3,3-(ethylenedioxy)-23,24-bisnor-5α-cholan-22-al | 191278-88-3

• 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: 3,3-(ethylenedioxy)-23,24-bisnor-5α-cholan-22-al
• 英文别名: (2S)-2-[(5S,8R,9S,10S,13S,14S,17R)-10,13-dimethylspiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]-17-yl]propanal
• CAS: 191278-88-3
• 化学式: C₂₄H₃₈O₃
• 分子量: 374.564
• InChiKey: MKGFUORHSVSTRJ-AOUZBUNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-(ethylenedioxy)-23,24-bisnor-5α-cholan-22-al 在 palladium on activated charcoal 盐酸 、 3 A molecular sieve 、 ammonium acetate 、 氢气 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 7.0h， 生成 24-amino-5α-cholestan-3-one
  参考文献：
  名称：

  The synthesis of spermine analogs of the shark aminosterol squalamine

  摘要：

  Aminosterols isolated from the dogfish shark Squalus acanthias are promising therapeutic agents in the treatment of infection and cancer. One of these, MSI-1436, has been shown to possess antimicrobial activity slightly better than squalamine. In this study, a series of analogs of MSI-1436 have been synthesized from stigmasterol. The 7alpha-hydroxy substituent of MSI-1436 was either omitted or the stereochemistry modified to the 7beta position. Also, analogs of MSI-1436 with 24-sultate, 24-amino, and 24-hydroxy substituents were synthesized in order to assess the importance of the side chain functional group on antimicrobial activity. All of the analogs possess significant antimicrobial activity, suggesting that substitution at C7 and C24 of the aminosterols plays a minor role in their antimicrobial potency. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00161-1
• 作为产物：
  描述：

  豆甾醇 在 氨 、 aluminum isopropoxide 、 lithium 、 对甲苯磺酸 、 臭氧 、 4-甲基-2-戊酮 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 3,3-(ethylenedioxy)-23,24-bisnor-5α-cholan-22-al
  参考文献：
  名称：

  The synthesis of spermine analogs of the shark aminosterol squalamine

  摘要：

  Aminosterols isolated from the dogfish shark Squalus acanthias are promising therapeutic agents in the treatment of infection and cancer. One of these, MSI-1436, has been shown to possess antimicrobial activity slightly better than squalamine. In this study, a series of analogs of MSI-1436 have been synthesized from stigmasterol. The 7alpha-hydroxy substituent of MSI-1436 was either omitted or the stereochemistry modified to the 7beta position. Also, analogs of MSI-1436 with 24-sultate, 24-amino, and 24-hydroxy substituents were synthesized in order to assess the importance of the side chain functional group on antimicrobial activity. All of the analogs possess significant antimicrobial activity, suggesting that substitution at C7 and C24 of the aminosterols plays a minor role in their antimicrobial potency. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00161-1

文献信息

• Practical Approaches to Remote Asymmetric Induction in Steroidal Side-Chains Utilizing Oxazaborolidine Reagents
  作者：Meenakshi N. Rao、Melissa A. McGuigan、Xuehai Zhang、Ze'ev Shaked、William A. Kinney、Michel Bulliard、Blandine Laboue、Nancy E. Lee

  DOI：10.1021/jo970227l

  日期：1997.6.1
• The synthesis of spermine analogs of the shark aminosterol squalamine
  作者：Youheng Shu、Stephen R Jones、William A Kinney、Barry S Selinsky

  DOI：10.1016/s0039-128x(01)00161-1

  日期：2002.3

  Aminosterols isolated from the dogfish shark Squalus acanthias are promising therapeutic agents in the treatment of infection and cancer. One of these, MSI-1436, has been shown to possess antimicrobial activity slightly better than squalamine. In this study, a series of analogs of MSI-1436 have been synthesized from stigmasterol. The 7alpha-hydroxy substituent of MSI-1436 was either omitted or the stereochemistry modified to the 7beta position. Also, analogs of MSI-1436 with 24-sultate, 24-amino, and 24-hydroxy substituents were synthesized in order to assess the importance of the side chain functional group on antimicrobial activity. All of the analogs possess significant antimicrobial activity, suggesting that substitution at C7 and C24 of the aminosterols plays a minor role in their antimicrobial potency. (C) 2002 Elsevier Science Inc. All rights reserved.