N-(3-(4-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide | 1301626-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-(4-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
• 英文别名: N-[3-(4-chlorophenyl)-1,4-dioxonaphthalen-2-yl]benzenesulfonamide
• CAS: 1301626-92-5
• 化学式: C₂₂H₁₄ClNO₄S
• 分子量: 423.876
• InChiKey: KBLCRHCFVIRBPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• 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

• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 、 cerium(III) chloride heptahydrate 、 palladium diacetate 、 碳酸氢钠 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 35.5h， 生成 N-(3-(4-chlorophenyl)-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