4-{2-[Methyl-(4-phenyl-thiazol-2-yl)-amino]-ethoxy}-benzaldehyde | 122320-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-{2-[Methyl-(4-phenyl-thiazol-2-yl)-amino]-ethoxy}-benzaldehyde
• 英文别名: 4-[2-[Methyl-(4-phenyl-1,3-thiazol-2-yl)amino]ethoxy]benzaldehyde
• CAS: 122320-89-2
• 化学式: C₁₉H₁₈N₂O₂S
• 分子量: 338.43
• InChiKey: COSXUTKNVMGBPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  70.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-{2-[Methyl-(4-phenyl-thiazol-2-yl)-amino]-ethoxy}-benzaldehyde 在 甲醇 、 碘 、 哌啶乙酸盐 、 magnesium 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 5-(4-{2-[N-methyl-N-(4-phenylthiazol-2-yl)amino]ethoxy}benzyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents

  摘要：

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.

  DOI：

  10.1021/jm00049a017
• 作为产物：
  描述：

  2-氯-4-苯基噻唑 在 sodium hydride 作用下， 反应 33.0h， 生成 4-{2-[Methyl-(4-phenyl-thiazol-2-yl)-amino]-ethoxy}-benzaldehyde
  参考文献：
  名称：

  [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents

  摘要：

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.

  DOI：

  10.1021/jm00049a017

文献信息

• Substituted thiazolidinedione derivatives
  申请人：BEECHAM GROUP PLC

  公开号：EP0842925A1

  公开（公告）日：1998-05-20

  Compounds of formula (I): or a tautomeric form thereof, or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof, wherein: A1 represents a substituted or unsubstituted aromatic heterocyclyl group; R1 represents a hydrogen atom, an alkyl group, an acyl group, an aralkyl group, wherein the aryl moiety may be substituted or unsubstituted, or a substituted or unsubstituted aryl group; R2 and R3 each represent hydrogen, or R2 and R3 together represent a bond; A2 represents a benzene ring having in total up to five substituents; and n represents an integer in the range of from 2 to 6; pharmaceutical compositions containing such compounds and the use of such compounds and compositions in medicine.

  式(I)的化合物，或其互变异构体，或其药学上可接受的盐，或其药学上可接受的溶剂化物，其中：A1代表取代或未取代的芳香杂环基团；R1代表氢原子、烷基团、酰基团、芳基烷基团，其中芳基部分可以是取代或未取代的，或取代或未取代的芳基基团；R2和R3各自代表氢，或R2和R3一起代表键；A2代表苯环，最多具有五个取代基；n代表在2到6范围内的整数；包含这种化合物的药学组合物以及这种化合物和组合物在医学上的用途。
• NOVEL COMPOUNDS
  申请人：Beecham Group p.1.c.

  公开号：US20020049240A1

  公开（公告）日：2002-04-25

  Compounds of formula (I): 1 or a tautomeric form thereof, or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof, wherein: A 1 represents a substituted or unsubstituted aromatic heterocyclyl group; R 1 represents a hydrocarbon atom, an alkyl group, an acyl grup, an aralkyl group, wherein the aryl moiety may be substituted or unsubstituted, or a substituted or unsubstituted aryl group; R 2 and R 3 each represent hydrogen, or R 2 and R 3 together represent a bond; A 2 represents a benzene ring having a total up to five substituents; and n represents an integer in the range of from 2 to 6; pharmaceutical compositions containing such compounds and the use of such compounds and compositions in medicine.

  化合物的式子（I）：其中1或其互变异构体，或其药学上可接受的盐，或其药学上可接受的溶剂盐，其中：A1代表取代或未取代的芳香杂环基团；R1代表碳氢原子，烷基，酰基，苯基烷基，其中芳基部分可能被取代或未取代，或者是取代或未取代的芳基基团；R2和R3分别代表氢，或者R2和R3一起代表一个键；A2代表苯环，具有最多五个取代基；n代表在2到6之间的整数；包含这种化合物的药物组合物以及这种化合物和组合物在医学上的用途。
• US5002953A
  申请人：——

  公开号：US5002953A

  公开（公告）日：1991-03-26
• US5194443A
  申请人：——

  公开号：US5194443A

  公开（公告）日：1993-03-16
• US5232925A
  申请人：——

  公开号：US5232925A

  公开（公告）日：1993-08-03