thiazolo[5,4-f ]quinazolin-9(8H)-one

• 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: thiazolo[5,4-f ]quinazolin-9(8H)-one
• 英文别名: 8H-thiazolo[5,4-f]quinazolin-9-one；thiazolo[5,4-f]quinazolin-9(8H)one；8h-Thiazolo[5,4-f]quinazolin-9-one；8H-[1,3]thiazolo[5,4-f]quinazolin-9-one
• 化学式: C₉H₅N₃OS
• 分子量: 203.224
• InChiKey: VVOGXEBGRUKPTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 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：
  82.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(((2R,3S),2-(2,4-二氟苯基)-3-甲基环氧乙烷-2-基)甲基)-1H-1,2,4-三唑 、 thiazolo[5,4-f ]quinazolin-9(8H)-one 在 N-甲基吡咯烷酮 、 potassium carbonate 作用下， 反应 72.0h， 以45%的产率得到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：

  2-氰基-4-硝基苯胺 在 吡啶 、 盐酸 、 溴 、 sodium hydride 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 22.0h， 生成 thiazolo[5,4-f ]quinazolin-9(8H)-one
  参考文献：
  名称：

  Multistep synthesis of thiazoloquinazolines under microwave irradiation in solution

  摘要：

  Thiazolo[5,4-f]quinazolines are synthesised in six or seven steps from 2-amino-5-nitrobenzonitrile. Both heterocyclic rings are fused onto the central benzene ring via imino-1,2,3-dithiazoles which are readily obtained from primary aromatic amines and 4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt). Four of the steps were improved in yield or reaction time or both, compared to conventional heating, by microwave irradiation of solutions of the reactants in a focused open microwave oven. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02221-2

文献信息

• Novel synthesis of angular thiazolo[5,4-f] and [4,5-h]quinazolines, preparation of their linear thiazolo[4,5-g] and [5,4-g]quinazoline analogs
  作者：Damien Hédou、Rémi Guillon、Charlotte Lecointe、Cédric Logé、Elizabeth Chosson、Thierry Besson

  DOI：10.1016/j.tet.2013.02.066

  日期：2013.4

  Synthesis of 9-oxo-8,9-dihydrothiazolo[5,4-f]quinazoline-2-carbonitrile (1) or 6-oxo-6,7-dihydrothiazolo[4,5-h]quinazoline-2-carbonitrile (2) was reinvestigated with the ambition of varying the position of the thiazole ring linked to the quinazolin-4-one moiety, in order to synthesize two novel linear tricyclic 8-oxo-7,8-dihydrothiazolo[4,5-g]quinazoline-2-carbonitrile (3) and 8-oxo-7,8-dihydrothiazolo[5

  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。
• 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。
• Efficient synthesis of thiazoloquinazolinone derivatives
  作者：François-René Alexandre、Amaya Berecibar、Roger Wrigglesworth、Thierry Besson

  DOI：10.1016/s0040-4039(03)01026-8

  日期：2003.6

  An original route to the rare 8H-thiazolo[5,4-f]quinazolin-9-one 1 and the novel 7H-thiazolo[4,5-h]quinazolin-6-one 2 is described. Access to the regioisomers was realized by fusion of a thiazole and a quinazoline ring via Appel's salt chemistry. Thermal reactions were carried Out using a focused microwave reactor. reducing the overall time of the multi-step synthesis. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 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.