrogen-containing derivatives

[0028] Dissolve 10mmol of amine, 5mmol of monochlorinated β-elemene and 10mmol of triethylamine in 5mL of N,N-dimethylformamide and reflux for 8-20h. The resulting triethylamine hydrochloride needle crystals were filtered out, and the filtrate was added with 10 mL of water, extracted 4 times with petroleum ether-diethyl ether, the extract was dried and concentrated, and separated by thin-layer preparation with silica gel.

Embodiment 3

[0029] Example 3 Synthesis

[0030] Using 2-methylpiperazine as a raw material, it was prepared according to the general method for the preparation of nitrogen-containing derivatives of β-elemene in Example 2. Add maleic acid acetone solution dropwise to form maleate to obtain white crystals, mp123.0-125.9°C. MS(m / z): 302[M + ]; 1 H-NMR (CDCl 3 )δ (ppm): 0.99 (3H, s), 1.03 (3H, d), 1.45-1.64 (6H, m), 1.71 (3H, s), 1.91-2.00 (4H, m), 2.72-2.95 (7H , m), 4.59-4.93 (6H, m), 5.81 (1H, dd)

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Abstract

This invention discloses beta-elemene nitrogen contained derivant. Nitrogen contain hetero atomic ring is brought in beta-elemene nitrogen structure to synthesize new structure beta-elemene nitrogen contained derivant. Its molecular structure formula is (I), R represents C1-C20 fatty amine group and aromatic amine group, C1-C20 contains hetero atomic ring amido group, cyclohexane backbone has three chirality centers. The derivent has some biological activities like alkaloid, it can increase polar at the same time, and make the synthesized derivent display certain alkalinity, so the goal of improve water-solubility by it with mineral acid or organic acid salt.

Description

Technical field: [0001] The present invention relates to new β-elemene nitrogen-containing derivatives and a preparation method thereof, to an intermediate for synthesizing said β-elemene nitrogen-containing derivatives and a preparation method thereof, and to said β-elemene nitrogen-containing derivatives Application of nitrogen derivatives. Background technique: [0002] The β-elemene (I) isolated from the volatile oil of Curcuma wenyujin Y.H.Chen et C.Ling (Curcuma wenyujin Y.H.Chen et C.Ling), also known as Wenzezhu, is a broad-spectrum anti-tumor drug elemene milk developed by my country. The main components of (Guo Yongming, Wu Xiuying, Chen Yuren. Isolation and identification of elemene in the volatile oil of Wen Zezhu [J]. Chinese Medicine Bulletin, 1983, 8(30): 31-33). β-Elemene has high selectivity to tumor cells, no myelosuppressive effect, no obvious liver and kidney toxicity, and has the "double effect" of selectively inhibiting tumor cell proliferation and impr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/25A61K31/495C07C211/46C07D207/04C07D211/14C07D235/28C07D277/28C07D295/03C07D333/10
Inventor 徐莉英黄金华景永奎王敏伟
Owner SHENYANG PHARMA UNIVERSITY
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