4-(tert-butyl)-N-phenylthiazol-2-amine

• 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-(tert-butyl)-N-phenylthiazol-2-amine
• 英文别名: 4-tert-butyl-2-(phenylamino)thiazole；4-tert-butyl-N-phenylthiazol-2-amine；4-tert-butyl-N-phenyl-1,3-thiazol-2-amine
• 化学式: C₁₃H₁₆N₂S
• mdl: MFCD00116797
• 分子量: 232.349
• InChiKey: OZPRKERRJSPXIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-苯酰基-3-苯基硫脲 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.17h， 生成 4-(tert-butyl)-N-phenylthiazol-2-amine
  参考文献：
  名称：

  Optimization of 2-aminothiazole derivatives as CCR4 antagonists

  摘要：

  A series of 2-aminothiazole-derived antagonists of the CCR4 receptor has been synthesized and their affinity for the receptor evaluated using a [I-125]TARC (CCL17) displacement assay. Optimization of these compounds for potency and pharmacokinetic properties led to the discovery of potent, orally bioavailable antagonists. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.126

文献信息

• Small Molecule Library Synthesis Using Segmented Flow
  作者：Christina M. Thompson、Jennifer L. Poole、Jeffrey L. Cross、Irini Akritopoulou-Zanze、Stevan W. Djuric

  DOI：10.3390/molecules16119161

  日期：——

  Flow chemistry has gained considerable recognition as a simple, efficient, and safe technology for the synthesis of many types of organic and inorganic molecules ranging in scope from large complex natural products to silicon nanoparticles. In this paper we describe a method that adapts flow chemistry to the synthesis of libraries of compounds using a fluorous immiscible solvent as a spacer between reactions. The methodology was validated in the synthesis of two small heterocycle containing libraries. The reactions were performed on a 0.2 mmol scale, enabling tens of milligrams of material to be generated in a single 200 mL reaction plug. The methodology allowed library synthesis in half the time of conventional microwave synthesis while maintaining similar yields. The ability to perform multiple, potentially unrelated reactions in a single run is ideal for making small quantities of many different compounds quickly and efficiently.

  流动化学作为一种简便、高效且安全的合成技术，已获得广泛认可，适用于多种有机和无机分子的制备，其规模从复杂的大型天然产物到硅纳米颗粒不等。本文介绍了一种利用流动化学合成化合物库的方法，该方法采用氟烃不溶性溶剂作为反应间的间隔物。我们在合成两个含小杂环的化合物库中验证了该方法。反应规模为0.2毫摩尔，单次200毫升反应插件即可生成数十毫克的物质。与传统微波合成相比，该方法在保持相似产率的同时，将化合物库合成时间缩短了一半。能够在单次运行中进行多个潜在不相关的反应，这为快速高效地制备少量多种不同化合物提供了理想条件。
• Synthesis of 2,4-Disubstituted Thiazoles from (<i>Z</i>)-(2-Acetoxyvinyl)phenyl-λ³-iodanes:  Nucleophilic Substitution of α-λ³-Iodanyl Ketones with Thioureas and Thioamides
  作者：Masahito Ochiai、Yoshio Nishi、Sakiko Hashimoto、Yoshimi Tsuchimoto、Da-Wei Chen

  DOI：10.1021/jo020759o

  日期：2003.10.1

  l-lambda(3)-iodanes react with thioureas or thioamides in MeOH to give 2,4-disubstituted thiazoles directly in good yields. The reaction probably involves generation of highly reactive alpha-lambda(3)-iodanyl ketones through ester exchange of the beta-acetoxy group with liberation of methyl acetate, followed by nucleophilic substitutions with thioureas or thioamides.

  在三乙胺的存在下，（Z）-（2-乙酰氧基-1-烯基）苯基-λ（3）-碘酮与硫脲或硫代酰胺在MeOH中反应，直接以高收率得到2,4-二取代噻唑。该反应可能涉及通过β-乙酰氧基的酯交换与乙酸甲酯的释放，然后用硫脲或硫代酰胺的亲核取代，来生成高反应性的α-lambda（3）-碘基酮。
• Application of Imidazopyridine Derivatives in Regenerative Medicine
  申请人：University of Heidelberg

  公开号：US20200062719A1

  公开（公告）日：2020-02-27

  A method of producing a pluripotent stem cell is provided. The method is comprising contacting a non-pluripotent donor cell obtained from a mammalian donor with a compound characterized by general formulas (1) and (3). Furthermore, methods for inducing OCT4 and NANOG, increasing histone 3 lysine methylation and the maintenance of pluripotency are provided.

  提供了一种制备多能干细胞的方法。该方法包括将从哺乳动物供体获得的非多能干细胞与具有一般式(1)和(3)特征的化合物接触。此外，还提供了诱导OCT4和NANOG，增加组蛋白3赖氨酸甲基化和维持多能性的方法。
• APPLICATION OF IMIDAZOPYRIDINE DERIVATIVES IN REGENERATIVE MEDICINE
  申请人：Universität Heidelberg

  公开号：EP3611256A1

  公开（公告）日：2020-02-19

  A method of producing a pluripotent stem cell is provided. The method is comprising contacting a non-pluripotent donor cell obtained from a mammalian donor with a compound characterized by general formulas (1) and (3). Furthermore, methods for inducing OCT4 and NANOG, increasing histone 3 lysine methylation and the maintenance of pluripotency are provided.

  提供了一种生产多能干细胞的方法。该方法包括将从哺乳动物供体获得的非多能供体细胞与通式（1）和（3）表征的化合物接触。此外，还提供了诱导 OCT4 和 NANOG、增加组蛋白 3 赖氨酸甲基化和维持多能性的方法。
• Modulation of CCR4 function
  申请人：Tularik Inc.

  公开号：US20020173524A1

  公开（公告）日：2002-11-21

  Compounds and compositions are provided that bind to the CCR4 chemokine receptor and which are useful for treating diseases associated with CCR4 activity, such as contact hypersensitivity.

  所提供的化合物和组合物与 CCR4 趋化因子受体结合，可用于治疗与 CCR4 活性相关的疾病，如接触过敏症。