4-(4,5-dihydrothiazol-2-yl)aniline | 774238-35-6

• 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: 4-(4,5-dihydrothiazol-2-yl)aniline
• 英文别名: 4-(thiazolin-2-yl) aniline；4-(4,5-Dihydro-thiazol-2-yl)-anilin；4-(4,5-dihydrothiazol-2-yl)phenylamine；4-(4,5-dihydro-1,3-thiazol-2-yl)aniline
• CAS: 774238-35-6
• 化学式: C₉H₁₀N₂S
• 分子量: 178.258
• InChiKey: FEAAKKFTSCOBQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4,5-dihydrothiazol-2-yl)aniline 在 盐酸 、 sodium nitrite 、 tin(ll) chloride 、 氢氧化钾 作用下， 以 水 为溶剂， 反应 1.0h， 生成 [4-(4,5-Dihydro-1,3-thiazol-2-yl)phenyl]hydrazine
  参考文献：
  名称：

  EP1612204

  摘要：

  公开号：
• 作为产物：
  描述：

  4-硝基-苯甲酸-(2-溴-乙基酰胺) 在 盐酸 、 tetraphosphorus decasulfide 、 铁粉 作用下， 生成 4-(4,5-dihydrothiazol-2-yl)aniline
  参考文献：
  名称：

  Aminophenyl Thiazolines and Thiazines

  摘要：

  DOI：

  10.1021/ja01290a044

文献信息

• N-Heterocycles Scaffolds as Quorum Sensing Inhibitors. Design, Synthesis, Biological and Docking Studies
  作者：Alfredo Fuentes-Gutiérrez、Everardo Curiel-Quesada、José Correa-Basurto、Alberto Martínez-Muñoz、Alicia Reyes-Arellano

  DOI：10.3390/ijms21249512

  日期：——

  Quorum sensing is a communication system among bacteria to sense the proper time to express their virulence factors. Quorum sensing inhibition is a therapeutic strategy to block bacterial mechanisms of virulence. The aim of this study was to synthesize and evaluate new bioisosteres of N-acyl homoserine lactones as Quorum sensing inhibitors in Chromobacterium violaceum CV026 by quantifying the specific production of violacein. Five series of compounds with different heterocyclic scaffolds were synthesized in good yields: thiazoles, 16a–c, thiazolines 17a–c, benzimidazoles 18a–c, pyridines 19a–c and imidazolines 32a–c. All 15 compounds showed activity as Quorum sensing inhibitors except 16a. Compounds 16b, 17a–c, 18a, 18c, 19c and 32b exhibited activity at concentrations of 10 µM and 100 µM, highlighting the activity of benzimidazole 18a (IC50 = 36.67 µM) and 32b (IC50 = 85.03 µM). Pyridine 19c displayed the best quorum sensing inhibition activity (IC50 = 9.66 µM). Molecular docking simulations were conducted for all test compounds on the Chromobacterium violaceum CviR protein to gain insight into the process of quorum sensing inhibition. The in-silico data reveal that all 15 the compounds have higher affinity for the protein than the native AHL ligand (1). A strong correlation was found between the theoretical and experimental results.

  广义上说，群体感知是细菌之间的一种通信系统，用于感知适当的时间来表达它们的毒力因子。群体感知抑制是一种阻断细菌毒力机制的治疗策略。本研究旨在合成和评估新的N-酰基同源半乳糖酮类生物同构体，作为Chromobacterium violaceum CV026中群体感知抑制剂，通过定量测定紫色素的特定产量。合成了五个不同杂环骨架的化合物系列，产率良好：噻唑类化合物16a–c，噻唑啉类17a–c，苯并咪唑类18a–c，吡啶类19a–c和咪唑啉类32a–c。所有15个化合物都显示出作为群体感知抑制剂的活性，除了16a。化合物16b，17a–c，18a，18c，19c和32b在浓度为10 µM和100 µM时表现出活性，突出显示了苯并咪唑18a（IC50 = 36.67 µM）和32b（IC50 = 85.03 µM）的活性。吡啶19c显示出最佳的群体感知抑制活性（IC50 = 9.66 µM）。对所有测试化合物在Chromobacterium violaceum CviR蛋白上进行了分子对接模拟，以深入了解群体感知抑制的过程。计算机辅助数据显示，所有15个化合物与蛋白的亲和力均高于天然的AHL配体（1）。理论结果与实验结果之间存在较强的相关性。
• A straightforward metal-free synthesis of 2-substituted thiazolines in air
  作者：Michael Trose、Faïma Lazreg、Mathieu Lesieur、Catherine S. J. Cazin

