JPH01160996A - Cycloartenol-7-one derivative - Google Patents
Cycloartenol-7-one derivativeInfo
- Publication number
- JPH01160996A JPH01160996A JP31792887A JP31792887A JPH01160996A JP H01160996 A JPH01160996 A JP H01160996A JP 31792887 A JP31792887 A JP 31792887A JP 31792887 A JP31792887 A JP 31792887A JP H01160996 A JPH01160996 A JP H01160996A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- reaction
- cycloartenol
- group
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000201 insect hormone Substances 0.000 abstract description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 229930193596 glycinoeclepin Natural products 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XZEUYTKSAYNYPK-UHFFFAOYSA-N 3beta-29-Norcycloart-24-en-3-ol Natural products C1CC2(C)C(C(CCC=C(C)C)C)CCC2(C)C2CCC3C(C)C(O)CCC33C21C3 XZEUYTKSAYNYPK-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical class C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000006416 CBr Chemical group BrC* 0.000 description 1
- RRTBTJPVUGMUNR-UHFFFAOYSA-N Cycloartanol Natural products C12CCC(C(C(O)CC3)(C)C)C3C2(CC)CCC2(C)C1(C)CCC2C(C)CCCC(C)C RRTBTJPVUGMUNR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000482313 Globodera ellingtonae Species 0.000 description 1
- HVXLSFNCWWWDPA-UHFFFAOYSA-N Isocycloartenol Natural products C1CC(O)C(C)(C)C2C31CC13CCC3(C)C(C(CCCC(C)=C)C)CCC3(C)C1CC2 HVXLSFNCWWWDPA-UHFFFAOYSA-N 0.000 description 1
- HXQRIQXPGMPSRW-UHZRDUGNSA-N Pollinastanol Natural products O[C@@H]1C[C@H]2[C@@]3([C@]4([C@H]([C@@]5(C)[C@@](C)([C@H]([C@H](CCCC(C)C)C)CC5)CC4)CC2)C3)CC1 HXQRIQXPGMPSRW-UHZRDUGNSA-N 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- ONQRKEUAIJMULO-YBXTVTTCSA-N cycloartenol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@@H](CCC=C(C)C)C)CC[C@@]3(C)[C@@H]1CC2 ONQRKEUAIJMULO-YBXTVTTCSA-N 0.000 description 1
- YNBJLDSWFGUFRT-UHFFFAOYSA-N cycloartenol Natural products CC(CCC=C(C)C)C1CCC2(C)C1(C)CCC34CC35CCC(O)C(C)(C)C5CCC24C YNBJLDSWFGUFRT-UHFFFAOYSA-N 0.000 description 1
- FODTZLFLDFKIQH-UHFFFAOYSA-N cycloartenol trans-ferulate Natural products C1=C(O)C(OC)=CC(C=CC(=O)OC2C(C3CCC4C5(C)CCC(C5(C)CCC54CC53CC2)C(C)CCC=C(C)C)(C)C)=C1 FODTZLFLDFKIQH-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明はａ薬として、殊にマメ科植物の生長に重大なｌ
９を与えるシスト線虫のふ化促進物質として知られるグ
リシノエクレビン類の合成中間体、又はエグタイソン類
やオオゲニオール類等の昆虫ホルモンの合成中間体とし
て、更にはそれ自体農薬としても有望視できる有用な新
規化合物に関する。[Detailed Description of the Invention] <Industrial Application Field> The present invention is useful as a drug, especially for the growth of leguminous plants.
It can be used as a synthetic intermediate for glycinoeclebins, which are known as hatch-promoting substances for cyst nematodes that give 9, or as a synthetic intermediate for insect hormones such as egtysons and ogeniols, and is also promising as a pesticide in itself. Concerning useful new compounds.
更に詳しくは１本発明は式（１）
（但し１式中Ｒ１は水素原子、低級アルキルカルボニル
基、低級アルキル基、ピラニル基を、Ｒ２，Ｒ。More specifically, the present invention is represented by the formula (1) (wherein R1 represents a hydrogen atom, a lower alkylcarbonyl group, a lower alkyl group, a pyranyl group, R2, R.
はハロゲン原子、ヒドロキシル基を、Ｘは水素原子、ヒ
ドロキシル基を示す）で示されるシクロアルテノール−
７−オン誘導体に関する。represents a halogen atom or a hydroxyl group, and X represents a hydrogen atom or a hydroxyl group)
7-one derivatives.
