Preparation method and application of 2-(4-beta-D-allose pyranoside-phenyl)-2,3-dihydroquinoline-4(1H) and 2-(4-(2,3,4,6-tetrabenzyl)-beta-D-allose pyranoside-phenyl)-2,3-benzodihydropyran

A technology of allopyranoside and dihydrobenzopyran, which is applied in the field of tofu glucoside derivatives, and can solve the problems of less side reactions, affecting the popularization and application of drugs, and good curative effect.

Inactive Publication Date: 2012-06-13
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Tofu fruit glycosides and excellent hypnotic and sedative drugs with acute effect, short half-life, good curative effect, less side effects, especially not affecting the patient's mental activity and memory are still available. A certain gap, such as: Wu Deyu et al. "Progress of hypnotic drugs" (Science Technology and Engineering 2005, 5(17), 1286), also affects the clinical application of the drug

Method used

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  • Preparation method and application of 2-(4-beta-D-allose pyranoside-phenyl)-2,3-dihydroquinoline-4(1H) and 2-(4-(2,3,4,6-tetrabenzyl)-beta-D-allose pyranoside-phenyl)-2,3-benzodihydropyran
  • Preparation method and application of 2-(4-beta-D-allose pyranoside-phenyl)-2,3-dihydroquinoline-4(1H) and 2-(4-(2,3,4,6-tetrabenzyl)-beta-D-allose pyranoside-phenyl)-2,3-benzodihydropyran
  • Preparation method and application of 2-(4-beta-D-allose pyranoside-phenyl)-2,3-dihydroquinoline-4(1H) and 2-(4-(2,3,4,6-tetrabenzyl)-beta-D-allose pyranoside-phenyl)-2,3-benzodihydropyran

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0017] Example 1: 2-(4- β-D -Allopyranoside-phenyl)-2,3-dihydroquinoline-4(1 H )-Synthesis of ketone (3a)

[0018]

[0019] In a 50mL round bottom flask, 0.6mmol L-proline was dissolved in 20mL absolute anhydrous methanol, and then 2mmol of tofu glucoside and 2mmol of o-aminoacetophenone were added successively, and the reaction was stirred at room temperature for 5 days. After the reaction, the crude product was separated and purified by column chromatography (dichloromethane:methanol=8:1) to obtain yellow-green solid 3a. Yield: 60%, m.p. 115-117℃; 1 H NMR (400MHz, DMSO-d 6 ) δ : 6.61~7.59(m, 8H), 5.15(d, J =8.0 Hz, 1H), 5.07(d, J =6.4 Hz, 1H), 4.95(d, J =3.6 Hz, 1H), 4.65~4.71(m, 2H), 4.49(t, J =4.0 Hz, 1H), 3.66~3.92(m, 3H), 3.36~3.47(m, 4H), 2.59~2.85(m, 2H); IR (KBr) ν : 3382, 2920, 1657, 1609, 1507, 1479, 1329, 1082,1037, 912, 836, 763; HRMS (ESI) calcd for C 21 h 23 NO 7 [M+H] + : 402.1547, found 402.1562; [M+Na] + : 424.1367, found 424.1368.

example 2

[0020] Example 2: 2-(4- β - D -Allopyranoside-phenyl)-2,3-dihydroquinoline-4(1 H )-Synthesis of methoxylamine (3b)

[0021]

[0022] Add 2mmol of 3a dissolved in 10mL of ethanol to a 25mL round bottom flask, then add 2mmol of methoxylamine hydrochloride (neutralized with dilute NaOH solution before addition) 2mmol under stirring, and reflux for 2h after the addition. After the reaction stopped, the solvent was spinned off, dissolved in ethyl acetate, washed with water, and the extract was washed with anhydrous Na 2 SO 4 Drying, rotary evaporation to remove the solvent, the crude product was separated and purified by column chromatography (dichloromethane: methanol = 8:1) to obtain yellow solid 3b, yield: 90%, m.p. 114-116°C; 1 H NMR (400MHz, DMSO-d 6 ) δ: 7.64(d, J =8.0 Hz, 1H), 7.35(d, J =8.4 Hz, 2H), 7.10(t, J =8.0 Hz, 1H), 7.00(d, J =8.0 Hz, 2H), 6.77(d, J =8.0 Hz, 1H), 6.59(t, J =8.0 Hz, 1H), 6.40(s, 1H), 5.07~5.12(m, 2H), 4.95(d, J =2.0 Hz, 1H), 4.66(d, ...

