3-chloro-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide | 516451-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-chloro-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide
• 英文别名: 3-chloro-N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]propanamide
• CAS: 516451-70-0
• 化学式: C₁₃H₁₃ClN₂O₂S
• mdl: MFCD03431672
• 分子量: 296.777
• InChiKey: KOFVOPGFGDROLD-UHFFFAOYSA-N

物化性质

• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氨基-1-苄基哌啶 、 3-chloro-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide 在 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以40%的产率得到3-((1-benzylpiperidin-4-yl)amino)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide
  参考文献：
  名称：

  合成，体外测定，分子对接，理论ADMET预测和评估4-甲氧基-苯基噻唑-2-胺衍生物作为乙酰胆碱酯酶抑制剂

  摘要：

  基于所报道化合物的胆碱能假设，N-（4-（4-甲氧基-苯基）噻唑-2-基）-3-（吡咯烷-1-基）丙酰胺对乙酰胆碱酯酶（AChE）具有良好的抑制活性），已设计并合成了作为AChE抑制剂（AChEI）的新型4-甲氧基-苯基噻唑-2-胺衍生物。它们的化学结构已通过质子核磁共振，碳13核磁共振，质谱和红外证实。此外，还通过Ellman分光光度法测试了其对AChE的体外抑制活性，抑制活性测试结果表明，大多数4-甲氧基-苯基噻唑-2-胺衍生物在体外均具有一定的AChE抑制活性。 IC 50化合物5g的（最大最大抑菌浓度）值为5.84μmol/ L，高于参考化合物利凡斯的明。而且，它对丁酰胆碱酯酶几乎没有抑制作用。另外，对化合物5g进行了酶抑制动力学实验，Lineweaver-Burk的V -1- [S] -1双倒数图的结果表明，化合物5g的作用类型为混合抑制类型。此外，化合物5g的AChE抑制活性机

  DOI：

  10.1007/s00044-019-02405-6
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 N,N-二异丙基乙胺 、 copper(ll) bromide 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 13.0h， 生成 3-chloro-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide
  参考文献：
  名称：

  合成，体外测定，分子对接，理论ADMET预测和评估4-甲氧基-苯基噻唑-2-胺衍生物作为乙酰胆碱酯酶抑制剂

  摘要：

  基于所报道化合物的胆碱能假设，N-（4-（4-甲氧基-苯基）噻唑-2-基）-3-（吡咯烷-1-基）丙酰胺对乙酰胆碱酯酶（AChE）具有良好的抑制活性），已设计并合成了作为AChE抑制剂（AChEI）的新型4-甲氧基-苯基噻唑-2-胺衍生物。它们的化学结构已通过质子核磁共振，碳13核磁共振，质谱和红外证实。此外，还通过Ellman分光光度法测试了其对AChE的体外抑制活性，抑制活性测试结果表明，大多数4-甲氧基-苯基噻唑-2-胺衍生物在体外均具有一定的AChE抑制活性。 IC 50化合物5g的（最大最大抑菌浓度）值为5.84μmol/ L，高于参考化合物利凡斯的明。而且，它对丁酰胆碱酯酶几乎没有抑制作用。另外，对化合物5g进行了酶抑制动力学实验，Lineweaver-Burk的V -1- [S] -1双倒数图的结果表明，化合物5g的作用类型为混合抑制类型。此外，化合物5g的AChE抑制活性机

  DOI：

  10.1007/s00044-019-02405-6

文献信息

• Synthesis, physicochemical characterization, cytotoxicity, antimicrobial, anti-inflammatory and psychotropic activity of new N-[1,3-(benzo)thiazol-2-yl]-ω-[3,4-dihydroisoquinolin-2(1H)-yl]alkanamides
  作者：Alla Zablotskaya、Izolda Segal、Athina Geronikaki、Tatiana Eremkina、Sergey Belyakov、Marina Petrova、Irina Shestakova、Liga Zvejniece、Vizma Nikolajeva

  DOI：10.1016/j.ejmech.2013.10.008

  日期：2013.12

  4-dihydroisoquinolin-2(1H)-yl]ethanamide is reported to determine its conformational feature. The investigated compounds were found to be active in psychotropic in vivo, anti-inflammatory in vivo and cytotoxicity in vitro screening. They possess marked sedative action, reveal high anti-inflammatory activity, have selective cytotoxic effects and NO-induction ability concerning tumour cell lines. Some of

