12-脱氧佛波醇-13-乙酸苯酯 | 58821-98-0

• 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: 12-脱氧佛波醇-13-乙酸苯酯
• 中文别名: 13-苯基乙酸-12-脱氧佛波醇酯
• 英文名称: 12-deoxyphorbol-13-phenylacetate
• 英文别名: 12-Deoxyphorbolphenylacetate；12-Deoxyphorbol 13-phenylacetate；[(1R,2S,6R,10S,11R,13S,15R)-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] 2-phenylacetate
• CAS: 58821-98-0
• 化学式: C₂₈H₃₄O₆
• 分子量: 466.574
• InChiKey: JAMGGIDPOXFRAM-XASYBOBESA-N

物化性质

• 沸点：
  529.38°C (rough estimate)
• 密度：
  1.0905 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 储存条件：
  存于阴凉干燥处。

反应信息

• 作为反应物：
  描述：

  高香草酸 、 12-脱氧佛波醇-13-乙酸苯酯 在 2-fluoro-methylpyridinium tosylate 、 三乙胺 作用下， 生成 Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8R,9aS)-4a,7b-dihydroxy-3-[2-(4-hydroxy-3-methoxy-phenyl)-acetoxymethyl]-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester
  参考文献：
  名称：

  Similarities and Differences in the Structure−Activity Relationships of Capsaicin and Resiniferatoxin Analogues

  摘要：

  Structure-activity relationships in analogues of the irritant natural product capsaicin have previously been rationalized by subdivision of the molecule into three structural regions (A, B, and C). The hypothesis that resiniferatoxin (RTX), which is a high-potency ligand for the same receptor and which has superficial structural similarities with capsaicin, could be analogously subdivided has been investigated. The effects of making parallel changes in the two structural series have been studied in a cellular functional assay which is predictive of analgesic activity. Parallel structural changes in the two series lead to markedly different consequences on biological activity; the 3- and 4-position aryl substituents (corresponding to the capsaicin 'A-region') which are strictly required for activity in capsaicin analogues are not important in RTX analogues. The homovanillyl C-20 ester group in RTX (corresponding to the capsaicin 'B-region') is more potent than the corresponding amide, in contrast to the capsaicin analogues. Structural variations to the diterpene moiety suggest that the functionalized 5-membered diterpene ring of RTX is an important structural determinant for high potency. Modeling studies indicate that the 3D position of the alpha-hydroxy ketone moiety in the 5-membered ring is markedly different in the phorbol (inactive) analogues and RTX (active) series. This difference appears to be due to the influence of the strained ortho ester group in RTX, which acts as a local conformational constraint. The reduced activity of an analogue substituted in this region and the inactivity of a simplified analogue in which this unit is entirely removed support this conclusion.

  DOI：

  10.1021/jm960139d
• 作为产物：
  描述：

  12-脱氧佛波醇-13-乙酸 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 高氯酸 、 barium hydroxide octahydrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 41.5h， 生成 12-脱氧佛波醇-13-乙酸苯酯
  参考文献：
  名称：

  [EN] DITERPENOID COMPOUNDS THAT ACT ON PROTEIN KINASE C (PKC)
  [FR] COMPOSÉS DITERPÉNOÏDES AGISSANT SUR LA PROTÉINE KINASE C (PKC)

  摘要：

  本公开涉及蛋白激酶C（PKC）调节化合物，使用这些化合物治疗癌症患者的方法，以及与第二治疗剂联合治疗的方法。

  公开号：

  WO2021062030A1

文献信息

• Process to Produce Prostratin and Structural or Functional Analogs Thereof
  申请人：Wender Paul A.

  公开号：US20090187046A1

  公开（公告）日：2009-07-23

  This invention concerns a process to convert a hydroxyl group (bold in R 3 C—OH) in a tigliane-type compound to a hydrogen (bold in R 3 C—H) to obtain deoxytigliane-type compounds or structural or functional analogs thereof. The process has wide application particularly to produce specific biologically active compounds in quantity for use as pharmaceuticals. In particular the process can be used to convert phorbol to a 12-deoxytigliane (prostrating which is a therapeutic lead for the treatment of AIDS. New compositions of matter are also disclosed.

