5-Bromopyridine-3-carbonyl isothiocyanate | 1154347-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-Bromopyridine-3-carbonyl isothiocyanate
• CAS: 1154347-66-6
• 化学式: C₇H₃BrN₂OS
• mdl: MFCD12189026
• 分子量: 243.084
• InChiKey: WUIMDTYJLCWJPS-UHFFFAOYSA-N

物化性质

• 沸点：
  334.2±27.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Bromopyridine-3-carbonyl isothiocyanate 、 4β-amino-4-deoxypodophyllotoxin 以 乙腈 为溶剂， 反应 2.0h， 以68%的产率得到N-[[(5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]carbamothioyl]-5-bromopyridine-3-carboxamide
  参考文献：
  名称：

  Design, synthesis and potent cytotoxic activity of novel podophyllotoxin derivatives

  摘要：

  Twenty new acyl thiourea derivatives of podophyllotoxin and 4'-demethylepipodophyllotoxin were prepared and screened for their cytotoxicity against four human tumor cell lines, A-549, DU-145, KB, and KBvin. With IC50 values of 0.098-1.13 mu M, compounds 13b, 13c, and 13o displayed much better cytotoxic activity than the control etoposide. Most importantly, 13b and 13o exhibited promising cytotoxicity against the drug resistant tumor cell line KBvin with IC50 values of 0.098 and 0.13 mu M, respectively, while etoposide lost activity completely. Structure-activity relationship (SAR) correlations of the new derivatives have been established. Compounds 13b and 13o merit further development as a new generation of epipodophyllotoxin-derived antitumor clinical trial candidates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.069

文献信息

• Design, synthesis and potent cytotoxic activity of novel podophyllotoxin derivatives
  作者：Wen-Qun Li、Xu-Li Wang、Keduo Qian、Ying-Qian Liu、Chih-Ya Wang、Liu Yang、Jin Tian、Susan L. Morris-Natschke、Xing-Wen Zhou、Kuo-Hsiung Lee

  DOI：10.1016/j.bmc.2013.01.069

  日期：2013.4

  Twenty new acyl thiourea derivatives of podophyllotoxin and 4'-demethylepipodophyllotoxin were prepared and screened for their cytotoxicity against four human tumor cell lines, A-549, DU-145, KB, and KBvin. With IC50 values of 0.098-1.13 mu M, compounds 13b, 13c, and 13o displayed much better cytotoxic activity than the control etoposide. Most importantly, 13b and 13o exhibited promising cytotoxicity against the drug resistant tumor cell line KBvin with IC50 values of 0.098 and 0.13 mu M, respectively, while etoposide lost activity completely. Structure-activity relationship (SAR) correlations of the new derivatives have been established. Compounds 13b and 13o merit further development as a new generation of epipodophyllotoxin-derived antitumor clinical trial candidates. (C) 2013 Elsevier Ltd. All rights reserved.