(Piperidin-4-yl)thiourea | 874618-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (Piperidin-4-yl)thiourea
• 英文别名: piperidin-4-ylthiourea
• CAS: 874618-79-8
• 化学式: C₆H₁₃N₃S
• 分子量: 159.255
• InChiKey: NHVCBXQSWYFUBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Piperidin-4-yl)thiourea 、 4,4'-二甲氧基苯酚酯 在 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.17h， 生成 5,5-Bis(4-methoxyphenyl)-3-piperidin-4-yl-2-sulfanylideneimidazolidin-4-one
  参考文献：
  名称：

  Evaluation of Aminohydantoins as a Novel Class of Antimalarial Agents

  摘要：

  Given the threat of drug resistance, there is an acute need for new classes of antimalarial agents that act via a unique mechanism of action relative to currently used drugs. We have identified a set of druglike compounds within the Tres Cantos Anti-Malarial Set (TCAMS) which likely act via inhibition of a Plasmodium aspartic protease. Structure-activity relationship analysis and optimization of these aminohydantoins demonstrate that these compounds are potent nanomolar inhibitors of the Plasmodium aspartic proteases PM-II and PM-IV and likely one or more other Plasmodium aspartic proteases. Incorporation of a bulky group, such as a cyclohexyl group, on the aminohydantion N-3 position gives enhanced antimalarial potency while reducing inhibition of human aspartic proteases such as BACE. We have identified compound 8p (CWHM-117) as a promising lead for optimization as an antimalarial drug with a low molecular weight, modest lipophilicity, oral bioavailability, and in vivo antimalarial activity in mice.

  DOI：

  10.1021/ml400412x

文献信息

• THIA(DIA)ZOLES AS FAST DISSOCIATING DOPAMINE 2 RECEPTOR ANTAGONISTS
  申请人：MacDonald Gregor James

  公开号：US20100120860A1

  公开（公告）日：2010-05-13

  The present invention relates to [1-(benzyl)-piperidin-4-yl]-([1,3,4]thiadiazol-2-yl)-amine and [1-(benzyl)-piperidin-4-yl]-(thiazol-2-yl)-amine derivatives of formula (I) that are fast dissociating dopamine 2 receptor antagonists, processes for preparing these compounds, pharmaceutical compositions comprising these compounds as an active ingredient. The compounds find utility as medicines for treating or preventing central nervous system disorders, for example schizophrenia, by exerting an antipsychotic effect without motor side effects.

  本发明涉及式(I)的[1-(苄基)-哌啶-4-基]-([1,3,4]噻二唑-2-基)-胺和[1-(苄基)-哌啶-4-基]-(噻唑-2-基)-胺衍生物，它们是快速解离的多巴胺2受体拮抗剂，制备这些化合物的方法，以及包含这些化合物作为活性成分的制药组合物。这些化合物可用作治疗或预防中枢神经系统疾病的药物，例如精神分裂症，通过产生抗精神病作用而不产生运动副作用。
• Dimeric Compounds Of Piperidine, Piperazine Or Morpholine Or Their 7-Membered Analogs Suitable For The Treatment Of Neurodegenerative Disorders
  申请人：Cik Miroslav

  公开号：US20070299109A1

  公开（公告）日：2007-12-27

  Formula (I″), the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof.
• US8933101B2
  申请人：——

  公开号：US8933101B2

  公开（公告）日：2015-01-13
• [EN] THIA(DIA)ZOLES AS FAST DISSOCIATING DOPAMINE 2 RECEPTOR ANTAGONISTS<br/>[FR] THIA(DIA)ZOLES EN TANT QU'ANTAGONISTES DU RÉCEPTEUR DE LA DOPAMINE À DISSOCIATION RAPIDE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2008128996A1

  公开（公告）日：2008-10-30

  [EN] The present invention relates to [1- (benzyl) -piperidin-4-yl] -( [1, 3,4] thiadiazol-2-yl) - amine and [1- (benzyl) -piperidin-4-yl] - (thiazol-2-yl) -amine derivatives of formula (I) that are fast dissociating dopamine 2 receptor antagonists, processes for preparing these compounds, pharmaceutical compositions comprising these compounds as an active ingredient. The compounds find utility as medicines for treating or preventing central nervous system disorders, for example schizophrenia, by exerting an antipsychotic effect without motor side effects.
  [FR] Cette invention concerne des dérivés de [1- (benzyl) -pipéridin-4-yl] -( [1, 3,4] thiadiazol-2-yl) - amine et de [1- (benzyl) -pipéridine-4-yl] - (thiazol-2-yl) -amine, représentés par la formule (I), qui sont des antagonistes du récepteur 2 de la dopamine à dissociation rapide, des procédés de préparation de ces composés et des compositions pharmaceutiques contenant ces composés comme principe actif. Ces composés conviennent pour le traitement ou la prévention des troubles du système nerveux central, notamment de la schizophrénie, par l'action anti-psychotique qu'ils exercent sans effets secondaires moteurs.
• Evaluation of Aminohydantoins as a Novel Class of Antimalarial Agents
  作者：Marvin J. Meyers、Micky D. Tortorella、Jing Xu、Limei Qin、Zhengxiang He、Xingfen Lang、Wentian Zeng、Wanwan Xu、Li Qin、Michael J. Prinsen、Francis M. Sverdrup、Christopher S. Eickhoff、David W. Griggs、Jonathan Oliva、Peter G. Ruminski、E. Jon Jacobsen、Mary A. Campbell、David C. Wood、Daniel E. Goldberg、Xiaorong Liu、Yongzhi Lu、Xin Lu、Zhengchao Tu、Xiaoyun Lu、Ke Ding、Xiaoping Chen

  DOI：10.1021/ml400412x

  日期：2014.1.9

  Given the threat of drug resistance, there is an acute need for new classes of antimalarial agents that act via a unique mechanism of action relative to currently used drugs. We have identified a set of druglike compounds within the Tres Cantos Anti-Malarial Set (TCAMS) which likely act via inhibition of a Plasmodium aspartic protease. Structure-activity relationship analysis and optimization of these aminohydantoins demonstrate that these compounds are potent nanomolar inhibitors of the Plasmodium aspartic proteases PM-II and PM-IV and likely one or more other Plasmodium aspartic proteases. Incorporation of a bulky group, such as a cyclohexyl group, on the aminohydantion N-3 position gives enhanced antimalarial potency while reducing inhibition of human aspartic proteases such as BACE. We have identified compound 8p (CWHM-117) as a promising lead for optimization as an antimalarial drug with a low molecular weight, modest lipophilicity, oral bioavailability, and in vivo antimalarial activity in mice.