1-(2-氨基乙基)-5-甲基嘧啶-2,4-二酮 | 34386-77-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-(2-氨基乙基)-5-甲基嘧啶-2,4-二酮
• 英文名称: N¹-(2-aminoethyl)thymine
• 英文别名: N-1-(2-aminoethyl)thymine；1-(2-aminoethyl)thymine；1-(2-amino-ethyl)-5-methyl-1H-pyrimidine-2,4-dione；1-(2-Aminoethyl)thymin；1-(2-aminoethyl)-5-methylpyrimidine-2,4-dione
• CAS: 34386-77-1
• 化学式: C₇H₁₁N₃O₂
• 分子量: 169.183
• InChiKey: VPONEJHNADKWPX-UHFFFAOYSA-N

物化性质

• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-氨基乙基)-5-甲基嘧啶-2,4-二酮 在 sodium carbonate 作用下， 反应 46.0h， 生成 N-[2-(Carbamoylmethyl-carbamoyl)-ethyl]-N-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-ethyl]-3-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-ethylamino]-propionamide
  参考文献：
  名称：

  Synthesis of nucleobase-functionalized β-peptoids and β-peptoid hybrids

  摘要：

  The solid-phase synthesis of a new class of nucleobase-modified peptide-mimetic oligomers is described. beta-Peptoids and P-peptoid hybrids bearing thymine on the side chain are prepared from N-Fmoc-N-[2-(thymin-l-yl)ethyl]-beta-alanine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.057
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 palladium on activated charcoal 叠氮基三甲基硅烷 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 245.5h， 生成 1-(2-氨基乙基)-5-甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  Alkylation of thymine with 1,2-dibromoethane

  摘要：

  Alkylation of thymine with 1,2-dibromoethane depends strongly on the reaction conditions. Various alkyl derivatives may be produced, including N-1- or N-5-monosubstituted alkylthymines and products of their cyclisation, as well higher molecular weight products resulting from intermolecular substitution of N-1- and N-3-mono- and N-1,N-3-dialkylthymines. We have identified two cyclic products 5 and 6 and the dialkylated derivative 7, for which detailed structural analyses have been performed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00277-0

文献信息

• Creation of polynucleotide-assisted molecular assemblies in organic solvents: general strategy toward the creation of artificial DNA-like nanoarchitectures
  作者：Munenori Numata、Kazunori Sugiyasu、Takanori Kishida、Shuichi Haraguchi、Norifumi Fujita、Sun Min Park、Young Ji Yun、Byeang Hyean Kim、Seiji Shinkai

  DOI：10.1039/b713354e

  日期：——

  complementary template for the gelator molecules to create the fibrous composites. Based on these findings, we can conclude that self-assembling modes and gelation properties of nucleobase-appended organogelators are controllable by the addition of their complementary polynucleotide in organic solvents. We believe, therefore, that the present system can open the new paths to accelerate development

  研究了添加的多核苷酸对核碱基附加的有机胶凝剂胶凝能力的影响。追加尿嘧啶的胆固醇胶凝剂在极性有机溶剂（例如正丁醇）中形成稳定的有机凝胶。已经发现，补充的聚腺苷酸（poly（A））的添加不仅稳定了凝胶，而且还在原始凝胶相中产生了螺旋结构。附加胸腺嘧啶和胸腺嘧啶的胶凝剂可以在非极性溶剂（例如苯）中形成稳定的凝胶，其中聚（A）-脂质复合物可以充当胶凝剂分子的互补模板，从而形成纤维复合材料。基于这些发现，我们可以得出结论，通过在有机溶剂中添加互补的多核苷酸，可以控制核碱基附加的有机胶凝剂的自组装模式和胶凝特性。我们相信，
• Pore formation in phospholipid bilayers by amphiphilic cavitands
  作者：Iman Elidrisi、Saeedeh Negin、Pralav V. Bhatt、Thavendran Govender、Hendrick G. Kruger、George W. Gokel、Glenn E. M. Maguire

  DOI：10.1039/c0ob01236j

  日期：——

  Five new cavitands were prepared that have four pendant n-undecyl chains and “headgroups” connected by 2-carbon spacers. The headgroups were ∼OCH2CONH-Ala-OCH3, 1; ∼OCH2CONH-Phe-OCH3, 2; ∼OCH2CONH-Ala-OH, 3; ∼OCH2CONH-Phe-OH, 4; and ∼OCH2CONHCH2CH2-thyminyl, 5. Pore formation by each cavitand was studied by use of the planar bilayer conductance experiment. All five compounds were found to form pores in asolectin bialyer membranes. Compounds 1–3 behaved in a generally similar fashion and exhibited open-close dynamics. Compounds 4 and 5 formed pores more rapidly, were more dynamic, and led more quickly to membrane rupture. Differences in the ion transport activity are rationalized in terms of structure and aggregate cavitand assemblies.