〈従来技術〉
グリシノエクレビン類は植物（インゲン）からの抽出（
現代化学１９８５年１６頁）あるいはシクロアステラガ
ロールを原料に合成可能（日本化学会１９８６年春季年
会講演要旨集ｌＮ４７．１００８頁）な物質であるが前
者は単離収率が低く（インゲン１トンから１ミリグラム
）後者は原料を生薬（トラガント）から抽出している為
経済的合成法とは言い難い、そこで、経済的に有利なグ
リシノエクレピン類の合成法の探索が望まれていた。<Prior art> Glycinoeclevins are extracted from plants (green beans) (
Gendai Kagaku 1985, p. 16) or cycloasteragallol (Chemical Society of Japan 1986 Spring Annual Meeting Abstracts IN 47, p. 1008), but the isolation yield of the former is low (Ingen 1). (1 milligram from a ton) The latter cannot be called an economical synthesis method because the raw material is extracted from a crude drug (tragacanth), so there was a desire to find an economically advantageous method for synthesizing glycinoecrepines. .
〈発明が解決した問題点〉
本発明者等は、米ヌカ油から工業的規模で抽出可能なシ
クロアルテノール類を原料とし、これを酸化することに
より得られる式（１）の化合物を使用すれば、グリシノ
エクレビン類が経済的に製し−うること、従って１式（
１）の化合物はグリジノエクレビン類の重要な中間体で
あることを見い出し本発明を完成した。<Problems Solved by the Invention> The present inventors have developed a method using a compound of formula (1) obtained by oxidizing cycloartenols, which can be extracted from rice bran oil on an industrial scale, as a raw material. For example, glycinoecrebins can be produced economically and therefore formula 1 (
The present invention was completed by discovering that the compound 1) is an important intermediate of glyzinoeclevins.
なお１式（１）の化合物に９反応に関与しない溶媒中で
、Ｐ−トルエンスルホン酸、硫酸等の有機酸或いは無機
酸を作用させシクロプロパン環を開裂させればグリシノ
エクレピン類に導くことができる。In addition, if the compound of formula (1) is treated with an organic or inorganic acid such as P-toluenesulfonic acid or sulfuric acid in a solvent that does not participate in the 9 reaction to cleave the cyclopropane ring, glycinoecrepines can be obtained. be able to.
〈発明の構成〉
本発明の式（１）の化合物は、シクロアルテノールから
容易に合成される下記式（１１）の公知化合物（Ｊ、ｃ
ｈｅｍ、Ｓｏｃ、、Ｐｅｒｋｉｎ Ｔｒａｎｓ、１１５
８７（１９７２） ）を原料としこれを酸化することに
より製される。<Configuration of the Invention> The compound of formula (1) of the present invention is a compound of the following formula (11) that is easily synthesized from cycloartenol (J, c
hem, Soc,, Perkin Trans, 115
87 (1972)) as a raw material and is produced by oxidizing it.
反応式で示せば下記の通りである。The reaction formula is as follows.
＆
（式中、 Ｒ，、Ｒ，及びＲ３は前記に同じ）反応は１
反応に関与しない溶媒に式（１１）の化合物を溶解し、
これに低濃度のオゾンを通ずる等酸化することにより行
なわれる。& (In the formula, R,, R, and R3 are the same as above) The reaction is 1
Dissolving the compound of formula (11) in a solvent that does not participate in the reaction,
Oxidation is carried out by passing a low concentration of ozone through this.
溶媒としては、クロロホルム、四塩化炭素、二塩化メチ
レン、酢酸エチルエステル、アセトン、メタノール等が
好ましい０反応温度は一９０℃〜０℃で行なわれるが低
温度（−９０℃〜−１Ｏ℃）が好ましく１反応を完結さ
せるには通常１〜２４時間必要である。As a solvent, chloroform, carbon tetrachloride, methylene dichloride, ethyl acetate, acetone, methanol, etc. are preferred.The reaction temperature is -90°C to 0°C, but lower temperatures (-90°C to -10°C) are preferable. Preferably, 1 to 24 hours are usually required to complete one reaction.
〈発明の効果〉
式（１）の化合物を使用すれば、グリシノエクレビン類
が従来の製法に比べより経済的に製しうることが可能と
なる。<Effects of the Invention> By using the compound of formula (1), glycinoeclevins can be produced more economically than with conventional production methods.
