A kind of spin-labeled cameline A compound, preparation method and use thereof

A spin-labeling, camelonine technology, applied in organic chemistry, drug combination, anti-tumor drugs, etc., can solve the problems of ineffective anti-tumor activity of derivatives, low anti-tumor activity, and narrow activity spectrum, etc. Achieve the effect of novel structure, high product purity and strong inhibitory effect

Active Publication Date: 2019-01-08
甘肃康扬医药科技有限公司
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Problems solved by technology

Although researchers have done a lot of research work on the derivative synthesis of camelline and the structure-activity relationship of anti-tumor in recent years, as an anti-tumor lead molecule, cameline A still has the problems of low anti-tumor activity and narrow activity spectrum. , even after derivation and structural modification, the antitumor activity of derivatives is not effectively improved or completely lost
However, up to now, there is still no effective modification and optimization strategy to improve the antitumor effect of such molecules.

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  • A kind of spin-labeled cameline A compound, preparation method and use thereof
  • A kind of spin-labeled cameline A compound, preparation method and use thereof
  • A kind of spin-labeled cameline A compound, preparation method and use thereof

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Embodiment Construction

[0013] One, the preparation method of the spin-labeled cameline compound of the present invention

[0014] The following is the best preparation method of the spin-labeled camelamine compound of the present invention:

[0015] 1) Synthesis of intermediate 2: phthalic anhydride (1.69eq) was placed in an appropriate amount of glacial acetic acid, and then benzylamine (2.3eq) was slowly added therein. After the mixture was heated to reflux for 5 hours, the hot reaction solution was directly poured into ice water, and a large amount of precipitation occurred. After suction filtration, the filter cake was rinsed several times with cold water, and compound 2 was obtained after drying (refer to Chemistry-AEuropean Journal, 2009,15(47):12960-12962), see formula 6.

[0016]

[0017]2) Synthesis of Intermediate 3: First, the entire reaction device was evacuated, and replaced with argon for 3 to 5 times, then methylmagnesium iodide (6eq) was injected into a round bottom flask with a ...

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Abstract

The invention discloses a spin-labeling luotonin A compound of formula (I) as shown in the specification, as well as a preparation method and application of the compound. In-vitro antitumor activity screening results show that compared with luotonin A, the spin-labeling luotonin A compound disclosed by the invention is relatively intense in inhibition activity on human lung adenocarcinoma cells (A549), human breast cancer cell lines (MDA-MB-468), human ovarian neoplasm cells (SKOV3) and human colon cancer cell lines (HCT 116), and has good application prospects.

Description

technical field [0001] The invention relates to a spin-labeled cameline A compound, a preparation method of the compound and its use in the preparation of antitumor drugs. It belongs to the field of medicine. Background technique [0002] Cameline A is a natural quinazoline alkaloid isolated from the Chinese medicinal plant Artemisia nigelastrum Bunge. in 1997. Researchers pay attention to cameline A, mainly because they found that cameline A has a similar chemical structure to camptothecin with anticancer activity, and has inhibitory effect on mouse tumor cell P388 cell line in vitro (IC 50 1.8 μg / mL), and demonstrated that it has camptothecin-like inhibitory topoisomerase I activity ((1) Molecules, 2011, 16, 4861-4883). Based on this, in recent years, using cameline A as the leading model, researchers have systematically carried out the research on the total synthesis, structure optimization and antitumor activity evaluation of cameline A and its derivatives ((1) Org.Bio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22A61P35/00
CPCC07D471/22
Inventor 刘映前王美娟宋子龙杨茜茹成丕乐赵永龙陈海乐李俊采
Owner 甘肃康扬医药科技有限公司
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