Bisbibenzyl Mannich base derivative, preparation method and application thereof

A bibibenzyl derivative technology, applied in the field of bibibenzyl Mannich base derivatives and its preparation, to achieve good preventive and therapeutic effects, improve pharmacokinetic parameters, and high yield

Active Publication Date: 2011-07-20
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Bisbenzyl derivatives of Mannich bases have not been reported yet

Method used

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  • Bisbibenzyl Mannich base derivative, preparation method and application thereof
  • Bisbibenzyl Mannich base derivative, preparation method and application thereof
  • Bisbibenzyl Mannich base derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the preparation of the dimethylamino derivatives of lamellarin D

[0034] The steps are: dissolving phyllonin D in methanol, adding 37% formaldehyde aqueous solution and dimethylamine, and reacting under reflux for 4 to 5 hours, evaporating the solvent to dryness under reduced pressure, and separating the residue by column chromatography (the eluent is dichloro Methane-methanol 20:1~1:1) to obtain its Mannich base derivative, dissolve the Mannich base derivative derivative in dry ethyl acetate, pass through hydrogen chloride, precipitate out, filter, and obtain the corresponding Mannich base hydrochloric acid Salt.

[0035] Its synthesis reaction is shown as follows:

[0036]

Embodiment 2

[0037] Embodiment 2: the preparation of the diethylamino derivative of lamellarin D

[0038] The steps are: dissolving phyllonin D in ethanol, adding 37% formaldehyde aqueous solution and dimethylamine, reflux reaction for 10 to 15 hours, evaporating the solvent to dryness under reduced pressure, and separating the residue by column chromatography (the eluent is dichloro Methane-methanol 40:1~1:1) to obtain its Mannich base derivative, the Mannich base derivative derivative was dissolved in dry ethyl acetate, and hydrogen chloride was passed through to precipitate out, filtered to obtain the corresponding Mannich base hydrochloric acid Salt.

[0039] Its synthesis reaction is shown as follows:

[0040]

[0041]

Embodiment 3

[0042] Example 3: Preparation of Dimethylamino Derivatives of Isophyllin C

[0043] The steps are: dissolving isophyllin C in ethanol, adding 37% aqueous formaldehyde and diethylamine, and reacting under reflux for 10 to 15 hours, then evaporating the solvent to dryness under reduced pressure, and separating the residue by column chromatography (the eluent is diethylamine) Chloromethane-methanol 40:1~1:1) to obtain its Mannich base derivative, dissolve the Mannich base derivative derivative in dry ethyl acetate, pass through hydrogen chloride, precipitate out, filter, and obtain the corresponding Mannich base salt salt.

[0044] Its synthesis reaction is shown as follows:

[0045]

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PUM

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Abstract

The invention discloses a bisbibenzyl Mannich base derivative, which is a compound with a structural formula shown in a general formula (I) or (II), or an officinal salt of the compound shown in the general formula (I), wherein NR1R2 is any one of dimethylamine, diethylamine, dipropylamine, diisopropylamine, tetrahydropyrrole, piperidine, morpholine or substituted piperazine; and R3 is H or NR1R2. A preparation method of the bisbibenzyl Mannich base derivative comprises the steps of: undergoing a Mannich reaction to riccardin D or isoriccardin C and secondary amine and a formaldehyde solution or paraformaldehyde in a common solvent, conventionally concentrating, and carrying out silicagel column chromatography to obtain the bisbibenzyl Mannich base derivative. The bisbibenzyl Mannich base derivative has a better application prospect in preparation of medicines for treating human osteoblastic sarcoma, cervical carcinoma, prostate glands cancer and other tumors.

Description

technical field [0001] The invention relates to a bibenzyl Mannich base derivative and a preparation method and application thereof. Background technique [0002] Bibenzyl compounds are more common in bryophytes, structurally with C 6 -C 2 -C 6 The dimer of the mother nucleus exists, and it is divided into different structural types based on the different connection methods between the benzene rings, usually named according to the plant source; due to the different substituents of the benzene rings, many compounds are produced, which are named in turn according to the structural type they belong to, such as Dichnin B-H, J-L, Leptin D, Isophyllin C, etc. (Qu Jianbo, Lou Hongxiang. Chemical Constituents and Biological Activities of Four Liverwort Plants. Doctoral Dissertation of Shandong University, 2008), (Susanne F, Ulrich HM, Brigirle DN, et al. Biosynthesis of Cyclic Bisbibenzyls in Marchantia polymorpha. Phytochemistry, 2001, 50(4):589-598.). So far, more than 100 bib...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/00A61K31/335A61P35/00
Inventor 娄红祥王莉宁王燕燕范培红薛霞程艳娜
Owner SHANDONG UNIV
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