9-oxo-8,9-dihydrothiazolo[5,4-f]quinazoline-2-carbonitrile | 1420990-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 9-oxo-8,9-dihydrothiazolo[5,4-f]quinazoline-2-carbonitrile
• 英文别名: 9-oxo-8H-[1,3]thiazolo[5,4-f]quinazoline-2-carbonitrile
• CAS: 1420990-57-3
• 化学式: C₁₀H₄N₄OS
• 分子量: 228.234
• InChiKey: ZNLPLIPPERRXEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-oxo-8,9-dihydrothiazolo[5,4-f]quinazoline-2-carbonitrile 在 N-甲基吡咯烷酮 、 氢溴酸 、 potassium carbonate 作用下， 反应 72.5h， 生成 8-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1,2,4-triazol-1-yl)propyl]thiazolo[5,4-f]quinazolin-9-one
  参考文献：
  名称：

  发现一种源自阿尔巴康唑的新型广谱抗真菌剂。

  摘要：

  严格合成阿尔巴康唑的结构类似物，其中喹唑啉酮环被噻唑部分稠合，导致发现了具有广谱抗真菌活性的新三唑。化合物I对致病性念珠菌和丝状真菌表现出很高的体外活性，并且在系统性念珠菌病小鼠模型中显示出初步的体内抗真菌功效。

  DOI：

  10.1021/ml300429p
• 作为产物：
  描述：

  6-硝基喹唑啉-4(3H)-酮 在 吡啶 、 aluminum (III) chloride 、 copper(l) iodide 、 palladium 10% on activated carbon 、 溴 、 甲酸铵 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0~140.0 ℃ 、101.33 kPa 条件下， 反应 6.58h， 生成 9-oxo-8,9-dihydrothiazolo[5,4-f]quinazoline-2-carbonitrile
  参考文献：
  名称：

  角噻唑并[5,4- f ]和[4,5- h ]喹唑啉的新型合成，其线性噻唑并[4,5- g ]和[5,4- g ]喹唑啉类似物的制备

  摘要：

  9-氧代8,9-二氢噻唑[5,4- f ]喹唑啉-2-腈（1）或6-氧代6,7-二氢噻唑[4,5 - h ]喹唑啉-2-腈（2）的合成）进行了重新研究，目的是改变与喹唑啉4-one部分相连的噻唑环的位置，以便合成两个新颖的线性三环式8-氧代-7,8-二氢噻唑并[4,5- g ]喹唑啉- 2-甲腈（3）和8-氧代7,8-二氢噻唑并[5,4 - g ]喹唑啉-2-甲腈（4）。本文描述的途径为获得有效的生物活性杂环化合物文库提供了各种替代和转化途径。

  DOI：

  10.1016/j.tet.2013.02.066

文献信息

• Photocatalyst-Free Visible Light-Mediated C-H Perfluoroalkylation of Quinazolin-4(3H)-ones with perfluoroalkyl iodides
  作者：Thomas Delouche、Abdoul Gadiry-Diallo、Thierry Besson、Sensuke Ogoshi、Corinne Fruit

  DOI：10.1055/a-2054-0482

  日期：——

  A practical and sustainable photocatalyst-free protocol for photo-induced synthesis of perfluoroalkylated quinazolin-4(3H)-ones is described starting from quinazolin-4(3H)-ones. A wide range of substituted or fused-quinazolinones is found to be compatible, providing the corresponding mono- and bis-perfluoroalkylated compounds in moderate yields. This visible-light mediated C-H perfluoroalkylation allows an environmentally friendly and straightforward access to an array of unprecedented functionalized quinazolinone scaffolds, presenting attractive features for drug discovery. The control experiments demonstrated that a radical mechanism is involved in the reaction mechanism.

