Preparation method of prodigiosin derivative

A technology for prodigiosin and derivatives, applied in the field of preparation of prodigiosin derivatives, capable of solving problems such as low yield and single product

Inactive Publication Date: 2013-06-12
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Compounds 1 and 2 are derived from the metabolic derivatives of actinomycetes. However, the extraction of these compounds by this method is limited by the characteristics of low yield and single product.

Method used

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  • Preparation method of prodigiosin derivative
  • Preparation method of prodigiosin derivative
  • Preparation method of prodigiosin derivative

Examples

Experimental program
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Embodiment 1

[0047] Embodiment 1, the preparation of prodigiosin derivative

[0048] The structural formula of the prepared prodigiosin derivative is shown in formula I-a.

[0049]

[0050] (Formula IV-a) (Formula III-a) (Formula V-a)

[0051]

[0052] (Formula VI-a) (Formula VII-a) (Formula I-a)

[0053] Dissolve 8.40 g of the compound represented by formula III-a in 110 mL of 4N sodium hydroxide solution and heat to 55°C. Dissolve 6.90 g of the compound represented by formula II-a in 110 mL of methanol, then drop this solution into the above-mentioned sodium hydroxide solution, and allow it to react at 55° C. for 12 hours after the addition is complete. Cool to room temperature, concentrate to remove the organic solvent, and then put it in the refrigerator (0° C.) for 24 hours to precipitate a white solid. After filtration and washing with water, 7.28 g of the compound represented by formula IV-a was obtained as a white solid (55%).

[0054] The structure confirmation results a...

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Abstract

The invention discloses a preparation method of prodigiosin derivative. The structural formula of the prodigiosin derivative compound is shown as a formula I. The preparation method comprises the following steps of: 1) in the presence of alkali, reacting a compound shown as a formula 2 and a compound shown as a formula 4; 2) carrying out a cyclization reaction on the obtained products in the presence of an acid catalyst; 3) carrying out a reduction reaction on the obtained products; and 4) carrying out a Weisimaisi reaction between the obtained products and a compound shown as a formula 7 to obtain a compound shown as a formula 1. The preparation method disclosed by the invention has the advantages of simple steps, mild reaction conditions and high yield, is easy to enlarge and convenient for products derivatization and has great industrial production potential.

Description

technical field [0001] The invention relates to a preparation method of prodigiosin derivatives. Background technique [0002] In 2008, the Fenical research group extracted a class of prodigiosin derivatives (1)(2) (Marineosins A and B) with a new carbon skeleton from a marine Streptomyces Actinomyces sediment (Streptomyces) (Org. Lett. 2008, 10, 5505-5508). The biological activity test of this alkaloid compound showed that: 1 and 2 showed better biological activity (IC 50 = 0.5 μM and IC 50 =46μM), and also has a good selective inhibitory activity on melanoma and leukemia cancer cells, so its research and transformation is expected to be used as a lead compound for the development of new anticancer clinical drugs. [0003] [0004] Compounds 1 and 2 are derived from the metabolic derivatives of actinomycetes. However, the extraction of these compounds by this method is limited by the characteristics of low yield and single product. By means of chemical synthesis, not...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107
Inventor 史一安李广李奇冯鹏举张勋
Owner INST OF CHEM CHINESE ACAD OF SCI
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