4-氨基-2-硝基-1-萘酚 | 319918-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-氨基-2-硝基-1-萘酚
• 英文名称: 4-amino-2-nitronaphthalen-1-ol
• 英文别名: 4-Amino-2-nitro-[1]naphthol；4-Amino-2-nitro-1-naphthol
• CAS: 319918-83-7
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: ANBUBGFZWBEEMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  92.1
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  4-氨基-2-硝基-1-萘酚 在 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 21.5h， 生成 1,1-dimethylethyl N-(3-amino-4-oxonaphthalen-1-ylidene)carbamate
  参考文献：
  名称：

  Initial development of a cytotoxic amino-seco-CBI warhead for delivery by prodrug systems

  摘要：

  Cyclopropabenzaindoles (CBIs) are exquisitely potent cytotoxins which bind and alkylate in the minor groove of DNA. They are not selective for cancer cells, so prodrugs are required. CBIs can be formed at physiological pH by Winstein cyclisation of 1-chloromethyl-3-substituted-5-hydroxy-2,3-dihydro-benzo[e] indoles (5-OH-seco-CBIs). Corresponding 5-NH2-seco-CBIs should also undergo Winstein cyclisation similarly. A key triply orthogonally protected intermediate on the route to 5-NH2-seco-CBIs has been synthesised, via selective monotrifluoroacetylation of naphthalene-1,3-diamine, Boc protection, electrophilic iodination, selective allylation at the trifluoroacetamide and 5-exo radical ring-closure with TEMPO. This intermediate has potential for introduction of peptide prodrug masking units (deactivating the Winstein cyclisation and cytotoxicity), addition of diverse indole-amide side-chains (enhancing non-covalent binding prior to alkylation) and use of different leaving groups (replacing the usual chlorine, allowing tuning of the rate of Winstein cyclisation). This key intermediate was elaborated into a simple model 5-NH2-seco-CBI with a dimethylaminoethoxyindole side-chain. Conversion to a bio-reactive entity and the bioactivity of this system were confirmed through DNA-melting studies (Delta T-m = 13 degrees C) and cytotoxicity against LNCaP human prostate cancer cells (IC50 = 18 nM). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.034
• 作为产物：
  描述：

  乙酸-1-萘酯 在 盐酸 、 乙酸酐 、 tin(ll) chloride 作用下， 生成 4-氨基-2-硝基-1-萘酚
  参考文献：
  名称：

  148.α-萘酚和α-萘甲醚的单硝化和2：4-二硝基-α-萘酚的单还原

  摘要：

  DOI：

  10.1039/jr9350000671

文献信息

• Fluorescent dye compounds, conjugates and uses thereof
  申请人：Life Technologies Corporation

  公开号：EP2371927A1

  公开（公告）日：2011-10-05

  The present teachings generally relate to fluorescent dyes, linkable forms of fluorescent dyes, energy transfer dyes, reagents labeled with fluorescent dyes and uses thereof.

  本教导一般涉及荧光染料、荧光染料的可连接形式、能量转移染料、用荧光染料标记的试剂及其用途。
• Fluorescent Dye Compounds, Conjugates and Uses Thereof
  申请人：Graham Ronald J.

  公开号：US20090093062A1

  公开（公告）日：2009-04-09

  The present teachings generally relate to fluorescent dyes, linkable forms of fluorescent dyes, energy transfer dyes, reagents labeled with fluorescent dyes and uses thereof.
• US7256292B2
  申请人：——

  公开号：US7256292B2

  公开（公告）日：2007-08-14
• US7985602B2
  申请人：——

  公开号：US7985602B2

  公开（公告）日：2011-07-26
• US8729267B2
  申请人：——

  公开号：US8729267B2

  公开（公告）日：2014-05-20