example 3

[0023] Example 3: 2-(4- β - D -Allopyranoside-phenyl)-2,3-dihydroquinoline-4(1 H )-Synthesis of Hydroxylamine (3c)

[0024] Add 2mmol of 3a dissolved in 10mL of ethanol to a 25mL round bottom flask, then add 2mmol of hydroxylamine hydrochloride (neutralized with dilute NaOH solution before addition) 2mmol under stirring, and reflux for 2h after the addition is complete. After the reaction stopped, the solvent was spinned off, dissolved in ethyl acetate, washed with water, and the extract was washed with anhydrous Na 2 SO 4 Drying, rotary evaporation to remove the solvent, the crude product was separated and purified by column chromatography (dichloromethane:methanol=8:1) to obtain a yellow solid 3c, yield: 80%, m.p. 118~120°C; 1 H NMR (400MHz, DMSO-d 6 ) δ : 10.86(s, 1H), 7.64(d, J =8.0 Hz, 1H), 7.35(d, J =8.4 Hz, 2H), 7.06(t, J =7.6 Hz, 1H), 7.00(d, J=8.2 Hz, 2H), 6.76(d, J =8.2 Hz, 1H), 6.59(t, J =7.6 Hz, 1H), 6.31(s, 1H), 5.07~5.12(m, 2H), 4.97(s, 1H), 4.68(...

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Abstract

The invention relates to a preparation method and an application of 2-(4-beta-D-allose pyranoside-phenyl)-2,3-dihydroquinoline-4(1H) (1) and 2-(4-(2,3,4,6-tetrabenzyl)-beta-D-allose pyranoside-phenyl)-2,3-benzodihydropyran (2). The invention discloses helicide derivatives with a central nervous system improving function, and a preparation method thereof. The compounds provided by the invention have good sedative, sleep-promoting, and convulsion-inhibiting functions. The compounds are collected in a Year 2000 version of Pharmacopoeia of PRC with a medicine name of helicide tablets. The helicide derivative novel medicines are represented by chemical formulas (1) and (2), wherein R1 can be hydrogen and acetyl, and R2 can be semicarbazide, hydroxylamine, and methoxylamine. Acording to the helicide derivatives provided by the invention, a plant active monomer helicide with sedative, sleep-promoting, and convulsion-inhibiting functions is adopted as a matrix compound, structural modification is carried out according to a medicine efficacy molecular principle, and compounds with high activities for improving central nervous system functions are designed and prepared.

Description

technical field [0001] The invention is to modify the structure of the plant active monomer tofu fruit glucoside with sedative and hypnotic activity, and obtain a series of tofu fruit glycoside derivatives with better curative effect. Background technique [0002] Tofu fruit glycoside, 4-formylphenyl-β-D-allosupranoside (4-fornylphenl-β-D-Allosupranoside) was firstly described by Chen Weixin in Liebigs.Ann.Chem., 1981, (10). It is reported that the active ingredient extracted from the fruit of the radish tree (Helicia Nilagirica Beed, synonym Helicia Erratica Hook) in Yunnan, my country, its structure is as shown: [0003] [0004] At present, there are many reports on using tofu glucoside as a preparation, and a patent is applied for. In the publication number CN1535690, a tofu fruit glucoside soft capsule and its preparation method are reported; in the publication number CN1535691, a tofu fruit glycoside powder injection and its preparation method are provided; Headach...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07H1/00A61K31/7048A61K31/706A61P25/20A61P25/08
Inventor 陈超李颖尹述凡
Owner SICHUAN UNIV
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