3,4-dihydro-7-nitro-4-propyl-2H-1,4-benzoxazine | 329229-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3,4-dihydro-7-nitro-4-propyl-2H-1,4-benzoxazine
• 英文别名: 7-Nitro-4-propyl-2H-1,4-benzoxazine；7-nitro-4-propyl-2,3-dihydro-1,4-benzoxazine
• CAS: 329229-16-5
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: MORPQEXENWSROL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-7-nitro-4-propyl-2H-1,4-benzoxazine 以36 mg (84%)的产率得到7-amino-3,4-dihydro-4-propyl-2H-1,4-benzoxazine
  参考文献：
  名称：

  Androgen receptor modulator compounds and methods

  摘要：

  化合物、药物组合物和调节类固醇受体介导过程的方法。具体描述了非类固醇化合物和组合物的制备和使用方法，这些化合物和组合物是雄激素受体（AR）的激动剂、部分激动剂和拮抗剂。此外，还描述了制备和使用关键中间体的方法，包括用于AR调节剂的立体选择性合成路线。

  公开号：

  US06462038B1
• 作为产物：
  描述：

  7-硝基-2H-1,4-苯并噁嗪-3-酮 在 dimethyl sulfide borane 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3,4-dihydro-7-nitro-4-propyl-2H-1,4-benzoxazine
  参考文献：
  名称：

  Novel Series of Potent, Nonsteroidal, Selective Androgen Receptor Modulators Based on 7H-[1,4]Oxazino[3,2-g]quinolin-7-ones

  摘要：

  Recent interest in orally available androgens has fueled the search for new androgens for use in hormone replacement therapy and as anabolic agents. In pursuit of this, we have discovered a series of novel androgen receptor modulators derived from 7H-[1,4]oxazino[3,2-g]quinolin-7-ones. These compounds were synthesized and evaluated in competitive binding assays and an androgen receptor transcriptional activation assay. A number of compounds from the series demonstrated single-digit nanomolar agonist activity in vitro. In addition, lead compound (R)-16e was orally active in established rodent models that measure androgenic and anabolic properties of these agents. In this assay, (R)-16e demonstrated full efficacy in muscle and only partially stimulated the prostate at 100 mg/kg. These data suggest that these compounds may be utilized as selective androgen receptor modulators or SARMs. This series represents a novel class of compounds for use in androgen replacement therapy.

  DOI：

  10.1021/jm061329j

文献信息

• [EN] ANDROGEN RECEPTOR MODULATOR COMPOUNDS AND METHODS<br/>[FR] COMPOSES DE MODULATION DU RECEPTEUR ANDROGENE ET PROCEDES D'UTILISATION
  申请人：LIGAND PHARM INC

  公开号：WO2001016139A1

  公开（公告）日：2001-03-08

  Compounds, pharmaceutical compositions, and methods for modulating processes mediated by steroid receptors. In particular, preparation and methods of use of non-steroidal compounds and compositions that are agonists, partial agonists, and antagonists for the androgen receptor (AR) are described. Further, described are the methods of making and use of critical intermediates including a stereoselective synthetic route to intermediates for the AR modulators.

  化合物、药物组合物和调节类固醇受体介导过程的方法。特别地，描述了非类固醇化合物和组合物的制备和使用方法，这些化合物和组合物是雄激素受体（AR）的激动剂、部分激动剂和拮抗剂。此外，还描述了制备和使用关键中间体的方法，包括用于AR调节剂的立体选择性合成路线的中间体。
• ANDROGEN RECEPTOR MODULATOR COMPOUNDS AND METHODS
  申请人：LIGAND PHARMACEUTICALS INCORPORATED

  公开号：EP1212330B1

  公开（公告）日：2006-04-19
• CATIONIC BENZOXAZINE DERIVATIVES AND USE IN HAIR DYEING
  申请人：L'OREAL

  公开号：US20170327690A1

  公开（公告）日：2017-11-16

  The invention relates to novel cationic benzoxazine-based compounds of formula (I) below, in which •R represents a hydrogen atom or a C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl radical, •—R 2 , R 3 , R 4 and R 5 independently represent: —a hydrogen atom, —a linear C 1 -C 4 or branched C 3 -C 4 alkyl radical, optionally substituted with a hydroxyl radical, •L represents a linear or branched, saturated C 1 -C 30 hydrocarbon-based chain, •CAT+ represents a cationic radical chosen from: —a cationic heterocyclic radical comprising 5 to 8 ring members containing at least one heteroatom chosen from O, N and S, —a tri(hydroxy)(C 1 -C 4 )alkylammonium radical, —a non-cationic heterocycle comprising 5 or 6 ring members containing at least one heteroatom chosen from O and N, such as pyrrolidine, substituted with a cationic radical, An− represents an anion or a mixture of anions which are organic or inorganic and are cosmetically acceptable.
• BENZOXAZINE DERIVATIVES AND USE IN HAIR DYEING
  申请人：L'OREAL

  公开号：US20180141922A1

  公开（公告）日：2018-05-24

  The invention relates to the use of a compound of formula (I) below, addition salts thereof, optical isomers, geometrical isomers and tautomers thereof and/or solvates thereof: Formula (I) in which: • R represents a hydrogen atom or a C1-C4 alkyl or C1-C4 hydroxyalkyl radical, preferably a hydrogen atom, • R 2 , R 3 , R 4 and R 5 independently represent: —a hydrogen atom, —a linear C1-C4 or branched C3-C4 alkyl radical, optionally substituted with a hydroxyl radical, • R 1 represents a linear C2-C10 or branched C3-C10 alkyl radical, optionally interrupted with one or more heteroatoms chosen from O or S or with one or more groups —NR′, said alkyl radical ending with a group —NX 1 X 2 or —OX 3 or a radical chosen from: Formula (II) —X 1 and X 2 independently denote ◯ a hydrogen atom ◯ a linear C1-C6 alkyl radical or a branched C3-C6 alkyl radical ◯ a linear C1-C6 hydroxyalkyl radical or a branched C3-C6 hydroxyalkyl radical, X 1 and X 2 may form, with the nitrogen atom that bears them, a saturated or unsaturated 5- to 8-membered heterocycle, in which one of the ring members may be a heteroatom chosen from O, S and N; said heterocycle possibly being substituted with one or more linear or branched C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl or dimethylamino radicals, —X 3 denotes a hydrogen atom or a linear C1-C6 or branched C3-C6 alkyl radical, —R′ denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical, for dyeing keratin fibres, especially human keratin fibres such as the hair.
• US6462038B1
  申请人：——

  公开号：US6462038B1

  公开（公告）日：2002-10-08