(3R)-6,7-bis(hydroxymethyl)-3-(4-hydroxyphenyl)-5-methyl-1H,3H-pyrrolo[1,2-c]thiazole | 1609535-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3R)-6,7-bis(hydroxymethyl)-3-(4-hydroxyphenyl)-5-methyl-1H,3H-pyrrolo[1,2-c]thiazole
• 英文别名: 4-[(3R)-6,7-bis(hydroxymethyl)-5-methyl-1,3-dihydropyrrolo[1,2-c][1,3]thiazol-3-yl]phenol
• CAS: 1609535-73-0
• 化学式: C₁₅H₁₇NO₃S
• 分子量: 291.371
• InChiKey: SOMPQJSPWKIIRN-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  90.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4R)-2-(4-hydroxyphenyl)thiazolidine-4-carboxylic acid 在 lithium aluminium tetrahydride 、 乙酸酐 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (3R)-6,7-bis(hydroxymethyl)-3-(4-hydroxyphenyl)-5-methyl-1H,3H-pyrrolo[1,2-c]thiazole
  参考文献：
  名称：

  Targeting triple-negative breast cancer cells with 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles

  摘要：

  Further studies on 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles as anticancer agents against breast cancer are reported, allowing to demonstrate the potential of these compounds for the therapy of the triple-negative breast cancer, the most challenging tumors in clinical practice. These compounds were assayed for their in vitro cytotoxicity on several human breast cancer cell lines (MCF7, HCC1954 and HCC1806 cell lines). Particularly interesting were the results obtained for 4-hydroxyphenyl substituted derivative, which proved to be the most promising compound regarding HCC1806 cell line, a triple-negative breast cancer. The effects of the two most active compounds on cell survival, viability, cell cycle, DNA damage and expression of proteins related to cell death pathways were studied. The reported results consolidate the potential of 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles for the therapy of breast cancer, particularly the triple-negative. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.008

文献信息

• Targeting triple-negative breast cancer cells with 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles
  作者：Kathleen Santos、Mafalda Laranjo、Ana Margarida Abrantes、Ana F. Brito、Cristina Gonçalves、Ana Bela Sarmento Ribeiro、M. Filomena Botelho、Maria I.L. Soares、Andreia S.R. Oliveira、Teresa M.V.D. Pinho e Melo

  DOI：10.1016/j.ejmech.2014.04.008

  日期：2014.5

  Further studies on 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles as anticancer agents against breast cancer are reported, allowing to demonstrate the potential of these compounds for the therapy of the triple-negative breast cancer, the most challenging tumors in clinical practice. These compounds were assayed for their in vitro cytotoxicity on several human breast cancer cell lines (MCF7, HCC1954 and HCC1806 cell lines). Particularly interesting were the results obtained for 4-hydroxyphenyl substituted derivative, which proved to be the most promising compound regarding HCC1806 cell line, a triple-negative breast cancer. The effects of the two most active compounds on cell survival, viability, cell cycle, DNA damage and expression of proteins related to cell death pathways were studied. The reported results consolidate the potential of 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles for the therapy of breast cancer, particularly the triple-negative. (c) 2014 Elsevier Masson SAS. All rights reserved.