3'-硝基-4'-羟基苯丙酮 | 50916-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3'-硝基-4'-羟基苯丙酮
• 英文名称: 4'-Hydroxy-3'-nitropropiophenone
• 英文别名: 1-(4-hydroxy-3-nitrophenyl)propan-1-one；3'-Nitro-4'-oxypropiophenon；4-Hydroxy-5-nitro-propiophenon；1-(4-Hydroxy-3-nitro-phenyl)-propan-1-on
• CAS: 50916-44-4
• 化学式: C₉H₉NO₄
• 分子量: 195.175
• InChiKey: ZXXQSUUUGORSCV-UHFFFAOYSA-N

物化性质

• 熔点：
  65.4–66.2°C
• 沸点：
  296.8±20.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  3'-硝基-4'-羟基苯丙酮 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 1-(2-Hydroxy-5-propanoylphenyl)-3-methylurea
  参考文献：
  名称：

  Studies on Antiulcer Drugs. II. Synthesis and Antiulcer Activities of Imidazo(1,2-a)pyridinyl-2-alkylaminobenzoxazoles and 5,6,7,8-Tetrahydroimidazo(1,2-a)pyridinyl Derivatives.

  摘要：

  合成了一系列咪唑[1, 2-a]吡啶基苯并噁唑（4）和5, 6, 7, 8-四氢咪唑[1, 2-a]吡啶基苯并噁唑（5），并在大鼠中测试了它们的抗压力溃疡活性。发现几种化合物的活性超过了对照化合物舒克糖铝、西咪替丁和雷尼替丁。其中一些化合物对乙醇诱导的胃损伤表现出强效的保护活性。讨论了这些化合物的合成及其构效关系。

  DOI：

  10.1248/cpb.40.371
• 作为产物：
  描述：

  4-羟基苯丙酮 在 硫酸 、 potassium nitrate 作用下， 反应 0.07h， 以69.3%的产率得到3'-硝基-4'-羟基苯丙酮
  参考文献：
  名称：

  INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF THEIR USE

  摘要：

  披露了调节或抑制吲哚胺2,3-双加氧酶（IDO）酶活性的化合物，包含所述化合物的药物组合物以及使用本披露的化合物治疗增殖性疾病的方法，如癌症、病毒感染和/或炎症性疾病。

  公开号：

  US20200069646A1

文献信息

• Studies on Antiulcer Drugs. I. Synthesis and Antiulcer Activities of Imidazo(1,2-a)pyridinyl-2-oxobenzoxazolidines-3-oxo-2H-1,4-benzoxazines and Related Compounds.
  作者：Yousuke KATSURA、Shigetaka NISHINO、Hisashi TAKASUGI

  DOI：10.1248/cpb.39.2937

  日期：——

  A series of imidazo[1, 2-α]pyridinyl-2-oxobenzoxazolidines (4a-i), -3-oxo-2H-1, 4-benzoxazines (5a-q), their thio-analogues (4j-p and 5r-t) and 5, 6, 7, 8-tetrahydroimidazo[1, 2-α]pyridinyl derivatives (8 and 9) were synthesized and tested for anti-stress ulcer activity in rats. Several compounds were found to be more active than the reference compounds, zolimidine, cimetidine and sucralfate. Among them, compound 4e, 5i and 5l also exhibited potent protective activity against ethanol-induced gastric lesion. The synthesis and structure-activity relationships of these compounds are discussed.

  合成了一系列咪唑[1, 2-α]吡啶基-2-氧苯并噁唑烷（4a-i）、-3-氧-2H-1, 4-苯并噁唑（5a-q）、它们的硫类类似物（4j-p 和 5r-t）以及5, 6, 7, 8-四氢咪唑[1, 2-α]吡啶衍生物（8和9），并对其在大鼠中进行抗应激溃疡活性测试。研究发现几个化合物的活性超过了参考化合物唑咪丁、西咪替丁和硫糖铝。其中，化合物4e、5i和5l对乙醇诱导的胃损伤表现出强大的保护活性。讨论了这些化合物的合成及结构-活性关系。
• Potential Antitumor Agents, XXII. Alkylating Agents fromp-Hydroxypropiophenone andp-Hydroxyacetophenone
  作者：Aldo Andreani、Daniela Bonazzi、Mirella Rambaldi、Giovanna Lelli、Rosaria Bossa、Iraklis Galatulas

  DOI：10.1002/ardp.19843170703

  日期：——

  the alkylating agents 18–25 from p‐hydroxypropiophenone, p‐hydroxyacetophenone and their nitro derivatives 14–17 is reported. The antitumor activities of these new compounds are compared to those of the previously reported analogs 2–13 of the local anesthetic ketocaine (1).

  报道了由对羟基苯乙酮、对羟基苯乙酮及其硝基衍生物 14-17 合成烷化剂 18-25。将这些新化合物的抗肿瘤活性与先前报道的局部麻醉剂酮卡因 (1) 的类似物 2-13 的抗肿瘤活性进行了比较。
• Inhibitors of indoleamine 2,3-dioxygenase and methods of their use
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US10959986B2

  公开（公告）日：2021-03-30

  There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the disclosure.

  本文公开了调节或抑制吲哚胺-2,3-二氧化酶（IDO）酶活性的化合物、含有上述化合物的药物组合物以及利用本公开化合物治疗增殖性疾病（如癌症、病毒感染和/或炎症性疾病）的方法。
• The Friedel—Crafts Reaction with o-Nitrophenol and Acyl Halides¹
  作者：Frances C. Brown

  DOI：10.1021/ja01209a050

  日期：1946.5
• Discovery of 2-Arylbenzoxazoles as Upregulators of Utrophin Production for the Treatment of Duchenne Muscular Dystrophy
  作者：Daniel R. Chancellor、Kay E. Davies、Olivier De Moor、Colin R. Dorgan、Peter D. Johnson、Adam G. Lambert、Daniel Lawrence、Cristina Lecci、Carole Maillol、Penny J. Middleton、Gary Nugent、Séverine D. Poignant、Allyson C. Potter、Paul D. Price、Richard J. Pye、Richard Storer、Jonathon M. Tinsley、Renate van Well、Richard Vickers、Julia Vile、Fraser J. Wilkes、Francis X. Wilson、Stephen P. Wren、Graham M. Wynne

  DOI：10.1021/jm200135z

  日期：2011.5.12

  A series of novel 2-arylbenzoxazoles that upregulate the production of utrophin in murine H2K cells, as assessed using a luciferase reporter linked assay, have been identified. This compound class appears to hold considerable promise as a potential treatment for Duchenne muscular dystrophy. Following the delineation of structure-activity relationships in the series, a number of potent upregulators were identified, and preliminary ADME evaluation is described. These studies have resulted in the identification of 1, a compound that has been progressed to clinical trials.