JPS598251B2 - Synthesis method of isoprenyl chalcone - Google Patents
Synthesis method of isoprenyl chalconeInfo
- Publication number
- JPS598251B2 JPS598251B2 JP4415274A JP4415274A JPS598251B2 JP S598251 B2 JPS598251 B2 JP S598251B2 JP 4415274 A JP4415274 A JP 4415274A JP 4415274 A JP4415274 A JP 4415274A JP S598251 B2 JPS598251 B2 JP S598251B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- chalcone
- isoprenyl
- methyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、イソプレニルカルコン類の合成法に関し、抗
消化性潰瘍活性を呈する物質の製法を提供するものであ
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for synthesizing isoprenyl chalcone, and provides a method for producing a substance exhibiting anti-peptic ulcer activity.
本発明は、
一般式
０．０、コ＝０゛′
（Ｉ’ ）
〔式中、Ｒ＾”は水素原子または水酸基、Ｒ＾２は３−
メチルー２−ブテニル基またはゲラニル基、Ｒ＾３はＲ
＾１、Ｒ＾２と異なつて水素原子または３−メチルー２
−ブテニル基を示す。The present invention is based on the general formula 0.0, co=0゛'(I') [wherein R^'' is a hydrogen atom or a hydroxyl group, and R^2 is 3-
Methyl-2-butenyl group or geranyl group, R^3 is R
Unlike ^1 and R^2, hydrogen atom or 3-methyl-2
- indicates a butenyl group.
〕で表わされる化合物を加熱転位させることにより、一
般式（式中、Ｒ１、Ｒ２、Ｒ３は前記と同義である。] By heating and rearranging the compound represented by the general formula (wherein R1, R2, and R3 have the same meanings as above).
）で表わされる化合物を得ることを特徴とするイソプレ
ニルカルコン類の合成法である。本発明の加熱転位は、
化合物『をジエチルアニリン、ジメチルフオルムアマイ
ドなどの溶剤に溶解もしくは懸濁し、あるいは溶剤を用
いることなしに窒素の存在下または非存在下に加熱する
ことによりおこるその１・１−ジメチルアリロキシ基の
転位であり、その結果、３−メチル−２−ブテニル基が
その隣位に導入されて化合物１が生成する。) is a method for synthesizing isoprenyl chalcone compounds. The heating dislocation of the present invention is
The formation of 1,1-dimethylallyloxy group by dissolving or suspending a compound in a solvent such as diethylaniline or dimethylformamide, or by heating it in the presence or absence of nitrogen without using a solvent. This is a rearrangement, resulting in the introduction of a 3-methyl-2-butenyl group to its adjacent position to form compound 1.
化合物「は、次の方法により製造することができる。Compound "can be produced by the following method.
すなわち、 一般式 （式中、Ｒ１およびＲ２は前記と同義である。That is, general formula (In the formula, R1 and R2 have the same meanings as above.
で表わされる化合物と、一般式 ） （式中、Ｒ３は前記と同義である。Compounds represented by and general formula ) (In the formula, R3 has the same meaning as above.
）で表わされる化合物とを有機溶剤（たとえば、メタノ
ール、エタノール、酢酸エチルなど）に溶解し、これに
アルカリ（たとえば、苛性ソーダ、苛性カリなど）また
は酸（たとえば、塩化水素、硫酸など）を加え、室温で
攪拌または還流して両者を縮合させることにより化合物
『を得る。) is dissolved in an organic solvent (e.g., methanol, ethanol, ethyl acetate, etc.), an alkali (e.g., caustic soda, caustic potash, etc.) or an acid (e.g., hydrogen chloride, sulfuric acid, etc.) is added thereto, and the mixture is heated at room temperature. By stirring or refluxing the mixture and condensing the two, the compound 'is obtained.
