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Synthesis and application of nitrosourea compounds modified by benzisoselenazocone

A technology of benzisoselenazole and compounds, which is applied in the field of preparation of nitrosourea compounds modified by benzisoselenazole, can solve problems such as pulmonary fibrosis

Active Publication Date: 2021-09-07
NANJING KEAISE MEDICINE & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And when administered long-term, can cause potentially fatal pulmonary fibrosis

Method used

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  • Synthesis and application of nitrosourea compounds modified by benzisoselenazocone
  • Synthesis and application of nitrosourea compounds modified by benzisoselenazocone
  • Synthesis and application of nitrosourea compounds modified by benzisoselenazocone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Embodiment 1 2, the preparation of 2'-diselenide bisbenzoic acid

[0083] 2Se+4NaOH+Na 2 S 2 o 4 →Na 2 Se 2 +2Na 2 SO 3 +2H 2 o

[0084]

[0085] (1) 16g of sodium hydroxide, 18g of sodium hydrosulfite, and 16g of selenium powder were added into water successively, and the temperature was raised to 50° C., and the reaction was completed to obtain a sodium diselenide solution.

[0086] (2) Under ice-bath conditions, 28 g of anthranilic acid was added to 80 ml of 1:1 hydrochloric acid and stirred and mixed, and an aqueous solution of 18.0 g of sodium nitrite was slowly added dropwise therein to obtain 2-benzoic acid diazonium chloride.

[0087] (3) Add the solution of 2-benzoic acid diazonium chloride obtained in step 1 dropwise into the sodium diselenide solution obtained in step 2 under stirring in an ice-water bath, and the mixture continues to stir. pH paper proves that the solution is alkaline. Filter with celite, adjust the pH to 3, filter, wash the fil...

Embodiment 2

[0089] The preparation of embodiment 2 2-selenium chlorobenzoyl chlorides

[0090]

[0091] 40g of 2,2'-diselenide bisbenzoic acid, 200ml of thionyl chloride and a few drops of DMF were stirred and refluxed. After the reaction was completed, excess thionyl chloride was removed by rotary evaporation, and the residue was recrystallized with petroleum ether to obtain yellow needle-like crystals.

[0092] 1 H NMR (400MHz, CDCl 3): δδ7.39(t, J=7.7Hz, 1H, Ar-H), 7.67(t, J=7.7Hz, 1H, Ar-H), 7.85(d, J=7.7Hz, 1H, Ar-H ), 8.09 (d, J=7.7Hz, 1H, Ar-H).

Embodiment 3

[0093] Example 3 Preparation of 5,5'-difluoro-2,2'-diselenide bisbenzoic acid

[0094] 2Se+4NaOH+Na 2 S 2 o 4 →Na 2 Se 2 +2Na 2 SO 3 +2H 2 o

[0095]

[0096] This compound was obtained in the same manner as in Example 1.

[0097] 1 H NMR (400MHz, DMSO-d 6 ): δδ7.23(m, 2H), 7.40(dd, 2H), 8.11(m, 2H), 13.93(s, br, 2H)

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Abstract

The invention relates to a nitrosourea compound modified by benzisoselenazocone and an application thereof. The nitrosourea compounds modified by benzisoselenazocone of the present invention are represented by the general formula I. The benzisoselazolone-modified nitrosourea compound of the invention has excellent antitumor activity and can be widely used in the preparation of antitumor drugs.

Description

technical field [0001] The invention relates to a preparation method and application of a nitrosourea compound modified by benzisoselazolone, belonging to the field of chemistry Background technique [0002] Nitrosourea antineoplastic drugs are widely used alkylating agents, which are used in the clinical treatment of brain tumors, leukemia, malignant lymphoma, glioma and other diseases. [0003] Most of the nitrosourea antineoplastic drugs are difunctional alkylating agents. Its mechanism of action is: nitrosoureas decompose rapidly in aqueous solution to produce azohydroxide intermediates. This intermediate can be further decomposed into carbocations. Since macromolecules such as DNA are electron-rich molecules, they can be combined with carbocations, such as O in guanine 6 bit or N 7 The formation of alkylation damage, and even further reaction to form covalent cross-links between complementary base pairs. These cross-links can damage DNA replication and eventually l...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D293/12A61K31/41A61P35/00A61P35/02
CPCC07D293/12
Inventor 叶索夫曾慧慧
Owner NANJING KEAISE MEDICINE & TECH CO LTD