(Z)-N-3-dihydroxytetrahydrofuran-3-carboximidamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (Z)-N-3-dihydroxytetrahydrofuran-3-carboximidamide
• 英文别名: N-hydroxytetrahydrofuran-3-carboxamidine；N'-hydroxyoxolane-3-carboximidamide
• 化学式: C₅H₁₀N₂O₂
• mdl: MFCD16707085
• 分子量: 130.147
• InChiKey: MQHAXHRKPMZBQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-N-3-dihydroxytetrahydrofuran-3-carboximidamide 、 2-乙酰氨基-4-甲基噻唑-5-甲酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以3%的产率得到N-{4-methyl-5-[3-(tetrahydrofuran-3-yl)-1,2,4-oxadiazol-5-yl]-1,3-thiazol-2-yl}acetamide
  参考文献：
  名称：

  Discovery of N-{5-[3-(3-hydroxypiperidin-1-yl)-1,2,4-oxadiazol-5-yl]-4-methyl-1,3-thiazol-2-yl}acetamide (TASP0415914) as an orally potent phosphoinositide 3-kinase γ inhibitor for the treatment of inflammatory diseases

  摘要：

  Class I phosphoinositide 3-kinases (PI3Ks), particularly PI3K gamma, have become attractive drug targets for inflammatory and autoimmune disorders such as rheumatoid arthritis. Herein, we describe the synthesis and the structure-activity relationships (SAR) of a series of 2-amino-5-oxadiazolyl thiazoles, culminating in the identification of 8j (TASP0415914), an orally potent inhibitor of phosphoinositide 3-kinase gamma (PI3K gamma). TASP0415914 demonstrated good potency in a cell-based assay and, furthermore, exhibited in vivo efficacy in a collagen induced arthritis (CIA) model in mice after oral administration. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.042
• 作为产物：
  描述：

  3-氰基-四氢呋喃 在 羟胺 作用下， 以 industrial methylated spirit 、 水 为溶剂， 反应 16.0h， 生成 (Z)-N-3-dihydroxytetrahydrofuran-3-carboximidamide
  参考文献：
  名称：

  [EN] CYCLOAMINO DERIVATIVES AS GPR119 AGONISTS
  [FR] DÉRIVÉS DE CYCLOAMINO COMME ANTAGONISTES DU GPR119

  摘要：

  公开号：

  WO2011147951A8

文献信息

• [EN] CYCLOAMINO DERIVATIVES AS GPR119 AGONISTS<br/>[FR] DÉRIVÉS DE CYCLOAMINO COMME ANTAGONISTES DU GPR119
  申请人：PROSIDION LTD

  公开号：WO2011147951A8

  公开（公告）日：2012-03-15
• Discovery of N-{5-[3-(3-hydroxypiperidin-1-yl)-1,2,4-oxadiazol-5-yl]-4-methyl-1,3-thiazol-2-yl}acetamide (TASP0415914) as an orally potent phosphoinositide 3-kinase γ inhibitor for the treatment of inflammatory diseases
  作者：Yusuke Oka、Tetsuya Yabuuchi、Takahiro Oi、Shoichi Kuroda、Yasuyuki Fujii、Hidenori Ohtake、Tomoyuki Inoue、Shunichi Wakahara、Kayo Kimura、Kiyoko Fujita、Mayumi Endo、Kyoko Taguchi、Yoshinori Sekiguchi

  DOI：10.1016/j.bmc.2013.10.042

  日期：2013.12

  Class I phosphoinositide 3-kinases (PI3Ks), particularly PI3K gamma, have become attractive drug targets for inflammatory and autoimmune disorders such as rheumatoid arthritis. Herein, we describe the synthesis and the structure-activity relationships (SAR) of a series of 2-amino-5-oxadiazolyl thiazoles, culminating in the identification of 8j (TASP0415914), an orally potent inhibitor of phosphoinositide 3-kinase gamma (PI3K gamma). TASP0415914 demonstrated good potency in a cell-based assay and, furthermore, exhibited in vivo efficacy in a collagen induced arthritis (CIA) model in mice after oral administration. (C) 2013 Elsevier Ltd. All rights reserved.