JPS63150225A - Carcinostatic agent containing hopane based compound - Google Patents
Carcinostatic agent containing hopane based compoundInfo
- Publication number
- JPS63150225A JPS63150225A JP29681086A JP29681086A JPS63150225A JP S63150225 A JPS63150225 A JP S63150225A JP 29681086 A JP29681086 A JP 29681086A JP 29681086 A JP29681086 A JP 29681086A JP S63150225 A JPS63150225 A JP S63150225A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- configuration
- anticancer agent
- hydrogen atom
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- ZRLNBWWGLOPJIC-PYQRSULMSA-N A'-neogammacerane Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1C(C)C ZRLNBWWGLOPJIC-PYQRSULMSA-N 0.000 title abstract description 6
- 230000003327 cancerostatic effect Effects 0.000 title abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- BJFPMDGPOFJGIR-UHFFFAOYSA-N Hopene I Natural products C1CCC(C)(C)C2CCC3(C)C4(C)CCC5=C(C(C)C)CCC5(C)C4CCC3C21C BJFPMDGPOFJGIR-UHFFFAOYSA-N 0.000 claims abstract 4
- BJFPMDGPOFJGIR-WWJAXWOYSA-N hop-17(21)-ene Chemical compound C1CCC(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CCC5=C(C(C)C)CC[C@]5(C)[C@H]4CC[C@@H]3[C@]21C BJFPMDGPOFJGIR-WWJAXWOYSA-N 0.000 claims abstract 3
- WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 claims abstract 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- PNJBOAVCVAVRGR-UDCAXGDQSA-N 22-Hopanol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1C(C)(O)C PNJBOAVCVAVRGR-UDCAXGDQSA-N 0.000 claims description 3
- DLTTWXWDLCGBRD-UHFFFAOYSA-N Hydroxyhopane Natural products CC12CCCC(C)(C)C1CCC1(C)C2CCC2C3(C)CCC(C(C)C)C3(O)CCC21C DLTTWXWDLCGBRD-UHFFFAOYSA-N 0.000 claims description 3
- -1 hydroxyisopropyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 7
- 229940041181 antineoplastic drug Drugs 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 11
- 239000004480 active ingredient Substances 0.000 abstract description 5
- 201000011510 cancer Diseases 0.000 abstract description 5
- 238000007911 parenteral administration Methods 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 241000124008 Mammalia Species 0.000 abstract description 2
- 230000003203 everyday effect Effects 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 125000000837 carbohydrate group Chemical group 0.000 abstract 1
- 238000007912 intraperitoneal administration Methods 0.000 abstract 1
- 238000001990 intravenous administration Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000007920 subcutaneous administration Methods 0.000 abstract 1
- 229940125904 compound 1 Drugs 0.000 description 7
- 206010003445 Ascites Diseases 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 241000985694 Polypodiopsida Species 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 238000002054 transplantation Methods 0.000 description 3
- 208000006268 Sarcoma 180 Diseases 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- ZRLNBWWGLOPJIC-FFIJSNRCSA-N hopane group Chemical group [C@H]12CC[C@@H]3[C@@]4(C)CCCC(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CCC1C(CC[C@]21C)C(C)C ZRLNBWWGLOPJIC-FFIJSNRCSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はシダ類から抽出されるホパン（ｈｏｐａｎｅ）
骨格を有する化合物を有効成分とする制癌剤に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to hopane extracted from ferns.
The present invention relates to an anticancer agent containing a compound having a skeleton as an active ingredient.
シダ類に由来する多くの化合物が研究されているが、純
粋に単離精製され、構造決定された化合物はあまり多く
ない。ホパン骨格を有する化合物のインビボ制癌活性に
ついては全く報告されていない。Although many compounds derived from ferns have been studied, only a few have been isolated, purified, and had their structures determined. There have been no reports on the in vivo anticancer activity of compounds having a hopane skeleton.
従って本発明はシダ類に由来するホパン骨格を有する化
合物を有効成分とする制癌剤を提供しようとするもので
ある。Therefore, the present invention aims to provide an anticancer agent containing a compound having a hopane skeleton derived from ferns as an active ingredient.
