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Fakalin alcohol compound enantiomer, method for synthesizing same and application of Fakalin alcohol compound enantiomer

An enantiomer and synthesis method technology, which is applied to the application field of anti-HeLa tumor cells, can solve the complex operation and processing procedures, the limited enantioselectivity of products in the scope of application, and the simple preparation and scale of fakarin alcohol compounds. Chemical production and other problems, to achieve the effects of high stereoselectivity, strong anti-HeLa tumor cell proliferation activity, and easy availability of raw materials

Pending Publication Date: 2019-01-04
SOUTHWEST MEDICAL UNIVERISTY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the chiral BINOL catalytic system, the Zn reagent used is very sensitive to humid air, the operation and treatment procedures are relatively complicated, and additional organic base additives need to be added to the catalytic system, which restricts the easy preparation and Scale-up; in addition, aldehydes are limited in both substrate scope and product enantioselectivity

Method used

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  • Fakalin alcohol compound enantiomer, method for synthesizing same and application of Fakalin alcohol compound enantiomer
  • Fakalin alcohol compound enantiomer, method for synthesizing same and application of Fakalin alcohol compound enantiomer
  • Fakalin alcohol compound enantiomer, method for synthesizing same and application of Fakalin alcohol compound enantiomer

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Example 1: (S)-1-(2-Bromophenyl)-5-(triisopropylsilyl)-pentane-2,4-diyn-1-ol and (R)-1-(2 Preparation of -bromophenyl)-5-(triisopropylsilyl)-pentane-2,4-diyn-1-ol, namely S-4 and R-4 (Entry 4)

[0046]1. Preparation of 1-(triisopropylsilyl)-1,3-butadiyne

[0047] At 0°C, 5 mL (97.6 mmol) of bromine was added dropwise to a saturated aqueous KOH solution and stirred for 30 minutes, then 10 mL (108.2 mmol) of 2-methyl-3-butyn-2-ol was added and stirring was continued for 30 minutes. The reaction mixture was extracted with ether, dried, evaporated to remove the solvent, and separated by silica gel column chromatography to obtain 4-bromo-2-methylbut-3-yn-2-ol as a yellow oily liquid for use in a yield of 90%. CuCl was added to the butylamine aqueous solution, 10 g of hydroxylamine hydrochloride and 40.3 g (220.8 mmol) of triisopropylsilyl acetylene were added, and the reaction was carried out. After the reaction was completed, it was cooled in an ice bath. After adding 30....

Embodiment 2

[0056] Example 2: (R)-1-(3-Methoxyphenyl)undecan-2,4-diyn-1-ol and (S)-1-(3-methoxyphenyl)undecane Preparation of alkane-2,4-diyn-1-ols, namely R-17 and S-17 (Entry17)

[0057] 1. Preparation of 1-(n-hexaneyl)-1,3-butadiyne

[0058] Same as the description in Example 1. The coupled alkyne described in Example 1 is 1-octyne, the yield is 89%, 1 H NMR (400MHz, CDCl3): δ2.26 (t, 2H, J=7.0Hz), 1.95 (s, 1H), 1.34 (m, 6H), 0.89 (t, 3H, J=6.6Hz), 1.54 ( p, 2H, J = 6.6 Hz).

[0059] 2. Preparation of R-17 and S-17

[0060] As described in Example 1, the added substrate was 3-methoxybenzaldehyde (1 equiv, 0.5 mmol), and the products R-17 and S-17 were obtained respectively in yields of 80% and 82%, and the products were detected by HPLC analysis , using a chiral Chiralcel OD column, the mobile phase n-hexane / isopropanol is 80 / 20, the flow rate is 0.9 mL / min, the detection wavelength is 254 nm, and the retention times are t 1 =5.5min, t 2 =7.2min, the enantioselectivity ee values...

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Abstract

The invention relates to a Fakalin alcohol compound enantiomer, a method for synthesizing the same and application of the Fakalin alcohol compound enantiomer. Structural general formulas of the Fakalin alcohol compound enantiomer are shown as formulas I and II. Zinc reagents, halides, chiral BINOL (binaphthol) reagents and Ti reagents are mixed with one another, asymmetric addition is carried outon aldehyde by 1, 3-diyne compounds under specific conditions, Fakalin alcohol compound enantiomers with serial specific structures can be synthesized in a high-selectivity manner, one of every two corresponding enantiomers is high in HeLa tumor cell anti-proliferation activity, and mixed components with different proportions of every two corresponding enantiomers and IC 50 values of the antitumorcell activity of the components have linear relations. The Fakalin alcohol compound enantiomer, the method and the application have the advantages that synthetic reaction conditions are mild, raw materials for chiral reagents are simple and are easily available, the Fakalin alcohol compound enantiomer and the method are high in stereo-selectivity, and the method is suitable for preparing chiral Fakalin alcohol compounds and producing the chiral Fakalin alcohol compounds on a large scale.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a method for synthesizing enantiomers of fakalinol compounds catalyzed by a binaphthol (BINOL) ligand and its application in anti-HeLa tumor cells. Background technique [0002] Chiral fakalinol compounds have a conjugated diacetylenic alcohol structure and have significant biological activities in antitumor, neuroprotection, antifungal and anti-inflammatory, and have great potential research value. There is a great relationship between its specific configuration and its biological activity, but due to the limitation of the types of structures of this type of compounds, its biological activity research is also limited, especially the steric structure of chiral fakalinol compounds has an impact on HeLa tumor cells. The effect of antiproliferative activity has not been reported. [0003] At present, the chemical synthesis of chiral conjugated diacetylenic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C07C33/04C07C33/12C07C33/14C07C33/44C07C33/48C07C43/23A61P35/00
CPCA61P35/00C07C33/04C07C33/12C07C33/14C07C33/44C07C33/483C07C43/23
Inventor 王钦杜曦张春王力韦思平张可何中洪
Owner SOUTHWEST MEDICAL UNIVERISTY
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