  DOI：10.1039/c5gc00286a

  日期：——

  A range of 2-substituted 4,5-dihydrothiazoles was easily synthesised from the reaction of nitriles with cysteamine in the presence of a catalytic amount of NaOH.

  一系列2-取代的4,5-二氢噻唑易于在催化剂量的NaOH存在下，通过腈与半胱氨酸的反应合成。
• Hydrazone derivative
  申请人：Kawagoe Keiichi

  公开号：US20060276433A1

  公开（公告）日：2006-12-07

  A compound represented by the following formula (I): wherein R 1 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R 2 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R 3 represents hydrogen, etc.; Ar represents a divalent group derived from aromatic hydrocarbon, etc.; X represents a single bond, linear or branched alkylene having from 1 to 3 carbon atoms which may have a substituent, etc.; and G represents halogen, a saturated or unsaturated 5- or 6-membered cyclic hydrocarbon group which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc., a salt thereof or a solvate thereof; and an agent for inhibiting aggregation and/or deposition of an amyloid protein or an amyloid-like protein, which comprises the compound, a salt thereof or a solvate thereof.

  以下是式子（I）所代表的化合物： 其中，R1代表氢、芳基（可能带有取代基）、饱和或不饱和的5-至7-成员杂环基（可能带有取代基）等； R2代表氢、芳基（可能带有取代基）、饱和或不饱和的5-至7-成员杂环基（可能带有取代基）等； R3代表氢等； Ar代表从芳香族碳氢化合物衍生的二价基团等； X代表单键、线性或支链烷基，具有1至3个碳原子，可能带有取代基等； G代表卤素、饱和或不饱和的5-或6-成员环烃基（可能带有取代基）、饱和或不饱和的5-至7-成员杂环基（可能带有取代基）等，其盐或溶剂化物；以及用于抑制淀粉样蛋白或类淀粉样蛋白的聚集和/或沉积的药剂，包括该化合物、其盐或溶剂化物。
• HYDRAZONE DERIVATIVE
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1612204A1

  公开（公告）日：2006-01-04

  A compound represented by the following formula (I): wherein R1 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R2 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R3 represents hydrogen, etc.; Ar represents a divalent group derived from aromatic hydrocarbon, etc.; X represents a single bond, linear or branched alkylene having from 1 to 3 carbon atoms which may have a substituent, etc.; and G represents halogen, a saturated or unsaturated 5- or 6-membered cyclic hydrocarbon group which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc., a salt thereof or a solvate thereof; and an agent for inhibiting aggregation and/or deposition of an amyloid protein or an amyloid-like protein, which comprises the compound, a salt thereof or a solvate thereof

  下式(I)所代表的化合物： 其中 R1 代表氢、可能具有取代基的芳基、可能具有取代基的饱和或不饱和 5 至 7 元杂环基团等；R2 代表氢、可能具有取代基的芳基、可能具有取代基的饱和或不饱和 5 至 7 元杂环基团等；R3 代表氢等。Ar 代表衍生自芳香烃的二价基团等；X 代表具有 1 至 3 个碳原子的单键、线性或支链亚烷基（可具有取代基）等；G 代表卤素、饱和或不饱和的 5 或 6 元环状烃基（可具有取代基）、饱和或不饱和的 5 至 7 元杂环基（可具有取代基）等、一种抑制淀粉样蛋白或类淀粉样蛋白聚集和/或沉积的制剂，其中包括该化合物、其盐或其溶液。
• Wagner; Winkelmann, Arzneimittel-Forschung/Drug Research, 1969, vol. 19, # 5, p. 719 - 730
  作者：Wagner、Winkelmann

  DOI：——

  日期：——