Tanshinone I derivatives and pharmaceutical application thereof

A derivative, the technology of tanshinone, applied in the field of medicine, can solve the problems that the molecular structure is difficult to modify, and the medicinal value of tanshinone I has not been fully developed, so as to improve bioavailability, bioavailability and curative effect, and biological Effect of Utilization and Enhancement of Efficacy

Inactive Publication Date: 2006-09-27
秦引林
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This new compound described in this patented formula helps improve how well we use certain drugs that are commonly used for treating diseases like cancer or heart disease. It does this because they have better absorption into our bodies compared to other medications currently available. Additionally, adding an ester group at one end allows them to be easily transported across cell membranes without being blocked up from moving around inside cells. Overall, these improvements make us safer ways to administer such molecules effectively while still maintaining their beneficant properties.

Problems solved by technology

This patented technical problem addressed by this patents describes how to modify the structure and improve the effectiveness of extracting tarsanilide (TSA) with high water solvable content without losing important properties such as potency.

Method used

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  • Tanshinone I derivatives and pharmaceutical application thereof
  • Tanshinone I derivatives and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1. 2-(cyclohexylamine) methyl-tanshinone I synthesis steps and structural confirmation

[0053] Mix 1.46g of tanshinone I, 0.5mL of 37% formaldehyde solution, 2.5g of cyclohexylamine, and 50mL of acetic acid, heat and reflux in an oil bath for 10 hours, remove the solvent from the mixture under reduced pressure to obtain a red solid, dissolve it in water, filter, and add alkali to the filtrate to adjust the pH to 9, filtered, the filter cake was dried, and separated by silica gel column chromatography (eluent: chloroform / methanol=15 / 1) to obtain 1.14 g (yield 55%) of the expected compound.

[0054] 1 H-NMR (CDCl 3 )δ9.13(d, 1H), 8.20(d, 1H), 7.85(d, 1H), 7.57(q, 1H), 7.24(d, 1H), 3.83(s, 2H), 3.21~3.38(m , 4H), 2.75(s, 3H), 2.31(s, 3H), 1.75~1.81(m, 4H), 1.52~1.69(m, 4H).

Embodiment 2

[0055] Example 2. 2-(2', 5'-dimethylpiperazine) methyl-tanshinone I synthesis steps and structural confirmation

[0056]Mix 1.46g of tanshinone I, 0.5mL of 37% formaldehyde solution, 2.8g of 2'5-dimethylpiperazine, and 50mL of acetic acid, and heat to reflux in an oil bath for 10 hours. Dissolve, filter, add alkali to the filtrate to adjust the pH to 9, filter, dry the filter cake, and separate by silica gel column chromatography (eluent: chloroform / methanol=15 / 1) to obtain 1.08 g (yield 51%) of the expected compound.

[0057] 1 H-NMR (CDCl3) δ9.28(d, 1H), 8.28(d, 1H), 7.85(d, 1H), 7.58(q, 1H), 7.25(d, 1H), 3.38~3.51(m, 2H ), 2.92~3.14(m, 4H), 3.73(s, 2H), 2.67(s, 3H), 2.28(s, 3H), 1.82(s, 1H), 1.52(s, 3H), 1.31(s, 3H).

Embodiment 3

[0058] Example 3. 2-(diallylamino)methyl-tanshinone I synthesis steps and structural confirmation

[0059] Mix 1.46g of tanshinone I, 0.5mL of 37% formaldehyde solution, 2.4g of diallylamine, and 50mL of acetic acid, heat and reflux in an oil bath for 10 hours, remove the solvent from the mixture under reduced pressure to obtain a red solid, add water to dissolve, filter, and add alkali to the filtrate Adjust the pH to 9, filter, dry the filter cake, and separate by silica gel column chromatography (eluent: chloroform / methanol=15 / 1) to obtain 1.03 g (yield 50%) of the expected compound.

[0060] 1 H-NMR (CDCl3) δ9.26(d, 1H), 8.27(d, 1H), 7.91(d, 1H), 7.48(q, 1H), 7.22(d, 1H), 5.42~5.58(m, 2H ), 4.75~4.91(m, 4H), 3.85(s, 2H), 2.81~2.98(m, 4H), 2.61(s, 3H), 2.12(s, 3H).

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Abstract

The invention discloses a tanshinoneIderivant and application in pharmacy, which is characterized by the following: the derivant constitutional formula is showed in the right chart: when R1 represents -Ar, R2,R3 represents hydrogen or alkyl with one to eight carbon atoms, cycloalkyl, aromatic nucleus or heterocyclic radical; or R2-N-R3 represents nitrogen saturation aza with nitrogen, imidazoline and its derivant, glyoxaline and its derivant, diethylenediamine and its derivant, piperidine and its derivant, morpholine and its derivant; when R1 represents -H, R2, R3 represents hydrogen and alkyl with three to eight carbon atoms, cycloalkyl, aromatic nucleus; or R2-N-R3 represents cyclohexylamine, imidazoline and its derivant, glyoxaline and its derivant, diethylenediamine derivant, piperidine derivant, morpholine derivant. The derivant can apply for preparing clinical preparation.

Description

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Claims

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Application Information

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Owner 秦引林
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