methyl 2-(2-amino-4,5-dihydrothiazol-4-yl)acetate | 103541-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: methyl 2-(2-amino-4,5-dihydrothiazol-4-yl)acetate
• 英文别名: methyl 2-amino-(2-thiazoline)-4-acetate；Methyl 2-(2-amino-4,5-dihydro-1,3-thiazol-4-yl)acetate
• CAS: 103541-12-4
• 化学式: C₆H₁₀N₂O₂S
• mdl: MFCD02656566
• 分子量: 174.224
• InChiKey: NCZBJXRNJWSONM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  90
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-amino-4,5-dihydrothiazol-4-yl)acetate 在 氢溴酸 作用下， 以 水 为溶剂， 以99%的产率得到2-(2-amino-4,5-dihydrothiazol-4-yl)acetic acid hydrobromide
  参考文献：
  名称：

  Five-Membered N-Heterocyclic Scaffolds as Novel Amino Bioisosteres at γ-Aminobutyric Acid (GABA) Type A Receptors and GABA Transporters

  摘要：

  Given the heterogeneity within the γ-aminobutyric acid (GABA) receptor and transporter families, a detailed insight into the pharmacology is still relatively sparse. To enable studies of the physiological roles governed by specific receptor and transporter subtypes, a series of GABA analogues comprising five-membered nitrogen- and sulfur-containing heterocycles as amine bioisosteres were synthesized and pharmacologically characterized at native and selected recombinant GABA_A receptors and GABA transporters. The dihydrothiazole and imidazoline analogues, 5-7, displayed moderate GAT activities and GABA_A receptor binding affinities in the mid-nanomolar range ( K_i, 90-450 nM). Moreover, they exhibited full and equipotent agonist activity compared to GABA at GABA_A-αβγ receptors but somewhat lower potency as partial agonists at the GABA_A-ρ₁ receptor. Stereoselectivity was observed for compounds 4 and 7 for the GABA_A-αβγ receptors but not the GABA_A-ρ₁ receptor. This study illustrates how subtle differences in these novel amino GABA bioisosteres result in diverse pharmacological profiles in terms of selectivity and efficacy.

  DOI：

  10.1021/acs.jmedchem.9b00026
• 作为产物：
  描述：

  4-溴-2-丁烯酸甲酯 在 碳酸氢钠 、 硫脲 作用下， 以 丙酮 为溶剂， 生成 methyl 2-(2-amino-4,5-dihydrothiazol-4-yl)acetate
  参考文献：
  名称：

  2-(2-amino-2-thiazolin-4-yl)acetic acid

  摘要：

  2-(2-氨基-2-噻唑啉-4-基)乙酸或其药用可接受的酸盐或阳离子盐，可用于从动物（包括人类）中去除过量的某些金属离子，并保护这些动物免受放射性物质的暴露。

  公开号：

  US04582907A1

文献信息

• [EN] NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS<br/>[FR] INHIBITEURS NON NUCLÉOSIDIQUES DE LA TRANSCRIPTASE INVERSE
  申请人：SALK INSTITUITE FOR BIOLOG STU

  公开号：WO2009061856A1

  公开（公告）日：2009-05-14

  Disclosed herein are antiviral agents, in particular non-nucleoside reverse transcriptase inhibitors (NNRTIs) of the formula. Also disclosed are methods of making the NNRTIs, as well as compositions that include such NNRTIs and methods of their use for treating viral infections, in particular retroviral infections, such as HIV infection.

  本文披露了抗病毒药物，特别是式中的非核苷类逆转录酶抑制剂（NNRTIs）。还披露了制备NNRTIs的方法，以及包含这些NNRTIs的组合物和它们用于治疗病毒感染的方法，特别是逆转录病毒感染，如HIV感染。
• Sirtuin modulating compounds
  申请人：Nunes J. Joseph

  公开号：US20070043050A1

  公开（公告）日：2007-02-22

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benfit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了一种新型的调节Sirtuin的化合物及其使用方法。这些Sirtuin调节化合物可用于增加细胞寿命，并治疗和/或预防各种疾病和疾病，包括与衰老或应激相关的疾病或疾病，糖尿病，肥胖症，神经退行性疾病，心血管疾病，血液凝固障碍，炎症，癌症和/或潮红，以及需要增加线粒体活性的疾病或疾病。此外，还提供了包含Sirtuin调节化合物与另一种治疗药物的组合物。
• CAMPBELL, M. M.
  作者：CAMPBELL, M. M.

  DOI：——

  日期：——
• US4582907A
  申请人：——

  公开号：US4582907A

  公开（公告）日：1986-04-15
• US7345178B2
  申请人：——

  公开号：US7345178B2

  公开（公告）日：2008-03-18