6-氨基-1,3-二甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-5-甲醛 | 54660-80-9

• 物质功能分类: 有机原料 - 有机膦化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-氨基-1,3-二甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-5-甲醛
• 中文别名: 6-氨基-1,3-二甲基-2,4-二羰基-1,2,3,4-四氢嘧啶-5-甲醛
• 英文名称: 6-amino-1,3-dimethyl-5-formyluracil
• 英文别名: 6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde；6-amino-5-formyl-1,3-dimethypyrimidine-2,4(1H,3H)-dione；1,3-dimethyl-6-amino-5-formyl uracil；6-amino-5-formyl-1,3-dimethyluracil；6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde；6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-carbaldehyd；4-amino-1,3-dimethyl-2,6-dioxopyrimidine-5-carbaldehyde
• CAS: 54660-80-9
• 化学式: C₇H₉N₃O₃
• mdl: MFCD00091834
• 分子量: 183.167
• InChiKey: LGXGZORRPBTMAO-UHFFFAOYSA-N

物化性质

• 熔点：
  191-192 °C(Solv: ethanol (64-17-5))
• 沸点：
  370.9±52.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• 海关编码：
  2933599090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  6-氨基-1,3-二甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-5-甲醛 在 sodium ethanolate 作用下， 生成 7-氨基-1,3-二甲基-2,4-二羰基-1,2,3,4-四氢吡啶并[2,3-d]嘧啶-6-甲腈
  参考文献：
  名称：

  Synthesis and pharmacology of pyrido[2,3-d]pyrimidinediones bearing polar substituents as adenosine receptor antagonists

  摘要：

  Amino-substituted pyrido[2,3-d]pyrimidinediones have previously been found to bind to adenosine A(1) and A(2A) receptors in micromolar concentrations. The present study was aimed at studying the structure-activity relationships of this class of compounds in more detail. Most of the investigated compounds were provided with polar substituents. such as ethoxycarbonyl groups and basic amino functions, in order to improve their water-solubility. The compounds were synthesized starting from 6-amino-1,3-dimethyfuracil via different reaction sequences involving (cyano)acetylation, Vilsmeier formylation, or reaction with diethyl ethoxymethylemalonate (EMME). The most potent and selective compound of the present series was 6-carbethoxy-1,2,3,4-tetrahydro-1.3-dimethyl-5-(2-naphthylmethyl) aminopyrido[2,3-d]pyrimidine-2,4-dione (11c) with a K-i value of 5 nM at rat and 25 nM at human A, receptors. The compound was more than 60-fold selective versus A(3) and more than 300-fold selective versus A2A receptors. It showed all over 300-fold improvement with respect to the lead compound. In GTP gamma S binding studies at membranes of Chinese hamster ovary cells recombinantly expressing the human adenosine A, receptor, 11c behaved as an antagonist with inverse agonistic activity. A regioisomer of 11c, 6-carbethoxy-1,2,3,4-tetrahydro-1,3-dimethyl-7-(2-naphthylmethyl)aminopyrido[2,3-d]pyrimidine-2,4-dione (7a) in which the 2-naphthylmethylamino substituent at position 5 of 11c was moved to the 7-position, was a relatively potent (K-i = 226 nM) and selective (> 20-fold) A(3) ligand. In the series of compounds lacking an electron-withdrawing ethoxycarbonyl or cyano substituent in the 6-position, compounds with high affinity for adenosine A(2A) receptors were identified. Such as 1,2,3,4-tetrahydro-1,3-dimethyl-5-(1-naphthyl)aminopyrido[2,3-d]pyrimidine-2,4-dioile 16b (K-i human A(2A) = 81.3 nM, K-i human A(1) = 153 nM, and K-i human A(3) > 10,000 nM). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.008
• 作为产物：
  描述：

  1,3-二甲基-5-氰基尿嘧啶 在 sodium hydroxide 作用下， 反应 7.0h， 以58%的产率得到6-氨基-1,3-二甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-5-甲醛
  参考文献：
  名称：

  Rearrangement of 5-Cyanouracils into 6-aminouracils by reaction with amines and hydroxide ion.

  摘要：

  用氨和烷基胺处理 5-氰基-1-苯基脲嘧啶衍生物 (1)，通过涉及开环和闭环过程的重排得到 6-氨基-5-亚氨基甲基脲嘧啶 (2)。当 3-未取代的 5-氰基-1-苯基脲嘧啶（1d）与氨和甲胺反应时，分离出开环产物 3-丙烯酰基-1-苯基脲（5a 和 5b），并很容易地再生成 6-氨基脲嘧啶（2j 和 2k）。用氢氧化钠代替胺进行类似的重排，得到 6-氨基-5-甲酰基尿嘧啶（7a-c）。

  DOI：

  10.1248/cpb.37.2008

文献信息

• A combined experimental and DFT investigation on the structure and CO-releasing properties of mono and binuclear fac-Re^I(CO)₃complexes with 5-pyridin-2-ylmethylene-amino uracils
  作者：Sonia B. Jiménez-Pulido、Nuria A. Illán-Cabeza、Francisco Hueso-Ureña、Carmen R. Maldonado、Purificación Sánchez-Sánchez、M. Paz Fernández-Liencres、Manuel Fernández-Gómez、Miguel N. Moreno-Carretero