育例底分
前記の目的は、次の一般式（■）：
〔式中、
ＲＩはメチル、又は糖残基であり；
Ｒ２は水素原子、又はメチル基であり；Ｒ３は水素原子
、又はメチル基であり：■、■、０及び◎において、■
と◎とが直接結合しており、そして■が水素原子、ヒド
ロキシル基もしくはメチル基であって０が水素原子であ
るか、又は■と◎及び■と◎がそれぞれ直接結合して２
重結合を構成しており；あるいは■と◎とが一緒になっ
てβ−配置の一〇−０−を構成しておりそして■と◎が
一緒になってα−配置の一〇−を構成しており；
［Ｆ］と◎において、［Ｆ］が水素原子又はメチル基で
あり、そして◎がイソプロピル基又はヒドロキシイソプ
ロピル基であり；あるいは［Ｆ］及び０がそれぞれ、α
−配置の次の式：
％式％
で表わされる基の０及び０に直接結合しており；そして
、
二二二は単結合又は２重結合のいずれかを表わす。但し
、■が水素原子、ヒドロキシル基又はメチル基である場
合、■がα−配置のときは◎はβ−配置であり、そして
Ａがβ〜配装のときはＧはα−配置である。〕
で表わされる化合物を含んで成る制癌剤により達成され
る。The above purpose is to obtain the following general formula (■): [In the formula, RI is methyl or a sugar residue; R2 is a hydrogen atom or a methyl group; R3 is a hydrogen atom or a methyl group. is a group: ■, ■, 0 and ◎, ■
and ◎ are directly bonded, and ■ is a hydrogen atom, hydroxyl group, or methyl group and 0 is a hydrogen atom, or ■ and ◎ and ■ and ◎ are each directly bonded, and 2
They constitute a double bond; or ■ and ◎ together constitute 10-0- in the β-configuration, and ■ and ◎ together constitute 10- in the α-configuration. In [F] and ◎, [F] is a hydrogen atom or a methyl group, and ◎ is an isopropyl group or a hydroxyisopropyl group; or [F] and 0 are α
- configuration of the following formula: % directly bonded to 0 and 0 of the group represented by the formula %; and 222 represents either a single bond or a double bond. However, when ■ is a hydrogen atom, a hydroxyl group, or a methyl group, when ■ is α-configuration, ◎ is β-configuration, and when A is β-configuration, G is α-configuration. ] This is achieved by an anticancer agent comprising a compound represented by the following.
前記一般式（Ｉ）中の糖残基として、例えば次の式： で示される基が挙げられる。As the sugar residue in the general formula (I), for example, the following formula: Examples include groups represented by.
一般式（１）で表わされる化合物として、次のような具
体例を挙げることができる。The following specific examples can be given as the compound represented by the general formula (1).
（１）ホブ−１７（２１）−エンオシニドＡ（ホペンー
オゾニドＡ） （化合物１〕
文献：第２１回天然有機化合物討論会講演要旨集、５７
６〜５８３頁、（１９７８）
（２）１７−ヒドロキシ−２４−〇−〔α−Ｌ−アラビ
ノフラノシル−（１→２））−（β−Ｄ−グルコピラノ
シル−（１→６）〕−β−Ｄ−グルコビラノシルーホパ
ン−２８、２２−オリド〔化合物２〕
ｉ１
文献： Ｃｈｅｍ、 Ｐｈａｒｍ、 Ｂｕｌｌ、 ３
０．３６３２−３６３９（１９８２）。(1) Hob-17(21)-eneosinide A (hopene-ozonide A) (Compound 1) Literature: Abstracts of the 21st Natural Organic Compounds Conference, 57
pp. 6-583, (1978) (2) 17-hydroxy-24-〇-[α-L-arabinofuranosyl-(1→2))-(β-D-glucopyranosyl-(1→6)]- β-D-glucobylanosylhopane-28,22-olide [Compound 2] i1 Literature: Chem, Pharm, Bull, 3
0.3632-3639 (1982).
（３）１７−ヒドロキシ−２４−０−Ｃα−Ｌ−アラビ
ノフラノシル−（１→２）〕−β−Ｄ−グルコピラノシ
ルーホパン−２８、２２−オリド〔化合物３〕
／ゝ
ぐＶ）
ｔＩ
文献： Ｃｈｅｍ、 Ｐｈａｒｍ、 Ｂｕｌｌ、 ３
０．３６３２−３６３９（１９Ｂ２）。(3) 17-hydroxy-24-0-Cα-L-arabinofuranosyl-(1→2)]-β-D-glucopyranosylhopane-28,22-olide [Compound 3] /ゝgu V) tI Literature: Chem, Pharm, Bull, 3
0.3632-3639 (19B2).
（４）ホパンー２２−オール（ヒドロキシホバン）〔化
合物４〕
文献：他旦匹籾畦旦■、 ２２ 、１８０１−１８０８
（１９８３）。(4) Hopan-22-ol (hydroxyphoban) [Compound 4] Literature: Others, 22, 1801-1808
(1983).
