(4-氯苯基)[4-(1-吡咯烷基甲基)苯基]甲酮 | 742085-16-1

• 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: (4-氯苯基)[4-(1-吡咯烷基甲基)苯基]甲酮
• 英文名称: (4-chlorophenyl)[4-(pyrrolidin-1-ylmethyl)phenyl]methanone
• 英文别名: (4-chlorophenyl)[4-(1-pyrrolidinylmethyl)phenyl]methanone；4-Chloro-4'-pyrrolidinomethyl benzophenone；(4-chlorophenyl)-[4-(pyrrolidin-1-ylmethyl)phenyl]methanone
• CAS: 742085-16-1
• 化学式: C₁₈H₁₈ClNO
• 分子量: 299.8
• InChiKey: CMCXXQWYALMYCH-UHFFFAOYSA-N

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：

  (4-氯苯基)[4-(1-吡咯烷基甲基)苯基]甲酮 在 氯化亚砜 、 碘 、 四氯化钛 、 二异丁基氢化铝 、 magnesium 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.33h， 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) 、 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 (4-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。
• Amine derivative
  申请人：Ishihara Yuji

  公开号：US20060128690A1

  公开（公告）日：2006-06-15

  The present invention provides a compound represented by the formula wherein Ar 1 is a cyclic group optionally having substituent(s); R is a hydrogen atom, an optionally halogenated C 1-6 alkyl, a phenyl optionally having substituent(s) or a pyridyl optionally having substituent(s); Ra 1 , Ra 2 , Ra 3 and Ra 4 are the same or different and each is a hydrogen atom, an optionally halogenated C 1-6 alkyl or the like; Ar is a monocyclic aromatic ring optionally having substituent(s); Y is an optionally halogenated alkylene group; and R 1 and R 2 are (1) the same or different and each is a hydrogen atom or a C 1-6 alkyl, (2) R 1 and R 2 form a nitrogen-containing heterocycle optionally having substituent(s) together with the adjacent nitrogen atom, or (3) R 1 and Y form a nitrogen-containing heterocycle optionally having substituent(s) together with the adjacent nitrogen atom, and R 2 is a hydrogen atom or a C 1-6 alkyl; provided that when the nitrogen-containing heterocycle formed by R 1 and R 2 together with the adjacent nitrogen atom is a piperazine, or when R is a C 1-4 alkyl, Ar 1 is a cyclic group having substituent(s), or a salt thereof, having a melanin-concentrating hormone antagonistic action and useful as an agent for the prophylaxis or treatment of obesity and the like.

  本发明提供了一种化合物，其表示为式子： 其中，Ar1是一个环状基团，可以具有取代基；R是氢原子，可选卤代的C1-6烷基，苯环，可以具有取代基，或者吡啶环，可以具有取代基；Ra1，Ra2，Ra3和Ra4相同或不同，每个都是氢原子，可选卤代的C1-6烷基或类似物；Ar是一个单环芳香环，可以具有取代基；Y是可选卤代的脂肪族烷基；R1和R2是（1）相同或不同，每个都是氢原子或C1-6烷基，（2）R1和R2与相邻的氮原子一起形成含氮杂环，可以具有取代基，或（3）R1和Y与相邻的氮原子一起形成含氮杂环，可以具有取代基，并且R2是氢原子或C1-6烷基；但是当R1和R2与相邻的氮原子一起形成哌嗪环，或当R是C1-4烷基，Ar1是具有取代基的环状基团或其盐时，该化合物具有黑色素浓集激素拮抗作用，可用作预防或治疗肥胖症等药物。
• AMINE DERIVATIVE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1593667A1

  公开（公告）日：2005-11-09

  The present invention provides a compound represented by the formula wherein Ar1 is a cyclic group optionally having substituent(s); R is a hydrogen atom, an optionally halogenated C1-6 alkyl, a phenyl optionally having substituent(s) or a pyridyl optionally having substituent(s); Ra1, Ra2, Ra3 and Ra4 are the same or different and each is a hydrogen atom, an optionally halogenated C1-6 alkyl or the like; Ar is a monocyclic aromatic ring optionally having substituent(s); Y is an optionally halogenated alkylene group; and R1 and R2 are (1) the same or different and each is a hydrogen atom or a C1-6 alkyl, (2) R1 and R2 form a nitrogen-containing heterocycle optionally having substituent(s) together with the adjacent nitrogen atom, or (3) R1 and Y form a nitrogen-containing heterocycle optionally having substituent(s) together with the adjacent nitrogen atom, and R2 is a hydrogen atom or a C1-6 alkyl; provided that when the nitrogen-containing heterocycle formed by R1 and R2 together with the adjacent nitrogen atom is a piperazine, or when R is a C1-4 alkyl, Ar1 is a cyclic group having substituent(s), or a salt thereof, having a melanin-concentrating hormone antagonistic action and useful as an agent for the prophylaxis or treatment of obesity and the like.

  本发明提供了一种由式表示的化合物 其中 Ar1 是任选具有取代基的环状基团； R 是氢原子、任选卤化的 C1-6 烷基、任选具有取代基的苯基或任选具有取代基的吡啶基； Ra1、Ra2、Ra3 和 Ra4 相同或不同，各自为氢原子、任选卤代的 C1-6 烷基或类似物； Ar 是单环芳香环，可选择具有取代基； Y 是任选卤代亚烷基；以及 R1 和 R2 (1) 相同或不同，且各自为氢原子或 C1-6 烷基；(2) R1 和 R2 组成含氮杂环，可选择与相邻氮原子一起具有取代基；或 (3) R1 和 Y 组成含氮杂环，可选择与相邻氮原子一起具有取代基，且 R2 为氢原子或 C1-6 烷基； 条件是当 R1 和 R2 与相邻氮原子一起形成的含氮杂环是哌嗪时，或当 R 是 C1-4 烷基时，Ar1 是具有取代基的环状基团或其盐，具有黑色素浓缩激素拮抗作用，可用作预防或治疗肥胖症等的药物。
• Exploring clotrimazole-based pharmacophore: 3D-QSAR studies and synthesis of novel antiplasmodial agents
  作者：Simone Brogi、Margherita Brindisi、Bhupendra P. Joshi、Salvatore Sanna Coccone、Silvia Parapini、Nicoletta Basilico、Ettore Novellino、Giuseppe Campiani、Sandra Gemma、Stefania Butini

  DOI：10.1016/j.bmcl.2015.09.007

  日期：2015.11

  We report herein the generation and validation of a 3D-QSAR model based on a set of antimalarials previously described by us and characterized by a clotrimazole-based pharmacophore. A novel series of derivatives was synthesized and showed activity against Plasmodium falciparum chloroquine-sensitive (CQ-S) and chloroquine-resistant (CQ-R) strains. Gratifyingly, compounds 35a-c showed interesting activity against P. falciparum CQ-R strains with improved predicted physico-chemical properties. (C) 2015 Elsevier Ltd. All rights reserved.
• EP1593667
  申请人：——

  公开号：——

  公开（公告）日：——