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(2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン

(2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン 化学構造式
119509-24-9
CAS番号.
119509-24-9
化学名:
(2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン
别名:
(2S,4S,5R)-1-(2,4-ジヒドロキシ-5,6-ジメトキシ-3-ピリジニル)-2,4-ジメチル-5,6-ジクロロ-1-ヘキサノン;アトペニンA5;(2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン;(2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチルヘキサン-1-オン;3-[(2S,4S,5R)-2,4-ジメチル-5,6-ジクロロヘキサノイル]-5,6-ジメトキシピリジン-2,4-ジオール
英語名:
atpenin A5
英語别名:
FO 125A5;atpenin A5;Antibiotic FO 125A5;Atpenin A5 (Synthetic);(2S,4S,5R)-5,6-Dichloro-1-(2,4-dihydroxy-5,6-dimethoxypyridin-3-yl)-2,4-dimethyl-1-hexanone;(2S,4S,5R)-1-(2,4-Dihydroxy-5,6-dimethoxy-3-pyridinyl)-2,4-dimethyl-5,6-dichloro-1-hexanone;3-[(2S,4S,5R)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone;2(1H)-Pyridinone, 3-[(2S,4S,5R)-5,6-dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-;preconditioning,sensitive,mKATP,Atpenin A 5,Atpenin A5,ischemia,potassium,complex II,Inhibitor,cardioprotective,channel,mitochondrial,Potassium Channel,KcsA,ATP,inhibit,reperfusion,Atpenin A-5
CBNumber:
CB71388223
化学式:
C15H21Cl2NO5
分子量:
366.24
MOL File:
119509-24-9.mol

(2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン 物理性質

融点 :
83-85℃
沸点 :
538.3±50.0 °C(Predicted)
比重(密度) :
1.31±0.1 g/cm3(Predicted)
貯蔵温度 :
-20°C Freezer, Under inert atmosphere
溶解性:
クロロホルム（微量）、エタノール（微量）、メタノール（微量、超音波処理）
酸解離定数(Pka):
4.50±1.00(Predicted)
外見 :
白色からオフホワイトの粉末。
色:
ホワイトからオフホワイト

安全性情報

(2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン 価格 もっと(1)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01MPB183357
Atpenin A5 		119509-24-9 1mg ￥84000 2018-12-26 購入

(2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン 化学特性,用途語,生産方法

説明

Enantioselective total synthesis of atpenin A5, a potent mitochondrial complex II (succinate-ubiquinone oxidoreductase) inhibitor, has been achieved by a convergent approach through a coupling reaction between 5-iodo-2,3,4,6-tetraalkoxypyridine and a side-chain aldehyde. The two key segments were synthesized through ortho-metalation/boronation with (MeO)3B/oxidation with mCPBA, ortho-iodination, halogen dance reaction, Sharpless epoxidation and regioselective epoxide-opening reaction.

定義

Atpenin A5 belongs to a class of antifungal antibiotics isolated from Penicillium sp. The atpenins are effective against filamentous fungi, particularly Trichophyton sp., and are specific and potent inhibitors of the succinate-ubiquinone reducatase activity of the mitochondrial complex II. Atpenin A5 is the most effective inhibitor against complex II from all the atpenins and has been shown to protect against cardiac-reperfusion injury in rat studies through the stimulation of mitochondrial KATP channels. Atpenin A5 is an inhibitor of SDHB, SDHC and SDHD.

生物活性

Mitochondrial complex II (succinate dehydrogenase or succinate:ubiquinone oxidoreductase) is a functional member of the Krebs cycle and the aerobic respiratory chain that couples the oxidation of succinate to fumarate with the reduction of quinone to quinol. Atpenin A5, an antifungal antibiotic isolated from Penicillium sp. found in soil, is a highly specific ubiquinone-binding site inhibitor of succinate dehydrogenase (IC50s = 12 and 3.7 nM in nematode and mammalian mitochondria, respectively, versus IC50s > 100 μM for inhibition of complex I and complex III enzymes). Atpenin A5 has cardioprotective effects against simulated ischemia-reperfusion injury in cardiomyocytes. Several mechanisms through which this occurs, including activation of mitochondrial ATP-sensitive potassium channels or modulation of mitochondrial reactive oxygen species generation, have been proposed.

(2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン 上流と下流の製品情報

原材料

準備製品

(2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン 生産企業

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(2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン  スペクトルデータ(1HNMR)

atpenin A5(119509-24-9)1HNMR

119509-24-9((2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン)キーワード:

(-)-4-ヒドロキシ-5,6-ジメトキシ-3-[(E)-2-メチル-1-オキソ-4-ヘキセニル]ピリジン-2(1H)-オン (2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン 7-クロロ-2-メチル-1-ヘプテン (2S,4S,5S)-5-クロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン (2S,4R)-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン 8-クロロ-2-メチル-1-オクテン
  • 119509-24-9
  • atpenin A5
  • (2S,4S,5R)-1-(2,4-Dihydroxy-5,6-dimethoxy-3-pyridinyl)-2,4-dimethyl-5,6-dichloro-1-hexanone
  • (2S,4S,5R)-5,6-Dichloro-1-(2,4-dihydroxy-5,6-dimethoxypyridin-3-yl)-2,4-dimethyl-1-hexanone
  • 3-[(2S,4S,5R)-5,6-Dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone
  • Antibiotic FO 125A5
  • FO 125A5
  • Atpenin A5 (Synthetic)
  • 2(1H)-Pyridinone, 3-[(2S,4S,5R)-5,6-dichloro-2,4-dimethyl-1-oxohexyl]-4-hydroxy-5,6-dimethoxy-
  • preconditioning,sensitive,mKATP,Atpenin A 5,Atpenin A5,ischemia,potassium,complex II,Inhibitor,cardioprotective,channel,mitochondrial,Potassium Channel,KcsA,ATP,inhibit,reperfusion,Atpenin A-5
  • (2S,4S,5R)-1-(2,4-ジヒドロキシ-5,6-ジメトキシ-3-ピリジニル)-2,4-ジメチル-5,6-ジクロロ-1-ヘキサノン
  • アトペニンA5
  • (2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチル-1-ヘキサノン
  • (2S,4S,5R)-5,6-ジクロロ-1-(2,4-ジヒドロキシ-5,6-ジメトキシピリジン-3-イル)-2,4-ジメチルヘキサン-1-オン
  • 3-[(2S,4S,5R)-2,4-ジメチル-5,6-ジクロロヘキサノイル]-5,6-ジメトキシピリジン-2,4-ジオール
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