(4-chlorophenyl)amino-3-methyluracil | 58137-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-chlorophenyl)amino-3-methyluracil
• 英文别名: 6-(4'-chloroanilino)-3-methylpyrimidine-2,4(1H,3H)-dione；6-(p-chloroanilino)-3-methyluracil；3-Methyl-6-(4-chlorophenylamino)uracil；3-Methyl-6-(p-chloranilino)uracil；6-(4-chloro-anilino)-3-methyl-1H-pyrimidine-2,4-dione；3-Methyl-6-(4-chloranilin)-uracil；6-(4-chloroanilino)-3-methyl-2,4(1H,3H)-pyrimidinedione；6-(4-chloroanilino)-3-methyl-1H-pyrimidine-2,4-dione
• CAS: 58137-45-4
• 化学式: C₁₁H₁₀ClN₃O₂
• 分子量: 251.672
• InChiKey: DHJODGLSYSYFJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-chlorophenyl)amino-3-methyluracil 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 8-(4-Chloro-phenyl)-3-methyl-2,4-dioxo-7-phenyl-2,3,4,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid
  参考文献：
  名称：

  Synthesis and properties of 2,3,4,8-tetrahydro-2,4-dioxopyrido(2,3-d)pyrimidines (5-deazalumazines) and their bis-compounds.

  摘要：

  乙基2, 3, 4, 8-四氢-3-甲基-2, 4-二氧吡啶[2, 3-d]嘧啶-6-羧酸酯（IV）及其双化合物（VI）是通过6-烷基或6-芳基氨基-3-甲基尿嘧啶（II）与适当的乙基3-氯-2-甲酰丙-2-烯酸酯（III）在二甲基甲酰胺中缩合合成的。将酯IV和VI在碱性条件下水解，会导致取代基（R2）在7位的重新排列，转移到6位的取代基上，生成对应的6-酰基-1, 2, 3, 4, 7, 8-六氢-3-甲基-2, 4, 7-三氧吡啶[2, 3-d]嘧啶（VII）及其双化合物（X）。对这种重新排列的机制进行了讨论。

  DOI：

  10.1248/cpb.32.1699
• 作为产物：
  描述：

  对氯苯胺 、 6-氯-3-甲基尿嘧啶 反应 0.17h， 以74%的产率得到(4-chlorophenyl)amino-3-methyluracil
  参考文献：
  名称：

  Nagamatsu, Tomohisa; Yamato, Hirotake; Ono, Masami, Journal of the Chemical Society. Perkin transactions I, 1992, # 16, p. 2101 - 2110

  摘要：

  DOI：

文献信息

• 3-Methyl-8-(substituted phenyl)-pteridine-2,4(3H,8H)-diones as Potential Antimalarials
  作者：PK Halladay、WB Cowden

  DOI：10.1071/ch9901449

  日期：——

  A series of 6,7,8-substituted 3-methylpteridine-2,4(3H,8H)- diones was synthesized by condensation of 5-amino-6-(substituted anilino )-3-methylpyrimidine-2,4(1H,3H)- dione with α- dicarbonyl reagents. These compounds were tested for antimalarial activity against the human parasite Plasmodium falciparum in culture, and lethal Plasmodium vinckei vinckei in mice. The 6,7-unsubstituted pteridinediones were active against cultured P. Falciparum ; however, none of the series was active against P. vinckei vinckei in mice.

  通过 5-氨基-6-（取代苯胺基）-3-甲基嘧啶-2,4(1H,3H)-二酮与α-二羰基试剂缩合，合成了一系列 6,7,8-取代的 3-甲基蝶啶-2,4(3H,8H)-二酮。这些化合物对培养的人类寄生虫恶性疟原虫和小鼠体内致命的 vinckei vinckei 疟原虫进行了抗疟活性测试。6,7-未取代的蝶啶二酮类化合物对培养的恶性疟原虫有活性，但对小鼠体内的 vinckei vinckei 疟原虫没有活性。
• Studies on Pyrimidine-Annulated Heterocycles: A Short Synthesis of Novel 6,9-Disubstituted Cyclohepta[b]pyrimido[5,4-d]pyrrole-8(6H),10(9H)-diones
  作者：Makoto Nitta、Yohei Tajima