（５）ホブ−１７（２１）エン（ホベンＩ） （化合
物５〕
文献：ハ旦匹的畦旦■、η、 １８０１−１８０８（１
９８３）。(5) Hob-17(21)ene (Hoben I) (Compound 5) Literature: Hob-17(21)ene (Hoben I) (Compound 5)
983).
（６）エピーフエルネン（ｅｐｉ−ｆｅｒｎｅｎｅ）〔
化合物１〕
文献： Ｊ、Ｃｈｅｍ、５ｏｃ（ｃ） １１０〜１１
６（１９７１）。(6) Epi-fernene [
Compound 1] Literature: J, Chem, 5oc(c) 110-11
6 (1971).
６週令のＩＣＲ雌性マウスの腹腔に、サルコーマ１８０
細胞を１０６細胞／マウスの量で移植し、移植後１日〜
５日、及び７日〜１１日の１０回にわたり０．１■／
ｋｇ・回〜１０■／ ｋｇ・回の被験化合物（化合物１
〜６）を、生理食塩水に分散した後、腹腔内に投与した
。対照として被験化合物を投与しない群を設けた。各実
験群につき、７匹ずつのマウスを使用した。この結果を
延命率、及び体重計測（腹水腫の増殖）により示す。Sarcoma 180 in the peritoneal cavity of a 6-week-old ICR female mouse.
Cells were transplanted at an amount of 106 cells/mouse, and from 1 day after transplantation.
0.1■/ over 10 times on the 5th and from the 7th to the 11th
kg・times ~ 10■/kg・times of test compound (compound 1
~6) was administered intraperitoneally after being dispersed in physiological saline. A group to which no test compound was administered was established as a control. Seven mice were used for each experimental group. The results are shown by the survival rate and body weight measurement (growth of ascites).
延命率を第１表に示す。Table 1 shows the life extension rate.
（＊）化合物６は純度約２０％。(*) Compound 6 has a purity of approximately 20%.
以上の結果、いずれの化合物も延命効果を示した。As a result, all compounds showed a life-prolonging effect.
マウスの体重増加により測定した腹水腫の増殖の程度を
第１図Ａ及び第１図Ｂに示す。この図から明らかなよう
にいずれの化合物にも腹水腫の増殖の抑制効果が認めら
れ、特に化合物１には強い抑制効果が認められた。The degree of ascites growth as measured by the weight gain of the mice is shown in FIGS. 1A and 1B. As is clear from this figure, all compounds were found to have an inhibitory effect on the growth of ascites, with Compound 1 having a particularly strong inhibitory effect.
大鼓１
６週令のＩＣＲ雌性マウスの左腋下皮下に、サルコーマ
１８０細胞を１０６細胞／マウス移植し、移植後１日〜
５日及び７日〜１１日の１０回にわたり、０．１■／
ｋｇ・回、又は１．０■／ ｋｇ・回の被験化合物（化
合物１又は化合物５）を、生理食塩水に分散した後に腹
腔内に投与した。対照として被験化合物を投与しない群
を設けた。各群に７匹ずつのマウスを使用した。移植後
の固形腫瘍の増殖を、腫瘍の長径及び短径を計測してサ
イズ（ｍｍ２）を求めることにより調べた。この結果を
相対癌増殖率として第２表に示す。Otsuzumi 1 Sarcoma 180 cells were subcutaneously transplanted into the left armpit of a 6-week-old female ICR mouse at 10 cells/mouse, and 1 day after transplantation.
0.1■/10 times on the 5th and from the 7th to the 11th
The test compound (Compound 1 or Compound 5) was administered intraperitoneally after being dispersed in physiological saline at a dose of 1.0 kg/kg/dose or 1.0 kg/dose. A group to which no test compound was administered was established as a control. Seven mice were used in each group. Growth of the solid tumor after transplantation was investigated by measuring the major and minor axes of the tumor to determine the size (mm2). The results are shown in Table 2 as relative cancer growth rates.
第一じし一表
化合物１ ０．１ｘ１０ １００ ７５ ５９
化合物５． １．０ 〃１００ ６６ ７１
＊日数は癌細胞接種後の日数を示す。First Table Compound 1 0.1x10 100 75 59
Compound 5. 1.0 〃100 66 71
*The number of days indicates the number of days after cancer cell inoculation.
大蔵ム
上記実験２を反復し、化合物１及び化合物５の固形腫瘍
の増殖抑制効果を確認した。第２図にこの結果を示す。Experiment 2 above was repeated to confirm the growth-inhibiting effects of Compound 1 and Compound 5 on solid tumor growth. Figure 2 shows the results.
