(+/-)-(3-chlorophenyl)[4-(pyrrolidin-1-ylmethyl)phenyl]methanol | 927690-07-1

• 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)[4-(pyrrolidin-1-ylmethyl)phenyl]methanol
• 英文别名: (3-Chlorophenyl)-[4-(pyrrolidin-1-ylmethyl)phenyl]methanol
• CAS: 927690-07-1
• 化学式: C₁₈H₂₀ClNO
• 分子量: 301.816
• InChiKey: DLLJBRKAYFNYBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-(3-chlorophenyl)[4-(pyrrolidin-1-ylmethyl)phenyl]methanol 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 22.0h， 生成 7-chloro-N-[3-[4-[3-[[(3-chlorophenyl)-[4-(pyrrolidin-1-ylmethyl)phenyl]methyl]amino]propyl]piperazin-1-yl]propyl]quinolin-4-amine
  参考文献：
  名称：

  Development of piperazine-tethered heterodimers as potent antimalarials against chloroquine-resistant P. falciparum strains. Synthesis and molecular modeling

  摘要：

  The design, synthesis, and antiplasmodial activity of antimalarial heterodimers based on the 1,4-bis(3-aminopropyl)piperazine linker is reported. In this series key structural elements derived from quinoline antimalarials were coupled to fragments capable of coordinating metal ions. Biological evaluation included determination of activity against chloroquine-sensitive and chloroquine-resistant Plasmodiunifaleiparum strains. Some of the novel compounds presented high activity in vitro against chloroquine-resistant strains, more potent than chloroquine and clotrimazole. Computational studies revealed that the activity is likely due to the ability of the compounds to assume a multisite iron coordinating geometry. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.077
• 作为产物：
  描述：

  (4-bromomethyl-phenyl)(3-chloro-phenyl)methanone 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 3.0h， 生成 (+/-)-(3-chlorophenyl)[4-(pyrrolidin-1-ylmethyl)phenyl]methanol
  参考文献：
  名称：

  Development of piperazine-tethered heterodimers as potent antimalarials against chloroquine-resistant P. falciparum strains. Synthesis and molecular modeling

  摘要：

  The design, synthesis, and antiplasmodial activity of antimalarial heterodimers based on the 1,4-bis(3-aminopropyl)piperazine linker is reported. In this series key structural elements derived from quinoline antimalarials were coupled to fragments capable of coordinating metal ions. Biological evaluation included determination of activity against chloroquine-sensitive and chloroquine-resistant Plasmodiunifaleiparum strains. Some of the novel compounds presented high activity in vitro against chloroquine-resistant strains, more potent than chloroquine and clotrimazole. Computational studies revealed that the activity is likely due to the ability of the compounds to assume a multisite iron coordinating geometry. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.077

文献信息

• 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.
• 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.
• Development of piperazine-tethered heterodimers as potent antimalarials against chloroquine-resistant P. falciparum strains. Synthesis and molecular modeling
  作者：Sandra Gemma、Gagan Kukreja、Giuseppe Campiani、Stefania Butini、Matteo Bernetti、Bhupendra P. Joshi、Luisa Savini、Nicoletta Basilico、Donatella Taramelli、Vanessa Yardley、Alessia Bertamino、Ettore Novellino、Marco Persico、Bruno Catalanotti、Caterina Fattorusso

  DOI：10.1016/j.bmcl.2007.04.077

  日期：2007.7

  The design, synthesis, and antiplasmodial activity of antimalarial heterodimers based on the 1,4-bis(3-aminopropyl)piperazine linker is reported. In this series key structural elements derived from quinoline antimalarials were coupled to fragments capable of coordinating metal ions. Biological evaluation included determination of activity against chloroquine-sensitive and chloroquine-resistant Plasmodiunifaleiparum strains. Some of the novel compounds presented high activity in vitro against chloroquine-resistant strains, more potent than chloroquine and clotrimazole. Computational studies revealed that the activity is likely due to the ability of the compounds to assume a multisite iron coordinating geometry. (c) 2007 Elsevier Ltd. All rights reserved.