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1-o-caffeoylquinic acid, its derivatives, preparation method and use thereof

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

Active Publication Date: 2021-07-06
WEDOCTOR INTELLIGENT INFORMATION & TECH BEIJING CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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, its derivatives, preparation method and use thereof
  • 1-o-caffeoylquinic acid, its derivatives, preparation method and use thereof
  • 1-o-caffeoylquinic acid, its derivatives, preparation method and use 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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Abstract

The present invention provides 1-O-caffeoylquinic acid derivatives shown in formula (II), and 1-O-caffeoylquinic acid, 1-O-caffeoylquinic acid shown in formula (II) Applications of derivatives and their salts. 1-O-caffeoylquinic acid, 1-O-caffeoylquinic acid derivatives and salts thereof shown in formula (II) have the effect of inhibiting the secretion of interleukin 17, especially interleukin 17F, and can prevent and treat Treat tumors. The experimental results show that when the concentration of 1‑O‑caffeoylquinic acid is 0.5 μM / L, the inhibition rate of interleukin 17F is close to 70%; , Pancreatic cancer, colorectal cancer, lung cancer and other tumors have good inhibitory effects, all exceeding 50%, and its derivatives also have good inhibitory effects on melanoma, pancreatic cancer, colorectal cancer, lung cancer and other tumors.

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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Patent Type & Authority Patents(China)
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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