3β-N-[tert-butyl N-(3-[4-aminobutyl])-1,3-diaminopropyl dicarbamate]-7α-(tert-butyloxycarbonyl)amino-23,24-bisnor-5α-cholan-22-ol | 1031391-34-0

• 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: 3β-N-[tert-butyl N-(3-[4-aminobutyl])-1,3-diaminopropyl dicarbamate]-7α-(tert-butyloxycarbonyl)amino-23,24-bisnor-5α-cholan-22-ol
• CAS: 1031391-34-0
• 化学式: C₄₄H₈₀N₄O₇
• 分子量: 777.142
• InChiKey: CEGXGFBQOCTHAM-NXOGNDMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.67
• 重原子数：
  55.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  138.46
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3β-N-[tert-butyl N-(3-[4-aminobutyl])-1,3-diaminopropyl dicarbamate]-7α-(tert-butyloxycarbonyl)amino-23,24-bisnor-5α-cholan-22-ol 在 吡啶 、 pyridine-SO3 complex 作用下， 反应 4.0h， 以92%的产率得到
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 7α-amino-23,24-bisnor-5α-cholan-22-ol derivatives

  摘要：

  A series of 7 alpha-aminobisnorsteroids were synthesized and their in vitro antimicrobial activity was evaluated regarding Gram-positive and Gram-negative bacteria. The stereoselective reductive amination of 7-ketosteroid 3 with NH4OAc, in the presence of NaBH3CN, afforded a high yield of 7 alpha-aminosteroid 4. The 3,7-diaminobisnorsteroids were obtained by the reductive amination of 4 with NH4OTf, Boc-spermidine, and Boc-spermine. 3 alpha,7 alpha-Diaminobisnorsterol dihydrochloride 15 showed the highest antimicrobial activity against Streptococcus pyogenes 308A with a MIC value of 1.6 mu g/mL. Hemolytic activities of the compounds 13-20 were determined. Compound 13 showed MHC value at 100 mu g/mL. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.042
• 作为产物：
  描述：

  7-(tert-butyloxycarbonyl)amino-3-keto-23,24-bisnor-5α-cholan-22-ol 、 N1,N5-双-Boc-亚精胺 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 3-N-[tert-butyl N-(3-[4-aminobutyl])-1,3-diaminopropyl dicarbamate]-7-(tert-butyloxycarbonyl)amino-23,24-bisnor-5α-cholan-22-ol 、 3β-N-[tert-butyl N-(3-[4-aminobutyl])-1,3-diaminopropyl dicarbamate]-7α-(tert-butyloxycarbonyl)amino-23,24-bisnor-5α-cholan-22-ol
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 7α-amino-23,24-bisnor-5α-cholan-22-ol derivatives

  摘要：

  A series of 7 alpha-aminobisnorsteroids were synthesized and their in vitro antimicrobial activity was evaluated regarding Gram-positive and Gram-negative bacteria. The stereoselective reductive amination of 7-ketosteroid 3 with NH4OAc, in the presence of NaBH3CN, afforded a high yield of 7 alpha-aminosteroid 4. The 3,7-diaminobisnorsteroids were obtained by the reductive amination of 4 with NH4OTf, Boc-spermidine, and Boc-spermine. 3 alpha,7 alpha-Diaminobisnorsterol dihydrochloride 15 showed the highest antimicrobial activity against Streptococcus pyogenes 308A with a MIC value of 1.6 mu g/mL. Hemolytic activities of the compounds 13-20 were determined. Compound 13 showed MHC value at 100 mu g/mL. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.042