(3-chlorophenyl)(pyridin-3-yl)methanol | 62247-14-7

• 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: (3-chlorophenyl)(pyridin-3-yl)methanol
• 英文别名: (3-pyridyl)(3-chlorophenyl)methanol；(3-chloro-phenyl)-pyridin-3-yl-methanol；α-(m-Chlorophenyl)-3-pyridinemethanol；3-Chlorphenyl-(3-pyridyl)-methanol；(3-Chlorophenyl)-pyridin-3-ylmethanol
• CAS: 62247-14-7
• 化学式: C₁₂H₁₀ClNO
• 分子量: 219.671
• InChiKey: SKGOOMJTKAHYPA-UHFFFAOYSA-N

物化性质

• 熔点：
  107-109 °C(Solv: benzene (71-43-2))
• 沸点：
  377.9±32.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-chlorophenyl)(pyridin-3-yl)methanol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 264.0h， 以78%的产率得到(3-氯苯)(吡啶-3-基)甲酮
  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：

  3-吡啶甲醛 、 间氯溴苯 在 magnesium 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.45h， 以74%的产率得到(3-chlorophenyl)(pyridin-3-yl)methanol
  参考文献：
  名称：

  标签上的格氏试剂：在流动条件下直接插入镁

  摘要：

  使用新的流程方案介绍了按需制备有机镁试剂的方法。新的柱上引发程序规避了与镁活化有关的风险。获得了需要量的精确滴定溶液。伸缩流动或间歇反应允许访问各种功能组。

  DOI：

  10.1021/acs.orglett.7b01590

文献信息

• US4116665A
  申请人：——

  公开号：US4116665A

  公开（公告）日：1978-09-26
• Grignard Reagents on a Tab: Direct Magnesium Insertion under Flow Conditions
  作者：Lena Huck、Antonio de la Hoz、Angel Díaz-Ortiz、Jesus Alcázar

  DOI：10.1021/acs.orglett.7b01590

  日期：2017.7.21

  An on-demand preparation of organomagnesium reagents is presented using a new flow protocol. The risks associated with the activation of magnesium are circumvented by a new on-column initiation procedure. Required amounts of solutions with a precise titration were obtained. Telescoped flow or batch reactions allow access to a diverse set of functional groups.

  使用新的流程方案介绍了按需制备有机镁试剂的方法。新的柱上引发程序规避了与镁活化有关的风险。获得了需要量的精确滴定溶液。伸缩流动或间歇反应允许访问各种功能组。
• 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.