benzyl sordaricin triflate | 250244-66-7

• 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: benzyl sordaricin triflate
• 英文别名: benzyl (1R,2S,4R,5R,8R,9S,11R)-9-formyl-5-methyl-13-propan-2-yl-2-(trifluoromethylsulfonyloxymethyl)tetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylate
• CAS: 250244-66-7
• 化学式: C₂₈H₃₃F₃O₆S
• 分子量: 554.628
• InChiKey: OMMZAAUAIJXLFL-SKHGXXIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  95.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl sordaricin triflate 在 palladium dihydroxide 氢气 、 sodium hydride 、 碳酸氢钠 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 生成 (1R,2S,4R,5R,8R,9S,11R)-2-[[(2R,4aR,7aR)-4-(2-chloroprop-2-enyl)-3,4a,5,6,7,7a-hexahydro-2H-cyclopenta[b][1,4]oxazin-2-yl]oxymethyl]-9-formyl-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid
  参考文献：
  名称：

  Identification of a broad-Spectrum azasordarin with improved pharmacokinetic properties

  摘要：

  The synthesis and antifungal activity of 5- and 5'-6'-substituted azasordarin derivatives are described. Modification of the 5'-position led to the discovery of the spirocyclopentyl analogue 7g, which is the first azasordarin to register single-digit MIC values versus Aspergillus spp. Further investigation identified the 5'-i-Pr derivative 7b, which displays superior pharmacokinetic properties compared to other azasordarins. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00161-6
• 作为产物：
  描述：

  三氟甲磺酸酐 、 sordaricin benzyl ester 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到benzyl sordaricin triflate
  参考文献：
  名称：

  Synthesis of Sordaricin Analogues as Potent Antifungal Agents against Candida albicans

  摘要：

  Sordaricin derivatives possessing a cyclohexane ring appendage attached via an ether. thioether. amine, oxime. ester or amide linkage were synthesized and their antifungal activity was evaluated in vitro. Compounds containing a thioether bond or an oxime bond as a linkage exhibited potent MICs (less than or equal to0.125 mug/mL) against four Candida albicans strains including azole-low-susceptible strains. They were also active (MIC less than or equal to0.125 mug/mL) against Candida glabrata. Their in vivo efficacy was confirmed in a murine intravenous infection model with Candida albicans. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00020-3

文献信息

• Synthesis of Sordaricin Analogues as Potent Antifungal Agents against Candida albicans
  作者：Satoru Kaneko、Takuya Uchida、Satoshi Shibuya、Takeshi Honda、Isao Kawamoto、Tamako Harasaki、Takashi Fukuoka、Toshiyuki Konosu

  DOI：10.1016/s0960-894x(02)00020-3

  日期：2002.3

  Sordaricin derivatives possessing a cyclohexane ring appendage attached via an ether. thioether. amine, oxime. ester or amide linkage were synthesized and their antifungal activity was evaluated in vitro. Compounds containing a thioether bond or an oxime bond as a linkage exhibited potent MICs (less than or equal to0.125 mug/mL) against four Candida albicans strains including azole-low-susceptible strains. They were also active (MIC less than or equal to0.125 mug/mL) against Candida glabrata. Their in vivo efficacy was confirmed in a murine intravenous infection model with Candida albicans. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Identification of a broad-Spectrum azasordarin with improved pharmacokinetic properties
  作者：Michael H. Serrano-Wu、Denis R.St. Laurent、Tina M. Carroll、Marco Dodier、Qi Gao、Patrice Gill、Claude Quesnelle、Anne Marinier、Charles E. Mazzucco、Alicia Regueiro-Ren、Terry M. Stickle、Dedong Wu、Hyekyung Yang、Zheng Yang、Ming Zheng、Mary E. Zoeckler、Dolatrai M. Vyas、Balu N. Balasubramanian

  DOI：10.1016/s0960-894x(03)00161-6

  日期：2003.4

  The synthesis and antifungal activity of 5- and 5'-6'-substituted azasordarin derivatives are described. Modification of the 5'-position led to the discovery of the spirocyclopentyl analogue 7g, which is the first azasordarin to register single-digit MIC values versus Aspergillus spp. Further investigation identified the 5'-i-Pr derivative 7b, which displays superior pharmacokinetic properties compared to other azasordarins. (C) 2003 Elsevier Science Ltd. All rights reserved.