  制备了五种新的腔体分子，这些腔体分子具有四个悬挂的正十一烷链和由两个碳间隔相连的“头部”。头部的结构分别为∼OCH2CONH-Ala-OCH3（1）；∼OCH2CONH-Phe-OCH3（2）；∼OCH2CONH-Ala-OH（3）；∼OCH2CONH-Phe-OH（4）；和∼OCH2CONHCH2CH2-胸苷基（5）。通过平面双层电导实验研究了每个腔体分子的孔形成。发现所有五种化合物均能在asolectin双层膜中形成孔。化合物1-3的行为一般相似，并显示出开闭动态。化合物4和5形成孔的速度更快，更具动态性，并且更快导致膜破裂。离子传输活性的差异可以从结构和聚集腔体分子组装的角度进行解释。
• Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility
  作者：Dan Yuan、Xuewen Du、Junfeng Shi、Ning Zhou、Abdulgader Ahmed Baoum、Bing Xu

  DOI：10.3762/bjoc.10.250

  日期：——

  This article reports the synthesis of a novel type of conjugate of three fundamental biological build blocks (i.e., saccharide, amino acids, and nucleobase) and their cell compatibility. The facile synthesis starts with the synthesis of nucleobase and saccharide derivatives, then uses solid-phase peptide synthesis (SPPS) to build the peptide segment (Phe-Arg-Gly-Asp or naphthAla-Phe-Arg-Gly-Asp with

  本文报道了三种基本生物构件（即糖、氨基酸和核碱基）的新型缀合物的合成及其细胞相容性。简便的合成从核碱基和糖衍生物的合成开始，然后使用固相肽合成 (SPPS) 构建具有完全保护基团的肽片段（Phe-Arg-Gly-Asp 或 naphthAla-Phe-Arg-Gly-Asp） ），然后，液相中的酰胺化反应将这三个部分连接在一起。这些多步合成的总产率约为34%。除了表现出优异的溶解性外，这些糖-氨基酸-核碱基（SAN）的缀合物，就像之前报道的核碱基-氨基酸-糖（NAS）和核碱基-糖-氨基酸（NSA）的缀合物一样，与哺乳动物细胞相容。
• Exploring hydrogen bonding and weak aromatic interactions induced assembly of adenine and thymine functionalised naphthalenediimides
  作者：Nagarjun Narayanaswamy、M. B. Avinash、T. Govindaraju

  DOI：10.1039/c3nj00060e

  日期：——

  Adenine and thymine functionalised naphthalenediimide (NDI) conjugates and complementary peptide nucleic acid (PNA) dimers are designed to exploit complementary hydrogen bonding and aromatic interactions for controllable molecular organization. These nucleobase appended NDIs organized into well-defined fibers, nanoribbons, porous spheres, belts and petal-like 2D sheets.

  腺嘌呤和胸腺嘧啶官能化萘二亚胺（NDI）共轭物和互补肽核酸（PNA）二聚体旨在利用互补氢键和芳香族相互作用实现可控的分子组织。这些附加核碱基的 NDI 组织成了定义明确的纤维、纳米带、多孔球、带状和花瓣状二维薄片。
• Bis(hydroxymethyl)phosphinic acid analogues of acyclic nucleosides; synthesis and incorporation into short DNA oligomers
  作者：B Nawrot、O Michalak、M Nowak、A Okruszek、M Dera、W.J Stec

  DOI：10.1016/s0040-4039(02)01067-5

  日期：2002.7

  nucleosides based on a bis(hydroxymethyl)phosphinic acid (BHPA) backbone were obtained by condensation of the bis(4,4′-dimethoxytrityl) derivative of BHPA with N-1- or N-3-(2-hydroxyethyl)thymine in the presence of MSNT, or by an Appel reaction with N-1- or N-3-(2-aminoethyl)thymine. After selective deprotection and phosphitylation they were used as monomers for automated solid support synthesis of short oligomers

  通过将BHPA的双（4,4'-二甲氧基三苯甲基）衍生物与N -1-或N -3-（2-羟乙基）缩合获得基于双（羟甲基）次膦酸（BHPA）骨架的无环核苷的新类似物。胸腺嘧啶在MSNT的存在下，或与N -1-或N -3-（2-氨基乙基）胸腺嘧啶的Appel反应。选择性脱保护和磷酸化后，它们被用作亚磷酰胺方法自动合成短寡聚物的固体支持物的单体。