ZM 147376 | 131131-34-5

• 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: ZM 147376
• 英文别名: 4-nitro-3-trifluoromethyl-N-(2-hydroxy-2-p-nitro-phenylpropionyl)aniline；4-nitro-3-trifluoromethyl-N-(2-hydroxy-2-p-nitrophenylpropionyl)aniline；2-hydroxy-2-(4-nitrophenyl)-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
• CAS: 131131-34-5
• 化学式: C₁₆H₁₂F₃N₃O₆
• 分子量: 399.283
• InChiKey: ALQKIFUMTRMSEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-hydroxy-2-(4-nitrophenyl)propionic acid 在 吡啶 、 氯化亚砜 作用下， 反应 34.5h， 生成 ZM 147376
  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

• Amide derivatives, process for their manufacture and pharmaceutical or veterinary compositions containing them
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0040932A1

  公开（公告）日：1981-12-02

  Novel 3,4-disubstituted-N-acylanilines of the formula: wherein Rl, R2 and ring A are defined in claim 1; wherein R3 is hydrogen or alkyl of up to 4 carbon atoms, or is joined to R5 as stated below; wherein R4 is alkyl of 2 to 4 carbon atoms, or has the formula -CX1X2X3 wherein X1, X2 and X3, which may be the same or different, each is hydrogen, fluorine or chlorine; wherein R5 is hydrogen, hydroxy or alkoxy or acyloxy each of up to 15 carbon atoms, or is joined to R3 to form an oxycarbonyl group such that together with the I -N-CO-C- part of the molecule it forms an oxazolidinedione group; and wherein R6 is hydrogen or halogen. These compounds possess antiandrogenic activity and are useful for the treatment of androgen dependent or prostatic diseases. Representative of the compounds is 3,4-dichloro-N-(2-hydroxy-2-p-nitrophenylpropionyl)aniline. Also disclosed are processes for the manufacture of the compounds and pharmaceutical and veterinary compositions containing them.

  式中的新型 3,4-二取代-N-酰基苯胺： 其中 Rl、R2 和环 A 在权利要求 1 中定义； 其中 R3 是氢或最多 4 个碳原子的烷基，或如下所述与 R5 连接； 其中 R4 是 2 至 4 个碳原子的烷基，或具有式 -CX1X2X3 其中 X1、X2 和 X3 可以相同或不同，各自是氢、氟或氯； 其中 R5 是氢、羟基或烷氧基或酰氧基，每个最多有 15 个碳原子，或与 R3 连接形成氧羰基，从而与分子的 I -N-CO-C- 部分一起形成噁唑烷二酮基团；以及 其中 R6 为氢或卤素。这些化合物具有抗雄激素活性，可用于治疗雄激素依赖性疾病或前列腺疾病。其中具有代表性的化合物是 3,4-二氯-N-(2-羟基-2-对硝基苯丙酰基)苯胺。此外，还公开了这些化合物的生产工艺以及含有这些化合物的药物和兽药组合物。
• 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：——
• US4386080A
  申请人：——

  公开号：US4386080A

  公开（公告）日：1983-05-31
• US5994362A
  申请人：——

  公开号：US5994362A

  公开（公告）日：1999-11-30