5-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carbaldehyde | 14161-00-3

• 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: 5-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carbaldehyde
• 英文别名: thymine-6-carboxaldehyde；6-formylthymine；5-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbaldehyde；5-Methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-carbaldehyd；6-Formyl-5-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin；5-methyl-2,4-dioxo-1H-pyrimidine-6-carbaldehyde
• CAS: 14161-00-3
• 化学式: C₆H₆N₂O₃
• 分子量: 154.125
• InChiKey: SZQDOUUFFRAZPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carbaldehyde 在 sodium tetrahydroborate 作用下， 以85%的产率得到6-(hydroxymethyl)-2,4-dihydroxy-5-methylpyrimidine
  参考文献：
  名称：

  Synthesis and enzymatic evaluation of pyridinium-Substituted uracil derivatives as novel inhibitors of thymidine phosphorylase

  摘要：

  A series of water soluble N(1)- and C(6)-substituted uracil pyridinium compounds were prepared as potential inhibitors of thymidine phosphorylase (TP). The C(6)-uracil substituted derivatives were the most active. 1-[(5-Chloro-2,4-dihydroxy-pyrimidin-6-yl)methyl]pyridinium chloride, was identified as the best inhibitor being 5-fold more potent than the known inhibitor, 6-amino-5-bromouracil. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00309-1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 5-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carbaldehyde
  参考文献：
  名称：

  Johnson; Cretcher, Journal of Biological Chemistry, 1916, vol. 26, p. 110

  摘要：

  DOI：

文献信息

• [EN] MONOCYCLIC PYRIMIDINE/PYRIDINE COMPOUNDS AS INHIBITORS OF P97 COMPLEX<br/>[FR] COMPOSÉS MONOCYCLIQUES PYRIMIDINE/PYRIDINE COMME INHIBITEURS DU COMPLEXE P97
  申请人：WUSTROW DAVID

  公开号：WO2015089218A1

  公开（公告）日：2015-06-18

  Monocyclic pyrimidine and pyridine compounds having a benzyl amine substituent at the 4 position and a 5:6 bicyclic heteroaryl substituent at the 2 position of the pyrimidine or pyridine ring as well as optional aliphatic, functional and/or aromatic components substituted at other positions of the ring are disclosed. These compounds are inhibitors of the AAA proteasome complex containing p97 and are effective medicinal agents for treatment of diseases associated with p97 bioactivity such as cancer.

  在4位上具有苄胺取代基的单环嘧啶和吡啶化合物，以及在2位上具有5:6双环杂芳基取代基的嘧啶或吡啶环，还可以在环的其他位置取代烷基、官能基和/或芳香基成分。这些化合物是含有p97的AAA蛋白酶复合物的抑制剂，并且是用于治疗与p97生物活性相关的疾病如癌症的有效药物。
• Recognition and cleavage at the DNA major groove
  申请人：——

  公开号：US20030119022A1

  公开（公告）日：2003-06-26

  DNA recognition agents based on the indole-based aziridinyl eneimine and the cyclopent[b]indole methide species are described. The recognition process involved either selective alkylation or intercalating interactions in the major groove. DNA cleavage resulted from phosphate backbone alkylation (hydrolytic cleavage) and N(7)-alkylation (piperidine cleavage). The formation and fate of the eneimine was studied using enriched 13 C NMR spectra and x-ray crystallography. The aziridinyl eneimine specifically alkylates the N(7) position of DNA resulting in direction of the aziridinyl alkylating center to either the 3′- or 5′-phosphate of the alkylated base. The eneimine species forms dimers and trimers that appear to recognize DNA at up to three base pairs. The cyclopent[b]indole quinone methide recognizes the 3′-GT-5′ sequence and alkylates the guanine N(7) and the thymine 6-carbonyl oxygen causing the hydrolytic removal of these bases. New classes of DNA recognition agents have been developed and the utility of 13 C-enrichment and 13 C-NMR to study DNA alkylation reactions is disclosed.

  本文介绍了基于吲唑烯烯胺和环戊[b]吲哚亚甲基物种的DNA识别剂。识别过程涉及到主沟槽中的选择性烷基化或插入作用。磷酸骨架烷基化（水解裂解）和N（7）烷基化（吡啶裂解）导致DNA裂解。使用富集的13C NMR光谱和X射线晶体学研究了烯烯胺的形成和命运。吲唑烯烯胺特异性烷基化DNA的N（7）位，从而将吲唑烯烷基化中心的方向定向到烷基化碱基的3'-或5'-磷酸。烯烯胺物种形成二聚体和三聚体，似乎能够识别DNA的最多三个碱基对。环戊[b]吲哚醌亚甲基物种识别3'-GT-5'序列，并烷基化鸟嘌呤N（7）和胸腺嘧啶6-羰基氧，导致这些碱基的水解去除。开发了新的DNA识别剂类别，并披露了13C富集和13C-NMR用于研究DNA烷基化反应的实用性。
• MONOCYCLIC PYRIMIDINE/PYRIDINE COMPOUNDS AS INHIBITORS OF P97 COMPLEX
  申请人：Cleave Biosciences, Inc.

  公开号：EP3080101A1

  公开（公告）日：2016-10-19
• US9868722B2
  申请人：——

  公开号：US9868722B2

  公开（公告）日：2018-01-16
• [EN] METHOD FOR THE SYNTHESIS OF HOMOLOGOUS COMPOUNDS OF AZANUCLEOSIDES<br/>[ES] PROCEDIMIENTO DE SÍNTESIS DE COMPUESTOS HOMÓLOGOS DE AZANUCLEÓSIDOS<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE COMPOSÉS HOMOLOGUES D'AZANUCLÉOSIDES
  申请人：UNIV ALICANTE

  公开号：WO2014154921A1

  公开（公告）日：2014-10-02

  La presente invención se refiere al procedimiento de síntesis de compuestos homólogos de azanucleósidos, a los compuestos obtenidos por dicho procedimiento y al uso de los mismos para la elaboración de medicamento para el tratamiento de enfermedades virales, bacterianas y cáncer.