(3-氯苯基)[4-(1-吡咯烷基甲基)苯基]甲酮 | 898776-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3-氯苯基)[4-(1-吡咯烷基甲基)苯基]甲酮
• 英文名称: (3-chlorophenyl)[4-(pyrrolidin-1-ylmethyl)phenyl]methanone
• 英文别名: (3-chloro-phenyl)(4-(pyrrolidin-1-ylmethyl)phenyl)methanone；3-Chloro-4'-pyrrolidinomethyl benzophenone；(3-chlorophenyl)-[4-(pyrrolidin-1-ylmethyl)phenyl]methanone
• CAS: 898776-32-4
• 化学式: C₁₈H₁₈ClNO
• 分子量: 299.8
• InChiKey: UVKZZQWHCZLWLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  432.0±35.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (3-氯苯基)[4-(1-吡咯烷基甲基)苯基]甲酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  3-氯-4-甲基苯甲酮 在 N-溴代丁二酰亚胺(NBS) 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三乙胺 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 4.0h， 生成 (3-氯苯基)[4-(1-吡咯烷基甲基)苯基]甲酮
  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

• NOVEL 4-AMINO-QUINOLINE DERIVATIVES USEFUL AS ANTI-MALARIA DRUGS
  申请人：Campiani Giuseppe

  公开号：US20100093726A1

  公开（公告）日：2010-04-15

  The present invention relates to clotrimazole/quinoline hybrids useful as active ingredients of anti-malaria drugs. The compounds show a remarkable in vitro biological activity especially against the chloroquine-resistant Plasmodium falciparum strains and in vivo activity against P. berghei.

  本发明涉及克霉唑/喹啉杂合物，可作为抗疟疾药物的活性成分。这些化合物在体外显示出显著的生物活性，特别是对氯喹耐药恶性疟原虫株的活性，以及对伯氏恶性疟原虫的体内活性。
• WO2007/104696
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2008/101891
  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.
• [EN] NOVEL 4-AMINO-QUINOLINE DERIVATIVES USEFUL AS ANTI-MALARIA DRUGS<br/>[FR] NOUVEAUX DÉRIVÉS DE 4-AMINO-QUINOLINE À UTILISER EN TANT QU'ANTIPALUDÉENS
  申请人：CAMPIANI GIUSEPPE

  公开号：WO2008101891A1

  公开（公告）日：2008-08-28

  [EN] The present invention relates to clotrimazole/quinoline hybrids useful as active ingredients of anti-malaria drugs. The compounds show a remarkable in vitro biological activity especially against the chloroquine-resistant Plasmodium falciparum strains and in vivoactivity against P.berghei.
  [FR] La présente invention concerne des hybrides clotrimazole/quinoline utiles en tant que principes actifs d'antipaludéens. Ces composés présentent une activité biologique in vitro remarquable en particulier contre les souches de Plasmodium falciparum résistant à la chloroquine ainsi qu'une activité in vivo contre l'espèce P.berghei.