5-fluoro-2-(methylthio)aniline | 439291-60-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-fluoro-2-(methylthio)aniline
• 英文别名: 5-fluoro-2-methylsulfanylaniline
• CAS: 439291-60-8
• 化学式: C₇H₈FNS
• 分子量: 157.212
• InChiKey: FWOIXOUAYRBKLM-UHFFFAOYSA-N

物化性质

• 沸点：
  238.2±25.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯甲基咪唑啉盐酸盐 、 5-fluoro-2-(methylthio)aniline 以 苯酚 为溶剂， 反应 1.5h， 以0.53 g的产率得到2'-methylthio-5'-fluoro-2-(anilinomethyl)imidazoline
  参考文献：
  名称：

  2-(Anilinomethyl)imidazolines as α₁ Adrenergic Receptor Agonists:  the Discovery of α_1a Subtype Selective 2‘-Alkylsulfonyl-Substituted Analogues

  摘要：

  A series of 2'-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of alpha-adrenergic receptor subtypes alpha(1a), alpha(1b), alpha(1d), alpha(2a), and alpha(2c). Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited alpha(1a) subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for alpha(1a) vs all other subtypes.

  DOI：

  10.1021/jm000542r
• 作为产物：
  描述：

  5-氯-2-甲基苯并噻唑 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 乙醇 、 乙二醇 为溶剂， 反应 2.75h， 生成 5-fluoro-2-(methylthio)aniline
  参考文献：
  名称：

  2-(Anilinomethyl)imidazolines as α₁ Adrenergic Receptor Agonists:  the Discovery of α_1a Subtype Selective 2‘-Alkylsulfonyl-Substituted Analogues

  摘要：

  A series of 2'-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of alpha-adrenergic receptor subtypes alpha(1a), alpha(1b), alpha(1d), alpha(2a), and alpha(2c). Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited alpha(1a) subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for alpha(1a) vs all other subtypes.

  DOI：

  10.1021/jm000542r

文献信息

• Process for the preparation of N-(phenylethyl) anilines salts and solvates thereof useful as serotonin 5-HT6 antagonists
  申请人：Laboratorios Del. Dr. Esteve, S.A.

  公开号：EP2103596A1

  公开（公告）日：2009-09-23

  The invention relates to a process for preparing N-(1-phenylethyl)anilines, salts, and solvates thereof, to novel intermediates, and to the use of the intermediates in the preparation of serotonin 5-HT6 antagonists.

  该发明涉及一种制备N-(1-苯乙基)苯胺，其盐和溶剂合物的过程，涉及新的中间体，并涉及在制备5-HT6受体拮抗剂中使用这些中间体。
• [EN] IMIDAZOLINE DERIVATIVES AS ALPHA-1A ADRENOCEPTOR LIGANDS<br/>[FR] DERIVES D'IMIDAZOLINE UTILISES COMME LIGANDS DU RECEPTEUR ADRENERGIQUE ALPHA-1A
  申请人：GLAXO GROUP LTD

  公开号：WO2000066563A1

  公开（公告）日：2000-11-09

  Compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof are disclosed. Formula (i) wherein R?2, R3, R4 and R5¿ are independently H, halogen, -OH, -C¿1-3?alkyl, -C1-3alkoxy, -SC1-2alkyl, or -CF3, with the proviso that at least 2 of R?2, R3, R4 and R5¿ are H; R6 is H or -CH¿3; R?1 is -S(O)¿nR?7 where n is 1 or 2, -S(O)¿2NHR?8, -C(O)R?9, -NR14R15, -C(R17)=NOR16¿, (a) or a 5,6, or 7 membered heteroalkyl or heteroaryl group optionally substituted. Such compounds are useful in the treatment of Alpha-1A mediated diseases or conditions such as urinary incontinence.

  公开了式(I)的化合物或其药学上可接受的盐或溶剂化物。式(I)中，R?2、R3、R4和R5¿独立地为H、卤素、-OH、-C¿1-3?烷基、-C1-3烷氧基、-SC1-2烷基或-CF3，但至少有2个R?2、R3、R4和R5¿为H；R6为H或-CH¿3；R?1为-S(O)¿nR?7，其中n为1或2，-S(O)¿2NHR?8，-C(O)R?9，-NR14R15，-C(R17)=NOR16¿，(a)或可选择取代的5、6或7成员杂烷基或杂芳基基团。这些化合物在治疗α-1A介导的疾病或病况，例如尿失禁方面有用。
• Imidazoline derivatives as alpha-1A adrenoceptor ligands
  申请人：Bigham Eric Cleveland

  公开号：US06884801B1

  公开（公告）日：2005-04-26

  Compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof are disclosed. Such compounds are useful in the treatment of Alpha-1A mediated diseases or conditions such as urinary incontinence.

  本发明公开了化学式(I)的化合物或其药学上可接受的盐或溶剂。这些化合物在治疗Alpha-1A介导的疾病或病状，如尿失禁方面非常有用。
• COMPOUND FOR TREATING OR PREVENTING BREAST CANCER
  申请人：Jiangsu Atom Bioscience And Pharmaceutical Co., Ltd

  公开号：EP3296294A1

  公开（公告）日：2018-03-21

  Disclosed are a class of compounds for treating or preventing breast cancer, in particular 2-phenyl benzoselenazole compounds, and a pharmaceutically acceptable salt thereof and an easily hydrolysable prodrug thereof. Further disclosed are a pharmaceutical composition containing these compounds and the use of such compounds for for treating or preventing breast cancer in mammals. The compounds of the present invention can effectively inhibit or reduce the growth or proliferation of mammalian breast cancer cells, and at the same time, such compounds do not inhibit the growth of partial test cells, apart from breast cancer cells in mammals, and have a good selectivity. Such compounds show a more obvious medicinal effect, and have high selectivivity, low toxicity and few side effects.

  公开了一类用于治疗或预防乳腺癌的化合物，特别是 2-苯基苯并硒唑化合物，及其药学上可接受的盐和易水解的原药。进一步公开的是含有这些化合物的药物组合物，以及这些化合物用于治疗或预防哺乳动物乳腺癌的用途。本发明的化合物可以有效地抑制或减少哺乳动物乳腺癌细胞的生长或增殖，同时，除了哺乳动物的乳腺癌细胞外，这类化合物不会抑制部分试验细胞的生长，具有良好的选择性。这类化合物的药效更明显，选择性高，毒性低，副作用小。
• IMIDAZOLINE DERIVATIVES AS ALPHA-1A ADRENOCEPTOR LIGANDS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1175406A1

  公开（公告）日：2002-01-30