benzhydryl (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 | 364377-69-5

• 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: benzhydryl (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: 364377-69-5
• 化学式: C₃₄H₃₇F₃O₆S
• 分子量: 630.725
• InChiKey: WBDUQPSIEFLHAN-YHTFFNHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  benzhydryl (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 在 potassium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,2S,4R,5R,8R,9S,11R)-2-[(cyclohexylideneamino)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：

  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
• 作为产物：
  描述：

  三氟甲磺酸酐 、 sordaricin benzhydryl ester 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 benzhydryl (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
  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.