2-hydroxy-N-methyl-4'-nitro-3'-trifluoromethylisobutyranilide | 52806-55-0

• 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: 2-hydroxy-N-methyl-4'-nitro-3'-trifluoromethylisobutyranilide
• 英文别名: 2-Hydroxy-2,N-dimethyl-N-(4-nitro-3-trifluoromethylphenyl)propionamide；2-hydroxy-N,2-dimethyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
• CAS: 52806-55-0
• 化学式: C₁₂H₁₃F₃N₂O₄
• 分子量: 306.241
• InChiKey: QZPMSPBDFFTFCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-methyl-4'-nitro-3'-(trifluoromethyl)aniline 在 sodium hydroxide 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 2-hydroxy-N-methyl-4'-nitro-3'-trifluoromethylisobutyranilide
  参考文献：
  名称：

  Non-steroidal antiandrogens. Design of novel compounds based on an infrared study of the dominant conformation and hydrogen-bonding properties of a series of anilide antiandrogens

  摘要：

  Antiandrogenic activity is observed in anilides containing a tertiary hydroxyl group, and these compounds are used to define a pharmacophore in terms of their physicochemical properties. Infrared spectroscopy shows that these anilides exist in a single conformation, which exerts a powerful influence on the hydrogen-bond donor ability of the hydroxyl group in a model system. Arguments are presented which suggest that hydrogen-bonding ability is an important contributor to biological activity. Compounds were synthesized that reproduced these properties in series not containing an amide bond. Such compounds were found to exhibit good antiandrogen activity. We suggest that quantitative information on hydrogen bonding might also be useful in other systems.

  DOI：

  10.1021/jm00105a067

文献信息

• Use of estrogens or antiandrogens for reversal of male sexual phenotype in poultry
  申请人：MERCK & CO. INC.

  公开号：EP0514056A2

  公开（公告）日：1992-11-19

  Fertilized poultry embryos are treated with estrogens or antiandrogens or estrogens in combination with antiandrogens during a period of embryonic development when the gonads are bipotential. This treatment causes genetic males to exhibit a female phenotype. When sex reversed male birds are crossed with normal male birds all offspring will be genotypically male.

  受精的家禽胚胎在胚胎发育期间，性腺处于双潜能期，此时使用雌激素或抗雄激素，或雌激素与抗雄激素联合使用。这种处理方法会使遗传雄性表现出雌性表型。当性别逆转的雄性鸟类与正常雄性鸟类杂交时，所有后代的基因型都是雄性。
• MORRIS, JEFFREY J.;HUGHES, LESLIE R.;GLEN, ALASDAIR T.;TAYLOR, PETER J., J. MED. CHEM., 34,(1991) N, C. 447-455
  作者：MORRIS, JEFFREY J.、HUGHES, LESLIE R.、GLEN, ALASDAIR T.、TAYLOR, PETER J.

  DOI：——

  日期：——
• US5994362A
  申请人：——

  公开号：US5994362A

  公开（公告）日：1999-11-30
• [EN] PHARMACEUTICAL COMBINATION FOR THE TREATMENT OF PROSTATIC CANCER CONTAINING A 5 ALPHA REDUCTASE INHIBITOR AND AN ANTIANDROGEN
  申请人：MERCK & CO., INC.

  公开号：WO1992016233A1

  公开（公告）日：1992-10-01

  (EN) Disclosed is a new treatment for men with prostatic cancer involving combination therapy of a 5$g(a)-reductase inhibitor, i.e., a 17$g(b)-substituted 4-azasteroid, a 17$g(b)-substituted non-azasteroid, 17$g(b)-acyl-3-carboxyandrost-3,5-diene, benzoylaminophenoxybutanoic acid derivative, fused benz(thio)amide or cinnamoylamide derivative, aromatic 1,2-diethers or thioethers, aromatic ortho acylaminophenoxy alkanoic acids, ortho thioalkylacylamino-phenoxy alkanoic acids, pharmaceutically acceptable salts and esters thereof, and particularly finasteride, in combination with an antiandrogen, i.e. flutamide. Pharmaceutical compositions useful for treatment are also disclosed.(FR) Nouveau traitement destiné à des hommes atteints d'un cancer de la prostate, impliquant la thérapie combinée à l'aide d'un inhibiteur de 5$g(a)-réductase, c'est à dire un 4-azastéroide 17$g(b)-substitué, un non-azastéroide 17$g(b)-substitué, 17$g(b)-acyl-3-carboxyandrost-3,5-diène, un dérivé d'acide benzoylaminophénoxybutanoique, un dérivé fusionné de benz(thio)amide ou de cinnamoylamide, des 1,2-diéthers ou thioéthers aromatiques, des acides alcanoiques aromatiques orthoacylaminophénoxy, leurs sels et leurs esters pharmaceutiquement acceptables, et en particulier un finastéride, en combinaison avec un antiandrogène, c'est à dire un flutamide. L'invention concerne également des compositions pharmaceutiques utilisées dans le traitement du cancer de la prostate.
• Non-steroidal antiandrogens. Design of novel compounds based on an infrared study of the dominant conformation and hydrogen-bonding properties of a series of anilide antiandrogens
  作者：Jeffrey J. Morris、Leslie R. Hughes、Alasdair T. Glen、Peter J. Taylor

  DOI：10.1021/jm00105a067

  日期：1991.1

  Antiandrogenic activity is observed in anilides containing a tertiary hydroxyl group, and these compounds are used to define a pharmacophore in terms of their physicochemical properties. Infrared spectroscopy shows that these anilides exist in a single conformation, which exerts a powerful influence on the hydrogen-bond donor ability of the hydroxyl group in a model system. Arguments are presented which suggest that hydrogen-bonding ability is an important contributor to biological activity. Compounds were synthesized that reproduced these properties in series not containing an amide bond. Such compounds were found to exhibit good antiandrogen activity. We suggest that quantitative information on hydrogen bonding might also be useful in other systems.