実施例１
２４．２５−ジブロモ−シクロアルタニルアセタート４
００ｍｇの無水クロロホルム１２００１λ溶液を一６０
℃に冷やし、２９６−オゾンを含む酸素ガスを通し溶液
が淡青色を呈する迄約１時間反応を行なった０反応終了
後窒素ガスを通して余分のオゾンを追い出し１鴎硫酸第
−鉄溶液で分解した。水洗後、クロロホルム層に無水硫
酸ナトリウムを加え脱水し、ついで溶媒を留去した。Example 1 24.25-dibromo-cycloartanyl acetate 4
00 mg of anhydrous chloroform 12001λ solution
The mixture was cooled to 0.degree. C., and oxygen gas containing 296-ozone was passed therethrough to react for about 1 hour until the solution turned pale blue. After the reaction was completed, nitrogen gas was passed through the solution to drive out excess ozone, followed by decomposition with a ferrous sulfate solution. After washing with water, the chloroform layer was dehydrated by adding anhydrous sodium sulfate, and then the solvent was distilled off.
粗反応生成物をシリカゲルカラムクロマトに付すと、ベ
ンゼン溶８部より ３β−アセトキシ２４゜２５−ジブ
ロモ〜シクロアルタン−７−オン１０８ｍｇが溶出した
。更にベンゼン−酢酸エチル（２０：１）ｉ出部より
３β−アセトキシ２４．２５−ジブロモ−シクロアルタ
ン−７−オン−８β−オール７４ｍｇが得られた３β−
アセトキシ２４．２５−ジブロモ−シクロアルタン−７
−オン
融点１９５〜１９６℃
ＩＲ（にＢｒ、ｃｍ−’）
ｖ １７３２ （ＯＡｃ） 、５４８ （Ｃ−Ｂｒ）
’ＨＮＭＲ（ｌｏＯＭＨｚ、ＣＤＣｈ）δ ０．２０
（ＩＨ，ｄ、Ｊ−５，９Ｈｚ、１９ ａ −ｔ（）０．
５４ （ＬＨ，ｄ、Ｊ−５，４８Ｚ、１９β−Ｈ）２．
０７ （３Ｈ，ｓ、０ＣＯ（：Ｈ，）２．７７ （ＩＨ
，ｓ、ＣＨ−Ｇｏ）
４．１６ （ｌ）１．ｍ、ｗ／２−２２．１５）１ｚ、
ＣＭ−Ｂｒ）４．８３ （１）１．ｍ、ｗ／２−２５．
７）１ｘ、ＣＨ−ＯＡｃ）Ｓ
ｍ／ｘ ８４０．２０９１（Ｍ”、Ｃ３２Ｈ５（，０
３Ｂｒ２）３β−アセトキシ２４．２５−ジブロモ−シ
クロアルタン−７−オン−８βオール
融点 １６７〜１６８℃
ＩＲ（にＢｒ、ｃｍ−１）
ｖ ３４１６（ＯＨ）、１７２８（ＯＡｃ）、１６８
４（Ｃ−０）’ＨＮＭＲ（１００ＭＨ２，ＣＤ（：ｈ）
６ ０．２８（ＩＨ，ｄ、Ｊ−６Ｈｘ、１９ａ−Ｈ）
０．５９（１１（、ｄ、Ｊ−６）１ｚ、１９β−Ｈ）２
．０１（３）ｔ、ｓ、０ＣＯＣＨｓ）３．２２（ＩＨ，
ｓ、ＣＨ）
４．０９（ＩＨ，ｍ、ｗ／２−２２．８Ｈｚ、Ｃ１（−
Ｂｒ）４．５６ （ｔＨ，ｍ、ｗ／２−２５．７８ｘ、
（：Ｈ−ＯＡｃ）Ｓ
ｍ／ｚ ６５Ｂ、２０３５（Ｍ”、Ｃ３２ＨｓｏＯＪ
ｒｚ）手続補正書（１劃
１、事件の表示
昭和６２年特許願第３１７９２８号
２、発明の名称
シクロアルテノール−７−オン誘導体
３、補正をする者
事件との関係 特許出願人
東京都中央区日本橋三丁目１４番１０号４、補正の対象
明細書（特許請求の範囲及び発明の詳細な説明）５、補
正の内容
（１）特許請求の範囲を別紙の通りに訂正する。When the crude reaction product was subjected to silica gel column chromatography, 108 mg of 3β-acetoxy 24°25-dibromo-cycloartan-7-one was eluted from 8 parts of the benzene solution. Furthermore, from the benzene-ethyl acetate (20:1) i output part
74 mg of 3β-acetoxy 24.25-dibromo-cycloartan-7-one-8β-ol was obtained.