実験２及び３の結果から化合物１及び５が固形腫瘍の増
殖を抑制することが確認された。The results of Experiments 2 and 3 confirmed that Compounds 1 and 5 suppressed the growth of solid tumors.
以上の実験結果から明らかなごとく、本発明の化合物は
固形癌及び腹水腫の両者に対して制癌効果を有する。本
発明の化合物は、制癌剤としてヒトを包含する哺乳類に
投与することができる。As is clear from the above experimental results, the compound of the present invention has an anticancer effect on both solid cancer and ascites. The compounds of the present invention can be administered to mammals, including humans, as anticancer agents.
経口投与又は非経口投与により投与され、非経口投与の
場合には、静脈内投与、腹腔内投与、皮下投与等により
行われる。非経口投与における投与量は患者の状態、癌
の種類等により異るが、１日に１〜３回投与され、その
量はおよそ０．０１〜１０■／ ｋｇ・日であり、毎日
又は隔日に投与される。It is administered orally or parenterally, and in the case of parenteral administration, it is administered intravenously, intraperitoneally, subcutaneously, etc. The dose for parenteral administration varies depending on the patient's condition, type of cancer, etc., but it is administered 1 to 3 times a day, and the amount is approximately 0.01 to 10 kg/day, every day or every other day. administered to
非経口投与剤は本発明の化合物を医薬として許容される
液状担体と共に含んでなり、又は使用直前に液状担体と
混合して使用するための固体組成物であってもよい。液
状担体としては生理食塩水、無毒性の種々の緩衝液、例
えばリン酸緩衝液を挙げることができる。Parenteral preparations may comprise a compound of the invention together with a pharmaceutically acceptable liquid carrier, or they may be solid compositions for mixing with a liquid carrier immediately prior to use. Liquid carriers include physiological saline and various non-toxic buffers, such as phosphate buffers.
経口投与剤は、常用の賦形剤、例えばラクトース、フラ
クトース等と共に調製された錠剤、カプセル剤等である
ことができる。Orally administered preparations can be tablets, capsules, etc. prepared with conventional excipients such as lactose, fructose, and the like.
本発明の制癌剤の有効酸物の毒性は低く、これをヒトに
投与するための制癌剤として使用することができる。The effective acid of the anticancer agent of the present invention has low toxicity and can be used as an anticancer agent for administration to humans.
第１図Ａ及び第１図Ｂは本発明の制癌剤の有効成分の、
腹水腫瘍による体重増加に対する抑制効果を示すグラフ
である。
第２図は本発明の制癌剤の有効成分の、固形癌のサイズ
の増加に対する効果を示すグラフである。FIG. 1A and FIG. 1B show the active ingredients of the anticancer agent of the present invention.
It is a graph showing the suppressive effect on weight gain due to ascites tumor. FIG. 2 is a graph showing the effect of the active ingredient of the anticancer agent of the present invention on increasing the size of solid cancer.
Claims (1)
（Ｄ）とが直接結合しており、そして（Ａ）が水素原子
、ヒドロキシル基もしくはメチル基であって（Ｃ）が水
素原子であるか、又は（Ａ）と（Ｃ）及び（Ｂ）と（Ｄ
）がそれぞれ直接結合して２重結合を構成しており；あ
るいは（Ａ）と（Ｃ）とが一緒になってβ−配置の−Ｏ
−Ｏ−を構成しておりそして（Ｂ）と（Ｄ）とが一緒に
なってα−配置の−Ｏ−を構成しており； （Ｆ）と（Ｇ）において、（Ｆ）が水素原子又はメチル
基であり、そして（Ｇ）がイソプロピル基又はヒドロキ
シイソプロピル基であり：あるいは（Ｆ）及び（Ｇ）が
それぞれ、α−配置の次の式： ▲数式、化学式、表等があります▼ で表わされる基の（Ｆ′）及び（Ｇ′）に直接結合して
おり、そして、 ■は単結合又は２重結合のいずれかを表わ す。但し、（Ａ）が水素原子、ヒドロキシル基又はメチ
ル基である場合、（Ａ）がα−配置のときは（Ｇ）はβ
−配置であり、そしてＡがβ−配置のときはＧはα−配
置である。〕 で表わされる化合物を含んで成る制癌剤。 ２、前記糖残基が次の式： ▲数式、化学式、表等があります▼ 又は、 ▲数式、化学式、表等があります▼ で表わされる特許請求の範囲第１項に記載の制癌剤。 ３、前記化合物が次の式（III） ▲数式、化学式、表等があります▼（III） で表わされるホプ−１７（２１）−エン オゾニドＡ（
ホペン−オゾニドＡ）である特許請求の範囲第１項に記
載の制癌剤。 ４、前記化合物が次の式（IV）： ▲数式、化学式、表等があります▼（IV） で表わされる１７−ヒドロキシ−２４−Ｏ−〔α−Ｌ−
アラビノフラノシル−（１→２）〕−〔β−Ｄ−グルコ
ピラノシル−（１→６）］−β−Ｄ−グルコピラノシル
−ホパン−２８，２２−オリドである特許請求の範囲第
１項又は第２項に記載の制癌剤。 ５、前記化合物が次の式（Ｖ） ▲数式、化学式、表等があります▼（Ｖ） で表わされる１７−ヒドロキシ−２４−Ｏ−〔α−Ｌ−
アラビノフラノシル−（１→２）〕−β−Ｄ−グルコピ
ラノシル−ホパン−２８，２２−オリドである特許請求
の範囲第１項又は第２項に記載の制癌剤。 ６、前記化合物が次の式（VI）： ▲数式、化学式、表等があります▼（VI） で表わされるホパン−２２−オール（ヒドロキシホパン
）である特許請求の範囲第１項に記載の制癌剤。 ７、前記化合物が次の式（VII） ▲数式、化学式、表等があります▼ で表わされるホプ−１７（２１）−エン（ホペン I ）
