Unlock instant, AI-driven research and patent intelligence for your innovation.

Desoxyribose nucleic acid dual intercalating agent using methyl iso thiourea cation as linker

A deoxyribonucleic acid, methyl isothiourea technology, applied in medical preparations containing active ingredients, organic active ingredients, organic chemistry, etc., can solve the problem of single linker, etc. The effect of damage ability

Inactive Publication Date: 2008-01-30
DALIAN UNIV OF TECH
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, although many DNA double intercalators have been reported, most of them are modified on the intercalation parent structure, and the choice of linker is relatively simple, usually using a flexible nitrogen-containing alkylamino chain
The molecular design concept of the methylisothiouronium cation involved in the present invention as the linker of the DNA double intercalator has not been reported so far

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Desoxyribose nucleic acid dual intercalating agent using methyl iso thiourea cation as linker
  • Desoxyribose nucleic acid dual intercalating agent using methyl iso thiourea cation as linker
  • Desoxyribose nucleic acid dual intercalating agent using methyl iso thiourea cation as linker

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] 10 grams of naphthalene anhydride and 6.1 grams of ethylenediamine were added to 60 milliliters of acetonitrile, stirred and heated, and kept at 60 ° C for 3 hours, then cooled to normal temperature, and solids were precipitated, filtered and dried to obtain 10.3 grams of intermediate product B1, the yield 85%; 5 grams of compound B1 were suspended in 100 milliliters of ethylene glycol monomethyl ether, 0.8 grams of carbon disulfide was added, stirred, heated to 120 ° C, kept for 2.5 hours, cooled, and solids were precipitated, filtered to obtain 5.1 grams of intermediate product C1, harvested The rate is 94%. Suspend 1 g of compound C1 in 30 ml of chloroform, add 0.24 g of dimethyl sulfate, stir, heat at 60 ° C, keep for 2 hours, cool to precipitate a solid, filter to obtain 0.8 g of product, DNA double intercalator D1, yield 71%.

[0016]

[0017] D1 melting point: 190-191°C; 1 H NMR: δδ9.40 (br s 2H), 8.46-8.44 (d, J = 8.4Hz, 8H), 7.87-7.83 (t, J = 7.6Hz, 4H), 4...

Embodiment 2

[0019] 10 grams of naphthalene anhydride and 7.5 grams of ethylenediamine were added to 60 milliliters of acetonitrile, stirred and heated, and kept at 60 ° C for 3 hours, then cooled to normal temperature, and solids were precipitated, filtered and dried to obtain 9.8 grams of intermediate product B2, the yield 76%; 5 grams of compound B1 were suspended in 100 milliliters of ethylene glycol monomethyl ether, 0.74 grams of carbon disulfide was added, stirred, heated to 120 ° C, kept for 2.5 hours, cooled, and solids were precipitated, filtered to obtain 5.2 grams of intermediate product C2, harvested The rate is 96%. Suspend 1 g of compound C2 in 30 ml of chloroform, add 0.23 g of dimethyl sulfate, stir, heat at 60°C, keep for 2 hours, cool to precipitate a solid, filter to obtain 0.82 g of product, DNA double intercalator D2, yield 77 %.

[0020]

[0021] D2 melting point: 147-148°C; 1 H NMR: δ 9.08 (br s 1H), 8.68 (br s, 1H), 8.42-8.36 (m, 8H), 7.84-7.79 (t, J=7.6Hz, 4H...

Embodiment 3

[0023] 10 grams of naphthalene anhydride and 11.8 grams of hexamethylenediamine were added to 60 milliliters of acetonitrile, stirred and heated, and kept at 60 ° C for 3 hours, then cooled to normal temperature, and solids were precipitated, filtered and dried to obtain 10.0 grams of intermediate product B1, yield 66 %; 5 grams of compound B3 were suspended in 100 milliliters of ethylene glycol monomethyl ether, 0.64 grams of carbon disulfide was added, stirred, heated to 120 ° C, kept for 2.5 hours, cooled, and solids were precipitated, filtered to obtain 5.2 grams of intermediate product C3, yield 98%. Suspend 1 g of compound C3 in 30 ml of chloroform, add 0.19 g of dimethyl sulfate, stir, heat at 60°C, keep for 2 hours, cool to precipitate a solid, filter to obtain 0.84 g of product, DNA double intercalator D3, yield 76 %.

[0024]

[0025] D3 melting point: 115-116°C; 1 H NMR: δ9.11 (br s 1H), 8.71 (br s, 1H), 8.42-8.36 (m, 8H), 7.84-7.79 (t, J=7.6Hz, 4H), 4.03-4.00 ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present invention relates to a naphthoylimines deoxyribonucleic acid (DNA) diintercalating agent by using methylisothiourea cation as linking group, its preparation method and biological application of its used as tumor inhibitor. Said DNA diintercalating agent uses methylisothiourea cation as linking group and is connected with two naphthoylimine structure units. Said invention also provides the concrete steps of its preparation method. Said DNA diintercalating agent has good activity for resisting tumor.

Description

Technical field: [0001] The invention relates to a class of naphthalimide deoxyribonucleic acid double intercalator with methylisothiouronium cation as linking group, its preparation method and its biological application as a tumor suppressor. Background technique: [0002] In recent years, the research and development of new anticancer drugs has been a hot spot in medicinal chemistry. Since the deoxyribonucleic acid (hereinafter referred to as DNA) of tumor cells and normal cells is significantly different, it is an ideal choice to use DNA as the target of anti-tumor drugs. DNA intercalators can intercalate into the middle of DNA base pairs, leading to changes in DNA topology, which in turn affects the recognition and action of topoisomerase on DNA. According to literature (Cur.Pharm.Design, 2001, 7, 1745) reports, different classes of DNA intercalators, such as anthracyclines, acridines, naphthalimides, actinomycins, etc., are used as Anti-tumor research; using them as a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/473A61P35/00C07D221/06
Inventor 肖义金礼吉
Owner DALIAN UNIV OF TECH