12-O-acetylphorbol 13-decanoate | 20839-15-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 12-O-acetylphorbol 13-decanoate
• 英文别名: 12-O-acetylphorbol-13-dodecanoate；12-O-Acetyl-phorbol-(13)-n-decanoat；N-6；Phorbol acetate, caprate；[(1S,2S,6R,10S,11R,13S,14R,15R)-14-acetyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] decanoate
• CAS: 20839-15-0
• 化学式: C₃₂H₄₈O₈
• 分子量: 560.728
• InChiKey: CSJWNHJJHIAAIG-SVOQZPEWSA-N

物化性质

• 沸点：
  547.92°C (rough estimate)
• 密度：
  1.0850 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

制备方法与用途

类别：有毒物品

刺激数据

• 皮肤（小鼠）：0.049 毫克，轻度刺激

可燃性危险特性

• 可燃；加热分解时释放刺激烟雾

储运特性

• 库房应通风、低温且干燥

灭火剂

• 干粉、泡沫、砂土、二氧化碳或雾状水

反应信息

• 作为反应物：
  描述：

  12-O-acetylphorbol 13-decanoate 在 silver(l) oxide 作用下， 生成 12-O-,20-O-diacetyl-4-O-methylphorbol 13-decanoate
  参考文献：
  名称：

  Inhibition of Cytopathic Effect of Human Immunodeficiency Virus Type-1 by Various Phorbol Derivatives.

  摘要：

  四十八种分子的phorbol（9）和isophorbol（14）被评估其对人类免疫缺陷病毒（HIV）-1诱导的细胞病变效应（CPE）在MT-4细胞上的抑制作用，以及其激活蛋白激酶C（PKC）的能力，分别作为抗HIV-1和肿瘤促进活性的指标。在这些化合物中，12-O-十四酸酯phorbol 13-醋酸酯（8）和12-O-乙酰phorbol 13-癸酸酯（6）显示出对CPE的最强抑制作用。前者也表现出最强的PKC激活活性，而后者在10 ng/ml时未显示活性。这两种活性通常是在具有A/B反式构型的phorbol衍生物中观察到的，而不是在具有A/B顺式构型的isophorbol衍生物中。对phorbol衍生物中的20-OH进行乙酰化显著降低了对CPE的抑制，正如在12-O-、20-O-二乙酰phorbol 13-癸酸酯（6a）（IC100=15.6 μg/ml）与化合物6（IC100=0.0076 μg/ml）之间的对比，以及在12-O-十四酸酯phorbol 13,20-二乙酸酯（8a）（IC100=15.6 μg/ml）与12-O-十四酸酯phorbol 13-醋酸酯（8）（IC100=0.00048 μg/ml）之间的对比，除了在12-O-癸酸酯phorbol 13-(2-甲基丁酸酯)（4）和phorbol 12,13-二乙酸酯（9c）情况下。C-3碳基团的去除突然降低了对CPE的抑制，正如在3β-羟基phorbol 12,13,20-三乙酸酯（9f）（IC100=500 μg/ml）与phorbol 12,13,20-三乙酸酯（9d）（IC100=62.5 μg/ml）之间的对比所观察到的。尽管8在抑制CPE和激活PKC方面具有同等效力，但20-OH的乙酰化和4-OH的甲基化（如在8a和4-O-甲基-12-O-十四酸酯phorbol 13,20-二乙酸酯（8b）中）都急剧降低了这两种活性。另一方面，其位置异构体（12-O-乙酰phorbol 13-十四酸酯（8c）则表现出两种活性均无）。在8中去除长的酰基团导致这两种活性的显著丧失，如在phorbol 13-醋酸酯（9b）中所示。在12-O-乙酰-13-O-酰基phorbol衍生物中，6显示出对CPE的最高抑制，C-13处具有十二酸酯残基。脂肪酸碳链数量的增加和减少均导致对CPE抑制作用的显著降低。

  DOI：

  10.1248/cpb.50.523
• 作为产物：
  描述：

  (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9a-三羟基-3-(羟基甲基)-1,1,6,8-四甲基-5-氧代-1a,1b,4,4a,5,7a,7b,8,9,9a-十氢-1H-环丙并[3,4]苯并[1,2-e]薁-9-基乙酸酯 、 癸酰氯 生成 12-O-acetylphorbol 13-decanoate
  参考文献：
  名称：

  克罗托诺尔斯的部分合成

  摘要：

  描述了在佛波醇的 α-二醇基团与乙酸和长链脂肪酸混合功能性佛波醇-(12,13)​​-二酯的部分合成。合成的六种佛波二酯与具有刺激性和促肿瘤作用的乙酰佛波酰化物 A 相同1- 一种4, 乙4和乙7从巴豆油中分离。异构佛波醇-(12,13)​​-二酯 A2和乙7以及ASA3和乙4是关于脂肪酸残基的位置异构体对。对于迄今为止从巴豆油中分离出来的所有 11 种佛波醇·(12,13)​​-二酯，A 基团的化合物在 C-13 处带有长链脂肪酸残基，在 C-13 处带有短链脂肪酸残基，这可以概括为-12。B组化合物显示这些脂肪酸残基的相反位置。A 型和 B 型的异构佛波二酯可以通过它们在薄层色谱中的 Rf 值、它们的 IR 和质谱以及它们的 20-[4'-硝基苯基偶氮苯甲酸-(4)]-酯的熔点来区分. 通过所描述的合成路线，具有确定化学结构的佛波醇-(12,13)​​-二酯现在很容易获得。

