4-氯-2-硝基-1-萘胺 | 91240-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-氯-2-硝基-1-萘胺
• 英文名称: 1-Amino-4-chlor-2-nitronaphthalin
• 英文别名: <4-Chlor-2-nitro-naphthyl-(1)>-amin；4-chloro-2-nitro-1-naphthylamine；4-Chlor-2-nitro-1-amino-naphthalin；4-Chlor-2-nitro-[1]naphthylamin；4-Chloro-2-nitronaphthalen-1-amine；4-chloro-2-nitronaphthalen-1-amine
• CAS: 91240-93-6
• 化学式: C₁₀H₇ClN₂O₂
• 分子量: 222.631
• InChiKey: AVPVVEHYUJTECG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯-2-硝基-1-萘胺 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 1,2-二氨基萘
  参考文献：
  名称：

  Synthesis and biological activity of splitomicin analogs targeted at human NAD+-dependent histone deacetylases (sirtuins)

  摘要：

  Small molecules interfering with posttranslational modification of histones are of interest as tools to study epigenetic regulation of gene transcription. Specifically, drugs that interfere with histone deacetylation could be useful to induce differentiation, growth arrest as well as apoptotic cell death in tumor cells. One class of histone deacetylases is known as sirtuins some of which (Saccharomyces cerevisiae Sir2) are for example inhibited by the lactone splitomicin leading to telomeric silencing in yeast. However, splitomicin is only a micromolar inhibitor of yeast Sir2 and does not inhibit human subtypes and the lactone is prone to hydrolytic ring opening. In preliminary SAR-studies, splitomicin analogs lacking this hydrolytically labile ring were described as inactive while the naphthalene moiety could successfully be replaced by smaller aromatic rings in a fragment-like dihydrocoumarin. Here we report the synthesis and biological activity of a series of hydrolytically stable analogs with activity against human SIRT1 and 2. These comparatively small compounds characterized by high ligand efficiency are used as a starting point toward the development of specific inhibitors of histone deacetylases from the class of sirtuins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.026
• 作为产物：
  描述：

  1-Acetamido-4-chlornaphthalin 在 盐酸 、 水 、 硝酸 、 溶剂黄146 作用下， 生成 4-氯-2-硝基-1-萘胺
  参考文献：
  名称：

  87.重氮萘的制备及4-溴乙酰-1-萘的硝化

  摘要：

  DOI：

  10.1039/jr9430000321

文献信息

• 164. The action of cuprous oxide on diazotised amines in ethyl-alcoholic acid solution
  作者：Herbert H. Hodgson、Harold S. Turner

  DOI：10.1039/jr9420000748

  日期：——
• 431. Salt formation of homonuclear naphthalene derivatives
  作者：Herbert H. Hodgson、Reginald L. Elliott

  DOI：10.1039/jr9350001850

  日期：——
• 32. Reactions of 3-nitro-1-naphthylamine. Part II. Chlorination, mercuration, coupling with diazo-compounds, and the preparation of some arsenicals
  作者：Herbert H. Hodgson、David E. Hathway

  DOI：10.1039/jr9450000123

  日期：——
• 328. Nitrous acid as a nitrating and oxidising agent. Part III. The nitration of 4-dimethylaminoaceto-1-naphthalide, of 4-chlorodimethyl-1-naphthylamine, and of dimethyl-β-naphthylamine
  作者：Herbert H. Hodgson、J. Harold Crook

  DOI：10.1039/jr9360001500

  日期：——
• 42. The action of cuprous oxide on diazotised amines. Part III. Action in sulphuric acid–glacial acetic acid
  作者：Herbert H. Hodgson、Stanley Birtwell、Ewart Marsden

  DOI：10.1039/jr9440000112

  日期：——