1-[(5-bromo-2-oxoindol-3-yl)amino]-3-prop-2-enylthiourea

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-[(5-bromo-2-oxoindol-3-yl)amino]-3-prop-2-enylthiourea
• 化学式: C₁₂H₁₁BrN₄OS
• 分子量: 339.216
• InChiKey: QUJVLFMGSZVEJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.52
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-溴丙酸乙酯 、 1-[(5-bromo-2-oxoindol-3-yl)amino]-3-prop-2-enylthiourea 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以74%的产率得到3-{[3-Allyl-5-methyl-4-oxo-thiazolidin-(2E)-ylidene]-hydrazono}-5-bromo-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Synthesis and Primary Cytotoxicity Evaluation of New 5-Bromo-3-substituted-hydrazono-1H-2-indolinones

  摘要：

  In this study a new series of 5-bromo-3-[(3-subtituted-5-methyl-4-thiazolidinone-2-lidene)-hydrazono]-1H-2-indolinones (3a-i) and 5-bromo-3-[(2-thioxo-3-substituted-4,5-imidazolidinedione-1-yl)imino]-1H-2-indolinones (4a-f) was synthesized by the cyclization of 5-bromo-3-(N-substituted-thiosemicarbazono)-1 H-2-indolinones (2 a-i) with ethyl 2-bromopropionate in anhydrous ethanolic medium and oxalyl cloride in anhydrous diethyl ether, respectively Six compounds chosen as prototypes were evaluated in the 3-cell line, one dose in vitro primary cytotoxicity assay. Four of them were evaluated against the full panel of 60 human tumor cell lines at a minimum of five concentrations at 10-fold dilutions. Among the compounds tested, the 4-fluorophenylthiosemicarbazone derivative 2f showed the most favorable cytotoxicity This compound demonstrated the most marked effects on a breast cancer cell line (BT-549, log(10)GI(50) value -6.40), a non small cell lung cancer cell line (NCl-H23, log(10)GI(50) value -6.10), and an ovarian cancer cell line (IGROV1, log(10)GI(50) value -6.02).

  DOI：

  10.1002/1521-4184(200211)335:8<374::aid-ardp374>3.0.co;2-k
• 作为产物：
  描述：

  4-丙烯基硫代氨基脲 、 5-溴靛红 以 乙醇 为溶剂， 反应 2.0h， 生成 1-[(5-bromo-2-oxoindol-3-yl)amino]-3-prop-2-enylthiourea
  参考文献：
  名称：

  Synthesis and Primary Cytotoxicity Evaluation of New 5-Bromo-3-substituted-hydrazono-1H-2-indolinones

  摘要：

  In this study a new series of 5-bromo-3-[(3-subtituted-5-methyl-4-thiazolidinone-2-lidene)-hydrazono]-1H-2-indolinones (3a-i) and 5-bromo-3-[(2-thioxo-3-substituted-4,5-imidazolidinedione-1-yl)imino]-1H-2-indolinones (4a-f) was synthesized by the cyclization of 5-bromo-3-(N-substituted-thiosemicarbazono)-1 H-2-indolinones (2 a-i) with ethyl 2-bromopropionate in anhydrous ethanolic medium and oxalyl cloride in anhydrous diethyl ether, respectively Six compounds chosen as prototypes were evaluated in the 3-cell line, one dose in vitro primary cytotoxicity assay. Four of them were evaluated against the full panel of 60 human tumor cell lines at a minimum of five concentrations at 10-fold dilutions. Among the compounds tested, the 4-fluorophenylthiosemicarbazone derivative 2f showed the most favorable cytotoxicity This compound demonstrated the most marked effects on a breast cancer cell line (BT-549, log(10)GI(50) value -6.40), a non small cell lung cancer cell line (NCl-H23, log(10)GI(50) value -6.10), and an ovarian cancer cell line (IGROV1, log(10)GI(50) value -6.02).

  DOI：

  10.1002/1521-4184(200211)335:8<374::aid-ardp374>3.0.co;2-k

文献信息

• Karah, Nilguen; Terzioglu, Nalan; Guersoy, Aysel, Arzneimittel-Forschung/Drug Research, 1998, vol. 48, # 7, p. 758 - 763
  作者：Karah, Nilguen、Terzioglu, Nalan、Guersoy, Aysel

  DOI：——

  日期：——