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Preparation methods of myrtuco mmulone J and Myrtucommuacetalone and their analogs

A technology of analogs and ketones, applied in the field of synthetic medicinal chemistry, can solve the problems of no chemical total synthesis, and achieve the effect of economical preparation methods

Active Publication Date: 2019-09-13
SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, their very complex ring system structure makes chemical synthesis very challenging, and there is still no report on chemical total synthesis

Method used

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  • Preparation methods of myrtuco mmulone J and Myrtucommuacetalone and their analogs
  • Preparation methods of myrtuco mmulone J and Myrtucommuacetalone and their analogs
  • Preparation methods of myrtuco mmulone J and Myrtucommuacetalone and their analogs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: Screening of reaction conditions

[0040] Taking the reaction of unsaturated ketone (compound 9, 0.2mmol) and isobutyrylphloroglucinol (compound 10, 0.2mmol) in solvent (3mL) as an example, investigate the influence of different solvents, acid catalysts and reaction temperature, the specific steps are as follows :

[0041] Dissolve unsaturated ketone (compound 9, 0.2mmol) and isobutyrylphloroglucinol (compound 10, 0.2mmol) in the solvent, add trifluoroacetic acid (50uL) or p-toluenesulfonic acid (0.02- 0.05mmol) at different temperatures. After the reaction was completed, the mixture was purified through a section of about 10 cm long silica gel chromatography column (n-hexane:ethyl acetate=5:1) to obtain the corresponding products Compounds 11 and 12. Spectral data: 1 H NMR (500MHz, CDCl 3 ):δ=14.03(brs,1H),13.92(brs,1H),6.15(brs,1H),5.93(s,1H),5.83(s,1H),4.00(dt,J=13.4,6.5Hz, 1H), 3.89(dt, J=13.6, 6.8Hz, 1H), 3.52(d, J=2.8Hz, 1H), 3.47(d, J=3.0Hz, 1H...

Embodiment 2

[0050] Example 2: Different unsaturated ketone compounds

[0051] The specific steps of synthesis are as follows:

[0052] Dissolve unsaturated ketone (compound 16, 0.2mmol) and isobutyrylphloroglucinol (compound 10, 0.2mmol) in toluene / tetrahydrofuran mixed solution (3mL, v:v=5:1), and add to the reaction system Add trifluoroacetic acid (50uL) or p-toluenesulfonic acid (0.02-0.05mmol) to react. After the reaction was completed, the mixture was purified through a silica gel chromatography column (n-hexane:ethyl acetate=5:1) about 10 cm long to obtain the corresponding products Compound 17 and Compound 18.

[0053]

[0054] 1-(6,8-Dihydroxy-2,2-dimethyl-3,4,4a,5-tetrahydro-2H-5,10a-propanopyrano[2,3-b]chromen-7-yl)-2-methylpropan- 1-one(compound 17a and 1-(6,8-dihydroxy-2,2-dimethyl-3,4,4a,5-tetrahydro-2H-5,10a-propanopyrano[2,3-b]chromen-9- yl)-2-methylpropan-1-one (compound 18a):

[0055]

[0056] 1 H NMR (500MHz, CDCl 3 ):δ=13.84(brs,1H),13.70(brs,1H),6.33(brs,1H...

Embodiment 3

[0076] Example 3: Different monoacylphloroglucinol compounds

[0077] When different monoacylphloroglucinol compounds 13a-13f were used as substrates, the target analogs could be efficiently obtained in very good yields under the conditions of trifluoroacetic acid as catalyst and toluene / THF as mixed solvent .

[0078] Two, when diformylphloroglucinol is used, p-toluenesulfonic acid is needed as a catalyst, toluene is used as a solvent, and the target product can be successfully obtained under the condition of heating at 60 degrees.

[0079]

[0080] Spectral data: 1-(5,7-Dihydroxy-2,2-dimethyl-2,3,3a,4-tetrahydro-4,9a-propanofuro[2,3-b]chromen-6-yl)etha none (compound 14a) 1-(5,7-dihydroxy-2,2-dimethyl-2,3,3a,4-tetrahydro-4,9a-propanofuro[2,3-b]chromen-8-yl)etha none (Compound 15a ):

[0081]

[0082] 1 H NMR (500MHz, CDCl 3 ):δ=13.87(s,1H),5.97(s,1H),5.97(s,1H),3.84(ddd,J=6.6,4.2,2.6Hz,1H),3.53(d,J=2.8Hz, 1H), 3.48(d, J=2.8Hz, 1H), 2.71(s, 3H), 2.70(s, 3H), 2.37-...

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Abstract

The invention discloses a preparation method of an antimicrobial compound Myrtucommulone J, an anticancer compound Myrtucommuacetalone and analogues of Myrtucommulone J and Myrtucommuacetalone. The method comprises the following steps: target products are prepared from unsaturated ketone compounds and monoacyl phloroglucinol compounds in a nonpolar solvent under the action of a trifluoroacetic acid, acetic acid or p-toluenesulfonic acid catalyst through a reaction. Biomimetic total synthesis is realized for the first time, the structure of Myrtucommulone J is further confirmed, and one efficient, reliable and economical preparation method is provided for abundant obtaining of Myrtucommulone J, Myrtucommuacetalone and the analogues of Myrtucommulone J and Myrtucommuacetalone as well as subsequent structure-function relationship and druggability based development and production.

Description

[0001] Technical field: [0002] The invention relates to the field of synthetic medicinal chemistry, in particular to a preparation method of an antibacterial compound Myrtuco mmulone J, an anticancer compound Myrtucommuacetalone and analogs thereof. [0003] Background technique: [0004] Phloroglucinol compounds have complex structures, novel diversity and broad-spectrum and significant biological activities, which have attracted extensive attention from synthetic and medicinal chemists in recent years. Myrtucommulone J is a novel and complex phloroglucinol compound isolated from Myrtuscommunis, the genus of Myrtaceae. The antibacterial activity evaluation shows that it has very significant antibacterial activity, and its MIC value is as low as 0.38uM, which is excellent. "Vancomycin", the last barrier of clinical antibacterial drugs; in addition, Myrtucommulone J's anti-Staphylococcus aureus activity has a selectivity factor as high as 35 times that of normal human cells, s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/08
Inventor 谭海波刘洪新霍璐琼王煜徐志防邱声祥
Owner SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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