(3R,3aR,4R,5R,7S,9R,9aR,12R)-5-hydroxy-3-methoxy-4,7,9,12-tetramethyl-7-vinyloctahydro-4,9a-propanocyclopenta[8]annulen-8(9H)-one | 76375-90-1

• 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: (3R,3aR,4R,5R,7S,9R,9aR,12R)-5-hydroxy-3-methoxy-4,7,9,12-tetramethyl-7-vinyloctahydro-4,9a-propanocyclopenta[8]annulen-8(9H)-one
• 英文别名: (1R,3aR,4R,6S,8R,9aR,9R,10R)-6-ethenyl-8-hydroxy-1-methoxy-4,6,9,10-tetramethyloctahydro-3a,9-propanocyclopenta[8]annulen-5(4H)-one；4-epimutilin；(1R,2R,4S,6R,7R,8S,9R,14R)-6-hydroxy-9-methoxy-2,4,7,14-tetramethyl-4-vinyl-1-tricyclo[5.4.3.0(1,8)]tetradecan-3-one；(1R,2R,4S,6R,7R,8R,9R,14R)-4-ethenyl-6-hydroxy-9-methoxy-2,4,7,14-tetramethyltricyclo[5.4.3.01,8]tetradecan-3-one
• CAS: 76375-90-1
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: GBRKURGUBRXTRD-STQREVBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,3aR,4R,5R,7S,9R,9aR,12R)-5-hydroxy-3-methoxy-4,7,9,12-tetramethyl-7-vinyloctahydro-4,9a-propanocyclopenta[8]annulen-8(9H)-one 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Boron-Pleuromutilins as Anti-Wolbachia Agents with Potential for Treatment of Onchocerciasis and Lymphatic Filariasis

  摘要：

  A series of pleuromutilins modified by introduction of a boron-containing heterocycle on C(14) of the polycyclic core are described. These analogs were found to be potent anti-Wolbachia antibiotics and, as such, may be useful in the treatment of filarial infections caused by Onchocerca volvulus, resulting in Onchocerciasis or river blindness, or Wuchereria bancrofti and Brugia malayi and related parasitic nematodes resulting in lymphatic filariasis. These two important neglected tropical diseases disproportionately impact patients in the developing world. The lead preclinical candidate compound containing 7-fluoro-6-oxybenzoxaborole (15, AN11251) was shown to have good in vitro anti-Wolbachia activity and physicochemical and pharmacokinetic properties providing high exposure in plasma. The lead was effective in reducing the Wolbachia load in filarial worms following oral administration to mice.

  DOI：

  10.1021/acs.jmedchem.8b01854
• 作为产物：
  描述：

  截短侧耳素 在 硫酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 51.5h， 生成 (3R,3aR,4R,5R,7S,9R,9aR,12R)-5-hydroxy-3-methoxy-4,7,9,12-tetramethyl-7-vinyloctahydro-4,9a-propanocyclopenta[8]annulen-8(9H)-one
  参考文献：
  名称：

  通过C–H酰胺化和随后的新型重排产物合成C-13功能化的截短侧耳素

  摘要：

  通过C–H酰胺化化学反应，在温和条件下合成了几克C-13功能化的截短侧耳素中间体。最初的工作是使用铑催化进行的。但是，使用银催化可获得最高的收率，导致形成立体选择性的恶唑烷酮。闭环是在C-12乙烯基存在下进行的，这使其与涉及饱和截短侧耳素骨架的历史方法有所区别。该乙烯基模板的亮点是独特的四环重排产物，可以通过用盐酸和热对其进行处理而生成。

  DOI：

  10.1016/j.tetlet.2011.06.028

文献信息

• 12-POSITION SUBSTITUTED MUTILIN DERIVATIVE
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：EP1832591A1

  公开（公告）日：2007-09-12

  A position 12-substituted mutilin derivative, a novel mutilin analogue, is provided that exhibits strong antimicrobial activity against a broad spectrum of Gram-positive or Gram-negative bacteria, including various drug-resistant bacteria, as well as intermediates for the production of such mutilin derivatives. Specifically, a mutilin derivative or an acid-addition salt thereof is provided that is represented by the following chemical formula (1): (wherein R1 is a hydrogen atom, a formyl group, a substituted or unsubstituted lower alkyl group, an aralkyl group whose aromatic ring may be optionally substituted, a heteroaralkyl group whose aromatic ring may be optionally substituted or a lower alkyloxycarbonyl group; and R2 is a hydrogen atom, a lower alkyl group or an aralkyl group whose aromatic ring may be optionally substituted) (R1 is neither an ethyl group nor a vinyl group).

  提供了一种位置12-取代的莫司林衍生物，一种新型莫司林类似物，对广谱的革兰氏阳性或阴性细菌，包括各种耐药细菌，表现出强大的抗微生物活性，以及用于生产这种莫司林衍生物的中间体。具体地，提供了一种莫司林衍生物或其酸盐加合物，其由以下化学式（1）表示：（其中R1是氢原子、甲酰基、取代或未取代的较低烷基基团、芳基烷基基团，其芳香环可能选择性取代、取代或未取代的杂芳烷基基团或较低烷氧羰基基团；R2是氢原子、较低烷基基团或其芳香环可能选择性取代的芳基烷基基团）（R1既不是乙基基团也不是乙烯基团）。
• Boron-containing small molecules
  申请人：ANACOR PHARMACEUTICALS, INC.

  公开号：US10611780B2

  公开（公告）日：2020-04-07

  Compounds, pharmaceutical formulations, and methods of treating bacterial infections are disclosed.

  公开了治疗细菌感染的化合物、药物制剂和方法。
• EP2149571
  申请人：——

  公开号：——

  公开（公告）日：——
• BORON-CONTAINING SMALL MOLECULES
  申请人：Anacor Pharmaceuticals, Inc.

  公开号：EP3423065B1

  公开（公告）日：2021-07-21