Acetoxy 24.25-dibromo-cycloartane-7
-on melting point 195-196°C IR (Br, cm-') v 1732 (OAc), 548 (C-Br)
'HNMR (loOMHz, CDCh) δ 0.20
(IH, d, J-5, 9Hz, 19 a-t()0.
54 (LH, d, J-5, 48Z, 19β-H)2.
07 (3H,s,0CO(:H,)2.77 (IH
, s, CH-Go) 4.16 (l)1. m, w/2-22.15) 1z,
CM-Br)4.83 (1)1. m, w/2-25.
7) 1x, CH-OAc)S m/x 840.2091(M”, C32H5(,0
3Br2) 3β-acetoxy 24.25-dibromo-cycloartan-7-one-8βol Melting point 167-168°C IR (Br, cm-1) v 3416 (OH), 1728 (OAc), 168
4(C-0)'HNMR (100MH2, CD(:h)
6 0.28 (IH, d, J-6Hx, 19a-H)
0.59(11(,d,J-6)1z,19β-H)2
．． 01(3)t,s,0COCHs)3.22(IH,
s, CH) 4.09 (IH, m, w/2-22.8Hz, C1(-
Br) 4.56 (tH, m, w/2-25.78x,
(:H-OAc)S m/z 65B, 2035(M”, C32HsoOJ
rz) Procedural Amendment (Part 1, Case Indication, 1988 Patent Application No. 317928, 2, Title of Invention, Cycloartenol-7-one Derivatives 3, Person Making the Amendment, Relationship with the Case, Patent Applicant, Tokyo Chuo) 3-14-10, Nihonbashi-ku, 4, Specification to be amended (Claims and Detailed Description of the Invention) 5, Contents of the Amendment (1) The scope of the claims will be corrected as shown in the attached sheet.
（２）明細書第２頁の構造式を下記の通りに訂正する
」
（３）同ｉ４４頁の構造式を下記の通りに訂正するｒＲ
？
別紙
「
２、特許請求の範囲
一般式
［式中Ｒ１は水素原子、低級アルキルカルボニル基、低
級アルキル基、ピラニル基を＋ ８２−ＩＨ３はハロゲ
ン原子、ヒドロキシル基を、Ｘは水素原子。(2) Correct the structural formula on page 2 of the specification as follows.'' (3) Correct the structural formula on page 44 of the specification as follows.rR
? Attachment ``2. Claims General formula [In the formula, R1 is a hydrogen atom, a lower alkylcarbonyl group, a lower alkyl group, or a pyranyl group + 82-IH3 is a halogen atom or a hydroxyl group, and X is a hydrogen atom.
ヒドロキシル基を示す］ で示されるシクロアルテノール−７−オン誘導体」Indicates hydroxyl group] Cycloartenol-7-one derivative represented by
Claims (1)
低級アルキル基、ピラニル基を、Ｒ＿２、Ｒ＿３はハロ
ゲン原子、ヒドロキシル基を、Ｘは水素原子、ヒドロキ
シル基を示す］ で示されるシクロアルテノール−７−オン誘導体[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R_1 is a hydrogen atom, a lower alkylcarbonyl group,
A cycloartenol-7-one derivative represented by a lower alkyl group or a pyranyl group, R_2 and R_3 represent a halogen atom or a hydroxyl group, and X represents a hydrogen atom or a hydroxyl group]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62317928A JP2557429B2 (en) | 1987-12-16 | 1987-12-16 | Cycloartenol-7-one derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62317928A JP2557429B2 (en) | 1987-12-16 | 1987-12-16 | Cycloartenol-7-one derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01160996A true JPH01160996A (en) | 1989-06-23 |
| JP2557429B2 JP2557429B2 (en) | 1996-11-27 |
Family
ID=18093599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62317928A Expired - Fee Related JP2557429B2 (en) | 1987-12-16 | 1987-12-16 | Cycloartenol-7-one derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2557429B2 (en) |
-
1987
- 1987-12-16 JP JP62317928A patent/JP2557429B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2557429B2 (en) | 1996-11-27 |
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