  DOI：10.1055/s-2000-6384

  日期：——

  A number of 6,9-disubstituted cyclohepta[b]pyrimido[5,4-d]pyrrole-8(6H),10(9H)-dione derivatives have been synthesized in good to moderate yields by the reaction of 6-amino-3-methyluracil derivatives with 2-chlorotropone in an enamine-alkylation process, subsequent condensation of the amino group with the carbonyl function, dehydrochlorination, and dehydration.

  合成了一系列6,9-二取代的环七氮[b]嘧啶[5,4-d]吡咯-8(6H),10(9H)-二酮衍生物，产率从良好到中等。这些衍生物是通过6-氨基-3-甲基尿嘧啶衍生物与2-氯托品在烯胺烷基化反应中反应而成，随后氨基与羰基功能的缩合、脱氯化氢和脱水反应。
• Alternative synthesis and novel oxidizing ability of 6,9-disubstituted cyclohepta[b]pyrimido[5,4-d]pyrrole-8(6H),10(9H)-dione derivatives
  作者：Shin-ichi Naya、Yusuke Iida、Makoto Nitta

  DOI：10.1016/j.tet.2003.11.004

  日期：2004.1

  Synthesis of 6,9-disubstituted cyclohepta[b]pyrimido[5,4-d]pyrrole-8(6H),10(9H)-diones 7a–g was accomplished by ring opening and ring closure sequences of 9-substituted cyclohepta[b]pyrimido[5,4-d]furan-8,10(9H)-dione derivatives induced by several amines. Furthermore, alternative synthetic methodology for compounds 7a–e was also accomplished by single-step reaction of 2-chlorotropone with 6-aminouracil

  6,9-二取代的环庚[ b ]嘧啶基[5,4 - d ]吡咯-8（6 H），10（9 H）-二酮7a – g的合成是通过9-取代的开环和闭环顺序完成的几种胺诱导的环庚[ b ]嘧啶基[5,4 - d ]呋喃-8,10（9 H）-二酮衍生物。此外，化合物7a - e的替代合成方法也可以通过在适度的条件下使2-氯托酮与6-氨基尿嘧啶衍生物进行一步反应来完成。7a的X射线晶体分析进行了澄清结构特征。通过紫外可见光谱和还原电势（相对于Ag / AgNO 3为−1.24至−1.39 V ）研究了7a – e的性质。在好氧条件下，进行了7a - d对某些胺的新型光诱导氧化反应，得到的亚胺的收率超过100％[基于化合物7a - d ]，表明该氧化反应发生在自动回收过程中。
• Compounds inhibiting the aggregation of superoxide dismutase-1
  申请人：Lansbury Peter

  公开号：US20060194821A1

  公开（公告）日：2006-08-31

  The invention is directed to methods of inhibiting the rate at which superoxide dismutse-1 (SOD) aggregates using compounds that stabilize SOD dimers. The methods are useful in the study and therapy of amyotrophic lateral sclerosis. The invention also includes assays that can be used to identify compounds that stabilize dimers and SOD molecules that have been modified for use in these assays.

  本发明涉及使用稳定SOD二聚体的化合物来抑制超氧化物歧化酶-1（SOD）聚集的速率的方法。该方法在进行肌萎缩侧索硬化的研究和治疗中非常有用。本发明还包括可用于识别稳定二聚体化合物和已经改性用于这些测定的SOD分子的测定方法。
• Nagamatsu, Tomohisa; Yamato, Hirotake; Ono, Masami, Journal of the Chemical Society. Perkin transactions I, 1992, # 16, p. 2101 - 2110
  作者：Nagamatsu, Tomohisa、Yamato, Hirotake、Ono, Masami、Takarada, Shigeki、Yoneda, Fumio

  DOI：——

  日期：——