3-Amino-1-[2-(pyridin-2-yl)ethyl]thiourea | 76609-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-Amino-1-[2-(pyridin-2-yl)ethyl]thiourea
• 英文别名: 1-amino-3-(2-pyridin-2-ylethyl)thiourea
• CAS: 76609-48-8
• 化学式: C₈H₁₂N₄S
• 分子量: 196.276
• InChiKey: UHPMTSNQAFFPSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-4-phenylpyridine-2-carboxaldehyde 、 3-Amino-1-[2-(pyridin-2-yl)ethyl]thiourea 以 乙醇 为溶剂， 反应 0.5h， 生成 1-[(3-Methyl-4-phenylpyridin-2-yl)methylideneamino]-3-(2-pyridin-2-ylethyl)thiourea
  参考文献：
  名称：

  Rahman, M. F., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 9, p. 828 - 830

  摘要：

  DOI：
• 作为产物：
  描述：

  C₈H₉N₂S₂^(1-)*Na⁽¹⁺⁾ 在 sodium chlorite 、 肼 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 生成 3-Amino-1-[2-(pyridin-2-yl)ethyl]thiourea
  参考文献：
  名称：

  Rahman, M. F., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 9, p. 828 - 830

  摘要：

  DOI：

文献信息

• Antibacterial agents
  申请人：Boyer Earl Frederick

  公开号：US20050288273A1

  公开（公告）日：2005-12-29

  Compounds of formula I and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula I as well as pharmaceutically acceptable compositions comprising compounds of formula I. Compounds of formula I as disclosed herein can be used in a variety of applications including use as antibacterial agents.

  本文披露了I式化合物及其制备方法。此外，还披露了制备具有生物活性的I式化合物的方法，以及包含I式化合物的药学上可接受的组合物的方法。本文所披露的I式化合物可以用于多种应用，包括用作抗菌剂。
• Synthesis and SAR of novel conformationally restricted oxazolidinones possessing Gram-positive and fastidious Gram-negative antibacterial activity. Part 2: Amino substitutions on heterocyclic D-ring system
  作者：Allison L. Choy、J.V.N. Vara Prasad、Frederick E. Boyer、Michael D. Huband、Michael R. Dermyer

  DOI：10.1016/j.bmcl.2007.05.085

  日期：2007.8

  A novel series of conformationally restricted oxazolidinones was synthesized, in which the heterocyclic D ring was substituted with various amino groups. Several analogs exhibited potent activity against both Gram-positive and fastidious Gram-negative organisms. Certain aniino-substituted analogs also exhibited improved aqueous solubility compared to the corresponding un-substituted heterocyclic D-ring analogs.(c) 2007 Elsevier Ltd. All rights reserved.
• Novel selective thiadiazine DYRK1A inhibitor lead scaffold with human pancreatic β-cell proliferation activity
  作者：Kunal Kumar、Peter Man-Un Ung、Peng Wang、Hui Wang、Hailing Li、Mary K. Andrews、Andrew F. Stewart、Avner Schlessinger、Robert J. DeVita

  DOI：10.1016/j.ejmech.2018.08.007

  日期：2018.9

  The Dual-Specificity Tyrosine Phosphorylation-Regulated Kinase 1A (DYRK1A) is an enzyme that has been implicated as an important drug target in various therapeutic areas, including neurological disorders (Down syndrome, Alzheimer's disease), oncology, and diabetes (pancreatic beta-cell expansion). Current small molecule DYRK1A inhibitors are ATP-competitive inhibitors that bind to the kinase in an active conformation. As a result, these inhibitors are promiscuous, resulting in pharmacological side effects that limit their therapeutic applications. None are in clinical trials at this time. In order to identify a new DYRK1A inhibitor scaffold, we constructed a homology model of DYRK1A in an inactive, DFG-out conformation. Virtual screening of 2.2 million lead-like compounds from the ZINC database, followed by in vitro testing of selected 68 compounds revealed 8 hits representing 5 different chemical classes. We chose to focus on one of the hits from the computational screen, thiadiazine I which was found to inhibit DYRK1A with IC50 of 9.41 mu m (K-d = 7.3 mu M). Optimization of the hit compound 1, using structure-activity relationship (SAR) analysis and in vitro testing led to the identification of potent thiadiazine analogs with significantly improved binding as compared to the initial hit (K-d = 71-185 nM). Compound 3-5 induced human beta-cell proliferation at 5 mu M while showing selectivity for DYRK1A over DYRK1B and DYRK2 at 10 mu M. This newly developed DYRK1A inhibitor scaffold with unique kinase selectivity profiles has potential to be further optimized as novel therapeutics for diabetes. (C) 2018 Published by Elsevier Masson SAS.
• RAHMAN M. F., INDIAN J. CHEM., 1980, B19, NO 9, 828-830
  作者：RAHMAN M. F.

  DOI：——

  日期：——
• US06008362
  申请人：——

  公开号：——

  公开（公告）日：——