(4-氯苯基)[4-(4-吗啉基甲基)苯基]甲酮 | 898769-96-5

• 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-(4-吗啉基甲基)苯基]甲酮
• 英文名称: (4-chlorophenyl){4-[(morpholin-4-yl)methyl]phenyl}methanone
• 英文别名: (4-chloro-phenyl){4-(morpholin-4-ylmethyl)phenyl}methanone；(4-chlorophenyl)[4-(morpholin-4-ylmethyl)phenyl]methanone；4-Chloro-4'-morpholinomethyl benzophenone；(4-chlorophenyl)-[4-(morpholin-4-ylmethyl)phenyl]methanone
• CAS: 898769-96-5
• 化学式: C₁₈H₁₈ClNO₂
• 分子量: 315.799
• InChiKey: XCNWUSCGOXDWMX-UHFFFAOYSA-N

物化性质

• 沸点：
  451.5±45.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (4-氯苯基)[4-(4-吗啉基甲基)苯基]甲酮 在 氯化亚砜 、 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 12.33h， 生成
  参考文献：
  名称：

  Exploring clotrimazole-based pharmacophore: 3D-QSAR studies and synthesis of novel antiplasmodial agents

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2015.09.007
• 作为产物：
  描述：

  吗啉 、 4-(4-chlorobenzoyl)benzyl bromide 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以81%的产率得到(4-氯苯基)[4-(4-吗啉基甲基)苯基]甲酮
  参考文献：
  名称：

  Clotrimazole Scaffold as an Innovative Pharmacophore Towards Potent Antimalarial Agents: Design, Synthesis, and Biological and Structure–Activity Relationship Studies

  摘要：

  We describe herein the design, synthesis, biological evaluation, and structure-activity relationship (SAR) studies of an innovative class of antimalarial agents based on a polyaromatic pharmacophore structurally related to clotrimazole and easy to synthesize by low-cost synthetic procedures. SAR studies delineated a number of structural features able to modulate the in vitro and in vivo antimalarial activity. A selected set of antimalarials was further biologically investigated and displayed low in vitro toxicity on a panel of human and murine cell lines. In vitro, the novel compounds proved to be selective for free heme, as demonstrated in the beta-hematin inhibitory activity assay, and did not show inhibitory activity against 14-alpha-lanosterol demethylase (a fungal P450 cytochrome). Compounds 2, 4e, and 4n exhibited in vivo activity against P. chabaudi after oral administration and thus represent promising antimalarial agents for further preclinical development.

  DOI：

  10.1021/jm701247k

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。
• 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.
• 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.