ethyl 4-(benzyloxy)-3-nitrobenzoate | 926028-17-3

• 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: ethyl 4-(benzyloxy)-3-nitrobenzoate
• 英文别名: Ethyl 3-nitro-4-phenylmethoxybenzoate
• CAS: 926028-17-3
• 化学式: C₁₆H₁₅NO₅
• 分子量: 301.299
• InChiKey: JMIRDOOKGBYIHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  465.2±30.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-(benzyloxy)-3-nitrobenzoate 在 tetrafluoroboric acid 、 tin (IV) chloride pentahydrate 、 sodium nitrite 作用下， 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of substituted 6H-benzo[c]chromenes: a palladium promoted ring closure of diazonium tetrafluoroborates

  摘要：

  A highly efficient palladium-catalysed phenyl diazonium tetrafluoroborate participation of C-H activation ring closure protocol has been developed. A series of 6H-benzo[c]chromenes have been synthesized by intramolecular cyclization of ortho diazonium salts tetrafluoroborate of benzyloxyphenyl (Method A), or phenoxymethyl phenyl (Method B). The transformation allows the synthesis of 6H-benzo[c]chromenes with a wide variety of functional groups and substitution patterns from simple and easily accessible precursors. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.038
• 作为产物：
  描述：

  4-羟基-3-硝基苯甲酸 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 ethyl 4-(benzyloxy)-3-nitrobenzoate
  参考文献：
  名称：

  Development of hypoxia-inducible factor (HIF)-1α inhibitors: Effect of ortho-carborane substituents on HIF transcriptional activity under hypoxia

  摘要：

  A series of substituted ortho-carboranylphenoxyacetanilides were synthesized and evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter assay in HeLa cells expressing the HRE-dependent firefly luciferase reporter construct (HRE-Luc) and constitutively expressing CMV-driven Renilla luciferase reporter, and their ability to inhibit cell growth (GI(50)) using the MTT assay. Among the compounds synthesized, 1g and 1l showed significant inhibition of hypoxia-induced HIF-1 transcriptional activity (IC50: 1.9 +/- 0.4 and 1.4 +/- 0.2 mu M, respectively). Both compounds suppressed HIF-1 alpha accumulation in a concentration-dependent manner. The porcine heart malate dehydrogenase (MDH) refolding assay revealed that compound 1l inhibited human Hsp60 chaperone activity (IC50: 6.80 +/- 0.25 mu M) and this inhibition activity was higher than that of ETB (IC50: 10.9 +/- 0.63 mu M). (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.081

文献信息

• [EN] SUBSTITUTED 4-BENZYLOXY-BENZOIC ACID AMIDE DERIVATIVES<br/>[FR] DERIVES AMIDES D'ACIDE 4-BENZYLOXY-BENZOIQUE SUBSTITUE
  申请人：BAYER HEALTHCARE AG

  公开号：WO2007017092A1

  公开（公告）日：2007-02-15

  [EN] The present invention relates to novel substituted 4-benzyloxy-benzoic acid amide derivatives, processes for their preparation, and their use in medicaments, especially for the prophylaxis and treatment of diseases associated with Cold Menthol Receptor 1 (CMR-1) activity, in particular for the treatment of urological diseases or disorders, such as detrusor overactivity (overactive bladder), urinary incontinence, neurogenic detrusor overactivity (detrusor hyperflexia), idiopathic detrusor overactivity (detrusor instability), benign prostatic hyperplasia, and lower urinary tract symptoms; chronic pain, neuropathic pain, postoperative pain, rheumatoid arthritic pain, neuralgia, neuropathies, algesia, nerve injury, ischaemia, neurodegeneration, stroke, and inflammatory disorders such as asthma and chronic obstructive pulmonary (or airways) disease (COPD).
  [FR] La présente invention concerne de nouveaux dérivés amides d'acide 4-benzyloxy-benzoïque substitué, leurs méthodes de préparation, et leur utilisation dans des médicaments, notamment pour la prophylaxie et le traitement de maladies associées à l'activité du récepteur au froid et au menthol 1 (CMR-1), en particulier pour le traitement de maladies ou de troubles urologiques, tels que l'hyperactivité du détrusor (vessie hyperactive), l'incontinence urinaire, l'hyperactivité neurogène du détrusor (hyperflexie du détrusor), l'hyperactivité idiopathique du détrusor (instabilité du détrusor), l'hyperplasie prostatique bénigne et les symptômes des voies urinaires inférieures, la douleur chronique, la douleur neuropathique, la douleur postopératoire, la douleur arthritique rhumatoïde, la névralgie, les neuropathies, l'algésie, la lésion nerveuse, l'ischémie, la neurodégénérescence, l'accident vasculaire cérébral, et des troubles inflammatoires, tels que l'asthme et la bronchopneumopathie chronique obstructive (obstruction des voies aériennes) (BPCO).
• Development of hypoxia-inducible factor (HIF)-1α inhibitors: Effect of ortho-carborane substituents on HIF transcriptional activity under hypoxia
  作者：Hiroyuki Nakamura、Yuka Yasui、Minako Maruyama、Hidemitsu Minegishi、Hyun Seung Ban、Shinichi Sato

  DOI：10.1016/j.bmcl.2012.11.081

  日期：2013.2

  A series of substituted ortho-carboranylphenoxyacetanilides were synthesized and evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter assay in HeLa cells expressing the HRE-dependent firefly luciferase reporter construct (HRE-Luc) and constitutively expressing CMV-driven Renilla luciferase reporter, and their ability to inhibit cell growth (GI(50)) using the MTT assay. Among the compounds synthesized, 1g and 1l showed significant inhibition of hypoxia-induced HIF-1 transcriptional activity (IC50: 1.9 +/- 0.4 and 1.4 +/- 0.2 mu M, respectively). Both compounds suppressed HIF-1 alpha accumulation in a concentration-dependent manner. The porcine heart malate dehydrogenase (MDH) refolding assay revealed that compound 1l inhibited human Hsp60 chaperone activity (IC50: 6.80 +/- 0.25 mu M) and this inhibition activity was higher than that of ETB (IC50: 10.9 +/- 0.63 mu M). (c) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of substituted 6H-benzo[c]chromenes: a palladium promoted ring closure of diazonium tetrafluoroborates
  作者：Jing Zhou、Liang-Zhu Huang、You-Qiang Li、Zhen-Ting Du

  DOI：10.1016/j.tetlet.2012.10.038

  日期：2012.12

  A highly efficient palladium-catalysed phenyl diazonium tetrafluoroborate participation of C-H activation ring closure protocol has been developed. A series of 6H-benzo[c]chromenes have been synthesized by intramolecular cyclization of ortho diazonium salts tetrafluoroborate of benzyloxyphenyl (Method A), or phenoxymethyl phenyl (Method B). The transformation allows the synthesis of 6H-benzo[c]chromenes with a wide variety of functional groups and substitution patterns from simple and easily accessible precursors. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.