3-(2-amino-4-fluorophenyl)-4-methyl-1,3-thiazole-2(3H)-thione | 1226711-12-1

• 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: 3-(2-amino-4-fluorophenyl)-4-methyl-1,3-thiazole-2(3H)-thione
• 英文别名: 3-(2-amino-4-fluorophenyl)-4-methyl-1,3-thiazole-2-thione
• CAS: 1226711-12-1
• 化学式: C₁₀H₉FN₂S₂
• 分子量: 240.325
• InChiKey: OUIWOPHIXRSALX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  86.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-amino-4-fluorophenyl)-4-methyl-1,3-thiazole-2(3H)-thione 以 甲醇 、 丙酮 为溶剂， 反应 12.0h， 生成 3,9-dimethyl-6-(trifluoromethyl)[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide
  参考文献：
  名称：

  通过噻唑并苯并咪唑并噻唑鎓盐的开环反应和烷氧基的C-O键裂解获得N-噻吩烯基和N-（邻-硫代）芳基-苯并咪唑-2-酮

  摘要：

  我们在这里报告通过噻唑并[3,2- a ]苯并咪唑鎓或苯并咪唑并[2,1- b ] [1,3]苯并噻唑的开环合成高度官能化的1,3-二氢-2H-苯并咪唑-2-酮-6-ium盐和醇盐异常的C–O键裂解。以高收率获得了多种带有原始N-硫代烯基或N-（邻硫代）芳基的苯并咪唑酮。先进的化学方法可快速有效地访问特权的苯并咪唑-2-酮骨架。

  DOI：

  10.1021/acs.joc.5b00221
• 作为产物：
  描述：

  4-氟-1,2-苯二胺 以 乙腈 为溶剂， 反应 14.0h， 生成 3-(2-amino-4-fluorophenyl)-4-methyl-1,3-thiazole-2(3H)-thione
  参考文献：
  名称：

  Novel phenyl(thio)ureas bearing (thio)oxothiazoline group as potential BACE-1 inhibitors: synthesis and biological evaluation

  摘要：

  We report the synthesis and the beta-site amyloid precursor protein cleaving enzyme-1 inhibitory properties of novel phenyl(thio) ureas bearing 2-(thio)oxothiazoline derivatives. A library of analogues was prepared according to specific synthetic schemes and the inhibitory activity was monitored using a fluorescence resonance energy transfer assay. Several analogues show potent inhibitory activities ranging between 1 and 0.01 mu M and the activity is related to the NH acidity of the (thio) urea motif. Our results illustrate once again the close relationship between molecular recognition, complexation of the active site in enzymatic system, and organocatalysis utilizing explicit hydrogen bonding.

  DOI：

  10.3109/14756366.2011.642375

文献信息

• PROCESS TO PREPARE NEW SUBSITUTED 1H-BENZO[d]IMIDAZOL-2(3H)-ONES, NEW INTERMEDIATES AND THEIR USE AS BACE 1 INHIBITORS
  申请人：Roussel Christian

  公开号：US20100120880A1

  公开（公告）日：2010-05-13

  The invention relates to a new process leading to new substituted 1H-benzo[d]imidazol-2(3H)-ones of formula III and III′, to pharmaceutical compositions comprising them and to their use as therapeutic agents, particularly as BACE 1 inhibitors in the treatment of Alzheimer disease.

  这项发明涉及一种新的过程，导致新的取代的1H-苯并[d]咪唑-2(3H)-酮，其化学式为III和III′，以及包含它们的药物组合物，以及它们作为治疗剂的用途，特别是作为治疗阿尔茨海默病的BACE 1抑制剂。
• Process to prepare new substituted 1H-benzo[d]imidazol-2(3H)-ones, new intermediates and their use as BACE 1 inhibitors
  申请人：Universite Paul Cezanne-Aix Marseille III

  公开号：US07906541B2

  公开（公告）日：2011-03-15

  The invention relates to a new process leading to new substituted 1H-benzo[d]imidazol-2(3H)-ones of formula III and III′, to pharmaceutical compositions comprising them and to their use as therapeutic agents, particularly as BACE 1 inhibitors in the treatment of Alzheimer disease.

  本发明涉及一种新的工艺，可导致新的取代1H-苯并[d]咪唑-2(3H)-酮III和III'，以及包含它们的制药组合物，以及它们作为治疗剂的用途，特别是作为BACE 1抑制剂用于治疗阿尔茨海默病。
• Process to prepare new substituted 1H-Benzo(d) imidazol-2(3h)-Ones, New intermediates and their use as bace 1 inhibitors
  申请人：UNIVERSITE PAUL CEZANNE AIX-MARSEILLE III

  公开号：EP2184276A1

  公开（公告）日：2010-05-12

  The invention relates to a new process leading to new substituted 1H-benzo[d]imidazol-2(3H)-ones of formula III and III', to pharmaceutical compositions comprising them and to their use as therapeutic agents, particularly as BACE I inhibitors in the treatment of Alzheimer disease.

  本发明涉及一种导致式 III 和 III'的新取代 1H-苯并[d]咪唑-2(3H)-酮的新工艺，涉及包含它们的药物组合物以及它们作为治疗剂的用途，特别是作为治疗阿尔茨海默病的 BACE I 抑制剂的用途。
• US7906541B2
  申请人：——

  公开号：US7906541B2

  公开（公告）日：2011-03-15
• [EN] PROCESS TO PREPARE NEW SUBSTITUTED 1H-BENZO [d] IMIDAZOL-2(3H)-ONES, NEW INTERMEDIATES AND THEIR USE AS BACE 1 INHIBITORS<br/>[FR] MÉTHODE POUR PRÉPARER DE NOUVELLES 1H-BENZO[D]IMIDAZOL-2(3H)-ONES SUBSTITUÉES, NOUVEAUX INTERMÉDIAIRES ET LEUR UTILISATION COMME INHIBITEURS DE BACE 1
  申请人：UNIV AIX MARSEILL III PAUL CEZANNE

  公开号：WO2010052670A1

  公开（公告）日：2010-05-14

  The invention relates to a new process leading to new substituted IH- benzo[