2-nitro-4-azidophenol | 51642-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-nitro-4-azidophenol
• 英文别名: 4-azido-2-nitrophenol；3-Nitro-4-oxy-diazobenzolimid
• CAS: 51642-26-3
• 化学式: C₆H₄N₄O₃
• mdl: MFCD09743673
• 分子量: 180.123
• InChiKey: ZDQFIUAWRBXXIE-UHFFFAOYSA-N

物化性质

• 熔点：
  91 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2929909090

反应信息

• 作为反应物：
  描述：

  2-nitro-4-azidophenol 在 甲醇 、 sodium hydroxide 、 potassium tert-butylate 作用下， 反应 0.25h， 生成 6-(2-nitro-4-azidophenoxy)hexanoic acid
  参考文献：
  名称：

  Aranda, G.; Lallemand, J. Y., Synthetic Communications, 1990, vol. 20, # 1, p. 85 - 96

  摘要：

  DOI：
• 作为产物：
  描述：

  2-硝基-4-氨基苯酚 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 0.45h， 以64%的产率得到2-nitro-4-azidophenol
  参考文献：
  名称：

  Dunkin, Ian R.; El Ayeb, Abdunaser A.; Gallivan, Sean L., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1997, # 8, p. 1419 - 1427

  摘要：

  DOI：

文献信息

• Synthesis of novel 1,2,3-triazole tagged pyrazolo[3,4-b]pyridine derivatives and their cytotoxic activity
  作者：Chavva Kurumurthy、Banda Veeraswamy、Pillalamarri Sambasiva Rao、Gautham Santhosh Kumar、Pamulaparthy Shanthan Rao、Velaturu Loka Reddy、Janapala Venkateswara Rao、Banda Narsaiah

  DOI：10.1016/j.bmcl.2013.12.107

  日期：2014.2

  3-triazole tagged pyrazolo[3,4-b]pyridine derivatives 3 and 4 were prepared respectively starting from 6-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-3-amine 1 via selective N-propargylation, followed by reaction with diverse substituted alkyl/perfluoroalkyl/aryl/aryl amide azides under Sharpless conditions. All the synthesized compounds 3 and 4 were screened for cytotoxic activity against four

  一系列新颖的1,2,3-三唑标记的吡唑并[3,4的b ]吡啶衍生物3和4被分别制备由6-苯基-4-（三氟甲基）-1 ħ -吡唑并[3,4- b通过选择性N-炔丙基化]吡啶3-胺1，然后在Sharpless条件下与各种取代的烷基/全氟烷基/芳基/芳基酰胺叠氮化物反应。筛选所有合成的化合物3和4对四种人类癌细胞系如U937，THP-1，HL60和B16-F10的细胞毒活性。化合物3e，4g，4i和4j 已经证明了显示出有希望的活动。
• Functional induction of P-glycoprotein efflux pump by phenyl benzenesulfonamides: Synthesis and biological evaluation of T0901317 analogs
  作者：Anil K. Padala、Abubakar Wani、Ram A. Vishwakarma、Ajay Kumar、Sandip B. Bharate

  DOI：10.1016/j.ejmech.2016.07.005

  日期：2016.10

  N-(2,2,2-Trifluoroethyl)-N-[4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyll-benzenesulfo- namide (T0901317, 6) is a potent activator of pregnane-X-receptor (PXR), which is a nuclear receptor controlling P-gp expression. Herein, we aimed to investigate P-gp induction activity of T0901317 and establish its structure-activity relationship. T0901317 along with a series of N-triazolyl-methylene-linked benzenesulfonamides were synthesized and screened for P-gp induction activity using a rhodamine-123 based efflux assay in the P-gp overexpressing human adenocarcinoma LS-180 cells, wherein several compounds showed potent P-gp induction activity at 5 mu M. Treatment with benzene sulphonamides led to the decrease in intracellular accumulation of a fluorescent P-gp substrate rhodamine-123 up to 48% (control 100%). In the western-blot studies, T0901317 (6) and its triazole linked analog 26e at 5 displayed induction of P-gp expression in LS180 cells. These compounds were non-toxic in LS-180 and human neuroblastoma SH-SY5Y cells (IC50 > 50 mu M). The compound 26e showed significant P-gp induction even at 0.3 mu M, indicating an excellent therapeutic window. These results clearly indicate promise of this class of compounds as potential agents to enhance amyloid-beta clearance in Alzheimers patients. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Design and synthesis by click triazole formation of paclitaxel mimics with simplified core and side-chain structures
  作者：Claire Le Manach、Aurélie Baron、Régis Guillot、Boris Vauzeilles、Jean-Marie Beau

  DOI：10.1016/j.tetlet.2011.01.081

  日期：2011.3

  A library of paclitaxel (taxol) mimics was obtained by a straightforward strategy involving rational design and an efficient synthesis of a simplified taxane core substitute, together with a click-chemistry combinatorial search for phenylisoserine side-chain surrogates. (c) 2011 Elsevier Ltd. All rights reserved.
• Forster; Fierz, Journal of the Chemical Society, 1907, vol. 91, p. 865
  作者：Forster、Fierz

  DOI：——

  日期：——
• Kumar, R. Naresh; Mallareddy; Nagender, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 11, p. 1361 - 1375
  作者：Kumar, R. Naresh、Mallareddy、Nagender、Rao, P. Sambasiva、Poornachandra、Ranjithreddy、Kumar, C. Ganesh、Narsaiah

  DOI：——

  日期：——