1-(5-乙酰基-2-氨基-4-羟基-3-丙基苯基)乙酮 | 79324-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(5-乙酰基-2-氨基-4-羟基-3-丙基苯基)乙酮
• 英文名称: 4,6-diacetyl-3-hydroxy-2-propylaniline
• 英文别名: 4,6-Diacetyl-3-amino-2-propylphenol；1-(5-Acetyl-2-amino-4-hydroxy-3-propylphenyl)ethan-1-one；1-(5-acetyl-2-amino-4-hydroxy-3-propylphenyl)ethanone
• CAS: 79324-47-3
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: KAOVWCZQHGBCJL-UHFFFAOYSA-N

物化性质

• 熔点：
  130.5 °C
• 沸点：
  464.6±45.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-乙酰基-2-氨基-4-羟基-3-丙基苯基)乙酮 在 盐酸 、 sodium hydroxide 、 sodium ethanolate 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 79.42h， 生成 disodium 4-oxo-6-(pentylamino)-10-propyl-4H-pyrano<3,2-g>quinoline-2,8-dicarboxylate
  参考文献：
  名称：

  Predictive structure-activity relationships in a series of pyranoquinoline derivatives. A new primate model for the identification of antiallergic activity

  摘要：

  A new primate model has been developed for the evaluation of antiallergic agents. Compounds are tested for their ability to inhibit anti-IgE induced histamine release from the bronchoalveolar mast cells lavaged from the lungs of Macaca arctoides infected with the parasite Ascaris suum. A number of 6-substituted pyranoquinoline derivatives have been evaluated and the activities were subjected to Hansch analysis. A highly significant correlation with lipophilicity (pi) and Hammett sigma p values was obtained. The relationship was used to predict further compounds for synthesis giving rise to new, potent analogues. Some apparently anomalous results could be explained by differences in the ionization of, or tautomerism in, the quinoline ring.

  DOI：

  10.1021/jm00402a033

文献信息

• Sulfonamides and derivatives thereof that modulate the activity of endothelin
  申请人：Texas Biotechnology Corporation

  公开号：US20010056183A1

  公开（公告）日：2001-12-27

  Thienyl-, furyl-, pyrrolyl- and phenylsulfonamides, formulations of pharmaceutically-acceptable derivatives thereof and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl)furylsulfonamides, N-(isoxazolyl)pyrrolylsulfonamides and N-(isoxazolyl)phenylsulfonamides, formulations thereof and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or pharmaceutically acceptable derivatives thereof that inhibit the activity of endothelin are also provided.

  提供了噻吩基、呋喃基、吡咯基和苯基磺酰胺，以及其药学上可接受的衍生物的配方和调节或改变内皮素家族肽活性的方法。具体而言，提供了N-(异噁唑基)噻吩基磺酰胺、N-(异噁唑基)呋喃基磺酰胺、N-(异噁唑基)吡咯基磺酰胺和N-(异噁唑基)苯基磺酰胺，以及这些磺酰胺的配方和使用这些磺酰胺通过与受体接触来抑制内皮素肽与内皮素受体的结合的方法。还提供了通过给予这些磺酰胺或药学上可接受的抑制内皮素活性的衍生物的有效量来治疗内皮素介导的疾病的方法。
• Certain diacetyl-amino-phenolic derivatives
  申请人：Fisons Limited

  公开号：US04414416A1

  公开（公告）日：1983-11-08

  There is described a process for the production of a 1,4-dihydro-4-oxo-quinoline-2-carboxylic acid, or a salt, ester or amide thereof, which comprises cyclization of a corresponding 2-aminobenzoyl pyruvic acid or an ester thereof, and if desired or necessary converting the resulting product to an appropriate salt, ester or amide thereof, or vice versa.

  描述了一种生产1,4-二氢-4-氧基-喹啉-2-羧酸或其盐、酯或酰胺的方法，该方法包括将相应的2-氨基苯甲酰丙酸或其酯环化，如果需要或必要，将所得产物转化为适当的盐、酯或酰胺，或者反之亦然。
• Process for preparing certain pyrano[3,2-g]quinoline 2,8-dicarboxylates
  申请人：Fisons Limited

  公开号：US04328341A1

  公开（公告）日：1982-05-04

  There is described a process for the production of a 1,4-dihydro-4-oxo-quinoline-2-carboxylic acid, or a salt, ester or amide thereof, which comprises cyclization of a corresponding 2-aminobenzoyl pyruvic acid or an ester thereof, and if desired or necessary converting the resulting product to an appropriate salt, ester or amide thereof, or vice versa.

  描述了一种生产1,4-二氢-4-氧基-喹啉-2-羧酸或其盐、酯或酰胺的过程，包括将相应的2-氨基苯甲酰丙酸或其酯环化，如有必要则将产物转化为适当的盐、酯或酰胺，反之亦然。
• Discovery, Modeling, and Human Pharmacokinetics of <i>N</i>-(2-Acetyl-4,6-dimethylphenyl)-3-(3,4-dimethylisoxazol-5-ylsulfamoyl)thiophene-2-carboxamide (TBC3711), a Second Generation, ET_A Selective, and Orally Bioavailable Endothelin Antagonist
  作者：Chengde Wu、E. Radford Decker、Natalie Blok、Huong Bui、Tony J. You、Junmei Wang、Andree R. Bourgoyne、Vippra Knowles、Kurt L. Berens、George W. Holland、Tommy A. Brock、Richard A. F. Dixon

  DOI：10.1021/jm030528p

  日期：2004.4.1

  Sitaxsentan (1) (Wu et al. J. Med. Chem. 1997, 40, 1690) is our first endothelin antagonist being evaluated in clinical trials. It has demonstrated biological effects in an acute hemodynamic study in CHF (Givertz et al. Circulation 2000, 101, 2922), an open-label 20-patient pulmonary hypertension trial (Barst et al. Chest 2002, 121, 1860-1868), and a 31-patient trial in essential hypertension (Calhoun et al. AHA Scientific Sessions 2000). In a phase 2b/3 pulmonary arterial hypertension trial, once a day treatment of 100 mg of sitaxsentan statistically significantly improved 6-min walk distance and NYHA class at 12 weeks (Barst et al. Am. J. Respir. Crit. Care Med. 2004, 169, 441). We have since reported on our efforts in generating follow-up compounds (Wu et al. J. Med. Chem. 1999, 42, 4485) and recently communicated that an ortho acyl group on the anilino ring enhanced oral absorption in this category of compounds (Wu et al. J. Med. Chem. 2001, 44, 1211). Here we report an expansion of this work by substituting a variety of electron-withdrawing groups at the ortho position and evaluating their effects on oral bioavailability as well as structure-activity relationships. As a result, TBC3711 (7z) was identified as our second endothelin antagonist to enter the clinic due to its good oral bioavailability (similar to100%) in rats, high potency (ETA IC50 = 0.08 nM), and optimal ETA/ETB selectivity (441 000-fold). Compound 7z has completed phase-I clinical development and was well tolerated with desirable pharmacokinetics in humans (t(1/2) = 6-7 h, oral availability > 80%).
• A New Efficient Route to 4-Oxo-1,4-dihydroquinoline-2-carboxylic Esters
  作者：Stephen C. W. Coltman、Stephen C. Eyley、Richard A. Raphael

  DOI：10.1055/s-1984-30762

  日期：——