3'-amino-4'-hydroxypropiophenone | 130521-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-amino-4'-hydroxypropiophenone
• 英文别名: 1-(3-amino-4-hydroxy-phenyl)-propan-1-one；1-(3-Amino-4-hydroxy-phenyl)-propan-1-on；3-amino-4-hydroxypropiophenone；1-(3-Amino-4-hydroxyphenyl)propan-1-one
• CAS: 130521-20-9
• 化学式: C₉H₁₁NO₂
• mdl: MFCD14552668
• 分子量: 165.192
• InChiKey: FPAAOAIXKHUNRT-UHFFFAOYSA-N

物化性质

• 熔点：
  144–145°C
• 沸点：
  366.6±27.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3'-amino-4'-hydroxypropiophenone 在 乙酸酐 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 7.0h， 生成 7-(3-cyano-2-methylpropionyl)-2,2-dimethyl-3,4-dihydro-3-oxo-1,4(2H)benzoxazine
  参考文献：
  名称：

  6-Benzoxazinylpyridazin-3-ones: potent, long-acting positive inotrope and peripheral vasodilator agents

  摘要：

  A series of 6-benzoxazinylpyridazin-3-ones was prepared and evaluated for inhibition of cardiac phosphodiesterase (PDE) fraction III in vitro and for positive inotropic activity in vivo. 6-[3,4-Dihydro-3-oxo-1,4(2H)-benzoxazin-7-yl]-2,3,4,5-tetrahydro-5 - methylpyridazin-3-one (bemoradan) was found to be an extremely potent and selective inhibitor of canine PDE fraction III and a long-acting, potent, orally active inotropic vasodilator agent in various canine models. Additional benzoxazin-6-yl and -8-yl compounds were also prepared. Altering the pyridazinone substitution from the 6-position to the 7-position produced a 14-fold increase in the iv cardiotonic potency (ED50) from 77 to 5.4 micrograms/kg while substitution at the 8-position reduced potency. Methyl substitution at various sites in the molecule was also examined. Positive inotropic activity was maintained for between 8 and 24 h after a single oral dose (100 micrograms/kg) of bemoradan in dogs, thus making it one of the most potent and long-acting orally effective inotropes yet described. Bemoradan is currently under development as a cardiotonic agent for use in the management of congestive heart failure.

  DOI：

  10.1021/jm00163a061
• 作为产物：
  描述：

  4-羟基苯丙酮 在 Iron(III) nitrate nonahydrate 、 铁粉 、 氯化铵 作用下， 以 industrial methylated spirit 为溶剂， 生成 3'-amino-4'-hydroxypropiophenone
  参考文献：
  名称：

  Discovery of 2-Arylbenzoxazoles as Upregulators of Utrophin Production for the Treatment of Duchenne Muscular Dystrophy

  摘要：

  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.

  DOI：

  10.1021/jm200135z

文献信息

• 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.
  作者：Yousuke KATSURA、Shigetaka NISHINO、Yoshikazu INOUE、Masaaki TOMOI、Hisashi TAKASUGI

  DOI：10.1248/cpb.40.371

  日期：——

  A series of imidazo[1, 2-a]pyridinylbenzoxazoles (4) and 5, 6, 7, 8-tetrahydroimidazo[1, 2-a]pyridinylbenzoxazoles (5) were synthesized and tested for anti-stress ulcer activity in rats. Several compounds were found to be more active than the reference compounds, sucralfate, cimetidine and ranitidine. Some of them 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-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。
• Unequivocal Preparation of 4- and 5-Acyl-2-aminophenols
  作者：Hocine Aichaoui、Isabelle Lesieur、Jean-Pierre Hénichart

  DOI：10.1055/s-1990-26979

  日期：——

  Unequivocal methods for the specific preparation of 4- or 5-acyl-2-aminophenols are reported. 5-Acyl-2-aminophenols are obtained by ring opening with dilute sodium hydroxide of 2(3H)-benzoxa-zolinones acylated at position 6. 4-Acyl-2-aminophenols are obtained by acylation of 2-acetamidophenol in the presence of aluminum chloride/dimethylformamide followed by a deprotection of the amino group.

  报道了一种用于特定制备4-或5-酰基-2-氨基苯酚的明确方法。5-酰基-2-氨基苯酚通过在稀氢氧化钠存在下开环来自位于6位酰基化的2(3H)-苯并恶唑啉酮。4-酰基-2-氨基苯酚通过在氯化铝/二甲基甲酰胺存在下酰基化2-乙酰氨基苯酚，然后脱保护氨基得到。
• 3-Alkylamino- alpha-aminomethyl-4-hydroxybenzyl alcohols
  申请人：SmithKline Corporation

  公开号：US03943173A1

  公开（公告）日：1976-03-09

  A series of 3-alkylamino-.alpha.-substituted aminomethyl-4-hydroxybenzyl alcohols are prepared. These compounds are .beta.-adrenergic stimulants, in particular as bronchodilators.

  制备了一系列3-烷基氨基-.alpha.-取代氨甲基-4-羟基苯甲醇。这些化合物是β-肾上腺素受体刺激剂，特别是作为支气管扩张剂。
• Comparing Individual-Level Returns with Aggregates a Historical Appraisal of the King Solution
  作者：Paul Bourke、Donald Debats、Thomas Phelan

  DOI：10.1080/01615440109598977

  日期：2001.1
• Edkins; Linnell, Quarterly Journal of Pharmacy and Pharmacology, 1936, vol. 9, p. 203,215
  作者：Edkins、Linnell

  DOI：——

  日期：——