5-(3-(trifluoromethyl)benzyl)thiazol-2-amine | 300819-51-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(3-(trifluoromethyl)benzyl)thiazol-2-amine
• 英文别名: 5-(3-Trifluoromethyl-benzyl)-thiazol-2-ylamine；5-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-2-amine
• CAS: 300819-51-6
• 化学式: C₁₁H₉F₃N₂S
• mdl: MFCD00709518
• 分子量: 258.267
• InChiKey: PABVEFOBZBIMQV-UHFFFAOYSA-N

物化性质

• 熔点：
  121-123 °C(Solv: chloroform (67-66-3); carbon tetrachloride (56-23-5))
• 沸点：
  340.5±37.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  5-(3-(trifluoromethyl)benzyl)thiazol-2-amine 在 亚硝酸特丁酯 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 以23%的产率得到2-Bromo-5-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazole
  参考文献：
  名称：

  Novel and potent inhibitors of stearoyl-CoA desaturase-1. Part II: Identification of 4-ethylamino-3-(2-hydroxyethoxy)-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide and its biological evaluation

  摘要：

  The continuing investigation of SAR studies of 3-(2-hydroxyethoxy)-N-(5-benzylthiazol-2-yl)-benzamides as stearoyl-CoA desaturase-1 (SCD-1) inhibitors is reported. Our prior hit-to-lead effort resulted in the identification of 1a as a potent and orally efficacious SCD-1 inhibitor. Further optimization of the structural motif resulted in the identification of 4-ethylamino-3-(2-hydroxyethoxy)-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide (37c) with sub nano molar IC(50) in both murine and human SCD-1 inhibitory assays. This compound demonstrated a dose-dependent decrease in the plasma desaturation index in C57BL/6J mice on a non-fat diet after 7 days of oral administration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.123
• 作为产物：
  描述：

  间三氟甲基重氮氯化物 在 copper dichloride 作用下， 以 乙醇 为溶剂， 生成 5-(3-(trifluoromethyl)benzyl)thiazol-2-amine
  参考文献：
  名称：

  Synthesis and antitumor activities of new N-(5-benzylthiazol-2-yl)-2-(heteryl-5-ylsulfanyl)-acetamides

  摘要：

  DOI：

  10.7124/bc.000971

文献信息

• Synthesis and BK channel-opening activity of 2-amino-1,3-thiazole derivatives
  作者：Xiao-Lei Qi、Heeji Jo、Xue-Ying Wang、Tong-Tong Ji、Hai-Xia Lin、Chul-Seung Park、Yong-Mei Cui

  DOI：10.1016/j.bmcl.2021.128083

  日期：2021.7

  activities in cell-based fluorescence assay and electrophysiological recording. The assay results indicated that the activities of the investigated compounds were influenced by the physicochemical properties of the substituent at benzene ring.

  合成了一系列 2-氨基-5-芳基甲基-或 5-杂芳基甲基-1,3-噻唑衍生物，并在基于细胞的荧光测定和电生理记录中评估了 BK 通道开放活动。测定结果表明，所研究化合物的活性受苯环取代基理化性质的影响。
• [EN] MODULATORS OF MYOCYTE LIPID ACCUMULATION AND INSULIN RESISTANCE AND METHODS OF USE THEREOF<br/>[FR] MODULATEURS D'ACCUMULATION DE LIPIDES DE MYOCYTES ET D'INSULINORÉSISTANCE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2017019772A1

  公开（公告）日：2017-02-02

  Formulations and methods for reducing blood glucose and/or increasing insulin signaling in a subject have been developed. The formulations include SBI-477 and compounds based on SBI-477 i.e., SBI-477 analogs (collectively, SBI-477 compounds) and/or Mondo family inhibitors, in an effective amount to inhibit intracellular lipid accumulation and/or increase cellular glucose uptake when compared to levels in a control subject not administered the composition. Also disclosed are methods of reducing intracellular lipid accumulation and/or increase glucose uptake in a subject in need thereof. The method includes administering to the subject an effective amount of SBI-477 compounds and/or Mondo family inhibitor to reducing intracellular lipid accumulation and/or increase glucose uptake in the subject. Also disclosed are method for treating one or more Myc-driven cancers, including neuroblastoma, lung squamous cell carcinoma/lung adenocarcinoma, liver hepatocellular carcinoma, colon adenocarcinoma, acute myeloid leukemia, and breast invasive carcinoma.

