2-Amino-4,5,6,7-tetrahydrobenzoxazole | 2933-42-8

• 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-4,5,6,7-tetrahydrobenzoxazole
• 英文别名: 4,5,6,7-tetrahydro-benzooxazol-2-ylamine；markiertes 2-Amino-4,5-tetramethylenoxazol；2-Amino-3,4,5,6-tetrahydro-benzoxazole；4,5-Tetramethylen-2-aminooxazol；4,5,6,7-Tetrahydro-1,3-benzoxazol-2-amine
• CAS: 2933-42-8
• 化学式: C₇H₁₀N₂O
• 分子量: 138.169
• InChiKey: WHPXIOARQDHUIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Amino-4,5,6,7-tetrahydrobenzoxazole 在 四氯化钛 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 26.5h， 生成 2-(4-Chlorophenyl)-5,6,7,8-tetrahydroimidazo[2,1-b][1,3]benzoxazole
  参考文献：
  名称：

  新型简便的咪唑并[2,1- b ]恶唑类化合物的合成

  摘要：

  利用氯化钛（IV）辅助环化反应，从2-氨基恶唑开发了一种高效，清洁的两步合成咪唑并[ 2,1- b ]恶唑的方法，各种咪唑并[ 2,1- b ]恶唑具有以高收率合成。通过X射线晶体学分析证实了一种产物的结构。

  DOI：

  10.1002/jhet.5570340241
• 作为产物：
  描述：

  环己酮 在 N-溴代丁二酰亚胺(NBS) 、 ammonium acetate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 8.5h， 生成 2-Amino-4,5,6,7-tetrahydrobenzoxazole
  参考文献：
  名称：

  Discovery and hit-to-lead optimization of novel allosteric glucokinase activators

  摘要：

  We report on a hit generation and hit-to-lead program of a novel class of glucokinase activators (GKAs). Hit compounds, activators at low glucose concentration only were identified by vHTS. Scaffold modification reliably afforded activators also at high substrate level. Potency was increased by introduction of a hydrogen bond acceptor as proposed by molecular docking. Replacement of the initial alkylene linkers with a rigid 1,2-phenylene motif followed by further studies eventually furnished a series of potent lead compounds exhibiting steep SAR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.128

文献信息

• Novel p53 Inactivators with Neuroprotective Action:  Syntheses and Pharmacological Evaluation of 2-Imino-2,3,4,5,6,7-hexahydrobenzothiazole and 2-Imino-2,3,4,5,6,7-hexahydrobenzoxazole Derivatives
  作者：Xiaoxiang Zhu、Qian-sheng Yu、Roy G. Cutler、Carsten W. Culmsee、Harold W. Holloway、Debomoy K. Lahiri、Mark P. Mattson、Nigel H. Greig

  DOI：10.1021/jm020044d

  日期：2002.11.1

  feature of several neurodegenerative disorders, including Alzheimer's disease, 2 and novel analogues (3-16) were synthesized to (i) assess the value of tetrahydrobenzothiazole analogues as neuroprotective agents and (ii) define the structural requirements for p53 inactivation. Not only did 2 exhibit neuroprotective activity in both tissue culture and in vivo stroke models but also compounds 6, 7, 10, 13

  肿瘤抑制蛋白p53是一种细胞内蛋白，在生化级联反应中至关重要，可通过凋亡导致细胞死亡。最近的研究确定了四氢苯并噻唑类似物pifithrin-alpha（2）作为p53抑制剂，可有效保护神经元细胞免受各种致命伤害并减少抗癌药物的副作用。由于p53的上调已被描述为包括阿尔茨海默氏病在内的几种神经退行性疾病的共同特征，因此合成了2种和新型类似物（3-16）以（i）评估四氢苯并噻唑类似物作为神经保护剂的价值，以及（ii）定义p53失活的结构要求。不仅2在组织培养和体内中风模型中均表现出神经保护活性，而且化合物6、7、10、13、15
• Thrombin inhibitors
  申请人：——

  公开号：US20030191139A1

  公开（公告）日：2003-10-09

  The invention relates to compounds of formula I D—CO—B—A-Het and pharmaceutically acceptable salts thereof where substituents in description have the specified meanings. The compounds are used as thrombin inhibitors.

  该发明涉及公式I的化合物D—CO—B—A-Het及其药用可接受的盐，其中描述中的取代基具有指定的含义。这些化合物被用作凝血酶抑制剂。
• Action of hydrogen peroxide on some 2-aminooxazoles and imidazolin-2-ones. Isolation of hydroperoxyimidazolidin-2-ones
  作者：M. Ginanneschi、M. Chelli、G. Rapi

  DOI：10.1002/jhet.5570220642

  日期：1985.11

  The reaction of some 2-aminooxazoles and imidazolidin-2-ones with hydrogen peroxide afforded stable trans-β-hydroxyhydroperoxy- or dihydroperoxyimidazolidin-2-ones according to the reaction conditions. In the case of 3a-hydroxy-7a-hydroperoxyoctahydro-2H-benzimidazolidin-2-one, the trans isomer is forbidden and cis adduct was isolated. A radical pathway to these hydroperoxides is proposed. From 2-

  根据反应条件，一些2-氨基恶唑和咪唑烷-2-酮与过氧化氢的反应提供了稳定的反式-β-羟基氢过氧-或二氢过氧咪唑烷-2-酮。在3a-羟基-7a-氢过氧八氢-2 H-苯并咪唑啉-2--2-的情况下，反式异构体被禁止并且顺式加合物被分离。提出了通向这些氢过氧化物的自由基途径。还从2-氨基-4-甲基恶唑和过氧化氢中分离出2-氨基-2-羟基-4-甲基恶唑烷丁-4-基过氧乙酸酯。
• Arylpiperazines as fatty acid transport protein 1 (FATP1) inhibitors with improved potency and pharmacokinetic properties
  作者：Tetsuyoshi Matsufuji、Mika Ikeda、Asuka Naito、Masakazu Hirouchi、Shoichi Kanda、Masanori Izumi、Jun Harada、Tsuyoshi Shinozuka

  DOI：10.1016/j.bmcl.2013.02.116

  日期：2013.5

  The discovery and optimization of a novel series of FATP1 inhibitors are described. Through the derivatization process, arylpiperazine derivatives 5k and 12a were identified as possessing potent in vitro activity against human and mouse FATP1s as well as excellent pharmacokinetic properties. In vivo evaluation of triglyceride accumulation in the liver, white gastrocnemius muscle and soleus is also described. (C) 2013 Elsevier Ltd. All rights reserved.
• GINANNESCHI, M.;CHELLI, M.;RAPI, G., J. HETEROCYCL. CHEM., 1985, 22, N 6, 1675-1678
  作者：GINANNESCHI, M.、CHELLI, M.、RAPI, G.

  DOI：——

  日期：——