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Indoline diketopiperazine spiro-compounds as well as preparation method and use thereof

A compound and composition technology, which is applied in the preparation of indoline diketopiperazine spiro compounds, indoline diketopiperazine spiro compounds, and the field of spiro compounds, and can solve problems that have not been documented, etc. question

Inactive Publication Date: 2013-08-14
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the molecule has the dimer molecular skeleton formed by the condensation and connection of the above-mentioned tetracyclic indoline diketopiperazine skeleton structure and 1-oxaspiro[4,5]decane skeleton structure involved in the present invention The indoline diketopiperazine spiro compound has not been documented so far

Method used

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  • Indoline diketopiperazine spiro-compounds as well as preparation method and use thereof
  • Indoline diketopiperazine spiro-compounds as well as preparation method and use thereof
  • Indoline diketopiperazine spiro-compounds as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Embodiment 1: Microbial fermentation culture and the preparation of compound 1 and compound 2

[0098] 1. Fermentation culture and extraction of fermented products

[0099] 1) Production strains

[0100] The toxin-producing bacteria used in this example to ferment and produce compounds 1 and 2 is Penicillium purpurogenum BD-1-3 (Penicillium purpurogenum BD-1-3) preserved in the General Microorganism Center of China Microbial Culture Collection Management Committee. The number is 4284 (CGMCC No.4283).

[0101] 2) Fermentation culture

[0102] From the slant of the test tube of PDA medium (composition: 2% glucose, 2% agar, 1.5% NaCl, prepared with 20% potato boiling liquid) of Penicillium purpura BD-1-3 stored in the refrigerator, use the inoculated Under aseptic conditions, appropriate amount of spores were scraped from the loop, streaked and inoculated on a newly prepared PDA solid medium plate, and activated and cultured in a 28°C incubator for 4 days. From the sl...

Embodiment 2

[0119] Example 2: Fermentation culture of Penicillium purpura 3-f-31 and separation and preparation of compound 1

[0120] 1. Fermentation culture and extraction of fermented products

[0121] 1) Production strains

[0122] The toxin-producing bacteria used to ferment and produce compound 1 in this example is the Penicillium purpurogenum 3-f-31 strain preserved in the General Microorganism Center of the China Microbiological Culture Collection Management Committee, and the preservation number is 7286 (CGMCC No. .7286).

[0123] 2) Fermentation culture

[0124] From the slant of the test tube of PDA medium (composition: 2% glucose, 2% agar, 1.5% NaCl, prepared with 20% potato boiling liquid) of Penicillium purpurea 3-f-31 stored in the refrigerator, inoculate with Scrape the appropriate amount of spores under aseptic conditions, streak and inoculate them on a newly prepared PDA solid medium plate, and cultivate them in a 28°C incubator for 3-5 days. When the spores are fo...

Embodiment 3

[0134] Embodiment 3: Derivatization preparation of other compounds of formula I of the present invention 1a-1i and 2a-2r

[0135] 1) Derivatization preparation of compound 1a-1i of formula I of the present invention

[0136] Weigh about 10 mg of Compound 1 prepared in the above-mentioned Example 1 and Example 2, dissolve it with 0.5 ml of acetone, add 50 mg of anhydrous K 2 CO 2 Mix well, and add 50 μl methyl iodide dropwise under magnetic stirring at 60°C to carry out methylation reaction for 6 h. The reaction product was separated and purified by preparative silica gel thin-layer chromatography (developed by chloroform-methanol volume ratio 93:7). In addition to recovering 5 mg of raw material compound 1, 1a (1.3 mg, positive ion ESI-MS m / z: 877 [M+H] + , negative ion ESI-MS m / z:875[M-H] - ).

[0137] Weigh about 10 mg of Compound 1 prepared in the above-mentioned Example 1 and Example 2, dissolve it with 0.5 ml of acetone, add 50 mg of anhydrous K 2 CO 2 Mix well, ...

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Abstract

The invention belongs to the field of medical and chemical industry, relates to indoline diketopiperazine spiro-compounds as well as a preparation method and use thereof, and in particular relates to compounds as shown in formula I or pharmaceutically acceptable salts of the compounds. The compounds have a framework dimerization molecular structure condensed by terracycloindoline diketopiperazine and 1-oxa spiro[4, 5] decane. Two ethylene oxide structures are arranged on the spiro hexatomic ring. The invention further relates to penicillium purpurogenum for preparing the compounds as shown in the formula I. Experiments show that the compounds can be used for preparing cytoskeletal protein inhibitors, apoptosis inducers, tumor cell proliferation inhibitors, tumor cell killing agents or antitumor drugs. The compounds provided by the invention have good antitumor activity.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and relates to a class of spiro compounds, in particular to indoline diketopiperazine spiro compounds, and the invention also relates to a composition comprising the indoline diketopiperazine spiro compounds, And the preparation method and application of indoline diketopiperazine spiro compound. Background technique [0002] Tumor is a new organism formed by the body under the action of various carcinogenic factors, a certain cell in the local tissue loses its normal regulation of its growth at the gene level, resulting in abnormal clonal proliferation. Tumors are generally divided into benign and malignant. All malignant tumors are collectively called cancer. [0003] The structure types of spiro compounds are very rich. Only spiro[4,5]decane compounds can form many different structural types because one or more of different positions on the spiro ring skeleton are replaced by he...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C12N1/14A61K31/4985A61P35/00A61P35/02C12R1/80
Inventor 崔承彬房士明李长伟王楠吴长景
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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