1-(3',4',5'-trimethoxyphenyl)-1,4-pentanedione | 1155102-56-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3',4',5'-trimethoxyphenyl)-1,4-pentanedione
• 英文别名: 1-(3,4,5-Trimethoxyphenyl)pentane-1,4-dione
• CAS: 1155102-56-9
• 化学式: C₁₄H₁₈O₅
• mdl: MFCD11926849
• 分子量: 266.294
• InChiKey: NWVVUCHKIWFAIO-UHFFFAOYSA-N

物化性质

• 沸点：
  406.9±45.0 °C(predicted)
• 密度：
  1.111±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-苯并噻唑基)苯胺 、 1-(3',4',5'-trimethoxyphenyl)-1,4-pentanedione 在 potassium hydrogensulfate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以83%的产率得到2-(4-(2-methyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole
  参考文献：
  名称：

  Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells

  摘要：

  By applying a methodology, a series of benzothiazole-pyrrole based conjugates (4a-r) were synthesized and evaluated for their antiproliferative activity. Compounds such as 4a, 4c, 4e, 4g-j, 4m, 4n, 4o and 4r exhibited significant cytotoxic effect in the MCF-7 cell line. Cell cycle effects were examined for these conjugates at 2 mu M as well as 4 mu M concentrations and FACS analysis show an increase of G2/M phase cells with concomitant decrease of G1 phase cells thereby indicating G2/M cell cycle arrest by them. Interestingly 4o and 4r are effective in causing apoptosis in MCF-7 cells. Moreover, 4o showed down regulation of oncogenic expression of Ras and its downstream effector molecules such as MEK1, ERK1/2, p38 MAPK and VEGF. The apoptotic aspect of this conjugate is further evidenced by increased expression of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in the highly malignant breast cancers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.068
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 丁烯酮 在 3-乙基-5-(2-羟乙基)-4-甲基噻唑溴化物 、 三乙胺 作用下， 反应 24.0h， 以47%的产率得到1-(3',4',5'-trimethoxyphenyl)-1,4-pentanedione
  参考文献：
  名称：

  1，5-二芳基吡咯衍生物、制备方法及其抗肿瘤 应用

  摘要：

  本发明属于新药研制领域，提供了一种具有抗肿瘤活性的1，5-二芳基吡咯衍生物，结构如通式I所示，其中：R1，R2，R3分别独立指氢、卤素、氰基、烷基、烷氧基、硝基、烷氧酰基、酰胺基或卤代烷基；Ar1，Ar2分别独立为取代苯基，且其中至少一个为3，4，5-三甲氧基芳基，其中取代苯基中的取代基团选自氢、卤素、氰基、硝基、烷氧基、胺基、羟基、酰胺基、磺酰胺基或氨基；上述烷基为C1-C6的烷基，烷氧基为C1-C6的烷氧基。本发明还提供了该类衍生物在制备治疗乳腺癌药物中的应用。

  公开号：

  CN103288701B

文献信息

• Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells
  作者：Ahmed Kamal、Shaikh Faazil、M. Janaki Ramaiah、Md. Ashraf、M. Balakrishna、S.N.C.V.L. Pushpavalli、Nibedita Patel、Manika Pal-Bhadra

  DOI：10.1016/j.bmcl.2013.07.068

  日期：2013.10

  By applying a methodology, a series of benzothiazole-pyrrole based conjugates (4a-r) were synthesized and evaluated for their antiproliferative activity. Compounds such as 4a, 4c, 4e, 4g-j, 4m, 4n, 4o and 4r exhibited significant cytotoxic effect in the MCF-7 cell line. Cell cycle effects were examined for these conjugates at 2 mu M as well as 4 mu M concentrations and FACS analysis show an increase of G2/M phase cells with concomitant decrease of G1 phase cells thereby indicating G2/M cell cycle arrest by them. Interestingly 4o and 4r are effective in causing apoptosis in MCF-7 cells. Moreover, 4o showed down regulation of oncogenic expression of Ras and its downstream effector molecules such as MEK1, ERK1/2, p38 MAPK and VEGF. The apoptotic aspect of this conjugate is further evidenced by increased expression of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in the highly malignant breast cancers. (C) 2013 Elsevier Ltd. All rights reserved.
• 1，5-二芳基吡咯衍生物、制备方法及其抗肿瘤 应用
  申请人：中南大学

  公开号：CN103288701B

  公开（公告）日：2016-01-27

  本发明属于新药研制领域，提供了一种具有抗肿瘤活性的1，5-二芳基吡咯衍生物，结构如通式I所示，其中：R1，R2，R3分别独立指氢、卤素、氰基、烷基、烷氧基、硝基、烷氧酰基、酰胺基或卤代烷基；Ar1，Ar2分别独立为取代苯基，且其中至少一个为3，4，5-三甲氧基芳基，其中取代苯基中的取代基团选自氢、卤素、氰基、硝基、烷氧基、胺基、羟基、酰胺基、磺酰胺基或氨基；上述烷基为C1-C6的烷基，烷氧基为C1-C6的烷氧基。本发明还提供了该类衍生物在制备治疗乳腺癌药物中的应用。