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O-carborane derivative, synthesis method and application thereof

A technology of o-carborane and synthesis method, which is applied in the field of o-carborane derivatives to achieve the effects of increasing cell affinity and increasing polarity

Active Publication Date: 2020-06-02
南京艾斯特医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But BPA has a disadvantage: once the BPA level in tumor cells rises, it will be excreted through the "anti-transport" mechanism, which makes BNCT somewhat limited

Method used

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  • O-carborane derivative, synthesis method and application thereof
  • O-carborane derivative, synthesis method and application thereof
  • O-carborane derivative, synthesis method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1~3

[0033] Embodiment 1~3 is the preparation embodiment of compound 1, compound 2

Embodiment 1

[0035] 1.48g of compound 1 (5-fluoro-2-methyl-1H-indene), 20ml of dichloromethane and 1.4g of aluminum trichloride were added to a 100ml single-necked flask, and the temperature of the system was reduced to 0-10 ℃, add 1.0g of 1-chloroacetic acid dropwise, the temperature rises to 15-20℃ and reacts for 4h. MgSO 4 After drying, the mother liquor was filtered and distilled under reduced pressure to obtain 1.9 g of compound 2, with a yield of 95%. The detection parameters are:

[0036] 1 H-NMR: 1.78 (s,3H), 2.93 (t, J = 5.5 Hz, 2H), 3.24 (t, J = 5.4 Hz, 2H), 5.37 (s, 1H), 6.67–6.68 (d, J = 8.5 Hz, 1H), 7.02 (s, 1H), 7.36–7.38 (d, J =8.7 Hz, 1H).

Embodiment 2

[0038] Roughly the same as Example 1, except that dichloromethane was replaced by chloroform to obtain 2.0 g of compound 2 with a yield of 98%.

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Abstract

The invention discloses an o-carborane derivative and a synthesis method thereof. The method includes: step 1, taking 5-fluoro-2-methyl-1H-indene or 5-trifluoromethyl-2-methyl-1H-indene as a reactioninitiator, adopting aluminum trichloride as a catalyst, and carrying out reaction with 1-chloroacetic acid to obtain an intermediate 2; step 2, reacting the intermediate 2 with N-bromosuccinimide by taking DMF as a reaction solvent to obtain an intermediate 3; and step 3, reacting the intermediate 3 with o-carborane in an organic solvent or ionic liquid under an alkaline condition to obtain the corresponding o-carborane derivative. According to the invention, fluorine ions and relative hydrophilic groups are introduced for modification through chemical synthesis, the purposes of reducing toxicity and increasing compound polarity and cell affinity are achieved, so that the technical effect of targeted enrichment and high concentration of boron ions in tumor cells is achieved, and then the technical bottleneck that p-borane phenylalanine (BPA) is discharged by an "anti-transport" mechanism after the concentration of the BPA in the tumor cells reaches a certain number 1 is solved.

Description

technical field [0001] The present application relates to the technical field of organic synthesis, in particular, to an o-carborane derivative, its synthesis method, and its application. Background technique [0002] Boron Neutron Capture Therapy, or BNCT for short, is applied to thermal neutron irradiation to target boron accumulated in tumors or cancer sites. After boron captures neutrons, heavy particles α particles (helium nuclei) and high-energy Li nuclei are produced. , and then selectively kill tumor and cancer cells. Tumor radiotherapy is a relatively popular treatment method in the medical field today. Its principle is to use the biological effects of ionizing radiation to emit radiation to directly or indirectly cause tumor cell damage. Under the irradiation of large doses of ionizing radiation, biological organisms and cell macromolecules will cause damage, leading to apoptosis or necrosis of tumor cells, which is a direct effect. The indirect effect is due to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/05A61P35/00
CPCA61P35/00C07F5/05Y02P20/54
Inventor 金峰金涛王雯王贵军何亚杰李仙洛金成福
Owner 南京艾斯特医药科技有限公司
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