化合物または化合物は、たとえば、インデイアン・ジヤ
ーナル・オブ・ケミストリーリヱ、１０７２（１９６９
）；同旦、１３２２（１９７１）；ヘミツシエ・ベリヒ
テ：１０５、８６３（１９７２）；同１０５、３５１１
（１９７２）；特開昭４９−５９５０号公報または同５
０−２４２５８号公報などに記載の公知の方法によつて
製造することができる。The compound or compounds are described, for example, in Indian Journal of Chemistry, 1072 (1969
); Same day, 1322 (1971); Hemitssie Berichte: 105, 863 (1972); Same day, 105, 3511
(1972); Japanese Patent Application Laid-Open No. 49-5950 or No. 5
It can be manufactured by a known method described in Japanese Patent No. 0-24258 and the like.
本発明で得られた化合物１は優れた抗消化性潰瘍活性を
示した。Compound 1 obtained according to the present invention showed excellent anti-peptic ulcer activity.
たとえば、ラツトに３０η／Ｋｇを投与した場合の幽門
結紮法による抑制率は、２′・４−ジハイドロキシ−３
−（３−メチル−２−ブテニル）−４′−（３−メチル
−２−ブテニロキシ）カルコンおよび４／−ゲラニロキ
シ一４−ハイドロキシ−３・５−ビス−（３−メチル−
２−ブテニル）カルコンにおいてそれぞれ８６．４％お
よび５３．５％であつた。For example, the inhibition rate by pylorus ligation when 30η/Kg was administered to rats was 2',4-dihydroxy-3
-(3-methyl-2-butenyl)-4'-(3-methyl-2-butenyloxy)chalcone and 4/-geranyloxy-4-hydroxy-3,5-bis-(3-methyl-
2-butenyl) chalcone was 86.4% and 53.5%, respectively.
以下、実施例を挙げて本発明を具体的に説明する。The present invention will be specifically described below with reference to Examples.
Claims (1)
メチル−２−ブテニル基またはゲラニル基、Ｒ＾３はＲ
＾１、Ｒ＾２と異なつて水素原子または３−メチル−２
−ブテニル基を示す。 〕で表わされる化合物を加熱転位させることにより、一
般式▲数式、化学式、表等があります▼ （式中、Ｒ＾１、Ｒ＾２、Ｒ＾３は前記と同義である。 ）で表わされる化合物を得ることを特徴とするイソプレ
ニルカルコン類の合成法。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 is a hydrogen atom or a hydroxyl group, R^2 is 3-
Methyl-2-butenyl group or geranyl group, R^3 is R
^1, unlike R^2, hydrogen atom or 3-methyl-2
- indicates a butenyl group. ] By heating and rearranging the compound represented by the formula ▲, there are mathematical formulas, chemical formulas, tables, etc. ▼ (wherein, R^1, R^2, and R^3 are the same as above. A method for synthesizing isoprenyl chalcone compounds, characterized by obtaining the compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4415274A JPS598251B2 (en) | 1974-04-19 | 1974-04-19 | Synthesis method of isoprenyl chalcone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4415274A JPS598251B2 (en) | 1974-04-19 | 1974-04-19 | Synthesis method of isoprenyl chalcone |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14358083A Division JPS5940810B2 (en) | 1983-08-05 | 1983-08-05 | Production method of isoprenyl chalcone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50140429A JPS50140429A (en) | 1975-11-11 |
| JPS598251B2 true JPS598251B2 (en) | 1984-02-23 |
Family
ID=12683645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4415274A Expired JPS598251B2 (en) | 1974-04-19 | 1974-04-19 | Synthesis method of isoprenyl chalcone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS598251B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ192641A (en) * | 1979-01-26 | 1984-10-19 | Hoffmann La Roche | Substituted acetophenones and pharmaceutical compositions |
| CA1137082A (en) * | 1979-05-23 | 1982-12-07 | Isao Umeda | Substituted acetophenones and process therefor |
| EP0292576A4 (en) * | 1986-12-12 | 1990-10-03 | Tsumura Juntendo, Inc. | Anti-ulcerous agent containing chalcone derivative as effective ingredient and novel chalcone derivatives |
-
1974
- 1974-04-19 JP JP4415274A patent/JPS598251B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50140429A (en) | 1975-11-11 |
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