  DOI：

  10.1515/znb-1968-0422

文献信息

• Method of Producing Progenitor Cells from Differentiated Cells
  申请人：Bhasin Vishal

  公开号：US20120121546A1

  公开（公告）日：2012-05-17

  The present invention provides a method of producing progenitor cells, such as cells capable of being differentiated into a plurality of different cell types, from differentiated cells. Methods of using progenitor cells in differentiation and/or tissue or organ repair and/or regeneration and/or building are also provides. Methods of using progenitor cells in treatment and prophylaxis of conditions alleviated by administering stem cells or tissue or organ derived from stem cells to a subject or by grafting stem cells or tissue or organ derived from stem cells into a subject or by transplanting stem cells or tissue or organ derived from stem cells into a subject are also provided. Also included are progenitor cells and differentiated cells and/or tissues and/or organs derived therefrom, and kits comprising same.
• METHOD OF PRODUCING PROGENITOR CELLS FROM DIFFERENTIATED CELLS
  申请人：Regenertech PTY Limited

  公开号：US20180171290A1

  公开（公告）日：2018-06-21

  The present invention provides a method of producing progenitor cells, such as cells capable of being differentiated into a plurality of different cell types, from differentiated cells. Methods of using progenitor cells in differentiation and/or tissue or organ repair and/or regeneration and/or building are also provided. Methods of using progenitor cells in treatment and prophylaxis of conditions alleviated by administering stem cells or tissue or organ derived from stem cells to a subject or by grafting stem cells or tissue or organ derived from stem cells into a subject or by transplanting stem cells or tissue or organ derived from stem cells into a subject are also provided. Also included are progenitor cells and differentiated cells and/or tissues and/or organs derived therefrom, and kits comprising same.
• US6268395B1
  申请人：——

  公开号：US6268395B1

  公开（公告）日：2001-07-31
• [EN] METHOD FOR INDUCING ENDOGENOUS PRODUCTION OF TISSUE PLASMINOGEN ACTIVATOR (tPA)
  申请人：MOSCATELLI, David, A.

  公开号：WO1988003030A1

  公开（公告）日：1988-05-05

  (EN) Method for achieving elevated circulating plasmin levels and thus causing the dissolution of blood clots. This method is particularly suited for the treatment of myocardial infarctions and other clotting disorders. This method involves in two phases the elevation of endogenous, circulating tissue plasminogen activator (tPA) levels through the administration of basic placenta angiogenic factor (PAF). In the first phase, a relatively high circulating concentration of basic PAF effects the release of tPA from sites in the vascular bed into the circulation. In the second phase, lower circulating concentrations are maintained for a period of time necessary to induce the synthesis and secretion of tPA. This induction will elevate the circulating concentrations of tPA, thus causing increases in the circulating levels of plasmin, an enzyme capable of dissolving blood clots. A method for accomplishing similar purposes is also disclosed which involves the administration of basic PAF in conjunction with heparin as the active ingredients in a pharmaceutical preparation.(FR) Procédé permettant d'obtenir des niveaux élevés de plasmine en circulation, provoquant la dissolution de caillots dans le sang. Ce procédé est particulièrement indiqué pour le traitement des infarctus du myocarde et d'autres troubles circulatoires à l'origine de caillots dans le sang. Ce procédé consiste à augmenter en deux phases les niveaux de l'activateur endogène de plasminogène tissulaire (tPA) en circulation par l'administration d'un facteur angiogène placentaire de base (PAF). Pendant la première phase, une concentration relativement élevée du PAF de base en circulation provoque la libération dans la circulation du tPA provenant de sites dans le lit vasculaire. Pendant la deuxième phase, on maintient en circulation des concentrations plus faibles pendant le temps nécessaire pour induire la synthèse et la sécrétion du tPA. Cette induction augmente les concentrations du tPA en circulation et provoque ainsi l'accroissement des niveaux de plasmine, une enzyme capable de dissoudre les caillots sanguins. Est également décrit un procédé permettant d'obtenir des résultats analogues et consistant à administrer le PAF de base en combinaison avec de l'héparine en tant qu'ingrédients actifs dans une préparation pharmaceutique.
• [EN] PROTEIN KINASE C MODULATORS, AND METHODS OF USE THEREOF<br/>[FR] MODULATEURS DE PROTEINE KINASE C ET PROCEDES PERMETTANT DE LES UTILISER
  申请人：UNIV GEORGETOWN

  公开号：WO2004007445A2

  公开（公告）日：2004-01-22

  One aspect of the present invention relates to amide-bearing substituted benzolactams, and individual stereoisomers thereof. A second aspect of the present invention relates to combinatorial libraries of the aforementioned amide-bearing substituted benzolactams, or individual stereoisomers thereof. Another aspect of the present invention relates to compositions, comprising an amide-bearing substituted benzolactam,and a pharmaceutically acceptable excipient. The present invention also encompasses methods of modulating the activity of PKC or enhancing the secretion of sAPPα or inducing hyperplasia in a mammal. Further, the present invention relates to methods of treating a mammal suffering from neuronal dysfunction, cognitive decline, neurodegeneration, stroke, Alzheimer’s disease, Parkinson’s disease, diabetes, heart disease, or cancer.