(4-isopropyl-benzenesulfonyl)-carbamic acid ethyl ester | 108247-95-6

• 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-isopropyl-benzenesulfonyl)-carbamic acid ethyl ester
• 英文别名: (4-Isopropyl-benzolsulfonyl)-carbamidsaeure-aethylester；ethyl N-(4-propan-2-ylphenyl)sulfonylcarbamate
• CAS: 108247-95-6
• 化学式: C₁₂H₁₇NO₄S
• 分子量: 271.337
• InChiKey: LINKAMLUPMVMCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (4-isopropyl-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"-isopropylphenylsulfonylurea)-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-异丙基苯磺酰胺 、 氯甲酸乙酯 生成 (4-isopropyl-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

• The Adamantyl Group in Medicinal Agents. I. Hypoglycemic N-Arylsulfonyl-N'-adamantylureas
  作者：Koert Gerzon、Eriks V. Krumkalns、Richard L. Brindle、Frederick J. Marshall、Mary A. Root

  DOI：10.1021/jm00342a029

  日期：1963.11
• US3933894A
  申请人：——

  公开号：US3933894A

  公开（公告）日：1976-01-20