(3aR,5aS,9aS,9bS)-2-hydroxy-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydronaphtho[1,2-d]oxaborole | 1376654-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (3aR,5aS,9aS,9bS)-2-hydroxy-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydronaphtho[1,2-d]oxaborole
• CAS: 1376654-46-4
• 化学式: C₁₅H₂₇BO₂
• 分子量: 250.189
• InChiKey: CEODFGRDNAAFHA-NZBPQXDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  香紫苏内酯 在 吡啶 、 碘苯二乙酸 、 碘 、 silver fluoride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 29.0h， 生成 (3aR,5aS,9aS,9bS)-2-hydroxy-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydronaphtho[1,2-d]oxaborole 、 borono-sclareolide
  参考文献：
  名称：

  [EN] ANTIMICROBIAL COMPOSITIONS AND USES FOR TREATMENT OF CLOSTRIDIOIDES DIFFICILE, MYCOBACTERIUM TUBERCULOSIS, AND ENTEROCOCCUS FAECALIS INFECTION
  [FR] COMPOSITIONS ANTIMICROBIENNES ET UTILISATIONS POUR LE TRAITEMENT D'INFECTIONS PAR CLOSTRIDIUM DIFFICILE, MYCOBACTERIUM TUBERCULOSIS ET ENTEROCOCCUS FAECALIS

  摘要：

  Provided herein are compositions to treat Clostridioid.es difficile (C. difficile), Mycobacterium tuberculosis (M. tuberculosis) and Enterococcus faecalis (E. faecalis). These compositions are related to the known compounds (+)-Puupehenone and (+)-ent-Chromazonarol, which are both naturally occurring products. The new compositions were shown to potently inhibit both growth and toxin production of C. difficile as well as inhibit the growth and survival of both replicating and dormant M. tuberculosis. In the United States the C. difficile burden is approximately 453,000 hospital cases and 29,000 deaths annually. Globally, about 10 million people fall ill from tuberculosis and 1.4 million died from the disease. In addition, the known compound (+)-ent-Chromazonarol (10) was found for the first time to strongly inhibit the growth of E. faecalis. E. faecalis has grown drug resistant to vancomycin. In 2017, Vancomycin-Resistant Enterococci (VRE) caused an estimated 54,500 infections among hospitalized patients and 5,400 estimated deaths in the United States.

  公开号：

  WO2023215619A2

文献信息

• Scalable, Divergent Synthesis of Meroterpenoids via “Borono-sclareolide”
  作者：Darryl D. Dixon、Jonathan W. Lockner、Qianghui Zhou、Phil S. Baran

  DOI：10.1021/ja303937y

  日期：2012.5.23

  A scalable, divergent synthesis of bioactive meroterpenoids has been developed. A key component of this work is the invention of "borono-sclareolide", a terpenyl radical precursor that enables gram-scale preparation of (+)-chromazonarol. Subsequent synthetic operations on this key intermediate permit rapid access to a variety of related meroterpenoids, many of which possess important biological activity.