6-methoxy-2-(4-(2-methyl-5-p-tolyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole | 1458715-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 6-methoxy-2-(4-(2-methyl-5-p-tolyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole
• 英文别名: 6-Methoxy-2-[4-[2-methyl-5-(4-methylphenyl)pyrrol-1-yl]phenyl]-1,3-benzothiazole；6-methoxy-2-[4-[2-methyl-5-(4-methylphenyl)pyrrol-1-yl]phenyl]-1,3-benzothiazole
• CAS: 1458715-50-8
• 化学式: C₂₆H₂₂N₂OS
• 分子量: 410.539
• InChiKey: NBWNIBZKJPPECG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-甲氧基-2-(4-硝基苯基)苯并噻唑 在 potassium hydrogensulfate 、 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 6-methoxy-2-(4-(2-methyl-5-p-tolyl-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

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.