(4-fluoro-benzenesulfonyl)-carbamic acid ethyl ester | 780-99-4

• 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: (4-fluoro-benzenesulfonyl)-carbamic acid ethyl ester
• 英文别名: (4-Fluor-benzolsulfonyl)-carbamidsaeure-aethylester；ethyl N-(4-fluorophenyl)sulfonylcarbamate
• CAS: 780-99-4
• 化学式: C₉H₁₀FNO₄S
• 分子量: 247.247
• InChiKey: HZCDQFDIHGLSLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-fluoro-benzenesulfonyl)-carbamic acid ethyl ester 、 (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-(4"-fluorophenylsulfonylurea)-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：

  4-氟苯磺酰胺 、 氯甲酸乙酯 生成 (4-fluoro-benzenesulfonyl)-carbamic acid ethyl ester
  参考文献：
  名称：

  Notes - Some N-Arylculfonyl-N '-alkylureas

  摘要：

  DOI：

  10.1021/jo01100a622

文献信息

• Design, synthesis, biological evaluation and docking studies of novel 2-substituted-4-morpholino-7,8-dihydro-5 H -thiopyrano[4,3- d ]pyrimidine derivatives as dual PI3Kα/mTOR inhibitors
  作者：Fei Lei、Chengyu Sun、Shan Xu、Qinqin Wang、Yiqiang OuYang、Chen Chen、Hui Xia、Linxiao Wang、Pengwu Zheng、Wufu Zhu

  DOI：10.1016/j.ejmech.2016.03.033

  日期：2016.6

  Four series of 2-substituted-4-morpholino- 7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine derivatives (9-28) were designed, synthesized and their structures were confirmed by 1H NMR, 13C NMR and MS spectrum. All compounds were evaluated for the IC50 values against three cancer cell lines (A549, PC-3 and MCF-7). And four selected compounds (10, 11, 24, 27) were further evaluated for the IC50 values against

  设计，合成了4个系列的2-取代-4-吗啉代-7,8-二氢-5H-硫代吡喃并[4,3-d]嘧啶衍生物（9-28），并通过1 H NMR，13 C NMR和1H NMR证实了它们的结构。 MS质谱图。评估了所有化合物对三种癌细胞系（A549，PC-3和MCF-7）的IC50值。然后进一步评估了四种选择的化合物（10、11、24、27）针对PI3Kalpha和mTOR激酶的IC50值。七个目标化合物针对这三种癌细胞系表现出中等至出色的抗肿瘤活性。最有前途的化合物11对A549，PC-3和MCF-7细胞系显示出良好的抗肿瘤潜能，IC50值分别为0.52 +/- 0.10μM，1.41 +/- 0.10μM，4.82 +/- 0.24μM，并具有中等的抗肿瘤活性PI3Kalpha / mTOR，IC50值为6.72 +/- 0.30μM和0.94 +/- 0.10μM。结构-活性关系（SARs）和对
• Design, Synthesis and Biological Evaluation of Novel Phenylsulfonylurea Derivatives as PI3K/mTOR Dual Inhibitors
  作者：Bingbing Zhao、Fei Lei、Caolin Wang、Binliang Zhang、Zunhua Yang、Wei Li、Wufu Zhu、Shan Xu

  DOI：10.3390/molecules23071553

  日期：——

  Five series of novel phenylsulfonylurea derivatives, 19a–d, 20a–d, 21a–d, 22a–d and 23a–d, bearing 4-phenylaminoquinoline scaffold were designed, synthesized and their IC50 values against four cancer cell lines (HepG-2, A549, PC-3 and MCF-7) were evaluated. Most compounds showed moderate cytotoxicity activity against the cancer cell lines. Structure–activity relationships (SARs) and pharmacological

  设计、合成了五个系列的新型苯磺酰脲衍生物，19a-d、20a-d、21a-d、22a-d 和 23a-d，带有 4-苯基氨基喹啉支架，并且它们对四种癌细胞系（HepG-2、 A549、PC-3 和 MCF-7) 进行了评估。大多数化合物对癌细胞系显示出中等的细胞毒性活性。构效关系（SAR）和药理学结果表明，4-氨基喹啉支架和苯磺酰脲支架的引入有利于抗肿瘤活性。此外，4-苯胺基部分的对甲氧基取代和苯磺酰脲的对卤素取代对不同系列的化合物有不同的影响。此外，
• Design, Synthesis, Activity and Docking Study of Sorafenib Analogs Bearing Sulfonylurea Unit
  作者：Chunjiang Wu、Min Wang、Qidong Tang、Rong Luo、Le Chen、Pengwu Zheng、Wufu Zhu

  DOI：10.3390/molecules201019361

  日期：——

  Structure-activity relationships (SARs) and docking studies indicated that the sulfonylurea unit was important to these kinds of compounds. None of the substitutions in the phenoxy group and small halogen atoms such as 2,4-difluoro substitution of the aryl group contributed to the activity. The results suggested that sulfonylurea sorafenib analogs are worthy of further study.

  合成了两个含有磺酰脲单元的新型索拉非尼类似物，并通过1 H-NMR，13 C-NMR，MS光谱和元素分析证实了它们的化学结构。评价合成的化合物对A549，Hela，MCF-7和PC-3癌细胞系的细胞毒性。一些化合物显示出中等的细胞毒活性，尤其是化合物1-（2,4-二氟苯基磺酰基）-3-（4-（2-（甲基氨基甲酰基）吡啶-4-基氧基）苯基）脲（6c）和1-（4-溴苯磺酰基）-3-（4-（2-（甲基氨基甲酰基）吡啶-4-基氧基）苯基）脲（6f）对四种癌细胞系的IC50值分别为16.54±1.22至63.92±1.81μM。为了研究这些化合物的靶标，在本文中进一步针对10μM的目标化合物执行了对血管内皮生长因子受体2（VEGFR2 / KDR）激酶的抑制率。结构活性关系（SARs）和对接研究表明，磺酰脲单元对这类化合物很重要。苯氧基和小的卤原子，例如芳基的2,4-二氟取代均无贡献。结果表明磺酰脲
• 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.