5H-naphth[1,8-cd]isothiazol-5-one,1,1-dioxide, 6-(phenylamino)

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5H-naphth[1,8-cd]isothiazol-5-one,1,1-dioxide, 6-(phenylamino)
• 英文别名: 6-(phenylamino)-5H-naphth[1,8-cd]isothiazol-5-one 1,1-dioxide；4-(phenylamino)-5H-naphtho[1,8-cd]isothiazol-5-one 1,1-dioxide；4-anilino-1,1-dioxo-1λ⁶-naphth[1,8-cd]isothiazol-5-one；4-Anilino-1,1-dioxo-1λ⁶-naphth[1,8-cd]isothiazol-5-on；6-Anilino-2,2-dioxo-2lambda6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(11),3,5,8(12),9-pentaen-7-one；6-anilino-2,2-dioxo-2λ6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(11),3,5,8(12),9-pentaen-7-one
• 化学式: C₁₆H₁₀N₂O₃S
• 分子量: 310.333
• InChiKey: XNWOABLRFSOLOR-UHFFFAOYSA-N

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：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5H-naphth[1,8-cd]isothiazol-5-one,1,1-dioxide, 6-(phenylamino) 以 乙醇 、 三氟乙酸 为溶剂， 以67%的产率得到5,8-dioxo-6-(phenylamino)-5,8-dihydronaphthalene-1-sulfonamide
  参考文献：
  名称：

  Regioselective one-pot C–N coupling of substituted naphthoquinones: selective intramolecular ring fusion of sulfonamides

  摘要：

  The first one-pot copper-catalyzed highly regioselective C - N bond formation between aryl/alkyl amines and sulfonamide-substituted naphthoquinones was accomplished. Facile chemoselective routes obtained diverse ring-opening 6-amino/anilino-naphthalen-dione-1-sulfonamides and ring-fused 6-amino/aniline5H-naphth[1,8-cd]isothiazol-5-one,1,1 -dioxides with great functional group tolerance. Regiochemistry was confirmed by 1D- and 2D-NMRs. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.041
• 作为产物：
  描述：

  1-萘磺酰胺 在 chromium(VI) oxide 、 copper(II) acetate monohydrate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 15.0h， 生成 5H-naphth[1,8-cd]isothiazol-5-one,1,1-dioxide, 6-(phenylamino)
  参考文献：
  名称：

  [EN] STAT3 INHIBITORS AND THEIR ANTICANCER USE
  [FR] INHIBITEURS DE STAT3 ET LEUR UTILISATION ANTICANCÉREUSE

  摘要：

  在一个方面，该发明涉及替代的替代6-氨基-5,8-二氧化-5,8-二氢萘磺酰胺类似物及其衍生物，替代的4-氨基-5H-萘并[1,8-cd]异噻唑酮-5-酮1,1-二氧化物类似物及其衍生物，以及相关化合物，这些化合物可用作STAT蛋白活性的抑制剂；制备这些化合物的合成方法；包含这些化合物的药物组合物；以及使用这些化合物和组合物治疗与STAT蛋白活性功能障碍相关的细胞不受控制增殖的疾病的方法。本摘要旨在作为在特定领域进行搜索的扫描工具，并不旨在限制本发明。

  公开号：

  WO2014028909A1

文献信息

• [EN] STAT3 INHIBITORS AND THEIR ANTICANCER USE<br/>[FR] INHIBITEURS DE STAT3 ET LEUR UTILISATION ANTICANCÉREUSE
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2014028909A1

  公开（公告）日：2014-02-20

  In one aspect, the invention relates to substituted substituted 6-amino-5,8-dioxo-5,8- dihydronaphthalene- 1 -sulfonamide analogs and derivatives thereof, substituted 4-amino-5H- naphtho[l,8-cd]isothiazol-5-one 1,1-dioxide analogs and derivatives thereof, and related compounds, which are useful as inhibitors of STAT protein activity; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating disorders of uncontrolled cellular proliferation associated with a STAT protein activity dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在一个方面，该发明涉及替代的替代6-氨基-5,8-二氧化-5,8-二氢萘磺酰胺类似物及其衍生物，替代的4-氨基-5H-萘并[1,8-cd]异噻唑酮-5-酮1,1-二氧化物类似物及其衍生物，以及相关化合物，这些化合物可用作STAT蛋白活性的抑制剂；制备这些化合物的合成方法；包含这些化合物的药物组合物；以及使用这些化合物和组合物治疗与STAT蛋白活性功能障碍相关的细胞不受控制增殖的疾病的方法。本摘要旨在作为在特定领域进行搜索的扫描工具，并不旨在限制本发明。
• STAT3 INHIBITORS AND THEIR ANTICANCER USE
  申请人：Ohio State Innovation Foundation

  公开号：US20150232434A1

  公开（公告）日：2015-08-20

  In one aspect, the invention relates to substituted 6-amino-5,8-dioxo-5,8-dihydronaphthalene-1-sulfonamide analogs and derivatives thereof, substituted 4-amino-5H-naphtho[1,8-cd]isothiazol-5-one 1,1-dioxide analogs and derivatives thereof, and related compounds, which are useful as inhibitors of STAT protein activity; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating disorders of uncontrolled cellular proliferation associated with a STAT protein activity dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本发明涉及替代的6-氨基-5,8-二氧代-5,8-二氢萘酚-1-磺酰胺类似物及其衍生物，替代的4-氨基-5H-萘并[1,8-cd]异噻唑-5-酮1,1-二氧化物类似物及其衍生物以及相关化合物，它们可用作STAT蛋白活性的抑制剂；制备这些化合物的合成方法；包含这些化合物的制药组合物；以及使用这些化合物和组合物治疗与STAT蛋白活性功能障碍相关的细胞不受控制增殖紊乱的方法。本摘要旨在作为特定领域搜索的工具，不限制本发明。
• Zincke, Justus Liebigs Annalen der Chemie, 1917, vol. 412, p. 100
  作者：Zincke

  DOI：——

  日期：——
• Discovery of Novel STAT3 Small Molecule Inhibitors via in Silico Site-Directed Fragment-Based Drug Design
  作者：Wenying Yu、Hui Xiao、Jiayuh Lin、Chenglong Li

  DOI：10.1021/jm400080c

  日期：2013.6.13

  Constitutive activation of signal transducer and activator of transcription 3 (STAT3) has been validated as an attractive therapeutic target for cancer therapy. To stop both STAT3 activation and dimerization, a viable strategy is to design inhibitors blocking its SH2 domain phosphotyrosine binding site that is responsible for both actions. A new fragment-based drug design (FBDD) strategy, in silico site-directed FBDD, was applied in this study. A designed novel compound, 5,8-dioxo-6-(pyridin-3-ylamino)-5,8-dihydronaphthalene-1-sulfonamide (LY5), was confirmed to bind to STAT3 SH2 by fluorescence polarization assay. In addition, four out of the five chosen compounds have IC50 values lower than 5 mu M for the U2OS cancer cells. 8 (LY5) has an IC50 range in 0.5-1.4 mu M in various cancer cell lines. 8 also suppresses tumor growth in an in vivo mouse model. This study has demonstrated the utility of this approach and could be used to other drug targets in general.
• US9783513B2
  申请人：——

  公开号：US9783513B2

  公开（公告）日：2017-10-10