4-ethoxycarbonylthiazole-2-yl isocyanate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-ethoxycarbonylthiazole-2-yl isocyanate
• 英文别名: ethyl 2-isocyanato-1,3-thiazole-4-carboxylate
• 化学式: C₇H₆N₂O₃S
• 分子量: 198.202
• InChiKey: JPJCLPMBKVNSBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-ethoxycarbonylthiazole-2-yl isocyanate 、 1,2,4-三甲氧基苯 在 四氯化锡 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以70%的产率得到2-[(2,4,5-三甲氧基苯甲酰基)氨基]-4-噻唑羧酸乙酯
  参考文献：
  名称：

  EP1489073

  摘要：

  公开号：
• 作为产物：
  描述：

  光气 、 2-氨基噻唑-4-甲酸乙酯 在 N,N-二甲基甲酰胺 氮气 、 氯苯 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以to yield 16.9 g of the title compound, where the purity was 80%的产率得到4-ethoxycarbonylthiazole-2-yl isocyanate
  参考文献：
  名称：

  Process for preparation of alkoxybenzamides and thiazolyl isocyanates

  摘要：

  通式（3）表示的烷氧基苯甲酰胺：（其中R1、R2、R3、R4和R5独立地表示氢原子、具有1至6个碳原子的烷基或具有1至6个碳原子的烷氧基；如果R3表示氢原子或具有1至6个碳原子的烷基，则R1表示具有1至6个碳原子的烷氧基，R4表示具有1至6个碳原子的烷基或烷氧基；两个相邻的取代基可以与交联基耦合形成环；R6表示杂环芳烃环；A表示氧原子或硫原子），通过在路易斯酸的存在下将通式（1）表示的烷氧基苯与通式（2）表示的异氰酸酯反应而制得：（其中R1、R2、R3、R4、R5、R6和A的定义如上；n表示1或2）。通式（2）表示的异氰酸酯中包括通式（5）表示的噻唑基异氰酸酯：（其中R1表示氢原子、具有1至6个碳原子的饱和或不饱和烷基、具有1至6个碳原子的卤代烷基、具有1至6个碳原子的烷氧基、烷氧羰基、或酰基；R2表示氢原子、卤素原子、具有1至6个碳原子的饱和或不饱和烷基、具有1至6个碳原子的卤代烷基、具有1至6个碳原子的烷氧羰基、酰基或取代或未取代的苯基；R1和R2均不表示氢原子；n表示1或2）。该噻唑基异氰酸酯由两个前体物质产生：氨基噻唑和羰基卤化物。本发明可以提供一种生产高产率烷氧基苯甲酰胺的方法，步骤更少，也可以提供噻唑基异氰酸酯，其在尿素、氨基甲酸酯和带有噻唑环的芳香酰胺的生产中有用。

  公开号：

  US20050143581A1

文献信息

• PROCESS FORPREPARATION OF ALKOXYBENZAMIDES AND THIAZOLYL ISOCYANATES
  申请人：MITSUI CHEMICALS, INC.

  公开号：EP1489073A1

  公开（公告）日：2004-12-22

  An alkoxybenzamide represented by the general formula (3): (wherein R1, R2, R3, R4, and R5 independently indicate a hydrogen atom, an alkyl group having one to six carbon atoms, or an alkoxy group having one to six carbon atoms; if R3 indicates a hydrogen atom or an alkyl group having one to six carbon atoms, R1 indicates an alkoxy group having one to six carbon atoms and R4 indicates an alkyl or alkoxy group having one to six carbon atoms; two adjacent substituents may be coupled with a cross-linking group to form a ring; R6 indicates a heteroaromatic ring; and A indicates an oxygen atom or a sulfur atom) is produced by reacting an alkoxybenzene represented by the general formula (1): (wherein R1, R2, R3, R4, and R5 are defined above) with an isocyanate represented by the general formula (2):         R6―N=C=A     (2) (wherein R6 and A are defined above; and n indicates 1 or 2) in the presence of a Lewis acid. Among isocyanates represented by the general formula (2) is a thiazolyl isocyanate represented by the general formula (5): (wherein R1 indicates a hydrogen atom, a saturated or unsaturated alkyl group having one to six carbon atoms, a haloalkyl group having one to six carbon atoms, an alkoxy group having one to six carbon atoms, an alkoxycarbonyl group, or an acyl group; R2 indicates a hydrogen atom, a halogen atom, a saturated or unsaturated alkyl group having one to six carbon atoms, a haloalkyl group having one to six carbon atoms, an alkoxycarbonyl group having one to six carbon atoms, an acyl group, or a substituted or unsubstituted phenyl group; both R1 and R2 do not indicate a hydrogen atom; and n indicates 1 or 2). This thiazolyl isocyanate is produced from two precursors: an aminothiazole and a carbonyl halide. The present invention can provide a method for producing a high yield of alkoxybenzamide with fewer steps, and can also provide thiazolyl isocyanates, which are useful in the production of ureas, carbamates, and aromatic amides having a thiazole ring.