  DOI：10.1039/c6dt02208a

  日期：——

  The synthesis, structure and CO-releasing properties of a number of new tricarbonyl rhenium(I) complexes with 5-substituted-6-amino-1,3-dimethyluracils are reported and their structural features discussed on the basis of both spectral and X-ray crystallographic analyses. The 5-substituent library includes –NCH-2py (DAAUPic) and –CHN–NCH-2py (FDUHzPic) as additional metal binding components and chloride

  报告了许多新的具有5-取代的6-氨基-1,3-二甲基尿嘧啶的三羰基rh（I）配合物的合成，结构和CO释放性质，并在光谱和X-的基础上讨论了它们的结构特征射线晶体学分析。5个取代基库包括–N CH-2py（DAAUPic）和–CH N–N CH-2py（FDUHzPic）作为其他金属结合成分，以及用作辅助配体的氯化物，乙腈或吡啶。该化合物已通过元素分析，NMR，MS和IR光谱法鉴定。另外，[ReCl（CO）3（DAAUPic）]，[Re（CO）3（FDUHzPic）py] ClO 4，[Re（CO）3（FDUHzPic）py] PF 6，[Re2 Cl 2（CO） 6（FDUHzPic）]和[Re 2 Cl（CO） 6（FDUHzPicH -1）（H 2O）]结构已通过X射线衍射法解决。这些研究清楚地表明，to的首选配位方式是通过（N1F，N52）-吡啶-2-基-亚甲基胺部分发生的，尿嘧啶配
• Pyrido[2,3-<i>d</i>]pyrimidines and pyrido[2,3-<i>d</i>; 5-<i>d</i>′]dipyrimidines as potential chemotherapeutic agents.<b>VIII</b>
  作者：Vishnu J. Ram、D. A. Vanden Berghe、A. J. Vlietinck

  DOI：10.1002/jhet.5570250133

  日期：1988.1

  ne-6-imino-1,3-dimethyluracil hydrochloride (1) with active methylene compounds 2 and 4 yielded bi- and tricyclic heterocyclic compounds 3 and 5. All the prepared compounds were screened for chemotherapeutical activities but none were active.

  5-二甲基氨基亚甲基-6-亚氨基-1,3-二甲基尿嘧啶盐酸盐（1）与活性亚甲基化合物2和4的反应生成双环和三环杂环化合物3和5。筛选所有制备的化合物的化学治疗活性，但没有活性。
• A Facile Entry to Fused Pyrimidines: Preparation of Pyrimido(4,5-<i>b</i>]quinoline and Pyrido(2,3-<i>d</i>: 6,5-<i>d</i>′]dipyrimidine Derivatives
  作者：Pedro Molina、Maria Jesús Vilaplana、Aurelia Pastor

  DOI：10.1055/s-1992-26236

  日期：——

  A number of pyrimido[4,5-b]quinolines 3 and pyrido[2,3-d:6,5-d]-dipyrimidines have been prepared by reaction of N,N-disubstituted barbituric acids with the iminophosphorane derived from o-azidobenzaldehyde or 6-amino-5-formyl-1,3-dimethyluracil.

  一些吡啶并[4,5-b]喹啉3和吡啶并[2,3-d:6,5-d]双吡啶嘧啶已经通过将N,N-二取代巴比妥酸与源自o-叠氮苯甲醛或6-氨基-5-呋喃基-1,3-二甲基尿嘧啶的亚胺膦烯反应制备而成。
• Stable thioaldehydes: Synthesis, structure assignment, and stability of 6-amino-5-thioformyluracils
  作者：Kosaku Hirota、Hironao Sajiki、Keiko Kubo、Masaru Kido、Kazuyuki Nakagawa

  DOI：10.1016/0040-4020(96)00533-9

  日期：1996.7

  Stable 6-amino-5-thioformyluracils 3a-e were synthesized starting from 6-amino-1,3-disubstituted uracils 1a-e in 23–98 % yields. According to the x-ray crystal structure, although the thioaldehyde 3c possesses reasonable double-bond character of the C=S bond, the length of C=S bond of the thioaldehyde 3c is longer than those of the kinetically stabilized thioaldehydes due to the mesomeric effect of

  稳定6-氨基-5- thioformyluracils 3A-E合成从6-氨基-1,3-二取代的尿嘧啶开始1A-E在23-98％的产率。根据X射线晶体结构，虽然硫醛3C拥有C = S键的合理双键字符时，硫醛的C = S键的长度3C是比那些动力学稳定的硫醛的较长由于内消旋6-氨基的作用。
• Synthesis and Antimicrobial Activity of Some New Heterocyclic Schiff Bases Derived from 2-Amino-3-formylchromone
  作者：Magdy A. Ibrahim、Kamelia M. El-Mahdy

  DOI：10.1080/10426500802625594

  日期：2009.10.30

  Some new hydrazone derivatives 3a–e have been obtained from 2-amino-3-formylchromone (1). Heterocyclization of thiocarbohydrazone derivative 3e via reaction with some electrophilic reagents afforded 1,2,4-triazoles 6–8 and 1,2,4-triazines 9–13. Condensation reactions of aldehyde 1 with o-aminoaldehydes and/or ketones afforded some new isolated and condensed heterocyclic systems 17, 19, and 20. The

  一些新的腙衍生物 3a-e 已从 2-amino-3-formylchromone (1) 中获得。通过与一些亲电试剂反应，硫代碳腙衍生物 3e 的杂环化得到 1,2,4-三唑 6-8 和 1,2,4-三嗪 9-13。醛 1 与邻氨基醛和/或酮的缩合反应提供了一些新的分离和稠合杂环系统 17、19 和 20。筛选了新合成的化合物的抗菌活性。