N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylbenzenesulfonamide | 850801-54-6

• 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)-4-methylbenzenesulfonamide
• 英文别名: N-(3-chloro-1,4-dioxonaphthalen-2-yl)-4-methylbenzenesulfonamide
• CAS: 850801-54-6
• 化学式: C₁₇H₁₂ClNO₄S
• 分子量: 361.806
• InChiKey: QSRSUCAEQDRWIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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)-4-methylbenzenesulfonamide 、 1-氨基-3,5-二甲苯 在 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 17.5h， 以25%的产率得到N-(3-((3,5-dimethylphenyl)amino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylbenzenesulfonamide
  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
• 作为产物：
  描述：

  对甲苯磺酰氯 在 N-甲基吗啉 、 吡啶 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.75h， 生成 N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  水中 1,4-萘醌的无金属 C–H 磺酰胺化

  摘要：

  开发了在水中无金属条件下使用N-甲氧基磺酰胺直接磺酰胺化 1,4-萘醌的方法。N-甲氧基磺酰胺的碱介导亲核加成，随后 N-O 键断裂，形成烯磺酰胺。此外，吡咯并萘醌的合成证明了该方法的实用性。

  DOI：

  10.1021/acs.joc.3c01409

文献信息

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

  公开号：US20170334842A1

  公开（公告）日：2017-11-23

  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.
• Structure–activity relationships and colorimetric properties of specific probes for the putative cancer biomarker human arylamine N-acetyltransferase 1
  作者：James E. Egleton、Cyrille C. Thinnes、Peter T. Seden、Nicola Laurieri、Siu Po Lee、Kate S. Hadavizadeh、Angelina R. Measures、Alan M. Jones、Sam Thompson、Amy Varney、Graham M. Wynne、Ali Ryan、Edith Sim、Angela J. Russell

  DOI：10.1016/j.bmc.2014.03.015

  日期：2014.6

  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.
• Metal-Free C–H Sulfamidation of 1,4-Naphthoquinone in Water
  作者：Pallaba Ganjan Dalai、Swayamprava Swain、Soumya Mohapatra、Niranjan Panda

  DOI：10.1021/acs.joc.3c01409

  日期：2023.10.6

  Direct sulfamidation of 1,4-naphthoquinones using N-methoxy sulfonamides under metal-free conditions in water was developed. Base-mediated nucleophilic addition of N-methoxy sulfonamides, followed by N–O bond cleavage allowed the formation of enesulfonamides. Further, the synthesis of pyrrolonaphthoquinones proved the practicability of the current approach.

  开发了在水中无金属条件下使用N-甲氧基磺酰胺直接磺酰胺化 1,4-萘醌的方法。N-甲氧基磺酰胺的碱介导亲核加成，随后 N-O 键断裂，形成烯磺酰胺。此外，吡咯并萘醌的合成证明了该方法的实用性。