2-amino-5,6,7,8-tetrahydro-4H-cycloheptathiazole hydroiodide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-amino-5,6,7,8-tetrahydro-4H-cycloheptathiazole hydroiodide
• 英文别名: 5,6,7,8-tetrahydro-4H-cyclohepta[d][1,3]thiazol-3-ium-2-amine;iodide
• 化学式: C₈H₁₂N₂S*HI
• 分子量: 296.175
• InChiKey: XNGUDUZJUSPICK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硫脲 、 环庚酮 在 碘 作用下， 以 乙醇 为溶剂， 以72%的产率得到2-amino-5,6,7,8-tetrahydro-4H-cycloheptathiazole hydroiodide
  参考文献：
  名称：

  2-Aminothiazoles: A new class of agonist allosteric enhancers of A1 adenosine receptors

  摘要：

  This report describes the synthesis and structure-activity relationships of a new class of A(1) adenosine receptor agonist allosteric enhancers, 2-aminothiazolium salts. The EC50 of compounds 6a, 6b, 7, and 8 were 0.3, 4.5, 3.8, and 1.2 muM, substantially lower than that of the 'Gold Standard' 2-amino-3-benzoyl thiophene (PD 81,723), which has an EC50 of 38 muM. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00236-6

文献信息

• Imino-tetrahydro-benzothiazole Derivatives as p53 Inhibitors:  Discovery of a Highly Potent in Vivo Inhibitor and Its Action Mechanism
  作者：Nicolas Pietrancosta、Anice Moumen、Rosanna Dono、Paul Lingor、Veronique Planchamp、Fabienne Lamballe、Mathias Bähr、Jean-Louis Kraus、Flavio Maina

  DOI：10.1021/jm060318n

  日期：2006.6.1

  Several neurological disorders manifest symptoms that result from the degeneration and death of specific neurons. p53 is an important modulator of cell death, and its inhibition could be a therapeutic approach to several neuropathologies. Here, we report the design, synthesis, and biological evaluation of novel p53 inhibitors based on the imino-tetrahydrobenzothiazole scaffold. By performing studies on their mechanism of action, we find that cyclic analogue 4b and its open precursor 2b are more potent than pifithrin-alpha (PFT-R), which is known to block p53 pro-apoptotic activity in vitro and in vivo without acting on other proapoptotic pathways. Using spectroscopic methods, we also demonstrate that open form 2b is more stable than 4b in biological media. Compound 2b is converted into its corresponding active cyclic form through an intramolecular dehydration process and was found two log values more active in vivo than PFT-alpha. Thus, 2b can be considered as a new prodrug prototype that prevents in vivo p53-triggered cell death in several neuropathologies and possibly reduces cancer therapy side effects.