2-[N-methyl-N-(2-benzoxazolyl)-amino]ethanol | 122320-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-[N-methyl-N-(2-benzoxazolyl)-amino]ethanol
• 英文别名: 2-(benzooxazol-2-ylmethylamino)ethanol；2-[(2-benzoxazolyl)methylamino]ethanol；2-(2-benzoxazolylmethylamino)ethanol；N-methyl-N-(2-benzoxazolyl)-2-aminoethanol；2-(Benzooxazol-2-yl-methyl-amino)-ethanol；2-[(benzoxazole-2-yl)-(methyl)amino]-ethanol；2-[1,3-benzoxazol-2-yl(methyl)amino]ethanol
• CAS: 122320-77-8
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: LITDWGSWBCBPDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[N-methyl-N-(2-benzoxazolyl)-amino]ethanol 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三甲基氯硅烷 、 sodium hydride 、 lithium diisopropyl amide 作用下， 反应 5.5h， 生成 Methyl 2-[4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl]-2-bromoacetate
  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：

  N-甲基-2-羟基乙胺 、 2-氯苯并恶唑 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以87%的产率得到2-[N-methyl-N-(2-benzoxazolyl)-amino]ethanol
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS AS AGONIST FOR PPAR GAMMA AND PPAR ALPHA, METHOD FOR PREPARATION OF THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
  [FR] NOUVEAUX COMPOSES AGONISTES DE PPAR DOLLAR G(G) ET PPAR DOLLAR G(A), LEUR METHODE DE PREPARATION ET COMPOSITION PHARMACEUTIQUE LES CONTENANT

  摘要：

  本发明涉及一种新型化合物，可加速过氧化物酶体增殖物激活受体γ（PPARϜ）和α（PPARα）的活性，以及制备这种化合物的方法，以及含有该化合物作为活性成分的药物组合物。

  公开号：

  WO2005040127A1

文献信息

• Antidiabetic agents
  申请人：——

  公开号：US20030171377A1

  公开（公告）日：2003-09-11

  The present invention provides compounds of Formula (I): 1 wherein A, X, Q, Y, B, D, Z, and E have any of the values defined in the specification, and pharmaceutically acceptable salt thereof, that are useful as antidiabetic agents. Also disclosed are pharmaceutical compositions comprising one or more compounds of Formula I, processes for preparing compounds of Formula I, and intermediates useful for preparing compounds of Formula I.

  本发明提供了式(I)的化合物： 1 其中A、X、Q、Y、B、D、Z和E具有规范中定义的任何值，以及药用可接受的盐，这些化合物作为抗糖尿病药是有用的。还公开了包含一个或多个式I化合物的药物组合物，制备式I化合物的方法，以及用于制备式I化合物的中间体。
• Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
  申请人：——

  公开号：US20030236227A1

  公开（公告）日：2003-12-25

  The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

  该发明提供了在治疗2型糖尿病中有用的药物化合物。这些化合物具有优势，因为它们可以被代谢药物解毒系统迅速代谢。特别地，设计了包含酯基的噻唑烷二酮类似物的化合物。该发明还涉及治疗疾病的方法，如糖尿病，包括给予经设计为能够被血清或细胞内酯酶代谢的化合物的治疗有效组合物。还教授了含酯基的噻唑烷二酮类似物的药物组合物。
• Compounds
  申请人：Beecham Group p.l.c.

  公开号：US05232925A1

  公开（公告）日：1993-08-03

  Compounds of formula (I): ##STR1## or a tautomeric form thereof, or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof, wherein: A.sup.1 represents a substituted or unsubstituted aromatic heterocyclyl group; R.sup.1 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; R.sup.2 and R.sup.3 each represent hydrogen, or R.sup.2 and R.sup.3 together represent a bond; A.sup.2 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：##STR1##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合物，其中：A.sup.1代表取代或未取代的芳香杂环基团；R.sup.1代表氢原子，烷基基团，酰基基团，芳基烷基基团，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；R.sup.2和R.sup.3各自代表氢，或R.sup.2和R.sup.3一起代表键；A.sup.2代表总共最多具有五个取代基的苯环；n代表范围为2至6的整数；含有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中的用途。
• Novel compounds
  申请人：Beecham Group p.l.c.

