12,13-二癸酸佛波醇 | 24928-17-4

• 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: 12,13-二癸酸佛波醇
• 英文名称: Phorbol-12,13-didecanoate
• 英文别名: 4-α-phorbol 12,13-didecanoate；4α-phorbol 12,13-didecanoate；4alpha-phorbol 12,13-didecanoate；phorbol 12,13-didecanoate；Phorbol didecanoate；[(1S,2S,6R,10S,11R,13S,14R,15R)-13-decanoyloxy-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] decanoate
• CAS: 24928-17-4
• 化学式: C₄₀H₆₄O₈
• 分子量: 672.943
• InChiKey: DGOSGFYDFDYMCW-MWRBZVGOSA-N

物化性质

• 沸点：
  604.62°C (rough estimate)
• 密度：
  1.0569 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

安全信息

• 危险等级：
  6.1(a)
• 危险品运输编号：
  UN 2928
• RTECS号：
  GZ0653000
• 包装等级：
  II
• 危险类别：
  6.1(a)
• 安全说明：
  S22,S24/25

反应信息

• 作为反应物：
  描述：

  高香草酸 、 12,13-二癸酸佛波醇 在 2-fluoro-methylpyridinium tosylate 、 三乙胺 作用下， 生成 phorbol 12,13-didecanoate 20 homovanillate
  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

文献信息

• 9, 10-SECOPREGNANE DERIVATIVE AND PHARMACEUTICAL
  申请人：Fujieda Hiroki

  公开号：US20100016263A1

  公开（公告）日：2010-01-21

  A main object of the invention is to provide a novel useful vitamin D 3 derivative, which has an excellent vitamin D 3 activity and, as compared with conventional vitamin D 3 derivatives, has a relatively small amount of influence on the systemic calcium metabolism. The invention includes a 9,10-secopregnane derivative of the following general formula [1] and a pharmaceutical composition containing it as active ingredient. In the general formula [1], the following partial structure between the 16-position and the 17-position means a single bond or a double bond: Y is a single bond, an alkylene, an alkenylene or phenylene; R 1 and R 2 are the same or different, each represents hydrogen, an alkyl or a cycloalkyl; or R 1 and R 2 , taken together with the adjacent carbon atom, form a cycloalkyl; R 3 is hydrogen or methyl; Z is hydrogen, hydroxy or —NR 11 R 12 .

  本发明的主要目的是提供一种新型有用的维生素D3衍生物，其具有优异的维生素D3活性，并且与传统的维生素D3衍生物相比，对全身钙代谢的影响较小。该发明包括以下通式[1]的9,10-secopregnane衍生物和含其作为活性成分的药物组合物。 在通式[1]中，16位和17位之间的以下部分结构表示单键或双键：Y表示单键、烷基、烯基或苯基；R1和R2相同或不同，每个代表氢、烷基或环烷基；或者R1和R2与相邻的碳原子结合形成环烷基；R3为氢或甲基；Z为氢、羟基或-NR11R12。
• 9,10-SECOPREGNANE DERIVATIVES AND MEDICINE
  申请人：Fujieda Hiroki

  公开号：US20100130454A1

  公开（公告）日：2010-05-27

  A novel useful vitamin D3 derivative which is reduced in influence on systemic calcium metabolism while retaining excellent vitamin D3 activity. The derivative is a 9,10-secopregnane derivative represented by the following general formula [1]. Also provided is a medicinal composition containing the derivative as an active ingredient. In the general formula [1], Y represents (1) a single bond, (2) alkylene (3) alkenylene, or (4) phenylene; R 1 and R 2 are the same or different and each represents (1) hydrogen, (2) alkyl, or (3) cycloalkyl, or R 1 and R 2 in combination represent cycloalkyl in cooperation with the adjacent carbon atom; R 3 represents hydrogen or methyl; and Z represents (1) hydrogen, (2) hydroxy, or (3) —NR 11 R 12 .

  一种新型有用的维生素D3衍生物，其对全身钙代谢的影响减少，同时保留了优异的维生素D3活性。该衍生物是一种9,10-secopregnane衍生物，其通式表示如下[1]。还提供了一种含有该衍生物作为活性成分的药物组合物。在通式[1]中，Y代表(1)单键，(2)烷基，(3)烯基或(4)苯基；R1和R2相同或不同，每个代表(1)氢，(2)烷基或(3)环烷基，或者R1和R2结合代表与相邻碳原子协作的环烷基；R3代表氢或甲基；Z代表(1)氢，(2)羟基或(3)-NR11R12。
• 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。