methyl 2-isothiocyanato-5-methyl-4-phenylthiophene-3-carboxylate | 588682-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: methyl 2-isothiocyanato-5-methyl-4-phenylthiophene-3-carboxylate
• CAS: 588682-00-2
• 化学式: C₁₄H₁₁NO₂S₂
• mdl: MFCD03944292
• 分子量: 289.379
• InChiKey: QLXOIMIFROYUOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  99
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-isothiocyanato-5-methyl-4-phenylthiophene-3-carboxylate 、 3-(4-甲基咪唑-1-基)丙烷-1-胺 生成 2,3-dihydro-6-methyl-3-(3-(4-methyl-1H-imidazol-1-yl)propyl)-5-phenyl-2-thioxothieno[2,3-d]pyrimidin-4(1H)-one
  参考文献：
  名称：

  Inhibitors of glutaminyl cyclase

  摘要：

  式(I)的化合物、其组合物和用于治疗疾病的用途，或其药学上可接受的盐、溶剂或多晶形式，包括其全部互变异构体和立体异构体，其中：R1表示，R2、R3、R4、R5、R6、X1、X2、X3、X4、Y和Z如本说明书和权利要求书中所定义。

  公开号：

  US09034907B2

文献信息

• NOVEL INHIBITORS OF GLUTAMINYL CYCLASE
  申请人：Buchholz Mirko

  公开号：US20080267911A1

  公开（公告）日：2008-10-30

  Compounds of formula (I), combinations and uses thereof for disease therapy, or a pharmaceutically acceptable salt, solvate or polymorph thereof, including all tautomers and stereoisomers thereof wherein: R 1 represents and R 2 , R 3 , R 4 , R 5 , R 6 , X 1 , X 2 , X 3 , X 4 , Y and Z are as defined throughout the description and the claims.

  式(I)的化合物，其组合物及用途用于疾病治疗，或其药学上可接受的盐、溶剂化合物或多晶形式，包括其所有互变异构体和立体异构体，其中： R1代表，而R2、R3、R4、R5、R6、X1、X2、X3、X4、Y和Z如描述和权利要求中所定义。
• Inhibitors for Human Glutaminyl Cyclase by Structure Based Design and Bioisosteric Replacement
  作者：Mirko Buchholz、Antje Hamann、Susanne Aust、Wolfgang Brandt、Livia Böhme、Torsten Hoffmann、Stephan Schilling、Hans-Ulrich Demuth、Ulrich Heiser

  DOI：10.1021/jm900969p

  日期：2009.11.26

  The inhibition of human glutaminyl cyclase (hQC) has come into focus as a new potential approach for the treatment of Alzheimer's disease. The hallmark of this principle is the prevention of the formation of A beta(3,11(pE)-40,42), as these A beta-species were shown to be of elevated neurotoxicity and likely to act as a seeding core leading to an accelerated formation of A beta-oligomers and fibrils. Starting from 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea, bioisosteric replacements led to the development of new classes of inhibitors. The optimization of the metal-binding group was achieved by homology modeling and afforded a first insight into the probable binding mode of the inhibitors in the hQC active site. The efficacy assessment of the hQC inhibitors was performed in cell culture, directly monitoring the inhibition of A beta(3,11(pE)-40,42) formation.
• THIOXOQUINAZOLINONE DERIVATIVES AS GLUTAMINYL CYCLASE INHIBITORS
  申请人：Probiodrug AG

  公开号：EP2160389A1

  公开（公告）日：2010-03-10
• US9034907B2
  申请人：——

  公开号：US9034907B2

  公开（公告）日：2015-05-19
• [EN] THIOXOQUINAZOLINONE DERIVATIVES AS GLUTAMINYL CYCLASE INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS
  申请人：PROBIODRUG AG

  公开号：WO2008128982A1

  公开（公告）日：2008-10-30

  [EN] The present invention relates to compounds of formula (I), combinations and uses thereof for disease therapy, or a pharmaceutically acceptable salt, solvate or polymorph thereof, including all tautomers and stereoisomers thereof wherein: R¹ represents (A) or (B) and R², R³, R⁴, R⁵, R⁶, X₁, X₂, X₃, X₄, Y and Z are as defined throughout the description and the claims.
  [FR] Composés de formule (I), combinaisons correspondantes, et leurs utulisations, à vocation thérapeutique en cas de maladie, y compris les sels, solvates ou polymorphes pharmaceutiquement acceptables des produits en question, dont l'ensemble des tautomères, stereoisomères et polymorphes correspondants, sachant que R¹ représente et que R², R³, R⁴, R⁵, R⁶, X₁, X₂, X₃, X₄, Y et Z sont tels que définis dans la description et les revendications.