4-amino-1-(2-hydroxyethyl)pyrimidin-2-one | 22441-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-amino-1-(2-hydroxyethyl)pyrimidin-2-one
• 英文别名: 1-(2-Hydroxyethyl)cytosine；4-amino-1-(2-hydroxy-ethyl)-1H-pyrimidin-2-one；1-(2-hydroxyethyl)-4-amino-2-1H-pyrimidinone；1-(2-Hydroxyaethyl)cytosin；1-(2-Hydroxyethyl)-cytosin；1-(2-hydroxyethyl)cytosin
• CAS: 22441-50-5
• 化学式: C₆H₉N₃O₂
• 分子量: 155.156
• InChiKey: ATQNWDREMOIFSG-UHFFFAOYSA-N

物化性质

• 熔点：
  228-229 °C
• 沸点：
  343.9±44.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-amino-1-(2-hydroxyethyl)pyrimidin-2-one 在 氯化亚砜 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 生成 1-(2-diallylaminoethyl)cytosine
  参考文献：
  名称：

  Two simple protocols for the preparation of diallylaminoethyl-substituted nucleic bases: a comparison

  摘要：

  The syntheses of pyrimidine and purine nucleic bases substituted with diallylaminoethyl groups are reported following two different protocols. A comparison is made between the yield, expense, and difficulty of each route. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.035
• 作为产物：
  描述：

  胞嘧啶 生成 4-amino-1-(2-hydroxyethyl)pyrimidin-2-one
  参考文献：
  名称：

  Macrolides with antibacterial activity

  摘要：

  该发明提供了具有改进生物性能和改进稳定性的新大环内酯类抗生素的公式(I)：其中R1为氢、氰基、—S(L)mR2、—S(O)(L)mR2或—S(O)2(L)mR2；L代表—(CH2)n—或—(CH2)nZ(CH2)n′—；m为0或1；n为1、2、3或4；n′为0、1、2、3或4；Z为O、S或NH；R2为氢、烷基、杂环烷基或芳基；其中杂环烷基和芳基基团可能进一步取代；*表示手性中心，为(R)或(S)形式，以及其药学上可接受的酸盐或体内可水解酯。

  公开号：

  US20030199459A1

文献信息

• Synthesis of L-Dioxolane Nucleosides and Related Chemistry
  作者：Chengyi Liang、Doo Won Lee、M. Gary Newton、Chung K. Chu

  DOI：10.1021/jo00111a012

  日期：1995.3

  (+)-L- or (+)-(2R,4S)-1-[4-(hydroxymethyl)-1,3-dioxolan-2-yl]-5-fluorouracil (25) and other novel classes of 1,3-dioxolane nucleosides have been synthesized. Coupling of 2-methoxy-4-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-dioxolane (23) or 2-methyl-1,3-dioxolane (9) with silylated g-fluorouracil, thymine, cytosine, and 5-chlorocytosine in the presence of TMSOTf gave the corresponding 1,3-dioxolane nucleosides. These nucleosides were decomposed and rearranged to the ring-opened products in certain reaction conditions. It was found that 5-fluorouricil nucleosides (12 and 25) were relatively more stable than the thymine or cytosine derivatives (10, 13, and 16). Bulky protecting group (TBDPS) at the 1,3-dioxolane moiety in compound 24 may also contribute the stability to the 1,3-dioxolane nucleosides. The structures of these novel 1,3-dioxolane nucleosides and ring-opened products have been assigned by NMR spectra, and the mechanisms of decomposition and rearrangement to the ring opened products were discussed.

  (+)-L-或(+)-(2R,4S)-1-[4-(羟甲基)-1,3-二氧戊环-2-基]-5-氟尿嘧啶（25）和其他新型1,3-二氧戊环核苷已被合成。2-甲氧基-4-[[(叔丁基二苯基硅基)氧基]甲基]-1,3-二氧戊环（23）或2-甲基-1,3-二氧戊环（9）与硅化的α-氟尿嘧啶、胸腺嘧啶、胞嘧啶和5-氯胞嘧啶在TMSOTf的存在下偶联，得到相应的1,3-二氧戊环核苷。这些核苷在某些反应条件下分解并重排为开环产物。发现5-氟尿嘧啶核苷（12和25）比胸腺嘧啶或胞嘧啶衍生物（10、13和16）相对更稳定。化合物24中1,3-二氧戊环部分的庞大保护基团（TBDPS）也可能为1,3-二氧戊环核苷的稳定性做出贡献。这些新型1,3-二氧戊环核苷和开环产物的结构已通过NMR光谱确定，并讨论了分解和重排到开环产物的机制。
• Synthesis and binding properties of monomeric and dimeric guanine and cytosine amine derivatives
  作者：Jonathan L. Sessler、Darren Magda、Hiroyuki Furuta

  DOI：10.1021/jo00029a008

  日期：1992.1

  The syntheses of the N-protected forms of the cytosine homodimer 1, the guanine cytosine heterodimer 2, and the guanine homodimer 3 are described. Derivatization of these dimers, as well as the protected monomers corresponding to 4 and 5, with omega-methoxypoly(ethylene glycol)-alpha-carboxylic acid 26 and subsequent deprotection formed the amides 29, 31, 33, 35, and 37. The binding properties of these solubilized compounds in DMSO-d(g) were examined using H-1 NMR.
• SESSLER, JONATHAN L.;MAGDA, DARREN;HUGDAHL, JEFF, J. NUCL. PHENOM., 7,(1989) N, C. 19-26
  作者：SESSLER, JONATHAN L.、MAGDA, DARREN、HUGDAHL, JEFF

  DOI：——

  日期：——
• USE OF MUTANT ALKYLTRANSFERASES FOR GENE THERAPY TO PROTECT FROM TOXICITY OF THERAPEUTIC ALKYLATING AGENTS
  申请人：THE PENN STATE RESEARCH FOUNDATION

  公开号：EP0910246B1

  公开（公告）日：2010-08-18
• NEW MACROLIDES WITH ANTIBACTERIAL ACTIVITY
  申请人：Basilea Pharmaceutica AG

  公开号：EP1313751A1

  公开（公告）日：2003-05-28