3-allyl-6-chlorouracil | 230630-82-7

• 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: 3-allyl-6-chlorouracil
• 英文别名: 6-chloro-3-prop-2-enyl-1H-pyrimidine-2,4-dione
• CAS: 230630-82-7
• 化学式: C₇H₇ClN₂O₂
• 分子量: 186.598
• InChiKey: FKNJRHRZTARNIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-allyl-6-chlorouracil 在 氢氧化钾 、 sodium periodate 、 四氧化锇 、 溴 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[5-Bromo-3-[(2,6-difluorophenyl)methyl]-4-ethyl-2,6-dioxopyrimidin-1-yl]acetaldehyde
  参考文献：
  名称：

  Identification of 1-Arylmethyl-3- (2-aminoethyl)-5-aryluracil as Novel Gonadotropin-Releasing Hormone Receptor Antagonists

  摘要：

  Based on SAR from hicyclic GnRH antagonists such as 6-aminomethyl-7-arylpyrrolo[1,2-a]pyrimid-4-ones (1) and 2-aryl-3-aminomethylimidazolo[1,2-a]pyrimid-5-ones (2a,b), a series of novel uracil compounds (4) were derived as the GnRH antagonists. Their syntheses and initial SAR are discussed herein. This is the first time that monocycle-based GnRH receptor antagonists are reported.

  DOI：

  10.1021/jm034041s
• 作为产物：
  描述：

  1-allylbarbituric acid 在 水 、 三氯氧磷 作用下， 以63%的产率得到3-allyl-6-chlorouracil
  参考文献：
  名称：

  Identification of 1-Arylmethyl-3- (2-aminoethyl)-5-aryluracil as Novel Gonadotropin-Releasing Hormone Receptor Antagonists

  摘要：

  Based on SAR from hicyclic GnRH antagonists such as 6-aminomethyl-7-arylpyrrolo[1,2-a]pyrimid-4-ones (1) and 2-aryl-3-aminomethylimidazolo[1,2-a]pyrimid-5-ones (2a,b), a series of novel uracil compounds (4) were derived as the GnRH antagonists. Their syntheses and initial SAR are discussed herein. This is the first time that monocycle-based GnRH receptor antagonists are reported.

  DOI：

  10.1021/jm034041s

文献信息

• 6-Anilinouracil-Based Inhibitors of <i>Bacillus </i><i>s</i><i>ubtilis</i> DNA Polymerase III:  Antipolymerase and Antimicrobial Structure−Activity Relationships Based on Substitution at Uracil N3
  作者：Paul M. Tarantino,、Chengxin Zhi、Joseph J. Gambino、George E. Wright、Neal C. Brown

  DOI：10.1021/jm980693i

  日期：1999.6.1

  analogues which selectively inhibit the DNA polymerase III of Bacillus subtilis and other Gram-positive bacteria. To enhance the potential of the 6-AUs as antimicrobial agents, a structure-activity relationship was developed involving substitutions of the uracil N3 position in two 6-AU platforms: 6-(3,4-trimethyleneanilino)uracil (TMAU) and 6-(3-ethyl-4-methylanilino)uracil (EMAU). Series of N3-alkyl

  6-苯胺尿嘧啶（6-AUs）是dGTP类似物，可选择性抑制枯草芽孢杆菌和其他革兰氏阳性细菌的DNA聚合酶III。为了增强6-AUs作为抗菌剂的潜力，开发了一种结构-活性关系，涉及两个6-AU平台中的尿嘧啶N3位置取代：6-（3,4-三亚甲基苯胺基）尿嘧啶（TMAU）和6- （3-乙基-4-甲基苯胺基）尿嘧啶（EMAU）。合成了两个6-AU的一系列N3-烷基衍生物，并测试了它们抑制纯化的枯草芽孢杆菌DNA聚合酶III和培养中枯草芽孢杆菌生长的能力。烷基的大小从乙基到己基不等，可以增强两个平台结合聚合酶的能力，除己基外，它们还可以显着增强其抗菌效力。用更多的亲水性羟烷基和甲氧基烷基基团对EMAU平台进行N3取代，虽然略微提高了抗聚合酶III的活性，但其抗菌效力却提高了数倍。总而言之，这些研究的结果表明6-茴香胺嘧啶的环N3可以耐受相当大的尺寸和结构变化的取代基，因此可以被操纵以显着增强这种新型
• [EN] GRAM-POSITIVE SELECTIVE ANTIBACTERIAL COMPOUNDS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT<br/>[FR] COMPOSES ANTIBACTERIENS A SELECTIVITE GRAM-POSITIF, COMPOSITIONS CONTENANT CES COMPOSES ET METHODES THERAPEUTIQUES
  申请人：MERCK & CO INC

  公开号：WO2001029010A1

  公开（公告）日：2001-04-26

  The compounds of formula (I) including pharmaceutically acceptable salts, stereoisomers or esters thereof are disclosed.
• Identification of 1-Arylmethyl-3- (2-aminoethyl)-5-aryluracil as Novel Gonadotropin-Releasing Hormone Receptor Antagonists
  作者：Yun-Fei Zhu、Timothy D. Gross、Zhiqiang Guo、Patrick J. Connors,、Yinghong Gao、Fabio C. Tucci、R. Scott Struthers、Greg J. Reinhart、John Saunders、Ta Kung Chen、Anne L. Killam Bonneville、Chen

  DOI：10.1021/jm034041s

  日期：2003.5.1

  Based on SAR from hicyclic GnRH antagonists such as 6-aminomethyl-7-arylpyrrolo[1,2-a]pyrimid-4-ones (1) and 2-aryl-3-aminomethylimidazolo[1,2-a]pyrimid-5-ones (2a,b), a series of novel uracil compounds (4) were derived as the GnRH antagonists. Their syntheses and initial SAR are discussed herein. This is the first time that monocycle-based GnRH receptor antagonists are reported.