2-amino-5-chlorophenyl 2-thienyl ketone | 41631-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-5-chlorophenyl 2-thienyl ketone
• 英文别名: 4-chloro-2-(2'-thienylcarbonyl)aniline；(2-amino-5-chloro-phenyl)-thiophen-2-yl-methanone；<5-Chlor-2-amino-phenyl>--keton；(2-Amino-5-chlorophenyl)(thiophen-2-yl)methanone；(2-amino-5-chlorophenyl)-thiophen-2-ylmethanone
• CAS: 41631-21-4
• 化学式: C₁₁H₈ClNOS
• 分子量: 237.71
• InChiKey: PYOYAYUOWCTPNL-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  438.3±40.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-5-chlorophenyl 2-thienyl ketone 在 氢氧化钾 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 反应 2.0h， 生成 4-Chloro-2-thiophen-2-ylmethyl-phenylamine
  参考文献：
  名称：

  Hunziker; Fischer; Kipfer, European Journal of Medicinal Chemistry, 1981, vol. 16, # 5, p. 391 - 398

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-5-氯苯甲酸 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.33h， 生成 2-amino-5-chlorophenyl 2-thienyl ketone
  参考文献：
  名称：

  Syntheses of 5-thienyl and 5-furyl-substituted benzodiazepines: probes of the pharmacophore for benzodiazepine receptor agonists

  摘要：

  The synthesis of 5-thienyl- and 5-furyl-substituted benzodiazepines is described. These compounds were employed to probe the lipophilic pocket (L(3)) of the benzodiazepine receptor (BzR) and to determine the effect of occupation of L(3) on biological activity. Of the new analogs synthesized, the 5-(2-thienyl)-benzodiazepines 6a and 7a displayed high affinity for the BzR (IC50 28 and 18 nM, respectively) and exhibited both anticonvulsant (ED(50) approximate to 9 and 3 mg/kg) and muscle relaxant (ED(50) approximate to 10 and 7 mg/kg) activity. The 5-(3-thienyl)benzodiazepines 6d and 7d displayed only moderate affinity for the BzR (IC50 140 and 110 nM) and exhibited no biological activity (no anticonvulsant or muscle relaxant activity) at doses up to 40 mg/kg. The 5-(2-furyl)benzodiazepines (6b, 7b, 19b and 20b) exhibit low affinities for the BzR. These in vitro and in vivo findings are consistent with our model suggesting that pocket L(3) is very sensitive to lipophilic effects. Thus, decreasing the lipophilicity of functional groups which occupy this region decreases ligand affinity at BzR. The 2'-halogen (F or Cl) substituent of the 5-phenylbenzodiazepines increases ligand affinity in vitro because the active conformation of the phenyl N(4)=C(5)-C(1')=C(2') moiety is syn rather than anti. The syn conformation permits the 2'-halogen (F or Cl) atom to interact at the hydrogen bonding site H-2 and form a stable three-centered hydrogen bond in the proposed ligand binding cleft. The 3-thienyl and 2-furyl groups decrease the lipophilicity of the substituent which occupies L(3) but do not form a hydrogen bond at H-2, thus resulting in a diminished affinity at BzR.

  DOI：

  10.1016/0223-5234(96)88259-6

文献信息

• [EN] NOVEL FUSED HETEROCYCLES AND USES THEREOF<br/>[FR] HETEROCYCLES FUSIONNES ET UTILISATIONS
  申请人：ASTRAZENECA AB

  公开号：WO2005111001A1

  公开（公告）日：2005-11-24

  This invention relates to novel compounds having the Formula (I) and to their pharmaceutical compositions and to their methods of use. These novel compounds provide a treatment or prophylaxis of H. pylori infection.

  本发明涉及具有公式(I)的新化合物，以及它们的药物组合物和使用方法。这些新化合物提供了治疗或预防幽门螺旋杆菌感染的方法。
• 2-Arylindoles: A New Entry to Transition Metal-free Synthesis of 2-Aminobenzophenones
  作者：Jin Yu、Hye Ran Moon、Beom Kyu Min、Jae Nyoung Kim

  DOI：10.1002/bkcs.10796

  日期：2016.6

  Various 2‐aminobenzophenones were synthesized from readily available 2‐arylindoles in DMSO under O2 balloon atmosphere. The synthesis was carried out without the aid of a transition metal catalyst or moisture‐sensitive organometallic reagents from 2‐arylindoles.

  在O 2气球气氛下，在DMSO中由易于获得的2-芳基吲哚合成了各种2-氨基二苯甲酮。合成过程无需借助过渡金属催化剂或对湿气敏感的2-芳基吲哚有机金属试剂进行。
• The Synthesis of Substituted 2-Aminophenyl Heterocyclic Ketones
  作者：R. I. Fryer、P. Zhang、R. Rios

  DOI：10.1080/00397919308013295

  日期：1993.4

  Abstract The synthesis of substituted 2-aminophenyl heterocyclic ketones, key intermediates to the preparation of 1,4-benzodiazepines has been achieved in one step and in good, yield from the corresponding anthranilic acid, by treatment with heterocyclic lithium reagents and chlorotrimethylsilane.

  摘要 取代的2-氨基苯基杂环酮是制备1,4-苯二氮卓类的关键中间体，通过杂环锂试剂和氯三甲基硅烷处理，一步合成，相应的邻氨基苯甲酸收率良好。
• Novel Fused Heterocycles and Uses Thereof
  申请人：Basarab Gregory

  公开号：US20070275954A1

  公开（公告）日：2007-11-29

  This invention relates to novel compounds having the Formula (I) and to their pharmaceutical compositions and to their methods of use. These novel compounds provide a treatment or prophylaxis of H. pylori infection.

  本发明涉及具有式（I）的新化合物，以及它们的药物组成物和使用方法。这些新化合物提供了治疗或预防H. pylori感染的方法。
• HUNZIKER, F.;FISCHER, R.;KIPFER, P.;SCHMUTZ, J.;BUERKI, H. R.;FICHENBERGE+, EUR. J. MED. CHEM.-CHIM. THER., 1981, 16, N 5, 391-398
  作者：HUNZIKER, F.、FISCHER, R.、KIPFER, P.、SCHMUTZ, J.、BUERKI, H. R.、FICHENBERGE+

  DOI：——

  日期：——