である特許請求の範囲第１項に記載の制癌剤。 ８、前記化合物が次の式（II） ▲数式、化学式、表等があります▼ で表わされるエピーフェルネンである特許請求の範囲第
１項に記載の制癌剤。[Claims] 1. The following general formula (I): ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R_1 is methyl or a sugar residue; R_2 is a hydrogen atom or a methyl group Yes; R_3 is a hydrogen atom or a methyl group; In (A), (B), (C) and (D), (B) and (D) are directly bonded, and (A) is hydrogen atom, hydroxyl group or methyl group, and (C) is a hydrogen atom, or (A) and (C) and (B) and (D
) are bonded directly to each other to form a double bond; or (A) and (C) are combined to form -O in the β-configuration.
-O-, and (B) and (D) together form -O- in the α-configuration; in (F) and (G), (F) is a hydrogen atom. or a methyl group, and (G) is an isopropyl group or a hydroxyisopropyl group: or (F) and (G) each have the following formula in the α-configuration: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ It is directly bonded to (F') and (G') of the represented group, and (2) represents either a single bond or a double bond. However, when (A) is a hydrogen atom, a hydroxyl group, or a methyl group, when (A) is in the α-configuration, (G) is in the β-configuration.
- configuration, and when A is in the β-configuration, G is in the α-configuration. ] An anticancer agent comprising a compound represented by: 2. The anticancer agent according to claim 1, wherein the sugar residue is represented by the following formula: ▲A mathematical formula, a chemical formula, a table, etc.▼ or ▲A mathematical formula, a chemical formula, a table, etc.▼. 3. The above compound is hop-17(21)-ene ozonide A (
The anticancer agent according to claim 1, which is hopene-ozonide A). 4. The above compound is 17-hydroxy-24-O-[α-L-
Claim 1 or Claim 1 which is arabinofuranosyl-(1→2)]-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranosyl-hopane-28,22-olide. The anticancer agent according to item 2. 5. The above compound is 17-hydroxy-24-O-[α-L-
The anticancer agent according to claim 1 or 2, which is arabinofuranosyl-(1→2)]-β-D-glucopyranosyl-hopane-28,22-olide. 6. The compound according to claim 1, wherein the compound is hopan-22-ol (hydroxyhopane) represented by the following formula (VI): ▲Mathical formula, chemical formula, table, etc.▼(VI) Anticancer drug. 7. The above compound is hop-17(21)-ene (hopen I) represented by the following formula (VII) ▲Mathematical formula, chemical formula, table, etc.▼
The anticancer agent according to claim 1. 8. The anticancer agent according to claim 1, wherein the compound is epifernene represented by the following formula (II) ▲ Numerical formula, chemical formula, table, etc. ▼.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29681086A JPS63150225A (en) | 1986-12-15 | 1986-12-15 | Carcinostatic agent containing hopane based compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29681086A JPS63150225A (en) | 1986-12-15 | 1986-12-15 | Carcinostatic agent containing hopane based compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63150225A true JPS63150225A (en) | 1988-06-22 |
Family
ID=17838437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29681086A Pending JPS63150225A (en) | 1986-12-15 | 1986-12-15 | Carcinostatic agent containing hopane based compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63150225A (en) |
-
1986
- 1986-12-15 JP JP29681086A patent/JPS63150225A/en active Pending
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