(6R, 7S)-N1,N4-di-tert-butoxycarbonyl-(6,7-O-isopropylidene)-6,7-dihydroxyspermine | 581777-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6R, 7S)-N1,N4-di-tert-butoxycarbonyl-(6,7-O-isopropylidene)-6,7-dihydroxyspermine
• 英文别名: tert-butyl N-[[(4S,5R)-5-[(3-aminopropylamino)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-N-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]carbamate
• CAS: 581777-42-6
• 化学式: C₂₃H₄₆N₄O₆
• 分子量: 474.641
• InChiKey: NZNFKCZANABMMV-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (6R, 7S)-N1,N4-di-tert-butoxycarbonyl-(6,7-O-isopropylidene)-6,7-dihydroxyspermine 在 盐酸 、 乙醇 作用下， 以84%的产率得到meso-6,7-dihydroxyspermine hydrochloride
  参考文献：
  名称：

  Synthesis of dihydroxylated polyamines from an erythronolactone

  摘要：

  The opening of protected erythronolactone by an amine or a diamine furnished hydroxy-amides. Their multistep functional conversion led to either selectively protected or free dihydroxy-polyamines. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00693-2
• 作为产物：
  描述：

  D-erythronolactone acetonide 在 lithium aluminium tetrahydride 、 TEA 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 134.0h， 生成 (6R, 7S)-N1,N4-di-tert-butoxycarbonyl-(6,7-O-isopropylidene)-6,7-dihydroxyspermine
  参考文献：
  名称：

  Synthesis of dihydroxylated polyamines from an erythronolactone

  摘要：

  The opening of protected erythronolactone by an amine or a diamine furnished hydroxy-amides. Their multistep functional conversion led to either selectively protected or free dihydroxy-polyamines. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00693-2

文献信息

• Targeting the Polyamine Transport System with Benzazepine- and Azepine-Polyamine Conjugates
  作者：Sophie Tomasi、Jacques Renault、Bénédicte Martin、Stephane Duhieu、Virginie Cerec、Myriam Le Roch、Philippe Uriac、Jean-Guy Delcros

  DOI：10.1021/jm1007648

  日期：2010.11.11

  The polyamine transport system (PTS) whose activity is up-regulated in cancer cells is an attractive target for drug design. Two heterocyclic (azepine and benzazepine) systems were conjugated to various polyamine moieties through an amidine bound to afford 18 compounds which were evaluated for their affinity for the PTS and their ability to use the PTS for cell delivery. Structure-activity relationship studies and lead optimization afforded two attractive PTS targeting compounds. The azepine-spermidine conjugate 14 is a very selective substrate of the PTS that may serve as a vector for radioelements used for diagnoses or therapeutics in nuclear medicine. The nitrobenzazepine-spermine conjugate 28 is a very powerful PTS inhibitor with very low intrinsic cytotoxicity, able to prevent the growth of polyamine depleted cells in presence of exogenous polyamines.
• Synthesis of dihydroxylated polyamines from an erythronolactone
  作者：Myriam Le Roch、Jacques Renault、Kristell Penlaë、Philippe Uriac

  DOI：10.1016/s0040-4039(03)00693-2

  日期：2003.4

  The opening of protected erythronolactone by an amine or a diamine furnished hydroxy-amides. Their multistep functional conversion led to either selectively protected or free dihydroxy-polyamines. (C) 2003 Elsevier Science Ltd. All rights reserved.