N-hydroxysuccinimidyl 4-azido-2-hydroxy-5-iodobenzoate | 99298-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-hydroxysuccinimidyl 4-azido-2-hydroxy-5-iodobenzoate
• 英文别名: 4-azido-2-hydroxy-5-iodobenzoic acid N-hydroxysuccinimide ester；2,5-Pyrrolidinedione, 1-[(4-azido-2-hydroxy-5-iodobenzoyl)oxy]-；(2,5-dioxopyrrolidin-1-yl) 4-azido-2-hydroxy-5-iodobenzoate
• CAS: 99298-06-3
• 化学式: C₁₁H₇IN₄O₅
• 分子量: 402.105
• InChiKey: LKYHKIASAGJOIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-hydroxysuccinimidyl 4-azido-2-hydroxy-5-iodobenzoate 在 盐酸 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 20.0h， 生成 3(R)-[(2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide N-(N'-(4-azido-2-hydroxy-5-iodobenzoyl)amino)ethyl hydrochloride
  参考文献：
  名称：

  Design and Synthesis of Photoaffinity-Labeling Ligands of the l-Prolyl-l-leucylglycinamide Binding Site Involved in the Allosteric Modulation of the Dopamine Receptor

  摘要：

  Pro-Leu-Gly-NH2 (PLG), in addition to its endocrine effects, possesses the ability to modulate dopamine D-2 receptors within the central nervous system. However, the precise binding site of PLG is unknown. Potential photoaffinity-labeling ligands of the PLG binding site were designed as tools to be used in the identification of the macromolecule that possesses this binding site. Six different photoaffinity-labeling ligands were designed and synthesized on the basis of the gamma-lactam PLG peptidomimetic 1. The 4-azidobenzoyl and 4-azido-2-hydroxybenzoyl photoaffinity-labeling moieties were placed at opposite ends of PLG peptidomimetic I to generate a series of ligands that potentially could be used to map the PLG binding site. All of the compounds that were synthesized possessed activity comparable to or better than PLG in enhancing [H-3]-N-propylnorapomorphine agonist binding to dopamine receptors. Photoaffinity ligands that were crosslinked to the receptor preparation produced a modulatory effect that was either comparable to or greater than the increase in agonist binding produced by the respective ligands that were not cross-linked to the dopamine receptor. The results indicate that these photoaffinity-labeling agents are binding at the same allosteric site as PLG and PLG peptidomimetic 1.

  DOI：

  10.1021/jm050644n
• 作为产物：
  描述：

  methyl 4-azido-2-hydroxy-5-iodobenzoate 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 19.0h， 生成 N-hydroxysuccinimidyl 4-azido-2-hydroxy-5-iodobenzoate
  参考文献：
  名称：

  Synthesis and biological activity of iodinated and photosensitive derivatives of tetrabenazine

  摘要：

  DOI：

  10.1016/0223-5234(90)90121-i

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。
• An improved procedure for the iodination of phenols using sodium iodide and tert-butyl hypochlorite
  作者：Tadashi Kometani、David S. Watt、Tae Ji、Tony Fitz

  DOI：10.1021/jo00225a079

  日期：1985.12
• Avermectin chemistry and action: ester- and ether-type candidate photoaffinity probes
  作者：Yoshihisa Tsukamoto、Loretta M. Cole、John E. Casida

  DOI：10.1016/s0968-0896(99)00259-x

  日期：2000.1

  Avermectin B-1a (1) is a potent anthelmintic, insecticide, miticide and chloride channel activator on interaction with a specific nerve membrane site analyzed by binding assays with [H-3]1. Candidate photoaffinity probes were prepared replacing the dioleandrosyl substituent with potential isosteric esters and ethers approximating the original overall atom length and terminating in a phenyl moiety substituted with azido, iodo or hydroxy. Several of the candidates met the goal of high potency on mouse, housefly and fruit fly brain chloride channels with IC50 values of 7-57 nM in competing for the [H-3]1 binding site. (C) 2000 Elsevier Science Ltd. All rights reserved.
• KOMETANI, TADASHI;WATT, D. S.;JI, TAE, TETRAHEDRON LETT., 1985, 26, N 17, 2043-2046
  作者：KOMETANI, TADASHI、WATT, D. S.、JI, TAE

  DOI：——

  日期：——
• Synthesis and biological activity of iodinated and photosensitive derivatives of tetrabenazine
  作者：G Aranda、JP Beaucourt、M Ponchant、MF Isambert、JP Henry

  DOI：10.1016/0223-5234(90)90121-i

  日期：1990.5