(5S,8R,9S,10S,13S,14S,17R)-17-[(2S)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one | 869729-62-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (5S,8R,9S,10S,13S,14S,17R)-17-[(2S)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 869729-62-4
• 化学式: C₂₈H₅₀O₂Si
• 分子量: 446.789
• InChiKey: XQYCSJSRNCVDBR-LBGFUSKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S,8R,9S,10S,13S,14S,17R)-17-[(2S)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one 在 对甲苯磺酸 作用下， 生成 3-keto-23,24-bisnor-5α-chol-22-ol
  参考文献：
  名称：

  Synthesis and antimicrobial activity of new 3α-Hydroxy-23,24-bisnorcholane polyamine carbamates

  摘要：

  3 alpha -Hydroxy-23,24-bisnorcholane spermidine and spermine carbamates 2-7 have been synthesized and their antimicrobial and hemolytic activities were evaluated. They exhibited excellent in vitro activities especially against methicillin-resistant Staphylococcus aureus. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00632-1
• 作为产物：
  描述：

  (20S)-21-羟基-20-甲基孕甾-4-烯-3-酮 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (5S,8R,9S,10S,13S,14S,17R)-17-[(2S)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of new 3α-Hydroxy-23,24-bisnorcholane polyamine carbamates

  摘要：

  3 alpha -Hydroxy-23,24-bisnorcholane spermidine and spermine carbamates 2-7 have been synthesized and their antimicrobial and hemolytic activities were evaluated. They exhibited excellent in vitro activities especially against methicillin-resistant Staphylococcus aureus. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00632-1

文献信息

• 一种3-烷基化的甾体中间体及其制备和应用
  申请人：上海彩迩文生化科技有限公司

  公开号：CN115974950A

  公开（公告）日：2023-04-18

  本发明公开了一种3‑烷基化的甾体中间体及其制备和应用，属于药物化学技术领域。该中间体利用合适的甾体底物，先在3位进行格氏化反应，引入3‑烷基或烯基，通过精制纯化，把3位手性杂质都去除掉，得到高品质3位手性烷基取代中间体。再将C22位官能团进行转化，生成C22醛中间体。上述中间体在药物合成中展现了良好应用前景，例如：氧化脱羧生成加奈索酮及其类似物；C20位进行其它转化，生成3‑烷基化系列产物。
• A concise synthesis and antimicrobial activities of 3-polyamino-23,24-bisnorcholanes as steroid–polyamine conjugates
  作者：Hong-Seok Kim、Sharaf N. Khan、Jyoti R. Jadhav、Ji-Woong Jeong、Kyungjin Jung、Jin-Hwan Kwak

  DOI：10.1016/j.bmcl.2011.05.048

  日期：2011.7

  A series of steroid-polyamine conjugates were synthesized and evaluated for their antimicrobial activity. This study was focused on the effect of stereochemistry at the C-3 and C-5 of steroids and types of polyamine at C-3 on activity against various human pathogens. All the conjugates exhibited strong antimicrobial activities against Gram-positive strains. Compound 18 was found to be the most potent in these series with a MIC value as low as 1 mu g/mL against the bacterium Staphylococcus aureus ATCC6538P. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and antimicrobial activity of new 3α-Hydroxy-23,24-bisnorcholane polyamine carbamates
  作者：Hong-Seok Kim、Kyung-Chan Kwon、Ki Soo Kim、Cheol Hae Lee

  DOI：10.1016/s0960-894x(01)00632-1

  日期：2001.12

  3 alpha -Hydroxy-23,24-bisnorcholane spermidine and spermine carbamates 2-7 have been synthesized and their antimicrobial and hemolytic activities were evaluated. They exhibited excellent in vitro activities especially against methicillin-resistant Staphylococcus aureus. (C) 2001 Elsevier Science Ltd. All rights reserved.