N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide | 63351-46-2

• 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)phenylacetamide
• 英文别名: phenyl-acetic acid-(3-chloro-1,4-dioxo-1,4-dihydro-[2]naphthylamide)；Phenyl-essigsaeure-(3-chlor-1,4-dioxo-1,4-dihydro-[2]naphthylamid)；N-(3-chloro-1,4-dioxonaphthalen-2-yl)-2-phenylacetamide
• CAS: 63351-46-2
• 化学式: C₁₈H₁₂ClNO₃
• 分子量: 325.751
• InChiKey: SLDFGKSFHLPJAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-呋喃硼酸 、 N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide 在 bis-triphenylphosphine-palladium(II) chloride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 以9%的产率得到N-(3-(furan-3-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide
  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：

  2,3-二氯-1,4-萘醌 在 ammonium hydroxide 、 乙醇 、 硫酸 作用下， 生成 N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide
  参考文献：
  名称：

  Preparation of Some Imidazole Derivatives of 1,4-Naphthoquinone

  摘要：

  DOI：

  10.1021/ja01645a028

文献信息

• ‘On water’: unprecedented nucleophilic substitution and addition reactions with 1,4-quinones in aqueous suspension
  作者：Vishnu K. Tandon、Hardesh K. Maurya

  DOI：10.1016/j.tetlet.2009.07.149

  日期：2009.10

  Unique nucleophilic substitution and addition reactions of 1,4-quinones in aqueous suspension with aromatic amines, primary aliphatic amines, amino acid, ester of amino acid, heterocyclic amines, hydrazine, amide, and thioethers are described in absence of catalyst against the traditional synthetic routes of these reactions in non-aqueous medium in presence of catalyst.

  在没有传统合成催化剂的催化剂的情况下，描述了水性悬浮液中1,4-醌与芳香胺，伯脂肪胺，氨基酸，氨基酸酯，杂环胺，肼，酰胺和硫醚的独特亲核取代和加成反应催化剂存在下在非水介质中进行这些反应的途径。
• Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of 2-substituted 3-chloro-1,4-naphthoquinone derivatives
  作者：Jin-Cherng Lien、Li-Jiau Huang、Jih-Pyang Wang、Che-Ming Teng、Kuo-Hsiung Lee、Sheng-Chu Kuo

  DOI：10.1016/s0968-0896(97)00133-8

  日期：1997.12

  A series of 2-substituted 3-chloro-1,4-naphthoquinones was synthesized, and the antiplatelet, antiinflammatory, and antiallergic activities of these compounds were evaluated. The structure-activity relationships in this series were also examined. Most of the 2-alkyl/arylcarboxamido derivatives of 3-chloro-1,4-naphthoquinone showed potent activities with similar trends in each of the activities evaluated. (C) 1997 Elsevier Science Ltd.
• 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.
• Preparation of Some Imidazole Derivatives of 1,4-Naphthoquinone
  作者：John R. E. Hoover、Allan R. Day

  DOI：10.1021/ja01645a028

  日期：1954.8