(4-hydroxybutyl)<<3-(1,1-dimethylethoxy)carbonylamino>propyl>carbamic acid, 1,1-dimethylethyl ester | 134935-52-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4-hydroxybutyl)<<3-(1,1-dimethylethoxy)carbonylamino>propyl>carbamic acid, 1,1-dimethylethyl ester
• 英文别名: O,O'-Di(tert-butyl)-N-(4-hydroxybutyl)-N,N'-(propan-1,3-diyl)bis；N,N'-bis(tert-butoxycarbonyl)-N-(4-hydroxybutyl)-1,3-diaminopropane；N-di-Boc-spermidine-ol；O,O'-Di(tert-butyl)-N-(4-hydroxybutyl)-N,N'-(propan-1,3-diyl)bis[carbamat]；[3-[[(1,1-Dimethyl-ethoxy)carbonyl]amino]propyl](4-hydroxybutyl)carbamic acid, 1,1-dimethylethyl ester；tert-butyl N-(4-hydroxybutyl)-N-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]carbamate
• CAS: 134935-52-7
• 化学式: C₁₇H₃₄N₂O₅
• 分子量: 346.467
• InChiKey: SOGPMEFVPZBOFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-hydroxybutyl)<<3-(1,1-dimethylethoxy)carbonylamino>propyl>carbamic acid, 1,1-dimethylethyl ester 在 ammonium hydroxide 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 48.17h， 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：

  N-(cyanoethyl)-4-aminobutanol 在 platinum(IV) oxide 盐酸 、 氢气 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 22.0 ℃ 、344.73 kPa 条件下， 反应 21.0h， 生成 (4-hydroxybutyl)<<3-(1,1-dimethylethoxy)carbonylamino>propyl>carbamic acid, 1,1-dimethylethyl ester
  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.
• Effect of spermine-derived AGEs on oxidative stress and polyamine metabolism
  作者：Ayumi Tsutsui、Ambara R. Pradipta、Shinobu Kitazume、Naoyuki Taniguchi、Katsunori Tanaka

  DOI：10.1039/c7ob01346a

  日期：——

  lysine dimer (MOLD). As a means to investigate and probe the ROS production pathways of AGEs, low molecular weight compounds carboxyethyl spermine (CES) and methylglyoxal-derived spermine dimer (MOSD) were synthesized, which replace lysine with another highly nucleophilic biological amine, spermine (SPM). Contrary to expectations, results show CES- and MOSD-induced oxidative stress proceeds through different

  蛋白质和碳水化合物之间的非酶糖基化（例如高级糖基化终产物（AGEs））是天然化合物，与衰老和许多退行性疾病有关。甲基乙二醛（MG）是AGE生物合成途径的中间产物，已知会与蛋白质的伯胺反应产生广泛的AGE修饰，例如羧乙基赖氨酸（CEL）和甲基乙二醛衍生的赖氨酸二聚体（MOLD） 。为了研究和探究AGEs的ROS生成途径，合成了低分子量化合物羧乙基精胺（CES）和甲基乙二醛衍生的精胺二聚体（MOSD），它们用另一种高度亲核的生物胺精胺（SPM）取代了赖氨酸。与预期相反，结果表明CES和MOSD诱导的氧化应激通过不同途径进行。
• 15-deoxyspergualin analogs, their method of preparation and their use in
  申请人：Fournier Industrie et Sante

  公开号：US05733928A1

  公开（公告）日：1998-03-31

  The present invention relates to a novel compound selected from the group consisting of: (i) the compounds of the formula ##STR1## in which: A is a group --CO--NH-- or a group --NH--CO--, R is a hydrogen atom or a methyl group, and *C, if R is not the hydrogen atom, is an asymmetric carbon of (R,S) or (R) configuration; and (ii) their addition salts. It further relates to the method of preparing this compound and to its use in therapeutics.

  本发明涉及一种新型化合物，所述化合物选自以下组中的一种：(i) 公式##STR1##中的化合物，其中：A是--CO--NH--基团或--NH--CO--基团，R是氢原子或甲基基团，如果R不是氢原子，则*C是(R,S)或(R)构型的不对称碳；以及(ii)它们的加合盐。它还涉及制备该化合物的方法以及其在治疗中的用途。
• Polyamine-Vectored Iron Chelators:  The Role of Charge
  作者：Raymond J. Bergeron、Neelam Bharti、Jan Wiegand、James S. McManis、Hua Yao、Laszlo Prokai

  DOI：10.1021/jm048974f

  日期：2005.6.1

  The utility of polyamines as vectors for the intracellular transport of iron chelators is further described. Consistent with earlier results with polyamine analogues, these studies underscore the importance of charge in the design of polyamine-vectored chelators. Four polyamine conjugates are synthesized, two of tereplithalic acid [N-1-(4-carboxy)benzoylspermine (7) and its methyl ester (6)] and two of (S)-2-(2,4-dihydroxyphenyl)-4,5-dihydro-4-methyl-4-thiazolecarboxylic acid [(S)-4'-(HO)-DADFT] [(S)-4,5-dihydro-2-[2-hydroxy-4-(12-amino-5,9-diazadodecyloxy)phenyl]-4-methyl-4-thiazolecarboxylic acid (10) and its ethyl ester (9)]. These four molecules were evaluated in murine leukemia L1210 cells for their impact on cell proliferation (48- and 96-h IC50 values), their ability to compete with spermidine for the polyamine transport apparatus (K-i), and their intracellular accumulation. The data revealed that when neutral molecules (cargo fragments) were fixed to the polyamine vector, the conjugates competed well with spermidine for transport and were accumulated intracellularly to millimolar levels. However, this was not the case when the cargo fragments were negatively charged. Metabolic studies of the polyamine-vectored (S)-4'-(HO)-DADFTs in rodents indicated that not only did the expected deaminopropylation step occur, but also a surprisingly high level of oxidative deamination at the terminal primary nitrogens took place. Finally, the iron-clearing efficiency of the (S)-4'-(HO)-DADFT conjugates was determined in a bile-duct-cannulated rodent model. Attaching the ligand to a polyamine vector had a profound effect on increasing the iron-clearing efficiency of this chelator relative to its parent drug.
• 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.