di-Boc-homoagmatine | 132502-77-3

• 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: di-Boc-homoagmatine
• 英文别名: N,N'-bis-Boc-N''-(5-aminopentyl)guanidine；tert-butyl N-[N'-(5-aminopentyl)-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• CAS: 132502-77-3
• 化学式: C₁₆H₃₂N₄O₄
• 分子量: 344.454
• InChiKey: BUYKGDWHJJZUHK-UHFFFAOYSA-N

物化性质

• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  di-Boc-homoagmatine 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl N-[(5S)-5-amino-6-[[(2S)-1-[5-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]pentylamino]-6-[(2-methylpropan-2-yl)oxycarbonylamino]-1-oxohexan-2-yl]amino]-6-oxohexyl]carbamate
  参考文献：
  名称：

  西尼罗河病毒NS2B / NS3丝氨酸蛋白酶的新型胍丁胺和类胍胺肽模拟物抑制剂

  摘要：

  该信息通报了西尼罗河病毒NS2B / NS3蛋白酶的新型非共价拟肽抑制剂的合成和抑制活性，该抑制剂含有脱羧化的P1精氨酸（胍丁胺； 4-氨基丁基胍）和相关类似物。一种胍丁胺肽模拟物（4-苯基-苯乙酰基-Lys-Lys-胍丁胺;化合物2）显示为竞争性抑制剂，结合亲和力为K i 2.05±0.13μM，对凝血酶没有活性（IC 50 > 100μM）。我们的结果表明，与含反应性亲电战斗部的抑制剂相比，由于它们的相对稳定性和化学合成的简便性，在P1位置具有胍丁胺的拟肽可能被用作设计非共价竞争性蛋白酶抑制剂的起始工具。

  DOI：

  10.1016/j.ejmech.2011.04.055
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 di-Boc-homoagmatine
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Minalemine A, a Guanidine Peptide from the Marine Tunicate Didemnum rodriguesi

  摘要：

  The total synthesis of the 3S,2S and 3R,2S diastereomers (1a and 1b) of minalemine A and the identification of the natural compound as the 3R,2S isomer is described. The key step in the synthesis is the preparation of the two enantiomers of the beta -amino diacid 3-(N-carboxymethyl)-aminodecanoic acid (Ncma), which were obtained by stereoselective alkylation with allyl bromide of two nonanoic acid imides bearing chiral oxazolidinones as chiral auxiliaries. Natural minalemine A shows identical (1)H NMR and very similar (13)C NMR spectra compared to the two synthetic diastereomers. Sufficient differences in their chromatographic behavior to allow conclusive identification were not found. However, the corresponding N-2-naphthoyl amides presented quite distinct circular dichroism spectra (CD), and these confirmed the 3R,2S configuration for the natural minalemines and the R configuration for the constituent beta -amino diacid, Ncma.

  DOI：

  10.1021/jo010076t

文献信息

• Preparation of l-proline based aeruginosin 298-A analogs: Optimization of the P1-moiety
  作者：Guijun Wang、Navneet Goyal、Branden Hopkinson

  DOI：10.1016/j.bmcl.2009.04.056

  日期：2009.7

  residue. The structure optimization was focused on modification of the P1 position. In choosing the P1 group, an effort was made to avoid using the highly basic guanidine groups present in nearly all naturally occurring aeruginosins. The synthesis and enzyme assays of these aeruginosin analogs against thrombin and trypsin are reported. We found that several compounds with neutral P1 groups exhibit excellent

  铜绿素是一族天然的寡肽，具有共同的双环氨基酸核心结构。该家族中的许多化合物都是丝氨酸蛋白酶的抑制剂，例如凝血酶和胰蛋白酶。凝血酶是凝血级联反应中的重要酶，并且是抗凝药物开发的有希望的靶标。为了了解结构-活性关系（SAR）并找到选择性的凝血酶抑制剂，我们合成了一系列铜绿菌素298-A类似物，其中P 2双环氨基酸被1-脯氨酸残基取代。结构优化的重点是修改P 1位置。在选择P 1时为了避免这种情况，人们努力避免使用几乎所有天然存在的铜绿素酶中都存在的高碱性胍基。报道了这些铜绿素类似物针对凝血酶和胰蛋白酶的合成和酶测定。我们发现几种具有中性P 1基团的化合物相对于胰蛋白酶表现出优异的选择性，并且对凝血酶具有良好的效力。此处获得的P 1基团的SAR数据可用于制备对胰蛋白酶具有更好选择性的其他凝血酶抑制剂。
• Macrocyclization of Di-Boc-guanidino-alkylamines Related to Guazatine Components: Discovery and Synthesis of Innovative Macrocyclic Amidinoureas
  作者：Daniele Castagnolo、Francesco Raffi、Gianluca Giorgi、Maurizio Botta

