(3-chlorophenyl)(pyrazin-2-yl)methanone | 118543-84-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-chlorophenyl)(pyrazin-2-yl)methanone
• 英文别名: (3-chlorophenyl)(2-pyrazinyl)methanone；(3-Chlorophenyl)-pyrazin-2-ylmethanone
• CAS: 118543-84-3
• 化学式: C₁₁H₇ClN₂O
• 分子量: 218.642
• InChiKey: GDTBMVJIFIHUPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3-(二甲基氨基)丙基]三苯基溴化磷 、 (3-chlorophenyl)(pyrazin-2-yl)methanone 、 三氟乙酸 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.25h， 生成 (3E)-4-(3-chlorophenyl)-N,N-dimethyl-4-(2-pyrazinyl)but-3-en-1-ammonium trifluoroacetate 、 (3Z)-4-(3-chlorophenyl)-N,N-dimethyl-4-(2-pyrazinyl)but-3-en-1-ammonium trifluoroacetate
  参考文献：
  名称：

  Chlorpheniramine Analogues Reverse Chloroquine Resistance in Plasmodium falciparum by Inhibiting PfCRT

  摘要：

  The emergence and spread of malaria parasites that are resistant to chloroquine (CQ) has been a disaster for world health. The antihistamine chlorpheniramine (CP) partially resensitizes CQ-resistant (CQR) parasites to CQ but possesses little intrinsic antiplasmodial activity. Mutations in the parasite's CQ resistance transporter (PfCRT) confer resistance to CQ by enabling the protein to transport the drug away from its site of action, and it is thought that resistance-reversers such as CP exert their effect by blocking this CQ transport activity. Here, a series of new structural analogues and homologues of CP have been synthesized. We show that these compounds (along with other in vitro CQ resistance-reversers) inhibit the transport of CQ via a resistance-conferring form of PfCRT expressed in Xenopus laevis oocytes. Furthermore, the level of PfCRT-inhibition was found to correlate well with both the restoration of CQ accumulation and the level of CQ resensitization in CQR parasites.

  DOI：

  10.1021/ml5000228
• 作为产物：
  描述：

  5-(3-Chloro-benzoyl)-pyrazine-2-carboxylic acid 在 铜 作用下， 以83%的产率得到(3-chlorophenyl)(pyrazin-2-yl)methanone
  参考文献：
  名称：

  A New, Convenient Synthesis of Monoaroylpyrazines via Homolytic Substitution

  摘要：

  2-吡嗪羧酸（1）与芳酰基反应生成 5-芳酰基-2-吡嗪羧酸 3，然后进行脱羧反应，可方便地获得芳基 2-吡嗪酮（2-芳酰基吡嗪）4。

  DOI：

  10.1055/s-1988-27484

文献信息

• Selective Acylation of Aryl- and Heteroarylmagnesium Reagents with Esters in Continuous Flow
  作者：Benjamin Heinz、Dimitrije Djukanovic、Maximilian A. Ganiek、Benjamin Martin、Berthold Schenkel、Paul Knochel

  DOI：10.1021/acs.orglett.9b04254

  日期：2020.1.17

  A selective acylation of readily accessible organomagnesium reagents with commercially available esters proceeds at convenient temperatures and short residence times in continuous flow. Flow conditions allow us to prevent premature collapse of the hemiacetal intermediates despite noncryogenic conditions, thus furnishing ketones in good yields. Throughout, the coordinating ability of the ester and/or

  易于获得的有机镁试剂与市售酯的选择性酰化反应可在方便的温度下以较短的停留时间连续进行。流动条件使我们能够防止半缩醛中间体过早坍塌，尽管非低温条件也是如此，因此可以提供高收率的酮。整个过程中，酯和/或格利雅（Grignard）的配位能力对于反应结果至关重要。通过使用2-羟基酯衍生物作为底物获得几种双芳基酮来利用这一点。
• Chlorpheniramine Analogues Reverse Chloroquine Resistance in <i>Plasmodium falciparum</i> by Inhibiting PfCRT
  作者：Karen J. Deane、Robert L. Summers、Adele M. Lehane、Rowena E. Martin、Russell A. Barrow

  DOI：10.1021/ml5000228

  日期：2014.5.8

  The emergence and spread of malaria parasites that are resistant to chloroquine (CQ) has been a disaster for world health. The antihistamine chlorpheniramine (CP) partially resensitizes CQ-resistant (CQR) parasites to CQ but possesses little intrinsic antiplasmodial activity. Mutations in the parasite's CQ resistance transporter (PfCRT) confer resistance to CQ by enabling the protein to transport the drug away from its site of action, and it is thought that resistance-reversers such as CP exert their effect by blocking this CQ transport activity. Here, a series of new structural analogues and homologues of CP have been synthesized. We show that these compounds (along with other in vitro CQ resistance-reversers) inhibit the transport of CQ via a resistance-conferring form of PfCRT expressed in Xenopus laevis oocytes. Furthermore, the level of PfCRT-inhibition was found to correlate well with both the restoration of CQ accumulation and the level of CQ resensitization in CQR parasites.
• A New, Convenient Synthesis of Monoaroylpyrazines via Homolytic Substitution
  作者：G. Heinisch、G. Lötsch

  DOI：10.1055/s-1988-27484

  日期：——

  Reactions of 2-pyrazinecarboxylic acid (1) with aroyl radicals to give 5-aroyl-2-pyrazinecarboxylic acids 3 followed by decarboxylation provide convenient access to aryl 2-pyrazinyl ketones (2-aroylpyrazines) 4.

  2-吡嗪羧酸（1）与芳酰基反应生成 5-芳酰基-2-吡嗪羧酸 3，然后进行脱羧反应，可方便地获得芳基 2-吡嗪酮（2-芳酰基吡嗪）4。