JPH0247992B2 - BENZOFUENONN22KARUBAMEETOJUDOTAI - Google Patents
BENZOFUENONN22KARUBAMEETOJUDOTAIInfo
- Publication number
- JPH0247992B2 JPH0247992B2 JP5138383A JP5138383A JPH0247992B2 JP H0247992 B2 JPH0247992 B2 JP H0247992B2 JP 5138383 A JP5138383 A JP 5138383A JP 5138383 A JP5138383 A JP 5138383A JP H0247992 B2 JPH0247992 B2 JP H0247992B2
- Authority
- JP
- Japan
- Prior art keywords
- lower alkyl
- alkyl group
- hydrogen atom
- formula
- reaction
- 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 - Lifetime
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- OMWSZDODENFLSV-UHFFFAOYSA-N (5-chloro-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 OMWSZDODENFLSV-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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】
本発明は次の一般式
（式中R1及びR2は同一又は異つて水素原子、低
級アルキル基又はフエニル基を意味し、R3は水
素原子、ハロゲン原子又は低級アルキル基を意味
する。）
で表わされる化合物に関する。
上式（）で表わされる本発明の化合物は、例
えば以下に示すように、２−ヒドロキシベンゾフ
エノン誘導体とイソシアナート類とをベンゼン、
アセトン、テトラヒドロフラン等の溶媒中好まし
くは、トリエチルアミン等の塩基の存在下、反応
させることにより容易に得ることができる。
かくして得られる本発明の化合物は癌細胞に対
する分化誘導作用を有し医薬として有用である。
実施例 １
２−ヒドロキシ−５−クロルベンゾフエノン
2.3ｇ、メチルイソシアナート0.6ｇおよび触媒量
のトリエチルアミンを、アセトン30mlに溶解し、
室温撹拌下５時間反応させる。反応後、溶媒を減
圧下除去し、残渣をｎ−ヘキサン、ベンゼンの混
合溶媒から再結晶して無色プリズム晶の５−クロ
ルベンゾフエノン−２−メチルカルバメート2.1
ｇを得た。収率73％、融点159〜161℃。
元素分析値 C15H12ClNO3として
Ｃ Ｈ Ｎ
理論値(%) 62.18 4.18 4.84
実測値(%) 62.28 4.21 4.78
上記と同様にして次表の化合物を得た。
実施例 ２〜10
実施例１と同様にして表の化合物を得た。
【表】[Detailed Description of the Invention] The present invention is based on the following general formula: (In the formula, R 1 and R 2 are the same or different and mean a hydrogen atom, a lower alkyl group, or a phenyl group, and R 3 means a hydrogen atom, a halogen atom, or a lower alkyl group.) The compound of the present invention represented by the above formula () is prepared by combining a 2-hydroxybenzophenone derivative and an isocyanate with benzene, for example, as shown below.
It can be easily obtained by reaction in a solvent such as acetone or tetrahydrofuran, preferably in the presence of a base such as triethylamine. The compound of the present invention thus obtained has a differentiation-inducing effect on cancer cells and is useful as a medicine. Example 1 2-hydroxy-5-chlorobenzophenone
2.3 g, methyl isocyanate 0.6 g and a catalytic amount of triethylamine were dissolved in 30 ml of acetone,
The reaction is allowed to proceed for 5 hours under stirring at room temperature. After the reaction, the solvent was removed under reduced pressure, and the residue was recrystallized from a mixed solvent of n-hexane and benzene to obtain colorless prismatic crystals of 5-chlorobenzophenone-2-methylcarbamate 2.1
I got g. Yield 73%, melting point 159-161°C. Elemental analysis value C 15 H 12 ClNO 3 C H N Theoretical value (%) 62.18 4.18 4.84 Actual value (%) 62.28 4.21 4.78 The compounds shown in the following table were obtained in the same manner as above. Examples 2 to 10 The compounds shown in the table were obtained in the same manner as in Example 1. 【table】
Claims (1)
級アルキル基又はフエニル基を意味し、R3は水
素原子、ハロゲン原子又は低級アルキル基を意味
する。） で表わされる化合物。[Claims] 1. General formula (In the formula, R 1 and R 2 are the same or different and mean a hydrogen atom, a lower alkyl group, or a phenyl group, and R 3 means a hydrogen atom, a halogen atom, or a lower alkyl group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5138383A JPH0247992B2 (en) | 1983-03-29 | 1983-03-29 | BENZOFUENONN22KARUBAMEETOJUDOTAI |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5138383A JPH0247992B2 (en) | 1983-03-29 | 1983-03-29 | BENZOFUENONN22KARUBAMEETOJUDOTAI |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59181251A JPS59181251A (en) | 1984-10-15 |
| JPH0247992B2 true JPH0247992B2 (en) | 1990-10-23 |
Family
ID=12885420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5138383A Expired - Lifetime JPH0247992B2 (en) | 1983-03-29 | 1983-03-29 | BENZOFUENONN22KARUBAMEETOJUDOTAI |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0247992B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0638899A (en) * | 1992-07-27 | 1994-02-15 | Kasen Plast Kk | Housing case |
| US11111869B2 (en) | 2019-07-31 | 2021-09-07 | Toyota Jidosha Kabushiki Kaisha | State detection system for internal combustion engine, data analysis device, and hybrid vehicle |
-
1983
- 1983-03-29 JP JP5138383A patent/JPH0247992B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0638899A (en) * | 1992-07-27 | 1994-02-15 | Kasen Plast Kk | Housing case |
| US11111869B2 (en) | 2019-07-31 | 2021-09-07 | Toyota Jidosha Kabushiki Kaisha | State detection system for internal combustion engine, data analysis device, and hybrid vehicle |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59181251A (en) | 1984-10-15 |
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