N-(4-(4-chlorophenyl)thiazol-2-yl)cinnamic acid amide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-(4-(4-chlorophenyl)thiazol-2-yl)cinnamic acid amide
• 英文别名: (E)-N-(4-(p-chlorophenyl)thiazol-2-yl)cinnamamide；N-[4-(4-chlorophenyl)thiazol-2-yl]-3-phenylacrylamide；N-(4-(4-chlorophenyl)thiazol-2-yl)cinnamamide；(E)-N-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-3-phenylprop-2-enamide
• 化学式: C₁₈H₁₃ClN₂OS
• 分子量: 340.833
• InChiKey: JSXNIUIBVUVOJT-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-(4-chlorophenyl)thiazol-2-yl)cinnamic acid amide 在 四氯苯醌 、 三乙胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醚 、 二氯甲烷 为溶剂， 生成 N-(4-(p-chlorophenyl)thiazol-2-yl)-4'-phenyl-1'H-pyrazole-3'-carboxamide
  参考文献：
  名称：

  Synthesis and antimicrobial activity of amido linked pyrrolyl and pyrazolyl-oxazoles, thiazoles and imidazoles

  摘要：

  A new class of amido linked bis heterocycles viz., pyrrolyl/pyrazolyl-oxazoles, thiazoles and imidazoles were prepared by 1,3-dipolar cycloaddition of TosMIC and diazomethane to the respective cinnamamide derivatives and screened for antimicrobial activity. The chlorosubstituted imidazolyl cinnamamide (6c) is the most potential antimicrobial agent as it displayed strong antibacterial activity against Bacillus subtilis and antifungal activity against Penicillium chrysogenum. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.032
• 作为产物：
  描述：

  2-氨基-4-(4-氯苯基)噻唑 、 3-苯基-2-丙烯酰氯 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以81%的产率得到N-(4-(4-chlorophenyl)thiazol-2-yl)cinnamic acid amide
  参考文献：
  名称：

  SPHINGOSINE KINASE INHIBITORS AND METHODS OF THEIR USE

  摘要：

  这项发明涉及化合物、其药物组合物以及抑制鞘氨醇激酶并治疗或预防过度增殖性疾病、炎症性疾病或血管生成性疾病的方法。

  公开号：

  US20070032531A1

文献信息

• SPHINGOSINE KINASE INHIBITORS AND METHODS OF THEIR USE
  申请人：Smith D. Charles

  公开号：US20070032531A1

  公开（公告）日：2007-02-08

  The invention relates to compounds, pharmaceutical compositions thereof, and methods for inhibiting sphingosine kinase and for treating or preventing hyperproliferative disease, inflammatory disease, or angiogenic disease,

  这项发明涉及化合物、其药物组合物以及抑制鞘氨醇激酶并治疗或预防过度增殖性疾病、炎症性疾病或血管生成性疾病的方法。
• 4-(4-Chlorophenyl)thiazol-2-amines as pioneers of potential neurodegenerative therapeutics with anti-inflammatory properties based on dual DNase I and 5-LO inhibition
  作者：Andrija Smelcerovic、Aleksandra Zivkovic、Budimir S. Ilic、Ana Kolarevic、Bettina Hofmann、Dieter Steinhilber、Holger Stark

  DOI：10.1016/j.bioorg.2019.103528

  日期：2020.1

  5-LO inhibitors with nanomolar IC50 values obtained in cell-free assay, with compound 20 being the most potent (IC50 = 50 nM). Molecular docking and molecular dynamics simulations into the binding site of 5-LO enzyme allowed us to clarify the binding mode of these dual DNase I/5-LO inhibitors. It was shown that compounds 18-20 uniquely show interactions with histidine residues in the catalytic site

  合成了11种新的4-（4-氯苯基）噻唑-2-胺，并与9种已知衍生物一起在体外评估了对牛胰腺DNase I的抑制特性。三种化合物（18-20）抑制DNase I的IC50值均低于100 µM，其中化合物19最有效（IC50 = 79.79 µM）。在没有“黄金标准”的情况下用作阳性对照的结晶紫显示出几乎弱了5倍的DNase I抑制作用。Pharma / E-State RQSAR模型阐明了与DNase I抑制有关的关键结构片段。分子对接和分子动力学模拟定义了4-（4-氯苯基）噻唑-2-胺与DNase I最重要的催化残基的相互作用。基于配体的药效团建模和虚拟筛选证实了DNase I抑制所需的4-（4-氯苯基）噻唑-2-胺的化学特征，并证明在可用数据库中不存在结构相似的分子。化合物18-20已显示为非常有效的5-LO抑制剂，在无细胞试验中具有纳摩尔IC50值，其中化合物20最有效（IC50 = 50
• Sphingosine Kinase Inhibitors and Methods of Their Use
  申请人：Smith Charles D.

  公开号：US20100137315A1

  公开（公告）日：2010-06-03

  The invention relates to compounds, pharmaceutical compositions thereof, and methods for inhibiting sphingosine kinase and for treating or preventing hyperproliferative disease, inflammatory disease, or angiogenic disease.

  该发明涉及化合物，其制药组合物以及抑制鞘氨醇激酶和治疗或预防过度增生性疾病，炎症性疾病或血管生成性疾病的方法。
• Treatment Of Ischemia-Reperfusion Injury
  申请人：Smith Charles D.

  公开号：US20120122870A1

  公开（公告）日：2012-05-17

  Ischemia-reperfusion injury remains a primary cause of morbidity and mortality in individuals who experience disruption of normal blood flow to one or more major organs. For example, there are no clinically proven strategies that prevent acute renal failure following cardiac surgery. The present invention provides a variety of methods for the treatment or prevention of ischemia-reperfusion injury. In one aspect of the invention, a method for treating or preventing ischemia-reperfusion injury includes administering to a subject an effective amount of a sphingosine kinase inhibitor. Sphingosine kinase inhibitors are very effective in the protection against IR-induced acute renal failure and liver failure. Moreover, the effects occur very early after administration, requiring only a very short time of treatment. Toxicology studies with sphingosine kinase inhibitors demonstrate that they have low toxicity, even in long-term treatment.
• [EN] SPHINGOSINE KINASE INHIBITORS AND METHODS OF THEIR USE<br/>[FR] INHIBITEURS DE LA SPHINGOSINE KINASE ET LEURS METHODES D'UTILISATION
  申请人：APOGEE BIOTECHNOLOGY CORP

  公开号：WO2007019251A2

  公开（公告）日：2007-02-15

  (EN) The invention relates to compounds, pharmaceutical compositions thereof, and methods for inhibiting sphingosine kinase and for treating or preventing hyperproliferative disease, inflammatory disease, or angiogenic disease.(FR) L'invention concerne des composés, des compositions pharmaceutiques contenant ces composés, ainsi que des méthodes destinées à l'inhibition de la sphingosine kinase et au traitement ou à la prévention de maladies hyperprolifératives, inflammatoires ou angiogéniques.