  已开发了用于降低血糖和/或增加受试者胰岛素信号的配方和方法。这些配方包括SBI-477和基于SBI-477的化合物，即SBI-477类似物（统称为SBI-477化合物）和/或Mondo家族抑制剂，以有效量抑制细胞内脂质积累和/或增加细胞葡萄糖摄取，与未施用该组合物的对照受试者相比。还公开了用于减少细胞内脂质积累和/或增加受试者葡萄糖摄取的方法。该方法包括向受试者施用足够量的SBI-477化合物和/或Mondo家族抑制剂，以减少受试者细胞内脂质积累和/或增加葡萄糖摄取。还公开了用于治疗一种或多种Myc驱动的癌症的方法，包括神经母细胞瘤、肺鳞状细胞癌/肺腺癌、肝细胞癌、结肠腺癌、急性髓系白血病和乳腺浸润性癌。
• Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents
  作者：Mariia Mishchenko、Sergiy Shtrygol、Danylo Kaminskyy、Roman Lesyk

  DOI：10.3390/scipharm88010016

  日期：——

  describe the synthesis and anticonvulsant activity of thiazole-bearing hybrids based on 2-imino-4-thiazolidinone and 2,4-dioxothiazolidine-5-carboxylic acid cores. The structure of target compounds was based on the following: (i) A combination of two thiazole cores; (ii) similarity to ralitolin’s structure; (iii) the compliance with structural requirements for the new anticonvulsants. Target compounds

  在这里，我们描述了基于2-亚氨基-4-噻唑烷酮和2,4-二氧噻唑烷-5-羧酸核的噻唑基杂化物的合成和抗惊厥活性。目标化合物的结构基于以下：（i）两个噻唑核的组合；（ii）与雷洛林的结构相似；（iii）符合新抗惊厥药的结构要求。通过已知的方法，基于Knoenavegel反应，烷基化反应和一锅三组分反应，合成目标化合物。在两种不同的模型中评估了化合物的抗惊厥特性-戊四唑诱导的癫痫发作和最大电击癫痫发作测试。在测试的化合物5Z-（3-硝基亚苄基）-2-（噻唑-2-ylimino）-噻唑烷-4-one Ib，2- [2，4-二氧-5-（噻唑-2-基氨基甲酰基甲基）-噻唑烷-3-基] -N-（2-三氟甲基苯基）乙酰胺IId和（2,4-二氧-5-（噻唑-2-基氨基甲酰基亚甲基）-噻唑烷-在这两个模型中，3-yl）乙酸乙酯IIj均显示出优异的抗惊厥活性。讨论了基于SAR方面的化合物修饰的方向。研究结果为
• NRF2 SMALL MOLECULE INHIBITORS FOR CANCER THERAPY
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US20160046616A1

  公开（公告）日：2016-02-18

  Small molecule inhibitors of Nrf2 and methods of their use are provided for treating or preventing a disease, disorder or condition associated with an Nrf2-regulated pathway. The compound can be administered as a single agent or can be administered to enhance the efficacy of a chemotherapeutic drug and/or radiation therapy.

  提供了Nrf2的小分子抑制剂及其使用方法，用于治疗或预防与Nrf2调节通路相关的疾病、疾患或病情。该化合物可以作为单一药剂使用，也可以用于增强化疗药物和/或放射治疗的疗效。
• Modulators of myocyte lipid accumulation and insulin resistance and methods of use thereof
  申请人：Sanford Burnham Prebys Medical Discovery Institute

  公开号：US11028061B2

  公开（公告）日：2021-06-08

  Formulations and methods for reducing blood glucose and/or increasing insulin signaling in a subject have been developed. The formulations include SBI-477 and compounds based on SBI-477 i.e., SBI-477 analogs (collectively, SBI-477 compounds) and/or Mondo family inhibitors, in an effective amount to inhibit intracellular lipid accumulation and/or increase cellular glucose uptake when compared to levels in a control subject not administered the composition. Also disclosed are methods of reducing intracellular lipid accumulation and/or increase glucose uptake in a subject in need thereof. The method includes administering to the subject an effective amount of SBI-477 compounds and/or Mondo family inhibitor to reducing intracellular lipid accumulation and/or increase glucose uptake in the subject. Also disclosed are method for treating one or more Myc-driven cancers, including neuroblastoma, lung squamous cell carcinoma/lung adenocarcinoma, liver hepatocellular carcinoma, colon adenocarcinoma, acute myeloid leukemia, and breast invasive carcinoma.

  用于降低受试者血糖和/或增加胰岛素信号传导的制剂和方法已经研制成功。这些制剂包括SBI-477和基于SBI-477的化合物，即SBI-477类似物（统称为SBI-477化合物）和/或蒙多家族抑制剂，与未施用该组合物的对照组相比，其有效量可抑制细胞内脂质积累和/或增加细胞葡萄糖摄取。还公开了减少有需要的受试者细胞内脂质积累和/或增加葡萄糖摄取的方法。该方法包括向受试者施用有效量的 SBI-477 化合物和/或蒙多家族抑制剂，以减少细胞内脂质积累和/或增加受试者的葡萄糖摄取。还公开了治疗一种或多种Myc驱动的癌症的方法，包括神经母细胞瘤、肺鳞癌/肺腺癌、肝肝细胞癌、结肠腺癌、急性髓性白血病和乳腺浸润性癌。