  这项发明涉及一种将蒽醌型化合物中的一个羟基（在R3C—OH中加粗）转化为氢（在R3C—H中加粗），以获得脱氧蒽醌型化合物或其结构或功能类似物的过程。该过程具有广泛的应用，特别是用于大量生产特定生物活性化合物，以用作药物。具体而言，该过程可用于将富尔酚转化为12-脱氧蒽醌（俯卧的，用于治疗艾滋病的治疗前导物）。还公开了新的物质组合。
• PROSTRATIN ANALOGS, BRYOSTATIN ANALOGS, PRODRUGS, SYNTHETIC METHODS, AND METHODS OF USE
  申请人：Wender Paul A.

  公开号：US20110014699A1

  公开（公告）日：2011-01-20

  Embodiments of the present disclosure provide for prostratin analogs, bryostatin analogs, prodrugs of prostratin and prostratin analogs, methods of making prostratin analogs, and methods of making prodrugs of prostratin and prostratin analogs, methods of use of prostratin analogs, bryostatin analogs, and prodrugs thereof, and the like.

  本公开的实施例提供了prostratin类似物、bryostatin类似物、prostratin和prostratin类似物的前药、制备prostratin类似物的方法，以及制备prostratin和prostratin类似物的前药的方法，使用prostratin类似物、bryostatin类似物及其前药的方法等。
• Prostratin and Structural or Functional Analogs Thereof
  申请人：Wender Paul A.

  公开号：US20120101283A1

  公开（公告）日：2012-04-26

  This invention concerns product and process to convert a hydroxyl group (bold in R 3 C—OH) in a tigliane-type compound to a hydrogen (bold in R 3 C—H) to obtain deoxytigliane-type compounds or structural or functional analogs thereof. The process has wide application particularly to produce specific biologically active compounds in quantity for use as pharmaceuticals. In particular the process can be used to convert phorbol to a 12-deoxytigliane (prostratin), which is a therapeutic lead for the treatment of AIDS. New compositions of matter are also disclosed.

  本发明涉及将三环戊二烯型化合物中的羟基基团（在R3C-OH中加粗）转化为氢（在R3C-H中加粗），以获得脱氧三环戊二烯型化合物或其结构或功能类似物的产品和过程。该过程具有广泛的应用，特别是用于生产特定的生物活性化合物，以用作药物。特别是，该过程可用于将富尔醇转化为12-脱氧三环戊二烯（普罗斯特林），后者是治疗艾滋病的治疗前导化合物。还披露了新的物质组成。
• Compositions and methods of use of phorbol esters for the treatment of stroke
  申请人：Biosuccess Biotech Co. Ltd.

  公开号：US10010519B2

  公开（公告）日：2018-07-03

  Methods and compositions containing a phorbol ester or a derivative of a phorbol ester are provided for the treatment and prevention of stroke and the sequelae of stroke. Additional compositions and methods are provided which employ a phorbol ester or derivative compound in combination with at least one additional agent to yield more effective treatment tools to treat or prevent stroke and the long term effects of stroke in mammalian subjects.

  本发明提供了含有植物醇酯或植物醇酯衍生物的方法和组合物，用于治疗和预防中风及中风后遗症。此外，还提供了其他组合物和方法，这些组合物和方法采用了与至少一种额外制剂相结合的植物醇酯或衍生物化合物，以产生更有效的治疗工具来治疗或预防哺乳动物中风和中风的长期后遗症。
• Compositions and methods of use of phorbol esters in the treatment of neoplasms
  申请人：Biosuccess Biotech Co. Ltd.

  公开号：US10278934B2

  公开（公告）日：2019-05-07

  Methods and compositions containing a phorbol ester or a derivative of a phorbol ester are provided for the treatment of chronic and acute conditions. Such conditions may be caused by disease, be symptoms, treatments, or sequelae of disease. The phorbol esters described are particularly useful in the treatment of neoplastic diseases and/or managing the side effects of chemotherapeutic and radiotherapeutic treatments of neoplastic diseases.

  本发明提供了含有植物醇酯或植物醇酯衍生物的方法和组合物，用于治疗慢性和急性疾病。这些病症可能由疾病引起，也可能是疾病的症状、治疗方法或后遗症。所述的植物醇酯特别适用于治疗肿瘤性疾病和/或控制肿瘤性疾病化疗和放疗的副作用。