N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide | 850189-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
• 英文别名: N-(3-chloro-1,4-dioxonaphthalen-2-yl)benzenesulfonamide
• CAS: 850189-76-3
• 化学式: C₁₆H₁₀ClNO₄S
• 分子量: 347.779
• InChiKey: SJRXNYPDZTYQGD-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  488.3±55.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 、 4-溴苯胺 在 cerium(III) chloride 作用下， 以 甲苯 为溶剂， 反应 49.0h， 以10%的产率得到N-(3'-(4"-bromophenylamino)-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
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 在 potassium phosphate 、 cerium(III) chloride heptahydrate 、 palladium diacetate 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 35.5h， 生成 N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Structure–activity relationships and colorimetric properties of specific probes for the putative cancer biomarker human arylamine N-acetyltransferase 1

  摘要：

  A naphthoquinone inhibitor of human arylamine N-acetyltransferase 1 (hNAT1), a potential cancer biomarker and therapeutic target, has been reported which undergoes a distinctive concomitant color change from red to blue upon binding to the enzyme. Here we describe the use of in silico modeling alongside structure-activity relationship studies to advance the hit compound towards a potential probe to quantify hNAT1 levels in tissues. Derivatives with both a fifty-fold higher potency against hNAT1 and a two-fold greater absorption coefficient compared to the initial hit have been synthesized; these compounds retain specificity for hNAT1 and its murine homologue mNat2 over the isoenzyme hNAT2. A relationship between pK(a), inhibitor potency and colorimetric properties has also been uncovered. The high potency of representative examples against hNAT1 in ZR-75-1 cell extracts also paves the way for the development of inhibitors with improved intrinsic sensitivity which could enable detection of hNAT1 in tissue samples and potentially act as tools for elucidating the unknown role hNAT1 plays in ER+ breast cancer; this could in turn lead to a therapeutic use for such inhibitors. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.03.015

文献信息

• INHIBITORS OF THE MITF MOLECULAR PATHWAY
  申请人：THE GENERAL HOSPITAL CORPORATION

  公开号：US20160130222A1

  公开（公告）日：2016-05-12

  Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.

  本文提供的是公式（IV）的化合物及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及其含有的药物组合物可用作MITF抑制剂、MITF通路抑制剂以及治疗癌症的药物。
• [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：WO2011055142A3

  公开（公告）日：2011-08-11
• BIOMARKERS PREDICTIVE OF CANCER CELL RESPONSE TO ML329 OR A DERIVATIVE THEREOF
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US20220128562A1

  公开（公告）日：2022-04-28

  The present invention is based in part on the identification of biomarkers, including NQO1, NRF2 and KEAP1, predictive of cancer cell responsiveness to treatment with ML 329 or a derivative thereof.
• US9745261B2
  申请人：——

  公开号：US9745261B2

  公开（公告）日：2017-08-29
• [EN] INHIBITORS OF THE MITF MOLECULAR PATHWAY<br/>[FR] INHIBITEURS DE LA VOIE MOLÉCULAIRE MITF
  申请人：GEN HOSPITAL CORP

  公开号：WO2014201016A2

  公开（公告）日：2014-12-18

  Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.