  合成了一系列新的N -[（苯并）噻唑-2-基] -2 / 3- [3,4-二氢异喹啉-2（1 H）-基]乙烷/丙酰胺衍生物，并用1 H，13 C表征NMR和IR光谱学和质谱。据报道，N-（1,3-苯并噻唑-2-基）-2- [3,4-二氢异喹啉-2（1 H）-基]乙酰胺的单晶X射线研究确定了其构象特征。发现所研究的化合物在体内具有精神活性，在体内具有抗炎作用，并且在体外具有细胞毒性。筛选。它们具有明显的镇静作用，具有很高的抗炎活性，对肿瘤细胞系具有选择性的细胞毒作用和NO诱导能力。某些合成的化合物显示出抗菌作用。试图使生物学结果与其结构特征和理化参数相关联。已经揭示了合成化合物的活性类型的一些特定组合。
• Synthesis and Biological Evaluation of New 4,5-Disubstituted-Thiazolyl Amides, Derivatives of 4-Hydroxy-Piperidine or of 4-N-Methyl Piperazine
  作者：A. Geronikaki、D. Hadjipavlou-Litina、C. Chatziopoulos、G. Soloupis

  DOI：10.3390/80600472

  日期：——

  4,5-disubstituted-thizolyl amides, derivatives of 4-hydroxy-piperidine and of 4-N-methyl piperazine, were synthesized and tested as anti-inflammatory agents. Log P values were theoretically calculated and experimentally determined. These compounds were tested for antioxidant activity, as hydroxyl radical scavengers and for their ability to interact with stable 1,1-diphenyl-2-picryl hydrazyl free radical

  4,5-二取代-噻唑基酰胺、4-羟基-哌啶和4-N-甲基哌嗪的衍生物被合成并作为抗炎剂进行测试。Log P 值是通过理论计算和实验确定的。测试了这些化合物的抗氧化活性、羟基清除剂以及它们与稳定的 1,1-二苯基-2-苦基肼自由基 (DPPH) 相互作用的能力。使用角叉菜胶诱导的小鼠爪水肿模型研究了合成化合物对炎症的影响。抗炎和抗氧化活性取决于合成化合物的一些结构特征。
• Aminothiazole derivatives with antidegenerative activity on cartilage
  作者：Anna Maria Panico、Athina Geronikaki、Remi Mgonzo、Venera Cardile、Barbara Gentile、Irini Doytchinova

  DOI：10.1016/s0968-0896(03)00149-4

  日期：2003.7

  A series of 2-dialkylamino-N-(4-substituted thiazolyl-2)acetamides and 3-dialkylamino-N-(4-substituted thiazolyl-2)propionamides were synthesized and evaluated for their anti-inflammatory activity. Encouraging results led us to investigate the effect of these compounds on NO production and GAGs release. Their effects were evaluated in vitro on the metabolism of pig cartilage, treated with IL-1beta. The amount of glycosaminoglycans (GAGs) and the production of nitric oxide (NO) in the culture medium were determined. The results, obtained, showed that all compounds, in the presence of IL-1beta, blocked the cartilage breakdown, with different behavior. A quantitative structure-activity relationship (QSAR) study was performed. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis and biological evaluation of new thiazolyl/benzothiazolyl-amides, derivatives of 4-phenyl-piperazine
  作者：Christina Papadopoulou、Athina Geronikaki、Dimitra Hadjipavlou-Litina

  DOI：10.1016/j.farmac.2005.06.014

  日期：2005.11

  A series of thiazolyl-N-phenyl piperazines has been synthesised and tested for anti-inflammatory activity. Their R(M) values were determined as an expression of their lipophilicity. Theoretical calculation of their lipophilicity, as clog P and logPsk also performed. The effect of the synthesised compounds on inflammation, using the carrageenin induced mouse paw oedema model was studied. In general, the studied compounds were found to be potent anti-inflammatory agents (44-74.1%). Anti-inflammatory activity was influenced by some structural characteristics of the synthesised compounds. An attempt was made to correlate their biological activity with some physicochemical parameters using a quantitative structure-activity relationship approach (QSAR).
• Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury
  作者：Lingfeng Chen、Hongjin Chen、Pengqin Chen、Wenxin Zhang、Chao Wu、Chuchu Sun、Wu Luo、Lulu Zheng、Zhiguo Liu、Guang Liang

  DOI：10.1016/j.ejmech.2018.09.068

  日期：2019.1

  Myeloid differentiation primary response protein 88 (MyD88), an essential adapter protein used by toll like receptors (TLR), is a promising target molecule for the treatment of respiratory inflammatory diseases. Previous studies explored the activities of novel 2-amino-4-phenylthiazole analogue (6) in inflammation-induced cancer, and identified the analogue as an inhibitor of MyD88 toll/interleukin-1 receptor (TIR) homology domain dimerization. Here, we describe the synthesis of 47 new analogues by modifying different sites on this lead compound and assessed their anti-inflammatory activities in lipopolysaccharide-induced mouse primary peritoneal macrophages (MPMs). The most promising compound, 15d, was found to effectively interact with MyD88 protein and prevented formation of the MyD88 homodimeric complex. Furthermore, 15d showed in vivo anti-inflammatory activity in LPS-caused model of acute lung injury. This work provides new candidates as MyD88 inhibitors to combat inflammation diseases. (C) 2018 Elsevier Masson SAS. All rights reserved.