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Germatrane compound as well as preparation method and application thereof

A compound and tricyclic technology, applied in the field of azazagermanium tricyclic compounds and their preparation

Active Publication Date: 2014-04-23
ANHUI HAIKANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Introducing the azazagermanium tricyclic structure into the structure of other natural products to obtain azazagermanium tricyclic compounds with higher activity has not been reported.

Method used

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  • Germatrane compound as well as preparation method and application thereof
  • Germatrane compound as well as preparation method and application thereof
  • Germatrane compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0129] Example 1 : Preparation of 3-(2,8,9-trioxa-5-aza-1-germaniumtricyclo[3.3.3.0]undecyl)-10-hydroxy-decanoic acid

[0130] (1) Preparation of trichlorogermanium form

[0131]According to the literature (Shangguan Guoqiang, Qin Mei. Synthesis, crystal structure and vibration spectrum of carboxyethyl germanium trichloride, Journal of Qufu Normal University, 1990, 16 (4): 54-58; Shangguan Guoqiang, Zhang Shugong, Ni Jiazuan, etc. . The synthesis of β-(phenol ester group) ethyl germanium sesquioxide and its effect on in vitro cultured cells, Applied Chemistry, 1989, 6(5):59-62), 6.0 grams of germanium dioxide (0.057mol) Mix well with 12.0 grams of sodium hypophosphite (0.136mol) and put it into a 125ml three-necked flask equipped with a stirrer, add 60mL of concentrated hydrochloric acid and 15ml of distilled water to it, install a spherical condenser, and make the temperature of the reaction solution 80~ After heating and stirring at 90°C for three hours, the solution beca...

Embodiment 2

[0144] Example 2 : 3-(2,8,9-trioxa-5-aza-1-germaniumtricyclo[3.3.3.0]undecyl)-10-hydroxy-decanoic acid methyl ester

[0145]

[0146] 3-(2,8,9-Trioxa-5-aza-1-germaniumtricyclo[3.3.3.0]undecyl)-10-hydroxy-decanoic acid 0.41 g (0.001 mol) and 50 ml methanol Add it to the reaction bottle, add 5 ml of thionyl chloride dropwise at room temperature, heat and reflux for 2 h after dropping, cool to room temperature, continue stirring for 5 h, distill off methanol and remaining thionyl chloride under reduced pressure, and recrystallize from ethanol to obtain white crystals Powder 0.40 g (0.88 mmol). The yield is 88.9%, and the molecular formula is C 17 h 33 o 6 GeN has a molecular weight of 420.13. EI-MS(m / z, %):421.09[M + , 92], 220[Ge(OCH 2 CH 2 ) 3 N, 100], 160[25], 146[12], 130[5], 116[5], 100[3] .

Embodiment 3

[0147] Example 3 : Preparation of 3-(2,8,9-trioxa-5-aza-1-germaniumtricyclo[3.3.3.0]undecyl)-10-hydroxy-decylamide

[0148]

[0149] 3-(2,8,9-Trioxa-5-aza-1-germaniumtricyclo[3.3.3.0]undecyl)-10-hydroxy-decanoic acid methyl ester 0.32 g (0.77 mmol) and 28 Add 20 ml of % ammonia water into the reaction flask, stir at room temperature for 3 h, extract with dichloromethane, concentrate to dryness, and recrystallize from ethyl acetate to obtain 0.22 g (0.54 mmol) of white crystals with the molecular formula C 16 h 32 o 5 GeN 2 , the molecular weight is 405.08. EI-MS(m / z, %):406.09[M + , 91], 220[Ge(OCH 2 CH 2 ) 3 N, 100], 160[22], 146[14], 130[4], 116[5], 100[3] .

[0150] Other compounds can be prepared with reference to the above examples.

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Abstract

The invention discloses a germatrane compound as well as a preparation method and application thereof. The germatrane compound has a structure shown as a formula (I). The method for preparing the germatrane compound comprises: enabling a royal jelly acid compound serving as a raw material to perform a Michael addition reaction, a nucleophilic substitution reaction and a transalkylation sequentially with germanium trichloroforme, sodium methoxide and triethanolamine. The germatrane compound has an excellent antitumor effect, so that the compound or pharmaceutically acceptable salt, hydrate, solvate or prodrug thereof can be used for preparing a cervical cancer inhibitor. The formula (I) is shown in the specification.

Description

technical field [0001] The invention belongs to the field of organic chemistry and medicinal chemistry, and in particular relates to a nitrogen-germanium tricyclic compound and a preparation method and application thereof. Background technique [0002] Cervical cancer occurs all over the world and is one of the most common cancers. It ranks first among female reproductive organ cancers, and its incidence rate has obvious regional differences. The geographical distribution of cervical cancer in my country is characterized by high-incidence areas that are often connected into patches. Cities and counties in relatively high-incidence areas of cervical cancer in various provinces are also often interconnected. The general trend is that the rural areas are higher than the cities, and the mountainous areas are higher than the plains. According to the retrospective survey of 29 provinces, municipalities, and autonomous regions, the death rate of cervical cancer in my country rank...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/30A61K31/555A61P35/00A61P15/00
Inventor 叶连宝欧小敏罗艳周玉平
Owner ANHUI HAIKANG PHARMA