4-叠氮基-2-羟基苯甲酸甲酯 | 87877-90-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-叠氮基-2-羟基苯甲酸甲酯
• 英文名称: methyl 4-azido-2-hydroxybenzoate
• 英文别名: methyl p-azidosalicylate；methyl-4-azidosalicylate；4-azido-2-hydroxy-benzoic acid methyl ester；4-Azido-2-hydroxy-benzoesaeure-methylester
• CAS: 87877-90-5
• 化学式: C₈H₇N₃O₃
• 分子量: 193.162
• InChiKey: APOODKUVHKLOFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-叠氮基-2-羟基苯甲酸甲酯 在 sodium hydroxide 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 1-(3-hydroxy-4-carboxyphenyl)-5-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Settimo, A. Da; Livi, O.; Biagi, G., Farmaco, Edizione Scientifica, 1983, vol. 38, # 10, p. 725 - 737

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氨基水杨酸 在 盐酸 、 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 50.33h， 生成 4-叠氮基-2-羟基苯甲酸甲酯
  参考文献：
  名称：

  An improved procedure for the iodination of phenols using sodium iodide and tert-butyl hypochlorite

  摘要：

  DOI：

  10.1021/jo00225a079

文献信息

• Iodination of phenols using chloramine T and sodium iodide
  作者：Tadashi Kometani、David S. Watt、Tae Ji

  DOI：10.1016/s0040-4039(00)94774-9

  日期：——

  A convenient procedure for the iodination of many substituted phenols uses chloramine T and sodium iodide in DMF, DMSO, or acetonitrile.

  许多取代的苯酚加碘的简便方法是在DMF，DMSO或乙腈中使用氯胺T和碘化钠。
• Studies on Specific Inhibition of Benzodiazepine Receptor Binding by Some C-Benzoyl-1,2,3-triazole Derivatives
  作者：G. Biagi、I. Giorgi、O. Livi、A. Lucacchini、C. Martini、V. Scartoni

  DOI：10.1002/jps.2600820906

  日期：1993.9

  activity, equivalent to that of the triazole acetic derivative 23, which is 4-benzyl substituted. Generally, the carboxymethyl radical in the 1-position of the triazole ring decreased the activity, probably because of intramolecular hydrogen bonding with the carbonyl function of the benzoyl substituent. The N-1 unsubstituted triazole derivatives 24 and 25 were ineffective; this result is in disagreement

  合成了某些新的（1-15）或先前描述的（16-25）以C-苯甲酰基取代基为特征的1,2,3-三唑衍生物，并测试了它们从牛脑膜置换[3H]氟硝西m的能力。带有中性和亲脂性取代基（分别为苯乙基和环己基）的化合物11a和9a显示出更高的活性。5-苯甲酰基异构体11b具有较低的活性，等同于被4-苄基取代的三唑乙酸衍生物23的活性。通常，三唑环的1-位上的羧甲基基团降低了活性，这可能是由于分子内的氢键与苯甲酰基取代基的羰基功能。N-1个未取代的三唑衍生物24和25无效；这个结果与我们以前的观察结果不一致。
• Syntheses of 1,2,3-triazolyl salicylamides with inhibitory activity on lipopolysaccharide-induced nitric oxide production
  作者：Jieun Yoon、Lan Cho、Sang Kook Lee、Jae-Sang Ryu

  DOI：10.1016/j.bmcl.2011.02.034

  日期：2011.4

  A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition and evaluated for their abilities to inhibit NO production in LPS-activated RAW264.7 macrophage cells. Among 28 analogues, 29g showed a significant inhibitory activity (IC50 = 12.8 mu M). The inhibitory effects of 29g on LPS-mediated NO production in macrophage cells appeared to be associated with the suppression of iNOS expression. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Activity of a Photoaffinity Etoposide Probe
  作者：Brian B. Hasinoff、Gaik-Lean Chee、Billy W. Day、Kwasi S. Avor、Norman Barnabé、Padmakumari Thampatty、Jack C. Yalowich

  DOI：10.1016/s0968-0896(01)00102-x

  日期：2001.7

  The epipodophyllotoxin etoposide is a potent and widely used anticancer drug that targets DNA topoisomerase II. The synthesis, photochemical, and biological testing of a photoactivatable aromatic azido analogue of etoposide also containing an iodo group is described. This azido analogue should prove useful for identifying the etoposide interaction site on topoisomerase II, Irradiation of the azido analogue and an aldehyde-conntaining azido precursor with UV light produced changes in their UV-visible spectra that were consistent with photoactivation. The azido analogue strongly inhibited topoisomerase II and inhibited the growth of Chinese Hamster Ovary cells. Azido analogue-induced topoisomerase II-DNA covalent complexes were significantly increased subsequent to UV irradiation of drug-treated human leukemia K562 calls as compared to etoposide-treated cells. These results suggest that the photoactivated form of etoposide is a more effective topoisomerase II poison either by interacting directly with the enzyme or with DNA subsequent to topoisnmerase II-mediated strand cleavage. (C) 2001 Elsevier Science Ltd. All rights reserved.
• An efficient synthesis of a class of heterobifunctional photo-reactive crosslinkers, labels, and probes
  作者：Kyle W Gano、Harold G Monbouquette、David C Myles

  DOI：10.1016/s0040-4039(01)00131-9

  日期：2001.3

  Aryl esters are selectively reduced with DIBAL-H in the presence of an azide functional group to provide access to 4-azido-2-alkoxybenzaldehydes in five steps with overall yields ranging from 72 to 78%. This methodology improves traditional approaches to this class of compounds, which suffer from poor overall yields (4-11%). Out approach can be used to synthesize a variety of new aryl azide cross-linkers, labels, and probes. (C) 2001 Elsevier Science Ltd. All rights reserved.