1,1'-{2,2'-[butane-1,4-diylbis(sulfanediyl)]bis(2,1-phenylene)}bis[3-(4-methoxyphenyl)urea] | 1131147-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1'-{2,2'-[butane-1,4-diylbis(sulfanediyl)]bis(2,1-phenylene)}bis[3-(4-methoxyphenyl)urea]
• 英文别名: 1-(4-Methoxyphenyl)-3-[2-[4-[2-[(4-methoxyphenyl)carbamoylamino]phenyl]sulfanylbutylsulfanyl]phenyl]urea
• CAS: 1131147-99-3
• 化学式: C₃₂H₃₄N₄O₄S₂
• 分子量: 602.778
• InChiKey: HIJMYPRRLWEXPH-UHFFFAOYSA-N

物化性质

• 沸点：
  629.9±55.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,2'-[1,4-butanediylbis(thio)]bisbenzenamine dihydrochloride 、 对甲氧基苯异氰酸酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以75%的产率得到1,1'-{2,2'-[butane-1,4-diylbis(sulfanediyl)]bis(2,1-phenylene)}bis[3-(4-methoxyphenyl)urea]
  参考文献：
  名称：

  QSAR modeling, synthesis and bioassay of diverse leukemia RPMI-8226 cell line active agents

  摘要：

  A rigorous QSAR modeling procedure employing CODESSA PRO descriptors has been utilized for the prediction of more efficient anti-leukemia agents. Experimental data concerning the effect on leukemia RPMI-8226 cell line tumor growth of 34 compounds (treated at a dose of 10 mu M) was related to their chemical structures by a 4-descriptor QSAR model. Four bis(oxy)bis-urea and bis(sulfanediyl)bis-urea derivatives (4a, 4b, 8, 11a) predicted as active by this model, together with 11b predicted to be of low activity, were synthesized and screened for anti-tumor activity utilizing 55 different tumor cell lines. Compounds 8 and 11a showed anti-tumor properties against most of the adopted cell lines with growth inhibition exceeding 50%. The highly promising preliminary anti-tumor properties of compounds 8 and 11a, were screened at serial dilutions (10(-4)-10(-8) mu M) for determination of their GI(50) and TGI against the screened human tumor cell lines. Compound 11a (GI(50) = 1.55, TGI = 8.68 mu M) is more effective than compound 8 (GI(50) = 58.30, TGI = >100 mu M) against the target leukemia RPMI-8226 cell line. Compound 11a also exhibits highly pronounced anti-tumor properties against NCI-H226, NCI-H23 (non-small cell lung cancer), COLO 205 (colon cancer), SNB-75 (CNS cancer), OVCAR-3, SK-OV-3 (ovarian cancer), A498 (renal cancer) MDA-MB-231/ATCC and MDA-MB-468 (breast cancer) cell lines (GI(50) = 1.95, 1.61, 1.38, 1.56, 1.30, 1.98, 1.18, 1.85, 1.08, TGI = 8.35, 6.01, 2.67, 8.59, 4.01, 7.01, 5.62, 6.38, 5.63 mu M, respectively). Thus 11a could be a suitable lead towards the design of broad spectrum anti-tumor active agents targeting various human tumor cell lines. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.033

文献信息

• QSAR modeling, synthesis and bioassay of diverse leukemia RPMI-8226 cell line active agents
  作者：Alan R. Katritzky、Adel S. Girgis、Svetoslav Slavov、Srinivasa R. Tala、Iva Stoyanova-Slavova

  DOI：10.1016/j.ejmech.2010.08.033

  日期：2010.11

  A rigorous QSAR modeling procedure employing CODESSA PRO descriptors has been utilized for the prediction of more efficient anti-leukemia agents. Experimental data concerning the effect on leukemia RPMI-8226 cell line tumor growth of 34 compounds (treated at a dose of 10 mu M) was related to their chemical structures by a 4-descriptor QSAR model. Four bis(oxy)bis-urea and bis(sulfanediyl)bis-urea derivatives (4a, 4b, 8, 11a) predicted as active by this model, together with 11b predicted to be of low activity, were synthesized and screened for anti-tumor activity utilizing 55 different tumor cell lines. Compounds 8 and 11a showed anti-tumor properties against most of the adopted cell lines with growth inhibition exceeding 50%. The highly promising preliminary anti-tumor properties of compounds 8 and 11a, were screened at serial dilutions (10(-4)-10(-8) mu M) for determination of their GI(50) and TGI against the screened human tumor cell lines. Compound 11a (GI(50) = 1.55, TGI = 8.68 mu M) is more effective than compound 8 (GI(50) = 58.30, TGI = >100 mu M) against the target leukemia RPMI-8226 cell line. Compound 11a also exhibits highly pronounced anti-tumor properties against NCI-H226, NCI-H23 (non-small cell lung cancer), COLO 205 (colon cancer), SNB-75 (CNS cancer), OVCAR-3, SK-OV-3 (ovarian cancer), A498 (renal cancer) MDA-MB-231/ATCC and MDA-MB-468 (breast cancer) cell lines (GI(50) = 1.95, 1.61, 1.38, 1.56, 1.30, 1.98, 1.18, 1.85, 1.08, TGI = 8.35, 6.01, 2.67, 8.59, 4.01, 7.01, 5.62, 6.38, 5.63 mu M, respectively). Thus 11a could be a suitable lead towards the design of broad spectrum anti-tumor active agents targeting various human tumor cell lines. (C) 2010 Elsevier Masson SAS. All rights reserved.