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Method for synthetizing allyl-substituted camptothecin compound

A technology of hydroxycamptothecin and allyl, which is applied in the field of drug synthesis and can solve problems such as highly toxic tin reagents

Inactive Publication Date: 2012-07-04
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Although this method can obtain high-purity compound 1, it requires the use of highly toxic tin reagents

Method used

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  • Method for synthetizing allyl-substituted camptothecin compound
  • Method for synthetizing allyl-substituted camptothecin compound
  • Method for synthetizing allyl-substituted camptothecin compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0026] 9-iodo-10-hydroxycamptothecin:

[0027] 10-Hydroxycamptothecin (2.0g, 5.5mmol) was dissolved in DMF (50ml), cooled to 0°C in an ice-water bath, N-iodosuccinimide (1.24g, 5.5mmol) was added, and reacted at room temperature for 2h After the reaction is completed, pour it into 200ml of ice water and adjust the pH value to 3-4 with 1N HCl. After fully stirring, filter with suction, wash with water, and dry to obtain 2.5 g of a yellow solid with a yield of 95%. 1 HNMR (DMSO-d 6 )(ppm) 11.2(1H, s), 8.72(1H, s), 8.07(1H, d), 7.63(1H, d), 7.28(1H, s), 6.50(1H, s), 5.42(2H, s), 5.29 (2H, s), 1.83-1.90 (2H, m), 0.88 (3H, t).

[0028] 9-iodo-10-methoxymethylcamptothecin:

[0029] Disperse 2.0g of 9-iodo-10-hydroxycamptothecin in 200ml of anhydrous dichloromethane, add 1.4ml of diisopropylethylamine, slowly add 0.4ml of chloromethyl ether to the system at room temperature, and Continue the reaction at room temperature for 2 hours. After the reaction is completed, pour it into ...

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Abstract

The invention discloses a method for preparing high-purity 9-allyl-10-hydroxycamptothecine (compound 1). The method comprises the following steps of: (1) reacting 10-hydroxycamptothecine with a halogenated reagent to obtain 9-bromine-10-hydroxycamptothecine and 9-iodine-10-hydroxycamptothecine; (2) protecting 10-position hydroxyl; (3) introducing a Suzuki reaction into the allyl; and (4) removingthe protective group to obtain the compound 1. The product has the characteristics of high purity and capability of meeting the clinical requirement.

Description

technical field [0001] The invention belongs to the field of medicine synthesis, and relates to a synthesis method of allyl-substituted camptothecin compounds, in particular to a synthesis method of 9-allyl-10-hydroxycamptothecin (1). [0002] Background technique [0003] Camptothecin (2) is an alkaloid, which was isolated by American scientist Wall from the unique Chinese plant camptothecin in 1966. Camptothecin has significant activity on rat leukemia L1210 system. Camptothecin compounds are important antitumor drugs. [0004] [0005] Studies have found that 9-allyl-10-hydroxycamptothecin (compound 1) has excellent anticancer activity both in vivo and in vitro, and is a new antitumor drug under development. [0006] At present, the compound has two synthetic methods: one is to use 10-hydroxycamptothecin (3) as a raw material and obtain it through two-step reactions, and its route is: [0007] [0008] Although this synthetic route is very simple, it will produ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/22
CPCY02P20/55
Inventor 吕伟黄颖梅铁文余善宝罗宇
Owner EAST CHINA NORMAL UNIV
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