  DOI：10.1002/ejoc.200801109

  日期：2009.1

  The synthesis of new and innovative macrocyclic amidinoureas from linear di-Boc-guanidino-alkylamines related to guazatine was accomplished. The macrocyclization reaction proceeds under mild conditions affording 11- to 16-membered rings with a new and previously undescribed structure in good yields. Enantiomerically pure macrocyclic amidinoureas were also synthesised. The strict correlation between

  完成了从与 guazatine 相关的线性二-Boc-胍基-烷基胺合成新的和创新的大环脒基脲。大环化反应在温和条件下进行，以良好的产率提供具有新的和以前未描述的结构的 11 至 16 元环。还合成了对映体纯的大环脒基脲。从生物学的角度来看，大环脒基脲和天然产物瓜扎汀之间的严格相关性也使它们非常具有活性。
• Concise total synthesis of phidianidine A and B
  作者：Jacob C. Buchanan、Brandon P. Petersen、Stephen Chamberland

  DOI：10.1016/j.tetlet.2013.08.063

  日期：2013.11

  total synthesis of cytotoxic indole alkaloids phidianidine A and B is described. Rapid assembly of the 1,2,4-oxadiazole core from a novel N-hydroxyguanidine and the corresponding indole-3-acetic acid chloride led to formal syntheses of phidianidine A and B in only three steps from known compounds. Deprotection under standard conditions provided the trifluoroacetate salts of phidianidine A and B in quantitative

  描述了最短的细胞毒性吲哚生物碱phidianidine A和B的总合成。由新颖的N-羟基胍和相应的吲哚-3-乙酸氯迅速组装成1,2,4-恶二唑核，仅需三步即可从已知化合物中正式合成phidianidine A和B。在标准条件下进行脱保护，以定量收率得到phidianidine A和B的三氟乙酸盐。
• Novel Hypotensive Agents from <i>Verbesina </i><i>c</i><i>aracasana</i>. 8. Synthesis and Pharmacology of (3,4-Dimethoxycinnamoyl)-<i>N</i>-agmatine and Synthetic Analogues¹
  作者：Marco Carmignani、Anna Rita Volpe、Bruno Botta、Romulo Espinal、Stella C. De Bonnevaux、Carlo De Luca、Maurizio Botta、Federico Corelli、Andrea Tafi、Rosario Sacco、Giuliano Delle Monache

  DOI：10.1021/jm001017v

  日期：2001.8.1

  The more polar metabolites from the Venezuelan plant Verbesina caracasana, i.e., N(3)-prenylagmatine, (3,4-dimethoxycinnamoyl)-N(1)-agmatine, agmatine, and galegine (prenylguanidine), previously reported (Delle Monache, G.; et al. BioMed. Chem. Lett. 1999, 9, 3249-3254), have been synthesized following a biosynthetic strategy. The pharmacologic profiles of various synthetic analogues of (3,4-dimetho

  来自委内瑞拉植物Verbesina caracasana的极性更强的代谢物，即以前报道的N（3）-prenylagmatine，（3,4-dimethoxycinnamoyl）-N（1）-胍丁胺，胍丁胺和半胱氨酸（异戊二烯胍） ；等； BioMed.Chem.Lett.1999，9，3249-3254）是按照生物合成策略合成的。还分析了（3,4-dimethoxycinnamoyl）-N（1）-胍丁胺（G5）的各种合成类似物的药理特性，以阐明这些化合物的构效关系。发现具有（E）-构型和/或具有对甲氧基苯甲酰基部分的衍生物可引起较高的降压作用，这与心脏正性肌力的轻微增加（在某些情况下与剂量无关）相关，且变化很大。并没有明显的计时反应，仅在较高剂量时，具有呼吸抑制作用。（E）-G5的烷基链中亚甲基数的增加（增加到6个）或减少（减少到2个）都没有改变血压反应，而正性正性变力反应却略有增加。在药理
• The Synthesis and Glycosidase Inhibitory Activity of Analogues of Tiruchanduramine
  作者：Patrick J. Murphy、Zackary J. R. Ashworth、Barbara Bartholomew、Daniel M. Evans、Josephine Forde-Thomas、Karl F. Hoffmann、Reece Murdoch、Robert J. Nash、Hazel Sharp、Helen Whiteland

  DOI：10.3987/com-20-14236

  日期：——

  Five analogues (7a-e) of the metabolite tiruchanduramine 1 were prepared. Compounds 7d and 7e were specific inhibitors of yeast alpha-glucosidase, whilst 7e specifically inhibited Bacillus alpha-glucosidase. Compounds 7b and 7c were the best inhibitors of beta-glucosidase. All 5 compounds inhibited beta-galactosidase, but once again 7e was the best inhibitor. It was apparent that different chain lengths in the compounds 7a-e affect the degree of inhibition. Some of the synthetic analogues show significantly improved inhibition of alpha-glucosidases when compared to tiruchanduramine 1 and also improved specificity.