(+/-)-2-(4-chlorophenyl)-2-phenyl-2-{4-[pyrrolidin-1-ylmethyl]phenyl}acetonitrile | 927690-02-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (+/-)-2-(4-chlorophenyl)-2-phenyl-2-{4-[pyrrolidin-1-ylmethyl]phenyl}acetonitrile
• 英文别名: 2-(4-Chlorophenyl)-2-phenyl-2-[4-(pyrrolidin-1-ylmethyl)phenyl]acetonitrile
• CAS: 927690-02-6
• 化学式: C₂₅H₂₃ClN₂
• 分子量: 386.924
• InChiKey: KMKBUNVVOGGALB-UHFFFAOYSA-N

物化性质

• 沸点：
  497.4±40.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(4-chlorophenyl)-2-phenyl-2-{4-[pyrrolidin-1-ylmethyl]phenyl}acetonitrile 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (+/-)-2-(4-chlorophenyl)-2-phenyl-2-{4-[(pyrrolidin-1-yl)methyl]phenyl}acetaldehyde
  参考文献：
  名称：

  Design and Synthesis of Potent Antimalarial Agents Based on Clotrimazole Scaffold:  Exploring an Innovative Pharmacophore

  摘要：

  Identification of new molecular scaffolds structurally unrelated to known antimalarials may represent a valid strategy to overcome resistance of P. falciparum (Pf) to currently available drugs. We describe herein the investigation of a new polycyclic pharmacophore, related to clotrimazole, to develop innovative antimalarial agents. This study allowed us to discover compounds characterized by a high in vitro potency, particularly against Pf CQ-resistant strains selectively targeting free heme, which are easy to synthesize by low-cost synthetic strategies.

  DOI：

  10.1021/jm061429p
• 作为产物：
  描述：

  4-氯-4-甲基苯甲酮 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 碘 、 四氯化钛 、 magnesium 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， 反应 20.33h， 生成 (+/-)-2-(4-chlorophenyl)-2-phenyl-2-{4-[pyrrolidin-1-ylmethyl]phenyl}acetonitrile
  参考文献：
  名称：

  Design and Synthesis of Potent Antimalarial Agents Based on Clotrimazole Scaffold:  Exploring an Innovative Pharmacophore

  摘要：

  Identification of new molecular scaffolds structurally unrelated to known antimalarials may represent a valid strategy to overcome resistance of P. falciparum (Pf) to currently available drugs. We describe herein the investigation of a new polycyclic pharmacophore, related to clotrimazole, to develop innovative antimalarial agents. This study allowed us to discover compounds characterized by a high in vitro potency, particularly against Pf CQ-resistant strains selectively targeting free heme, which are easy to synthesize by low-cost synthetic strategies.

  DOI：

  10.1021/jm061429p

文献信息

• WO2007/104696
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] ANTIMALARIAL AGENTS HAVING POLYAROMATIC STRUCTURE<br/>[FR] AGENTS ANTIMALARIAUX DE STRUCTURE POLYAROMATIQUE
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2007104696A1

  公开（公告）日：2007-09-20

  [EN] Antimalarial agents having a novel pharmacophore of formula (I) are herein described. These polycyclic compounds are able to inhibit chloroquine-sensitive and chloroquine-resistant strains ofPlasmodium falciparum (Pf). Furthermore, the synthesis of these compounds involves few steps from commercial products with low cost of production.
  [FR] La présente invention concerne des agents antimalariaux comportant un nouveau pharmacophore de formule (I). Ces composés polycycliques sont susceptibles d'inhiber les souches sensibles à la chloroquine et résistantes à la chloroquine de Plasmodium falciparum (Pf). En outre, la synthèse de ces composés est peu onéreuse et implique peu d'étapes à partir des produits commerciaux.
• Design and Synthesis of Potent Antimalarial Agents Based on Clotrimazole Scaffold:  Exploring an Innovative Pharmacophore
  作者：Sandra Gemma、Giuseppe Campiani、Stefania Butini、Gagan Kukreja、Bhupendra P. Joshi、Marco Persico、Bruno Catalanotti、Ettore Novellino、Ernesto Fattorusso、Vito Nacci、Luisa Savini、Donatella Taramelli、Nicoletta Basilico、Giulia Morace、Vanessa Yardley、Caterina Fattorusso

  DOI：10.1021/jm061429p

  日期：2007.2.1

  Identification of new molecular scaffolds structurally unrelated to known antimalarials may represent a valid strategy to overcome resistance of P. falciparum (Pf) to currently available drugs. We describe herein the investigation of a new polycyclic pharmacophore, related to clotrimazole, to develop innovative antimalarial agents. This study allowed us to discover compounds characterized by a high in vitro potency, particularly against Pf CQ-resistant strains selectively targeting free heme, which are easy to synthesize by low-cost synthetic strategies.