1-重氮基-2-羟基-4-硝基萘 | 33670-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-重氮基-2-羟基-4-硝基萘
• 英文名称: 1-diazo-2-hydroxy-4-nitronaphthalene
• 英文别名: 2-hydroxy-4-nitro-naphthalene-1-diazonium-betaine；2-Hydroxy-4-nitro-naphthalin-1-diazonium-betain；4-Nitro-2-oxo-1-diazo-1.2-dihydro-naphthalin；4-Nitro-naphthochinon-(1.2)-diazid-(1)；4-Nitro-1-diazo-naphthol-(2)；1-Diazo-4-nitro-2(1H)naphthalenon；4-Nitro-1,2-naphthochinon-1-diazid；1-diazonio-4-nitronaphthalen-2-olate
• CAS: 33670-65-4
• 化学式: C₁₀H₅N₃O₃
• 分子量: 215.168
• InChiKey: IFLRCTVJOIQGFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 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：
  97
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-重氮基-2-羟基-4-硝基萘 在 乙醇 作用下， 生成 4-硝基萘-2-醇
  参考文献：
  名称：

  Morgan; Evens, Journal of the Chemical Society, 1919, vol. 115, p. 1141

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2,4-二硝基萘-1-基)乙酰胺 在 硫酸 、 sodium nitrite 作用下， 反应 0.25h， 以80%的产率得到1-重氮基-2-羟基-4-硝基萘
  参考文献：
  名称：

  Hydrazinonaphthalene and Azonaphthalene Thrombopoietin Mimics Are Nonpeptidyl Promoters of Megakaryocytopoiesis

  摘要：

  High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC50 values in the region of 1-20 nM.

  DOI：

  10.1021/jm010283l

文献信息

• Morgan; Evens, Journal of the Chemical Society, 1919, vol. 115, p. 1141
  作者：Morgan、Evens

  DOI：——

  日期：——
• 87. Preparation of diazo-naphthols and nitration of 4-bromoaceto-1-naphthalide
  作者：Herbert H. Hodgson、Stanley Birtwell

  DOI：10.1039/jr9430000321

  日期：——
• Hydrazinonaphthalene and Azonaphthalene Thrombopoietin Mimics Are Nonpeptidyl Promoters of Megakaryocytopoiesis
  作者：Kevin J. Duffy、Michael G. Darcy、Evelyne Delorme、Susan B. Dillon、Daniel F. Eppley、Connie Erickson-Miller、Leslie Giampa、Christopher B. Hopson、Yifang Huang、Richard M. Keenan、Peter Lamb、Lynnette Leong、Nannan Liu、Stephen G. Miller、Alan T. Price、Jon Rosen、Rakhi Shah、Tony N. Shaw、Heather Smith、Kenneth C. Stark、Shin-Shay Tian、Curtis Tyree、Kenneth J. Wiggall、Lily Zhang、Juan I. Luengo

  DOI：10.1021/jm010283l

  日期：2001.10.1

  High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC50 values in the region of 1-20 nM.
• 126.—Preparation of 4-halogeno-2-naphthols and 4-nitro-2-naphthol, with a note on the resonance structure of the internal diazo-oxides (diazo-naphthols)
  作者：Herbert H. Hodgson、Stanley Birtwell

  DOI：10.1039/jr9430000468

  日期：——