2-chloro-6-methyl-N-phenylpyrimidin-4-amine | 51944-25-3

• 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: 2-chloro-6-methyl-N-phenylpyrimidin-4-amine
• 英文别名: (2-chloro-6-methyl-pyrimidin-4-yl)-phenyl-amine
• CAS: 51944-25-3
• 化学式: C₁₁H₁₀ClN₃
• 分子量: 219.673
• InChiKey: YSEHCMSEPMBOGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 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：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-硝基-苯磺酰基)-哌嗪盐酸盐 、 2-chloro-6-methyl-N-phenylpyrimidin-4-amine 以 异丙醇 为溶剂， 反应 1.0h， 以92%的产率得到6-methyl-2-(4-((4-nitrophenyl)sulfonyl)piperazin-1-yl)-N-phenylpyrimidin-4-amine
  参考文献：
  名称：

  Antiplasmodial activity of piperazine sulfonamides

  摘要：

  A high-throughput screening program identified two piperazine sulfonamides with activity against Plasmodium falciparum. Both screening positives had three structural features with potential liabilities: furanyl, thiourea and nitrophenyl groups. The furan could be replaced with no loss of activity, replacement of the nitrophenyl led to some loss of activity, and any attempt to replace the thiourea led to a significant decrease in activity, which implicates this reactive functional group's role in the antiplasmodial activity of this compound class. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.130
• 作为产物：
  描述：

  6-甲基尿嘧啶 在 三氯氧磷 作用下， 以 水 为溶剂， 反应 0.67h， 生成 2-chloro-6-methyl-N-phenylpyrimidin-4-amine
  参考文献：
  名称：

  Anilinopyrimidines作为新型抗结核药。

  摘要：

  已经发现了一些新的苯胺基嘧啶类似物对结核分枝杆菌具有微摩尔活性。在与耐多药结核病作斗争中，这可能会产生新的先导化合物。

  DOI：

  10.1016/s0960-894x(03)00241-5

文献信息

• Synthesis, antimalarial activity, heme binding and docking studies of 4-aminoquinoline–pyrimidine based molecular hybrids
  作者：Deepak Kumar、Shabana I. Khan、Babu L. Tekwani、Prija Ponnan、Diwan S. Rawat

  DOI：10.1039/c4ra09768h

  日期：——

  A series of novel 4-aminoquinoline–pyrimidine hybrids was synthesized and evaluated for their antimalarial activity.

  一系列新颖的4-氨基喹啉-嘧啶杂合物被合成并评估其抗疟活性。
• Regioselective 2-Amination of Polychloropyrimidines
  作者：Sean M. Smith、Stephen L. Buchwald

  DOI：10.1021/acs.orglett.6b00799

  日期：2016.5.6

  The regioselective amination of substituted di- and trichloropyrimidines affording the 2-substituted products is reported. While aryl- and heteroarylamines require the use of a dialkylbiarylphosphine-derived palladium catalyst for high efficiency, more nucleophilic dialkylamines produce 2-aminopyrimidines under noncatalyzed SNAr conditions. The key is the use of 5-trimethylsilyl-2,4-dichloropyrimidine

  报道了提供2-取代产物的取代的二氯和三氯嘧啶的区域选择性胺化。尽管芳基胺和杂芳基胺需要使用二烷基联芳基膦衍生的钯催化剂才能实现高效率，但更多的亲核性二烷基胺在未催化的S N Ar条件下会产生2-氨基嘧啶。关键是使用5-三甲基甲硅烷基-2,4-二氯嘧啶作为母体二氯嘧啶的替代物。对于更具挑战性的情况，制备了2-氯-4-硫代甲氧基甲氧基类似物，并专门提供了所需的2-氨基-4-硫代甲氧基嘧啶产物。
• Synthesis and antiplasmodial activity of novel 2,4-diaminopyrimidines
  作者：Derek C. Martyn、Amarjit Nijjar、Cassandra A. Celatka、Ralph Mazitschek、Joseph F. Cortese、Erin Tyndall、Hanlan Liu、Maria M. Fitzgerald、Thomas J. O’Shea、Sanjay Danthi、Jon Clardy

  DOI：10.1016/j.bmcl.2009.10.133

  日期：2010.1

  Two sets of diaminopyrimidines, totalling 45 compounds, were synthesized and assayed against Plasmodium falciparum. The SAR was relatively shallow, with only the presence of a 2-(pyrrolidin-1-yl)ethyl group at R-2 significantly affecting activity. A subsequent series addressed high Log D values by introducing more polar side groups, with the most active compounds possessing diazepine and N-benzyl-4-aminopiperidyl groups at R-1/R-2. A final series attempted to address high in vitro microsomal clearance by replacing the C6-Me group with CF3, however antiplasmodial activity decreased without any improvement in clearance. The C6-CF3 group decreased hERG inhibition, probably as a result of decreased amine basicity at C2/C4. (C) 2009 Elsevier Ltd. All rights reserved.
• Anilinopyrimidines as novel antituberculosis agents
  作者：Jody Morgan、Rachada Haritakul、Paul A. Keller

  DOI：10.1016/s0960-894x(03)00241-5

  日期：2003.5

  A selection of novel anilinopyrimidine analogues have been found to have micromolar activity against Mycobacterium tuberculosis. This could potentially generate new lead compounds in the fight against multi-drug resistant tuberculosis.

  已经发现了一些新的苯胺基嘧啶类似物对结核分枝杆菌具有微摩尔活性。在与耐多药结核病作斗争中，这可能会产生新的先导化合物。
• Antiplasmodial activity of piperazine sulfonamides
  作者：Derek C. Martyn、Joseph F. Cortese、Erin Tyndall、Justin Dick、Ralph Mazitschek、Benito Munoz、Jon Clardy

  DOI：10.1016/j.bmcl.2009.10.130

  日期：2010.1

  A high-throughput screening program identified two piperazine sulfonamides with activity against Plasmodium falciparum. Both screening positives had three structural features with potential liabilities: furanyl, thiourea and nitrophenyl groups. The furan could be replaced with no loss of activity, replacement of the nitrophenyl led to some loss of activity, and any attempt to replace the thiourea led to a significant decrease in activity, which implicates this reactive functional group's role in the antiplasmodial activity of this compound class. (C) 2009 Elsevier Ltd. All rights reserved.