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1-O-caffeoylquinic acid and derivative, preparing method and application thereof

A technology of caffeoylquinic acid and its derivatives, which is applied in the field of preparation of its derivatives, 1-O-caffeoylquinic acid, can solve the problems of not describing the synthesis conditions and yield in detail

Active Publication Date: 2018-05-08
WEDOCTOR INTELLIGENT INFORMATION & TECH BEIJING CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis conditions and yields are not described in detail in the article

Method used

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  • 1-O-caffeoylquinic acid and derivative, preparing method and application thereof
  • 1-O-caffeoylquinic acid and derivative, preparing method and application thereof
  • 1-O-caffeoylquinic acid and derivative, preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0116] Example 1: (1S,3R,4R,5R)-1-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4,5- Preparation of Trihydroxycyclohexanecarboxylic Acid (Compound 1-1)

[0117]

[0118] Step B:

[0119] Add caffeic acid (36.0g, 0.2mol) into the reaction flask, add 1mol / L sodium hydroxide aqueous solution (440ml) to dissolve, cool the system to 0°C, slowly add acetic anhydride (80ml, 0.84mol) dropwise, and keep at 0°C React for 1 h, filter, wash the filter cake until neutral, recrystallize the crude product with ethanol, and dry to obtain 44.87 g of SM white powder, yield: 84.98%, mp: 182-184 °C.

[0120] Step A:

[0121] D-(-)-Quinic acid (30.0g, 0.156mol, according to the literature Valentina Sinisi.Et al., "Interaction of chlorogenic acids and quinides from coffee with human serum malbumin", Food Chemistry, 2015 (168): 332-340 Method preparation), p-toluenesulfonic acid monohydrate (1.50g, 7.8mmol), acetone (1200.0ml) were put into a one-necked bottle, and a Soxhlet extractor with...

Embodiment 2

[0128] Embodiment 2 (preparation of compound 1-4)

[0129]

[0130] Step A:

[0131] Add intermediate 1b (10.0g, 21.72mmol) and DCM (100.0ml) successively to a 100ml three-necked flask, stir to dissolve, then add H 2 O (20.0ml), and trifluoroacetic acid (37.0ml) was slowly added dropwise in an ice-water bath, stirred at room temperature for 5min-15min after the dripping, and the reaction was monitored by sampling TLC. Concentrate the reaction system under reduced pressure with an oil pump at room temperature, add trifluoroacetic acid to toluene, and obtain 7.2 g of yellow foamy solid 1-4a.

[0132] Step B:

[0133] Under the protection of nitrogen, the intermediate 1-4a (5.0g, 11.89mmol) was added to the reaction flask, anhydrous DMF (50.0ml) was added to dissolve, the system was cooled to 0°C, and sodium hydride (1.2g, 29.72mmol) was added in batches , 60% mineral oil), stirred for 30min, slowly added dropwise a DMF solution (10.0ml) containing 2-bromopropane (3.2g, 26....

Embodiment 3

[0136] Embodiment 3 (preparation of compound 1-9)

[0137]

[0138] Step D:

[0139] The intermediate 1b (1.60 g, 3.48 mmol) of Example 1 was added into the reaction flask, methanol (20.0 ml) was added, and stirred at room temperature to dissolve. Sodium methoxide (0.23 g, 4.17 mmol) was added into the reaction system, and the reaction was stirred at room temperature for 1 h. TLC showed the starting material was completely reacted. Add saturated aqueous ammonium chloride solution (15.0ml) to the reaction system, concentrate under reduced pressure, and extract the residue three times with ethyl acetate, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, spin under reduced pressure The steamed crude product was purified by column chromatography to obtain intermediate 1-9d, 1.13g. Yield: 79.66%. MS (ESI+): m / z = 408.2.

[0140] Step E:

[0141] Add compound 1-9d (500mg, 1.22mmol) into the reaction flask, add tetrahyd...

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PUM

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Abstract

The invention provides a derivative of 1-O-caffeoylquinic acid shown in the formula II, 1-O-caffeoylquinic acid and of the derivative and application of 1-O-caffeoylquinic acid shown in the formula IIand salt thereof. 1-O-caffeoylquinic acid, the derivative of 1-O-caffeoylquinic acid showing in the formula II and salt thereof have the effect of inhibiting interleukin 17, particularly secretion ofinterleukin 17F, and can also prevent and treat tumors. An experiment result shows that when the concentration of 1-O-caffeoylquinic acid is 0.5 MUM / L, the inhibition rate of interleukin 17F is closeto 70%; when the dose of 1-O-caffeoylquinic acid is 20 mg / kg, 1-O-caffeoylquinic acid has a good inhibiting effect on melanoma and tumors like pancreatic cancer, colorectal cancer and lung cancer, the inhibition rates all exceed 50%, and the derivative of 1-O-caffeoylquinic acid also has a good inhibiting effect on melanoma and the tumors like pancreatic cancer, colorectal cancer and lung cancer,wherein the formula II is shown in the formula II.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to 1-O-caffeoylquinic acid, its derivatives, a preparation method and an application thereof. Background technique [0002] The interleukin 17 (IL-17) family includes six interleukins (IL-17A, IL-17B, IL-17C, IL-17D, IL-17E and IL-17F) and their receptors ( IL-17RA, IL-17RB, IL-17RC, IL-17RD, IL-17RE and IL-17RF) (Gaffen, S.L. et al., Nature reviews. Immunology 9 (2009):556-567). IF-17F, also known as IL-24 or ML-1, is a member of the IL-17 cytokine family. IF-17F is approximately 55% identical to IL-17A and is thought to share the same receptor with IL-17A (Kolls and Linden 2004, Immunity, 21, 467-476; Hymowitz et al., 2001, EMBO J.20(19), 5332 -5341; Kuestner et al., 2007, Journal of Immunology, 179, 5462-5473). Both can form homodimeric and heterodimeric proteins, both produced by activated human CD4+ T cells (Wright et al., 2007, J Biol Chem. 282(18), ...

Claims

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Application Information

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IPC IPC(8): C07C69/757C07C69/732C07D307/00C07D317/46C07D317/72C07D493/08C07D493/10A61P35/00A61P37/00
CPCC07C69/732C07C69/757C07D307/00C07D317/46C07D317/72C07D493/08C07D493/10
Inventor 廖杰远陈晓光孙志国邹德超陈先红季鸣金晶谈敦潮
Owner WEDOCTOR INTELLIGENT INFORMATION & TECH BEIJING CO LTD
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