佛波醇-12,13-二苯甲酸酯 | 25405-85-0

• 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
• 中文名称: 佛波醇-12,13-二苯甲酸酯
• 英文名称: phorbol-12,13-dibenzoate
• 英文别名: PDB；phorbol 12,13-dibenzoate；Phorbol dibenzoate；Phorbol-12,13-dibenzoat；Phorbol-12.13-dibenzoat；[(1S,2S,6R,10S,11R,13S,14R,15R)-13-benzoyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] benzoate
• CAS: 25405-85-0
• 化学式: C₃₄H₃₆O₈
• 分子量: 572.655
• InChiKey: FQHYQCXMFZHLAE-PNEATKGUSA-N

物化性质

• 沸点：
  594.83°C (rough estimate)
• 密度：
  1.1098 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.441
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  佛波醇-12,13-二苯甲酸酯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以57%的产率得到6,7-epoxyphorbol 12,13-dibenzoate
  参考文献：
  名称：

  Tyler, Margaret I.; Howden, Merlin E. H., Australian Journal of Chemistry, 1987, vol. 40, # 1, p. 193 - 200

  摘要：

  DOI：
• 作为产物：
  描述：

  phorbol 20-trityl 在 吡啶 作用下， 以 溶剂黄146 为溶剂， 生成 佛波醇-12,13-二苯甲酸酯
  参考文献：
  名称：

  Hecker,E. et al., Justus Liebigs Annalen der Chemie, 1969, vol. 725, p. 130 - 141

  摘要：

  DOI：

文献信息

• Polybenzoate und -acetate des Phorbols und Phorbol-3-ols und funktionelle Derivate der Allylgruppierung des Phorbols
  作者：Hans Ulrich Schairer、Heinz Walter Thielmann、Michael Gschwendt、Gert Kreibich、Rainer Schmidt、Erich Hecker

  DOI：10.1515/znb-1968-1106

  日期：1968.11.1

  Base catalysed transesterification of phorbol-12,13,20-tribenzoate yields phorbol-12,13-dibenzoate. By base catalysed transesterification of phorbol-pentaacetate phorbol-9,12,13-triacetate is obtained. This can be re-acetylated to give phorbol-9,12,13,20-tetraacetate which is also obtained by treatment of phorbol-12,13,20-triacetate with acetic anhydride/p-toluene-sulfonic acid.

  Reduction of phorbol-12,13,20-triacetate with LiAlH₄ yields phorbol-3-ol which reduces Fehling's and Tollen's reagent. Reduction of the 3-keto group alone can be accomplished with sodium borohydride. From all phorbol-esters investigated only in phorbol-pentaacetate an acetyl migration is observed during the sodium borohydride reduction leading to phorbol-3-ol-3,9,12,13,20-pentaacetate. By these findings those two tertiary hydroxyl groups of phorbol which are not acetylated with acetic anhydride/pyridine at room temperature were further characterized.

  Oxidation of phorbol-12,13-diacetate with activated manganese dioxide yields phorbol-20-al-12,13-diacetate. By evaluation of nmr-spectra of this aldehyde and of some of its derivatives as well as of the epoxide of phorbol-12,13-diacetate and of 6-oxo-7-hydroxy- and 6,7-diacetoxy-20-nor-phorbol-12,13-diacetate the sequence of C-atoms around the allylic alcohol group of phorbol is further characterized.

  苯丙二酸酯的碱催化转酯化反应可得到苯丙二酸酯。苯丙五酸酯的碱催化转酯化反应可得到苯丙-9,12,13-三乙酸酯。这可以重新乙酰化以得到苯丙-9,12,13,20-四乙酸酯，该化合物也可以通过苯丙-12,13,20-三乙酸酯与乙酸酐/对甲苯磺酸的处理获得。 用LiAlH4还原苯丙-12,13,20-三乙酸酯可得到苯丙-3-醇，该化合物可还原费林试剂和托伦试剂。仅还原3-酮基团可使用硼氢化钠完成。在所有研究的苯丙酯中，仅在苯丙五酸酯中观察到钠硼氢化物还原过程中的乙酰迁移，导致苯丙-3-醇-3,9,12,13,20-五乙酸酯的形成。通过这些发现，苯丙醇中未被乙酸酐/吡啶在室温下乙酰化的两个三级羟基进一步被表征。 用活性二氧化锰氧化苯丙-12,13-二乙酸酯可得到苯丙-20-醛-12,13-二乙酸酯。通过评估该醛及其某些衍生物、苯丙-12,13-二乙酸酯的环氧化物以及6-氧代-7-羟基-和6,7-二乙酰氧基-20-去甲基苯丙-12,13-二乙酸酯的nmr光谱，进一步表征了苯丙烯醇羟基周围的C原子序列。
• Ester Prodrugs of Prostratin and Related Phorbol Compounds
  申请人：Xu Rensheng

  公开号：US20110251421A1

  公开（公告）日：2011-10-13

  The present disclosure provides analogs and derivatives of phorbol compounds for the treatment of viral infections, neoplastic diseases, inflammatory reactions, and use as analgesics.

  本公开提供了类似于并生物衍生物的茂丙烷化合物，用于治疗病毒感染、肿瘤性疾病、炎症反应，并用作镇痛剂。
• ESTER PRODRUGS OF PROSTRATIN AND RELATED PHORBOL COMPOUNDS
  申请人：Xu Rensheng

  公开号：US20090163587A1

  公开（公告）日：2009-06-25

  Ester prodrugs of phorbol compounds for the treatment of viral infections, neoplastic diseases, inflammatory reactions, and use as analgesics, wherein the phorbol compounds are derivatized with a -x-o-c(o)-R′ group linked to the 6-carbon of the phorbol residue.

  Ester前药是指与Phorbol化合物衍生物一起用于治疗病毒感染、肿瘤疾病、炎症反应和用作镇痛剂的化合物，其中Phorbol化合物经过衍生化处理，与Phorbol残基的6-碳连接，形成-x-o-c(o)-R'基团。
• DNA encoding rabbit TNF, vector having said DNA inserted thereinto, host transformed with said vector, rabbit TNF polypeptide, and process for production thereof
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0146026A2

  公开（公告）日：1985-06-26

  A novel cloned DNA encoding a rabbit Tumor Necrosis Factor (TNF) or a principal portion thereof, a vector having said DNA inserted thereinto, a host transformed with said vector, a novel polypeptide having or containing the rabbit TNF or a principal portion thereof, and a process for producing said polypeptide comprising cultivating said transformed host.

  一种编码兔肿瘤坏死因子（TNF）或其主要部分的新型克隆DNA，一种插入了所述DNA的载体，一种用所述载体转化的宿主，一种具有或含有兔TNF或其主要部分的新型多肽，以及一种生产所述多肽的工艺，包括培养所述转化宿主。
• DNA encoding human tumor necrosis factor and human tumor necrosis factor polypeptide
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0155549A2

  公开（公告）日：1985-09-25

  A novel cloned DNA encoding a human tumor necrosis factor (TNF), a vector having said DNA inserted thereinto, a host transformed with said vector and a novel human TNF polypeptide, and processes for producing them.

  一种编码人肿瘤坏死因子（TNF）的新型克隆 DNA、一种插入了所述 DNA 的载体、一种用所述载体转化的宿主和一种新型人 TNF 多肽，以及生产它们的工艺。