  公开号：US05002953A1

  公开（公告）日：1991-03-26

  Compounds of formula (I): ##STR1## or a tautomeric form thereof, or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof, wherein: A.sup.1 represents a substituted or unsubstituted aromatic heterocyclyl group; R.sup.1 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; R.sup.2 and R.sup.3 each represent hydrogen, or R.sup.2 and R.sup.3 together represent a bond; A.sup.2 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：##STR1##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合物，其中：A.sup.1代表取代或未取代的芳香杂环基团；R.sup.1代表氢原子，烷基基团，酰基基团，芳基烷基基团，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；R.sup.2和R.sup.3各自代表氢，或R.sup.2和R.sup.3一起代表键；A.sup.2代表苯环，总共有多达五个取代基；n代表范围在2到6之间的整数；含有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中的用途。
• Heterocyclic compounds and their use in the treatment of Type-II diabetes
  申请人：SmithKline Beecham PLC

  公开号：US05589492A1

  公开（公告）日：1996-12-31

  A compound of the formula A.sup.1 --X--(CH.sub.2).sub.n --O--A.sup.2 --A.sup.3 --CO.R.sup.2 (I) or a tautomeric form thereof and/or a pharmaceutically acceptable salt thereof, and/or a pharmaceutically acceptable solvate thereof, wherein: A.sup.1 represents a substituted or unsubstituted aromatic heterocyclyl group; A.sup.2 represents a benzene ring having three optional substituents; A.sup.3 represents a moiety of formula --(CH.sub.2).sub.m --CHR.sup.1 -- wherein R.sup.1 represents a halogen atom or a moiety of formula S(O).sub.p A.sup.4 wherein A.sup.4 represents hydrogen, substituted or unsubstituted alkyl, aryl, aralkyl, alkylcarbonyl or an aromatic heterocyclyl group and p represents zero or an integer 1 or 2 and m represents zero or an integer in the range of from 1 to 5, or A.sup.3 represents a moiety of formula --CH.dbd.CR.sup.1 -- wherein R.sup.1 is as defined above; R.sup.2 represents OR.sup.3 wherein R.sup.3 represents hydrogen, alkyl, aryl or aralkyl, or R.sup.2 represents --NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 each independently represent hydrogen or alkyl or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a heterocyclic ring; X represents O, S or NR wherein R 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; and n represents an integer in the range of from 2 to 6; a process for the preparation of such a compound, a pharmaceutical composition comprising such a compound and the use of such a compound and composition in medicine.

  一种具有以下结构的化合物：A.sup.1 --X--(CH.sub.2).sub.n --O--A.sup.2 --A.sup.3 --CO.R.sup.2 (I)或其互变异构体和/或其药学上可接受的盐，和/或其药学上可接受的溶剂，其中：A.sup.1代表取代或未取代的芳香杂环基团；A.sup.2代表具有三个可选取代基团的苯环；A.sup.3代表具有式--(CH.sub.2).sub.m --CHR.sup.1 --的基团，其中R.sup.1代表卤素原子或式S(O).sub.p A.sup.4的基团，其中A.sup.4代表氢、取代或未取代的烷基、芳基、芳基烷基、烷基羰基或芳香杂环基团，p代表零或整数1或2，m代表零或范围在1到5之间的整数，或A.sup.3代表具有式--CH.dbd.CR.sup.1 --的基团，其中R.sup.1如上定义；R.sup.2代表OR.sup.3，其中R.sup.3代表氢、烷基、芳基或芳基烷基，或R.sup.2代表--NR.sup.4 R.sup.5，其中R.sup.4和R.sup.5各自独立地代表氢或烷基，或R.sup.4和R.sup.5与它们连接的氮原子一起形成杂环环；X代表O、S或NR，其中R代表氢原子、烷基、酰基、芳基烷基，其中芳基可能是取代或未取代的，或取代或未取代的芳基；n代表范围在2到6之间的整数；一种制备这种化合物的方法，包括这种化合物的药物组合物和这种化合物及组合物在医学中的用途。