Naphthyl-(2)-sulfonsaeure-aethoxycarbonylamid | 92029-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Naphthyl-(2)-sulfonsaeure-aethoxycarbonylamid
• 英文别名: ethyl N-naphthalen-2-ylsulfonylcarbamate
• CAS: 92029-80-6
• 化学式: C₁₃H₁₃NO₄S
• 分子量: 279.317
• InChiKey: JRWGBIIVGFLGBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Naphthyl-(2)-sulfonsaeure-aethoxycarbonylamid 、 (5R,5aR,8aS,9S)-9-amino-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one 以 甲苯 为溶剂， 生成 4β-N-(2"-naphthylsulfonylurea)-4-deoxy-4'-demethyl-epipodophyllotoxin
  参考文献：
  名称：

  Design, synthesis and cytotoxic activity of novel sulfonylurea derivatives of podophyllotoxin

  摘要：

  Three series of novel sulfonylurea podophyllotoxin derivatives were designed, synthesized, and evaluated for in vitro cytotoxicity against four tumor cell lines (A-549, DU-145, KB and KBvin). Compounds 14c (IC50: 1.41-1.76 mu M) and 14e (IC50: 1.72-2.01 mu M) showed superior cytotoxic activity compared with etoposide (IC50: 2.03 to >20 mu M), a clinically available anticancer drug. Significantly, most of the compounds exhibited comparable cytotoxicity against the drug-resistant tumor cell line KBvin, while etoposide lost activity completely. Preliminary structure-activity relationship (SAR) correlations indicated that the 4'-O-methyl functionality in podophyllotoxin analogues may be essential to maintain cytotoxic activity, while an arylsulfonylurea side chain at podophyllotoxin's 4 beta position can significantly improve cytotoxic activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.035
• 作为产物：
  描述：

  2-naphthalenesulfinyl chloride 在 氢氧化钾 作用下， 以 苯 为溶剂， 生成 Naphthyl-(2)-sulfonsaeure-aethoxycarbonylamid
  参考文献：
  名称：

  Levchenko,E.S. et al., Journal of general chemistry of the USSR, 1961, vol. 31, p. 2218 - 2222

  摘要：

  DOI：

文献信息

• Synthesis, biological activities and structure−activity relationships for new avermectin analogues
  作者：Jian Zhang、Xiang Nan、Hai-Tao Yu、Pi-Le Cheng、Yan Zhang、Ying-Qian Liu、Shao-Yong Zhang、Guan-Fang Hu、Huanxiang Liu、An-Liang Chen

  DOI：10.1016/j.ejmech.2016.05.056

  日期：2016.10

  LC50 values of 7.744, 5.634, 6.809, 7.939 and 52.234 μM, respectively. Furthermore, QSAR analysis showed that the molecular shape, size, connectivity degree and electronic distribution of avermectin analogues had substantial effects on insecticidal potency. These preliminary results provided useful insight in guiding further modifications of avermectin in the development of potential new insecticides.

  为了发现具有良好杀虫活性的新分子，合成了40多种新的阿维菌素衍生物，并评估了它们对三种物种的蜘蛛，昆虫和线虫的生物活性，这些物种分别是朱砂叶螨（Tetranychus Cinnabarinus），蚜虫（Aphis craccivora）和松柏xylophilus。所有测试的化合物均显示出对三种昆虫的有效抑制活性。值得注意的是，大多数化合物对朱砂毛虫表现出高选择性，其中一些与阿维菌素相比具有更好的选择性。特别是化合物9j（LC 50：0.005μM）和16d（LC 50：0.002μM）对朱砂丁香的活性分别比阿维菌素（LC 50： 0.013μM ）高2.5倍和4.7倍。此外，化合物9B，9D-F ，9H，9J，9升，9N，9P，9R，9V和17D显示了优良的活性与LC 50个相比的2.959-5.013μM的值1（LC 50： 6.746μM）对乙。松材线虫。同时，化合物9f，9g，9h和9m的杀虫活性针对A
• Naphthalene/quinoline amides and sulfonylureas as potent and selective antagonists of the EP4 receptor
  作者：Jason D. Burch、Julie Farand、John Colucci、Claudio Sturino、Yves Ducharme、Richard W. Friesen、Jean-François Lévesque、Sébastien Gagné、Mark Wrona、Alex G. Therien、Marie-Claude Mathieu、Danielle Denis、Erika Vigneault、Daigen Xu、Patsy Clark、Steve Rowland、Yongxin Han

  DOI：10.1016/j.bmcl.2010.12.014

  日期：2011.2

  Two new series of EP4 antagonists based on naphthalene/quinoline scaffolds have been identified as part of our on-going efforts to develop treatments for inflammatory pain. One series contains an acidic sulfonylurea pharmacophore, whereas the other is a neutral amide. Both series show subnanomolar intrinsic binding potency towards the EP4 receptor, and excellent selectivity towards other prostanoid receptors. While the amide series generally displays poor pharmacokinetic parameters, the sulfonylureas exhibit greatly improved profile. MF-592, the optimal compound from the sulfonylurea series, has a desirable overall preclinical profile that suggests it is suitable for further development. (C) 2010 Elsevier Ltd. All rights reserved.
• HOWBERT, J. JEFFRY;GROSSMAN, C. SUE;CROWELL, THOMAS A.;RIEDER, BRENT J.;H+, J. MED. CHEM., 33,(1990) N, C. 2393-2407
  作者：HOWBERT, J. JEFFRY、GROSSMAN, C. SUE、CROWELL, THOMAS A.、RIEDER, BRENT J.、H+

  DOI：——

  日期：——