(3R)-3-deoxo-11-deoxy-3-methoxy-11-oxo-4-epi-mutilin 14-chloroformate | 193536-85-5

• 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)-3-deoxo-11-deoxy-3-methoxy-11-oxo-4-epi-mutilin 14-chloroformate
• 英文别名: (3R,3aS,4R,SR,7S,9R,9aR,12R)-3-methoxy-4,7,9,12-tetramethyl-8-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl carbonochloridate；4-epi-mutilin 14-chloroformate；[(1R,2R,4S,6R,7R,8S,9R,14R)-4-ethenyl-9-methoxy-2,4,7,14-tetramethyl-3-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] carbonochloridate
• CAS: 193536-85-5
• 化学式: C₂₂H₃₃ClO₄
• 分子量: 396.955
• InChiKey: BWSVWXWDAQULHZ-LGEBSIRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R)-3-deoxo-11-deoxy-3-methoxy-11-oxo-4-epi-mutilin 14-chloroformate 在 盐酸羟胺 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到(3R)-3-deoxo-11-deoxy-3-methoxy-11-oxo-4-epi-mutilin 14-(N-hydroxycarbamate)
  参考文献：
  名称：

  Pleuromutilins. Part 1 The identification of novel mutilin 14-carbamates

  摘要：

  A novel series of mutilin 14-carbamates has been discovered as a result of structure-activity studies on the naturally occurring antibiotic pleuromutilin (1). In particular, the 4-methoxybenzoylcarbamate, SE-222734 (15o) displays potent antibacterial activity against a number of bacterial pathogens which are resistant to currently used agents and shows enhanced metabolic stability when compared to earlier pleuromutilin derivatives. Such derivatives therefore have the potential to provide a new class of antibacterial agents for human therapy which address the threat of bacterial resistance. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00338-2
• 作为产物：
  描述：

  (3R,3aS,4R,5R,7S,9R,9aR,12R)-3-methoxy-4,7,9,12-tetramethyl-8-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl 2-hydroxyacetate 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 (3R)-3-deoxo-11-deoxy-3-methoxy-11-oxo-4-epi-mutilin 14-chloroformate
  参考文献：
  名称：

  具有新型C（14）侧链的截短侧耳素衍生物的合成和抑菌活性

  摘要：

  为了找到具有优异抗菌活性和克服多药耐药性的新型抗菌剂，合成了一系列具有新型C（14）侧链的截短侧耳素衍生物，并对其体外抗菌活性进行了评估。抗菌作用的结果表明，大多数衍生物显示出对革兰氏阳性生物体的有效活性。特别是，与截短侧耳素和利奈唑胺相比，化合物10d表现出最强的抑制活性，是潜在的分子，需要进一步研究。

  DOI：

  10.1016/j.cclet.2011.10.002

文献信息

• [EN] BORON-CONTAINING SMALL MOLECULES<br/>[FR] PETITES MOLÉCULES CONTENANT DU BORE
  申请人：ANACOR PHARMACEUTICALS INC

  公开号：WO2017151489A1

  公开（公告）日：2017-09-08

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

  化合物、药物配方和治疗细菌感染的方法被披露。
• 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。
• Design, synthesis, and structure–activity relationship studies of conformationally restricted mutilin 14-carbamates
  作者：Liqiang Fu、Xin Liu、Chenyu Ling、Jianjun Cheng、Xingsheng Guo、Huili He、Shi Ding、Yushe Yang

  DOI：10.1016/j.bmcl.2011.12.063

  日期：2012.1

  We report herein the design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates based on the structure of SB-222734. The antibacterial activities of these newly synthesized compounds were also evaluated and compared with linezolid and retapamulin. Results showed that most of the target compounds exhibit good potency in inhibiting the growth of Gram-positive bacteria including Methicillin-susceptible Staphylococcus aureus MSSA (MIC: 0.0625-2 mu g/mL), Methicillin-resistant S. aureus MRSA (MIC: 0.0625-2 mu g/mL), Methicillin-susceptible Staphylococcus epidermidis MSSE (MIC: 0.0625-2 mu g/mL), Methicillin-resistant S. epidermidis MRSE (MIC: 0.0625-2 mu g/mL), and Streptococcus pneumonia (MIC: 0.0625-4 mu g/mL). In particular, three remarkable compounds of this series (12l, 12m, and 21l) exhibited comparable in vitro antibacterial profiles to that of retapamulin. (C) 2011 Elsevier Ltd. All rights reserved.
• Process Development for A Novel Pleuromutilin-Derived Antibiotic
  作者：Yemane Andemichael、Jun Chen、Jacalyn S. Clawson、Wenning Dai、Ann Diederich、Susan V. Downing、Alan J. Freyer、Peng Liu、Lynette M. Oh、Daniel B. Patience、Sonja Sharpe、Joseph Sisko、Julie Tsui、Frederick G. Vogt、Jun Wang、Lori Wernersbach、Edward C. Webb、James Wertman、Leon Zhou

  DOI：10.1021/op900104g

  日期：2009.7.17

  A scalable synthesis of a novel pleuromutilin-based antibiotic is reported. The synthesis features the scale-up of an interesting skeletal rearrangement of the pleuromutilin core and isolation. of a highly purified product despite starting with relatively impure pleuromutilin. The use of Design of Experiment (DoE) and Principal Component Analysis (PCA) tools to achieve these goals is also discussed. Furthermore, the novel coupling of a carbamate and N-acyl-imidazole to produce the imidodicarbonate portion of the target molecule is described.
• BORON-CONTAINING SMALL MOLECULES
  申请人：Anacor Pharmaceuticals, Inc.

  公开号：EP3423065B1

  公开（公告）日：2021-07-21