  由通式(3)代表的烷氧基苯甲酰胺： (其中 R1、R2、R3、R4 和 R5 分别独立地表示氢原子、具有 1 至 6 个碳原子的烷基或具有 1 至 6 个碳原子的烷氧基；如果 R3 表示氢原子或具有 1 至 6 个碳原子的烷基，R1 表示具有 1 至 6 个碳原子的烷氧基，R4 表示具有 1 至 6 个碳原子的烷基或烷氧基；相邻的两个取代基可与交联基团结合形成环；R6 表示杂芳香环；A 表示氧原子或硫原子）通过与通式（1）所代表的烷氧基苯反应而制得： (其中 R1、R2、R3、R4 和 R5 如上定义）与通式(2)所代表的异氰酸酯反应而制得： R6-N=C=A (2) (其中 R6 和 A 如上定义；n 表示 1 或 2）在路易斯酸存在下进行反应。在通式（2）所代表的异氰酸酯中，有通式（5）所代表的噻唑基异氰酸酯： (其中 R1 表示氢原子、具有 1 至 6 个碳原子的饱和或不饱和烷基、具有 1 至 6 个碳原子的卤代烷基、具有 1 至 6 个碳原子的烷氧基、烷氧羰基或酰基；R2 表示氢原子、卤素原子、具有 1 至 6 个碳原子的饱和或不饱和烷基、具有 1 至 6 个碳原子的卤代烷基、具有 1 至 6 个碳原子的烷氧羰基、酰基或取代或未取代的苯基；R1 和 R2 均不表示氢原子；n 表示 1 或 2）。这种噻唑基异氰酸酯由两种前体生成：氨基噻唑和羰基卤化物。本发明可以提供一种以较少步骤生产高产率烷氧基苯甲酰胺的方法，还可以提供噻唑基异氰酸酯，这种异氰酸酯可用于生产具有噻唑环的脲类、氨基甲酸酯和芳香族酰胺。
• Diarylurea derivatives comprising 2,4-diarylpyrimidines: Discovery of novel potential anticancer agents via combined failed-ligands repurposing and molecular hybridization approaches
  作者：Ahmed Karam Farag、Ahmed H.E. Hassan、Kyung-Sook Chung、Jeong-Hun Lee、Hyo-Sun Gil、Kyung-Tae Lee、Eun Joo Roh

  DOI：10.1016/j.bioorg.2020.104121

  日期：2020.10

  A series of diarylurea derivatives comprising 2,4-diarylpyrimidines were synthesized based on a combination of postulated molecular hybridization design and failed-ligands repurposing approaches, which enabled the discovery of novel potential antiproliferative agents. Towards credible biological evaluation, an in vitro anticancer activity assay was conducted employing a library of 60 cancer cell lines constituting nine panels representing blood, lung, colon, CNS, skin, ovary, renal, prostate, and breast cancers. The results revealed high effectiveness and broad-spectrum anticancer activity of compounds 4m and 4g. Five-dose assay of compounds 4m and 4g proved their high potency that surpassed that of four standard kinase inhibitors FDA-approved anticancer drugs against many cancer cells. Towards the identification of their molecular target, screening of kinase inhibitory profile employing a panel of 51 kinases involved in cancer revealed inhibition of several kinases from the platelet-derived growth factor/vascular endothelial growth factor receptor (PVR) kinase family, which might mediate, at least in part, the antiproliferative activity. Molecular docking of 4g into the crystal structure of the Feline McDonough Sarcoma (FMS) kinase predicted that it binds to a pocket formed by the juxtamembrane domain, the catalytic loop, and the aE helix, thus stabilizing the inhibited conformation of the kinase. Flow cytometric study of the cytotoxic effects of compound 4g in A549 cells showed it induces dose- and timedependent apoptotic events leading to cell death. Collectively, this work presents compound 4g as a potential broad-spectrum anticancer agent against multiple cancer types.
• EP1489073
  申请人：——

