O,O'-Di(tert-butyl)-N-<4-(mesyloxy)butyl>-N,N'-(propan-1,3-diyl)bis | 134935-53-8

• 英文名称: O,O'-Di(tert-butyl)-N-<4-(mesyloxy)butyl>-N,N'-(propan-1,3-diyl)bis
• 英文别名: 4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl methanesulfonate
• CAS: 134935-53-8
• 化学式: C₁₈H₃₆N₂O₇S
• 分子量: 424.559
• InChiKey: RISORPVTHSANRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  111.24
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  O,O'-Di(tert-butyl)-N-<4-(mesyloxy)butyl>-N,N'-(propan-1,3-diyl)bis 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 N1,N4-双-Boc-亚精胺
  参考文献：
  名称：

  Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 1. Structural Modifications of the Hydroxyglycine Moiety

  摘要：

  A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent currently commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Using the general concept of bioisosteric replacement, variations of the hydroxyglycine central "C" region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. By this way, the malonic derivative 13a was discovered as the first example of a new series of potent immunosuppressive agents encompassing a retro-amide bond linked to the hexyl-guanidino moiety. Structure-activity relationships of this series were studied by synthesizing compounds 13g-i and 13k-s. Variation of the "right-amide" of 13a led to the urea 19a and the carbamates 23 and 27a which proved to be equally active as DSG in our GVHD model. Finally 27a was found to be the most potent derivative, being slightly more active than DSG in a heart allotransplantation model in rats. Due to the absence of chiral center in its structure and to its improved chemical stability compared to DSG, 27a was selected as a candidate for clinical evaluation.

  DOI：

  10.1021/jm980431g
• 作为产物：
  描述：

  碳酸二叔丁酯 在 sodium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 O,O'-Di(tert-butyl)-N-<4-(mesyloxy)butyl>-N,N'-(propan-1,3-diyl)bis
  参考文献：
  名称：

  合成冯Ñ 1，4-二（p -cumaroyl）精胺，einemmöglichenBiogenese-Vorläufer冯Aphelandrin †

  摘要：

  的合成Ñ 1，4-二（p -coiimaroyl）精胺，Aphelandrine的可能的生物遗传前体

  DOI：

  10.1002/hlca.19910740322

文献信息

• The synthesis of deuterium-labeled spermine, N1-acetyl-spermine and N1-acetylspermidine
  作者：Vijay Gawandi、Paul F. Fitzpatrick

  DOI：10.1002/jlcr.1381

  日期：2007.6

  The synthesis of deuterium-labeled spermine, N1-acetylspermine and N1-acetylspermidine is reported. 1,1,3,3-2H4-N1-Acetylspermine hydrochloride, 1,1,3,3-2H4-N1-acetylspermidine hydrochloride and 1,1,3,3,10,10,12,12-2H8-spermine dihydrochloride were obtained in seven, four and three steps, respectively. All the syntheses were carried out by simple protection and deprotection steps from commonly used selective protecting reagents. These deuterium-labeled compounds can be used as mechanistic probes of polyamine oxidizing enzymes. Copyright © 2007 John Wiley & Sons, Ltd.

  报道了氘标记的精胺、N1-乙酰精胺和N1-乙酰精胺的合成。分别通过七步、四步和三步反应获得了1,1,3,3-2H4-N1-乙酰精胺盐酸盐、1,1,3,3-2H4-N1-乙酰精胺盐酸盐和1,1,3,3,10,10,12,12-2H8-精胺二盐酸盐。所有合成均通过从常用选择性保护试剂进行简单的保护和去保护步骤完成。这些氘标记化合物可用作聚胺氧化酶的机制探针。版权所有 © 2007 John Wiley & Sons, Ltd.
• Synthesis and Cytotoxic Activity of Polyamine Analogues of Camptothecin
  作者：Sabrina Dallavalle、Giuseppe Giannini、Domenico Alloatti、Andrea Casati、Elena Marastoni、Loana Musso、Lucio Merlini、Gabriella Morini、Sergio Penco、Claudio Pisano、Stella Tinelli、Michelandrea De Cesare、Giovanni Luca Beretta、Franco Zunino

  DOI：10.1021/jm060285b

  日期：2006.8.1

  A number of derivatives of camptothecin with a polyamine chain linked to position 7 of camptothecin via an amino, imino, or oxyiminomethyl group were synthesized and tested for their biological activity. All compounds showed marked growth inhibitory activity against the H460 human lung carcinoma cell line. In particular, the iminomethyl derivatives where the amino groups of the chain were protected with Boc groups exhibited a high potency, with IC50 values of similar to 10(-8) M. The pattern of DNA cleavage in vitro and the persistence of the cleavable ternary complex drug-DNA-topoisomerase I observed with polyamine conjugates containing free amino groups support a contribution of specific drug interaction with DNA as a determinant of activity. Modeling of compound 7c in the complex with topoisomerase 1 and DNA is consistent with this hypothesis. The lack of a specific correlation between stabilization of the cleavable complex and growth inhibition likely reflects multiple factors including the cellular pharmacokinetic behavior related to the variable lipophilicity of the conjugate, and the nature and linkage of the polyamine moiety.
• Synthesis of an azido spermidine equivalent
  作者：Alexander L. Weis、Tamas Bakos、Ivan Alferiev、Xuehai Zhang、Bin Shao、William A. Kinney

  DOI：10.1016/s0040-4039(99)00896-5

  日期：1999.6

  The synthesis and conversion of a new spermidine equivalent (2) to squalamine is reported. It is prepared in a practical manner, is stable to sodium borohydride reduction, is converted to spermidine under mild conditions, and is not prone to internal cyclization reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.