N-(3'-(4"-tert-butylphenylamino)-1',4'-dioxo-1',4'-dihydronaphthalen-2'-yl)benzenesulphonamide | 1218995-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3'-(4"-tert-butylphenylamino)-1',4'-dioxo-1',4'-dihydronaphthalen-2'-yl)benzenesulphonamide
• 英文别名: N-(3-(4-tert-butylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulphonamide；N-[3-(4-tert-butylanilino)-1,4-dioxonaphthalen-2-yl]benzenesulfonamide
• CAS: 1218995-98-2
• 化学式: C₂₆H₂₄N₂O₄S
• 分子量: 460.554
• InChiKey: VFFGMKLFAGYCGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 、 4-叔丁基苯胺 在 cerium(III) chloride 作用下， 以 甲苯 为溶剂， 反应 49.0h， 以60%的产率得到N-(3'-(4"-tert-butylphenylamino)-1',4'-dioxo-1',4'-dihydronaphthalen-2'-yl)benzenesulphonamide
  参考文献：
  名称：

  Small Molecule Colorimetric Probes for Specific Detection of Human Arylamine N-Acetyltransferase 1, a Potential Breast Cancer Biomarker

  摘要：

  The identification, synthesis, and evaluation of a series of naphthoquinone derivatives as selective inhibitors of human arylamine N-acetyltransferase 1 and mouse arylamine N-acetyltransferase 2 are described. The compounds undergo a distinctive color change (red -> blue) upon binding to these human and mouse NAT isoenzymes driven by a proton transfer event. No color change is observed in the presence of functionally distinct but highly similar isoenzymes which are >70% identical. These molecules may be used as sensors to detect the presence of human NAT1 in cell lysates.

  DOI：

  10.1021/ja909165u

文献信息

• [EN] 1,4-QUINONES AND THEIR SULFUR ANALOGUES USEFUL AS LIGANDS OF N-ACETYLTRANSFERASES<br/>[FR] 1,4-QUINONES ET LEURS ANALOGUES SOUFRÉS UTILES EN TANT QUE LIGANDS DE N-ACÉTYLTRANSFÉRASES
  申请人：ISIS INNOVATION

  公开号：WO2011055142A2

  公开（公告）日：2011-05-12

  The invention provides 1,4-quinones, 1,4-naphthoquinones and their sulphur analogues as inhibitors of hNAT1, an enzyme which is both a diagnostic marker and drug target for breast cancer. Some of the compounds of the invention are also chromogenic in the presence of hNAT1. The compounds of the invention are used for detecting for and/or measuring hNAT1 and for inhibiting hNAT1 in the treatment of disease.
• Small Molecule Colorimetric Probes for Specific Detection of Human Arylamine <i>N</i>-Acetyltransferase 1, a Potential Breast Cancer Biomarker
  作者：Nicola Laurieri、Matthew H. J. Crawford、Akane Kawamura、Isaac M. Westwood、James Robinson、Ai M. Fletcher、Stephen G. Davies、Edith Sim、Angela J. Russell

  DOI：10.1021/ja909165u

  日期：2010.3.17

  The identification, synthesis, and evaluation of a series of naphthoquinone derivatives as selective inhibitors of human arylamine N-acetyltransferase 1 and mouse arylamine N-acetyltransferase 2 are described. The compounds undergo a distinctive color change (red -> blue) upon binding to these human and mouse NAT isoenzymes driven by a proton transfer event. No color change is observed in the presence of functionally distinct but highly similar isoenzymes which are >70% identical. These molecules may be used as sensors to detect the presence of human NAT1 in cell lysates.