  公开号：——

  公开（公告）日：——
• Process for preparation of alkoxybenzamides and thiazolyl isocyanates
  申请人：Awano Hirokazu

  公开号：US20050143581A1

  公开（公告）日：2005-06-30

  An alkoxybenzamide represented by the general formula (3): (wherein R1, R2, R3, R4, and R5 independently indicate a hydrogen atom, an alkyl group having one to six carbon atoms, or an alkoxy group having one to six carbon atoms; if R3 indicates a hydrogen atom or an alkyl group having one to six carbon atoms, R1 indicates an alkoxy group having one to six carbon atoms and R4 indicates an alkyl or alkoxy group having one to six carbon atoms; two adjacent substituents may be coupled with a cross-linking group to form a ring; R6 indicates a heteroaromatic ring; and A indicates an oxygen atom or a sulfur atom) is produced by reacting an alkoxybenzene represented by the general formula (1): (wherein R1, R2, R3, R4, and R5 are defined above) with an isocyanate represented by the general formula (2): (wherein R6 and A are defined above; and n indicates 1 or 2) in the presence of a Lewis acid. Among isocyanates represented by the general formula (2) is a thiazolyl isocyanate represented by the general formula (5): (wherein R1 indicates a hydrogen atom, a saturated or unsaturated alkyl group having one to six carbon atoms, a haloalkyl group having one to six carbon atoms, an alkoxy group having one to six carbon atoms, an alkoxycarbonyl group, or an acyl group; R2 indicates a hydrogen atom, a halogen atom, a saturated or unsaturated alkyl group having one to six carbon atoms, a haloalkyl group having one to six carbon atoms, an alkoxycarbonyl group having one to six carbon atoms, an acyl group, or a substituted or unsubstituted phenyl group; both R1 and R2 do not indicate a hydrogen atom; and n indicates 1 or 2). This thiazolyl isocyanate is produced from two precursors: an aminothiazole and a carbonyl halide. The present invention can provide a method for producing a high yield of alkoxybenzamide with fewer steps, and can also provide thiazolyl isocyanates, which are useful in the production of ureas, carbamates, and aromatic amides having a thiazole ring.

  通式（3）表示的烷氧基苯甲酰胺：（其中R1、R2、R3、R4和R5独立地表示氢原子、具有1至6个碳原子的烷基或具有1至6个碳原子的烷氧基；如果R3表示氢原子或具有1至6个碳原子的烷基，则R1表示具有1至6个碳原子的烷氧基，R4表示具有1至6个碳原子的烷基或烷氧基；两个相邻的取代基可以与交联基耦合形成环；R6表示杂环芳烃环；A表示氧原子或硫原子），通过在路易斯酸的存在下将通式（1）表示的烷氧基苯与通式（2）表示的异氰酸酯反应而制得：（其中R1、R2、R3、R4、R5、R6和A的定义如上；n表示1或2）。通式（2）表示的异氰酸酯中包括通式（5）表示的噻唑基异氰酸酯：（其中R1表示氢原子、具有1至6个碳原子的饱和或不饱和烷基、具有1至6个碳原子的卤代烷基、具有1至6个碳原子的烷氧基、烷氧羰基、或酰基；R2表示氢原子、卤素原子、具有1至6个碳原子的饱和或不饱和烷基、具有1至6个碳原子的卤代烷基、具有1至6个碳原子的烷氧羰基、酰基或取代或未取代的苯基；R1和R2均不表示氢原子；n表示1或2）。该噻唑基异氰酸酯由两个前体物质产生：氨基噻唑和羰基卤化物。本发明可以提供一种生产高产率烷氧基苯甲酰胺的方法，步骤更少，也可以提供噻唑基异氰酸酯，其在尿素、氨基甲酸酯和带有噻唑环的芳香酰胺的生产中有用。