5-(4-chlorophenyl)thieno[3,2-d][1,3]thiazol-2-amine | 1347758-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻唑类
• 英文名称: 5-(4-chlorophenyl)thieno[3,2-d][1,3]thiazol-2-amine
• 英文别名: 5-(4-Chlorophenyl)thieno[3,2-d][1,3]thiazol-2-amine
• CAS: 1347758-62-6
• 化学式: C₁₁H₇ClN₂S₂
• 分子量: 266.775
• InChiKey: YXISNOIPYPBXGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)thieno[3,2-d][1,3]thiazol-2-amine 在 四氢吡咯 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 2-{[5-(4-chlorophenyl)thieno[3,2-d][1,3]thiazol-2-yl]imino}-5-(2-naphtylidene)-1,3-thiazolidin-4-one
  参考文献：
  名称：

  2-(Thienothiazolylimino)-1,3-thiazolidin-4-ones inhibit cell division cycle 25 A phosphatase

  摘要：

  Cell division cycle dual phosphatases (CDC25) are essential enzymes that regulate cell progression in cell cycle. Three isoforms exist as CDC25A, B and C. Over-expression of each CDC25 enzyme is found in cancers of diverse origins. Thiazolidinone derivatives have been reported to display anti-proliferative activities, bactericidal activities and to reduce inflammation process. New 2-(thienothiazolylimino)-1,3-thiazolidin-4-ones were synthesized and evaluated as inhibitors of CDC25 phosphatase. Among the molecules tested, compound 6 inhibited CDC25A with an IC50 estimated at 6.2 +/- 1.0 mu M. The binding of thiazolidinone derivative 6 onto CDC25A protein was reversible. In cellulo, compound 6 treatment led to MCF7 and MDA-MB-231 cell growth arrest. To our knowledge, it is the first time that such 4-thiazolidinone derivatives are characterized as CDC25 potential inhibitor. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.04.063
• 作为产物：
  描述：

  4-isothiocyanato-2-(4-chlorophenyl)thiophene 在 ammonium hydroxide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 5-(4-chlorophenyl)thieno[3,2-d][1,3]thiazol-2-amine
  参考文献：
  名称：

  新型2-氨基噻吩并[3,2 - d ]噻唑和硒代[3,2- d ]噻唑的合成

  摘要：

  在这项工作中，我们描述了从3-氨基硒吩（使用硫光气）开始的3-isothiocyanatoselenophenes的合成。然后在氢氧化铵存在下将那些化合物转化为相应的硫脲。使用DDQ在2-氨基硒代[3,2- d ]噻唑中环化。使用相同的途径从3-异硫氰酸根合噻吩获得2-氨基噻吩并[3,2- d ]噻唑。

  DOI：

  10.1016/j.tet.2011.09.134

文献信息

• 2-(Thienothiazolylimino)-1,3-thiazolidin-4-ones inhibit cell division cycle 25 A phosphatase
  作者：Sophie Huber-Villaume、Germain Revelant、Estelle Sibille、Stéphanie Philippot、Angelica Morabito、Sandrine Dunand、Patrick Chaimbault、Denyse Bagrel、Gilbert Kirsch、Stéphanie Hesse、Hervé Schohn

  DOI：10.1016/j.bmc.2016.04.063

  日期：2016.7

  Cell division cycle dual phosphatases (CDC25) are essential enzymes that regulate cell progression in cell cycle. Three isoforms exist as CDC25A, B and C. Over-expression of each CDC25 enzyme is found in cancers of diverse origins. Thiazolidinone derivatives have been reported to display anti-proliferative activities, bactericidal activities and to reduce inflammation process. New 2-(thienothiazolylimino)-1,3-thiazolidin-4-ones were synthesized and evaluated as inhibitors of CDC25 phosphatase. Among the molecules tested, compound 6 inhibited CDC25A with an IC50 estimated at 6.2 +/- 1.0 mu M. The binding of thiazolidinone derivative 6 onto CDC25A protein was reversible. In cellulo, compound 6 treatment led to MCF7 and MDA-MB-231 cell growth arrest. To our knowledge, it is the first time that such 4-thiazolidinone derivatives are characterized as CDC25 potential inhibitor. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis of novel 2-aminothieno[3,2-d]thiazoles and selenolo[3,2-d]thiazoles
  作者：Germain Revelant、Stéphanie Hesse、Gilbert Kirsch

  DOI：10.1016/j.tet.2011.09.134

  日期：2011.12

  3-aminoselenophenes (using thiophosgene). Those compounds were then converted to the corresponding thioureas in the presence of ammonium hydroxide. Cyclization in 2-aminoselenolo[3,2-d]thiazoles was achieved using DDQ. 2-Aminothieno[3,2-d]thiazoles were obtained from 3-isothiocyanatothiophenes using the same pathway.

  在这项工作中，我们描述了从3-氨基硒吩（使用硫光气）开始的3-isothiocyanatoselenophenes的合成。然后在氢氧化铵存在下将那些化合物转化为相应的硫脲。使用DDQ在2-氨基硒代[3,2- d ]噻唑中环化。使用相同的途径从3-异硫氰酸根合噻吩获得2-氨基噻吩并[3,2- d ]噻唑。