N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide | 63351-45-1

• 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)benzamide
• 英文别名: 2-benzoylamino-3-chloro-[1,4]naphthoquinone；2-benzoylamino-3-chloro-1,4-naphthoquinone；N-(3-chloro-1,4-dioxonaphthalen-2-yl)benzamide
• CAS: 63351-45-1
• 化学式: C₁₇H₁₀ClNO₃
• 分子量: 311.724
• InChiKey: ADHBVWXFMCERTO-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  498.5±45.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide 以 乙二醇 为溶剂， 生成 2-苯基萘并[2,3-d]恶唑-4,9-二酮
  参考文献：
  名称：

  Hammam,A.S.; Osman,A.-M., Journal fur praktische Chemie (Leipzig 1954), 1977, vol. 319, p. 254 - 258

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-3-氯-1,4-萘醌 、 苯甲酰氯 在 sodium hydride 作用下， 生成 N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide
  参考文献：
  名称：

  1,2-二取代萘[2,3-d]咪唑-4,9-二酮及相关化合物的合成及细胞毒性。

  摘要：

  在继续寻找对缓慢生长的实体瘤具有选择性的潜在抗癌药物候选药物的过程中，我们合成了一系列铅结构的1-乙基和2-取代衍生物，即1-乙基-2-甲基萘[2,3-]。 d]咪唑-4，9-二酮（5）。据报道，它们在美国国家癌症研究所的体外癌细胞系中具有细胞毒活性。通常，各种烷基，苯基或苄基部分的取代不会提高活性，并且化合物5仍然是活性最高的萘并[2,3-d]咪唑-4,9-二酮衍生物。但是，发现几种相关的2-（酰基氨基）-3-氯-1,4-萘醌（2f-j）具有较高的活性和选择性。化合物2i，2-[（（2-氟苯基）乙酰胺基] -3-氯-1,4-萘醌，

  DOI：

  10.1021/jm950247k

文献信息

• Naphthoquinone antitumor compound and method
  申请人：The University of North Carolina at Chapel Hill

  公开号：US05789431A1

  公开（公告）日：1998-08-04

  The invention provides 1,4-naphthoquinone compounds and a method for inhibiting tumor cell growth in a subject by administering such compounds. The compounds are represented by the structures: ##STR1## where R.sub.1 is lower alkyl, halogenated lower alkyl, phenyl, benzyl, phenethyl, or --(CH.sub.2).sub.m COOX where m is 2 or 3 and X is H, methyl, or ethyl; R.sub.2 is halo or NHY, where Y is hydrogen, lower alkyl, halogenated lower alkyl, hydroxylated lower alkyl, lower dialkylaminoalkyl, phenyl, benzyl, or phenethyl; R.sub.3 is lower alkyl, halogenated lower alkyl, phenyl, benzyl, phenethyl, or --(CH.sub.2).sub.m COOX, where m and X are as defined for R.sub.1 above; and R.sub.4 is hydrogen, lower alkyl, lower aminoalkyl, halogenated lower alkyl, phenyl, benzyl, or phenethyl.

  这项发明提供了1,4-萘醌化合物以及一种通过给予这些化合物来抑制体内肿瘤细胞生长的方法。这些化合物由以下结构表示： 其中R.sub.1为较低烷基、卤代较低烷基、苯基、苄基、苯乙基或--(CH.sub.2).sub.m COOX，其中m为2或3，X为H、甲基或乙基；R.sub.2为卤素或NHY，其中Y为氢、较低烷基、卤代较低烷基、羟基化较低烷基、较低二烷基氨基烷基、苯基、苄基或苯乙基；R.sub.3为较低烷基、卤代较低烷基、苯基、苄基、苯乙基或--(CH.sub.2).sub.m COOX，其中m和X如上所述；R.sub.4为氢、较低烷基、较低氨基烷基、卤代较低烷基、苯基、苄基或苯乙基。
• 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。
• 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.
• [EN] INHIBITORS OF THE MITF MOLECULAR PATHWAY<br/>[FR] INHIBITEURS DE LA VOIE MOLÉCULAIRE MITF
  申请人：GEN HOSPITAL CORP

  公开号：WO2014201016A3

  公开（公告）日：2015-02-05
• Synthesis and evaluation of Hsp90 inhibitors that contain the 1,4-naphthoquinone scaffold
  作者：M. Kyle Hadden、Stephanie A. Hill、Jason Davenport、Robert L. Matts、Brian S.J. Blagg

  DOI：10.1016/j.bmc.2008.11.064

  日期：2009.1

  High-throughput screening of a library of diverse molecules has identified the 1,4-naphthoquinone scaffold as a new class of Hsp90 inhibitors. The synthesis and evaluation of a rationally-designed series of analogues containing the naphthoquinone core scaffold has provided key structure-activity relationships for these compounds. The most active inhibitors exhibited potent in vitro activity with low micromolar IC50 values in anti-proliferation and Her2 degradation assays. In addition, 3g, 12, and 13a induced the degradation of oncogenic Hsp90 client proteins, a hallmark of Hsp90 inhibition. The identification of these naphthoquinones as Hsp90 inhibitors provides a new scaffold upon which improved Hsp90 inhibitors can be developed. (C) 2008 Elsevier Ltd. All rights reserved.