  介绍了一种实用的、可持续的、不含光催化剂的光诱导合成全氟烷基化喹唑啉-4(3H)-酮的方法，该方法从喹唑啉-4(3H)-酮开始。该方法可兼容多种取代或融合的喹唑啉酮，并能以中等产率提供相应的单-全氟烷基化和双-全氟烷基化化合物。这种以可见光为介质的 C-H 全氟烷基化反应允许以环境友好的方式直接获得一系列前所未有的官能化喹唑啉酮支架，为药物发现提供了极具吸引力的特征。对照实验表明，反应机理涉及自由基机制。

• Maturation of hepatocyte-like cells derived from human pluripotent stem cells
  申请人：Takara Bio Europe AB

  公开号：US10294457B2

  公开（公告）日：2019-05-21

  The present invention relates to directed differentiation and maturation of hepatocyte-like cells. In particular, the present invention relates to exposure of hepatocyte-like cells to an activator of a retinoic acid responsive receptor, such as retinoic acid (RA), optionally in combination with an inhibitor of GSK-3 (Glycogen synthase kinase 3) or activator of Wnt signalling and/or with the overlay of the cells with one or more components characteristic of the mammalian extracellular matrix (matrix overlay). The present invention also relates to exposure of hepatocyte-like cells to an activator of a retinoic acid responsive receptor, such as retinoic acid (RA), optionally in combination with an inhibitor of a cycline dependent kinase (CDK) and/or with the overlay of the cells with one or more components characteristic of the mammalian extracellular matrix (matrix overlay). The hepatocyte-like cells obtained in accordance with the present invention show a phenotype which is more similar to that of primary hepatocytes than previously shown.

  本发明涉及肝细胞样细胞的定向分化和成熟。特别是，本发明涉及将肝细胞样细胞暴露于视黄酸反应受体的激活剂，如视黄酸（RA），可选择与 GSK-3（糖原合酶激酶 3）抑制剂或 Wnt 信号激活剂结合使用，和/或将细胞与哺乳动物细胞外基质的一种或多种特征成分（基质覆盖）结合使用。本发明还涉及将肝细胞样细胞暴露于视黄酸反应受体的激活剂，如视黄酸（RA），可选择与细胞周期依赖性激酶（CDK）抑制剂结合使用，和/或将细胞与哺乳动物细胞外基质的一种或多种特征成分覆盖（基质覆盖）。根据本发明获得的肝细胞样细胞显示出的表型比以前显示的更类似于原代肝细胞的表型。
• MATURATION OF HEPATOCYTE-LIKE CELLS DERIVED FROM HUMAN PLURIPOTENT STEM CELLS
  申请人：Takara Bio Europe AB

  公开号：EP2925859A1

  公开（公告）日：2015-10-07
• [EN] MATURATION OF HEPATOCYTE-LIKE CELLS DERIVED FROM HUMAN PLURIPOTENT STEM CELLS<br/>[FR] MATURATION DE CELLULES DE TYPE HÉPATOCYTE DÉRIVÉES DE CELLULES SOUCHES PLURIPOTENTES HUMAINES
  申请人：CELLECTIS SA

  公开号：WO2014083132A1

  公开（公告）日：2014-06-05

  The present invention relates to directed differentiation and maturation of hepatocyte-like cells. In particular, the present invention relates to exposure of hepatocyte-like cells to an activator of a retinoic acid responsive receptor, such as retinoic acid (RA), optionally in combination with an inhibitor of GSK-3 (Glycogen synthase kinase 3) or activator of Wnt signalling and/or with the overlay of the cells with one or more components characteristic of the mammalian extracellular matrix (matrix overlay).The present invention also relates to exposure of hepatocyte-like cells to an activator of a retinoic acid responsive receptor, such as retinoic acid (RA), optionally in combination with an inhibitor of a cycline dependent kinase (CDK) and/or with the overlay of the cells with one or more components characteristic of the mammalian extracellular matrix (matrix overlay). The hepatocyte-like cells obtained in accordance with the present invention show a phenotype which is more similar to that of primary hepatocytes than previously shown.