4-<2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy>aniline | 103788-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-<2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy>aniline
• 英文别名: 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]aniline；5-Methyl-4-p-aminophenoxyethyl-2-phenyl-1,3-oxazole；4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxyl]-aniline；4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]aniline
• CAS: 103788-87-0
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: YDHOOEPQXCENPV-UHFFFAOYSA-N

物化性质

• 沸点：
  510.6±60.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-<2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy>aniline 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 potassium tert-butylate 、 乙酸酐 作用下， 以 氯仿 、 二甲基亚砜 、 xylene 为溶剂， 反应 35.0h， 生成 Methyl 2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-1,1,2',5'-tetraoxospiro[1,2-benzothiazole-3,4'-pyrrolidine]-3'-carboxylate
  参考文献：
  名称：

  Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents

  摘要：

  Compounds from two novel series of spirosuccinimides were prepared. Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group. These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats. Many members from the isoindolone series 2, particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency. The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer. Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg). Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone. However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.

  DOI：

  10.1021/jm00102a016
• 作为产物：
  描述：

  N-苯甲酰基-L-天门冬氨酸 4-甲酯 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 sodium hydride 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.5h， 生成 4-<2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy>aniline
  参考文献：
  名称：

  抗糖尿病药的研究。11.新型的噻唑烷二酮衍生物作为有效的降血糖药和降血脂药。

  摘要：

  在新型抗糖尿病吡格列酮的进一步化学修饰过程中（AD-4833，U-72,107），一系列5- [4-（2-或4-偶氮烷氧基）苄基或亚苄基] -2,4-噻唑烷二酮制备并评估了胰岛素抵抗，遗传性肥胖和糖尿病KKA（y）小鼠的降血糖和降血脂活性。吡格列酮的2-吡啶基部分被2-或4-恶唑基或2-或4-噻唑基部分取代大大增强了体内效力。相应的5-亚苄基型化合物也具有有效的生物活性，其中次甲基用作苯环和噻唑烷二酮环之间的连接基。在合成的化合物中，5- [4- [2-（5-甲基-2-苯基-4-恶唑基）乙氧基]苄基] -2,4-噻唑烷二酮（18）表现出最强的活性，是其的100倍以上吡格列酮。

  DOI：

  10.1021/jm00092a012

文献信息

• Ether and amide compounds and preparation of thereof as antidiadetics.
  申请人：——

  公开号：US20010008898A1

  公开（公告）日：2001-07-19

  Ether and amide derivatives are disclosed, which are represented by the following formula (I) and its pharmaceutical acceptable salt, and which are useful for the treatment of diabetes. 1 (with the provisos that (i) when A is —O—, then n is 2 or 3 (ii) when A is 2 then n is 1 or 2. R 3 is OH—, CH 3 SO 2 NH—, CF 3 SO 2 NH—, CH 3 SO 2 NHCH 2 —, CF 3 SO 2 NHCH 2 —, HOOC—, CH 3 OOC—, 3 HOOC—CH 2 SO 2 NH—, CF 3 —CH 2 SO 2 NH—, 4 R 8 —NHSO 2 —, R 8 —NHSO 2 —CH 2 —, HOOC—CH 2 —O—, HSO 3 N═CH—, or R 9 —SO 2 NHCO—; R 4 is H, OH, O-alkyl or O—CH 2 OCH 3 ; R 5 is H, halogen atom, —CH 2 COOH or OH; R 6 and R 7 are hydrogen, t-butyl or pyrolidyl; R 8 is hydrogen or lower alkyl; R 9 is alkyl or thienyl; R 10 is lower alkyl) or a pharmaceutically acceptable salt.

  乙醚和酰胺衍生物被披露，其由以下式(I)及其药用可接受盐所代表，并且对于糖尿病的治疗是有用的。 1 （在以下情况下，附加条件为：(i) 当A为—O—时，n为2或3 (ii) 当A为 2 时，n为1或2。R 3 为OH—，CH 3 SO 2 NH—，CF 3 SO 2 NH—，CH 3 SO 2 NHCH 2 —，CF 3 SO 2 NHCH 2 —，HOOC—，CH 3 OOC—， 3 HOOC—CH 2 SO 2 NH—，CF 3 —CH 2 SO 2 NH—， 4 R 8 —NHSO 2 —，R 8 —NHSO 2 —CH 2 —，HOOC—CH 2 —O—，HSO 3 N═CH—，或R 9 —SO 2 NHCO—； R 4 为H，OH，O-烷基或O—CH 2 OCH 3 ； R 5 为H，卤原子，—CH 2 COOH或OH； R 6 和R 7 为氢，叔丁基或吡咯烷基； R 8 为氢或较低烷基； R 9 为烷基或噻吩基； R 10 为较低烷基） 或药用可接受盐。
• Amino-thiazolidinediones useful in the treatment of insulin resistance and hyperglycemia
  申请人：——

  公开号：US06214842B1

  公开（公告）日：2001-04-10

  This invention provides compounds of Formula I having the structure wherein: R is hydrogen or alkyl of 1-6 carbon atoms; A is R1, R2, R3 are each, independently, hydrogen, alkoxy of 1-6 carbon atoms, thioalkyl of 1-6 carbon atoms, trifluoromethyl, R4 is hydrogen, alkyl of 1-6 carbon atoms, halogen, or alkoxy of 1-6 carbon atoms; R5 is phenyl, naphthyl, thienyl, furyl, wherein R5 may be optionally mono-, di-, or tri-substituted with a sustituent selected from the group consisting of alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, trifluoromethyl, halogen, alkoxycarbonyl of 2-7 carbon atoms, alkylamino of 1-6 carbon atoms, and dialkylamino in which each of the alkyl groups is of 1-6 carbon atoms, nitro, cyano, —CO2H, alkylcarbonyloxy of 2-7 carbon atoms, and alkylcarbonyl of 2-7 carbon atoms; m=1-4; n=1-4; and X=O, S, or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.

  该发明提供了具有结构的化合物I，其中：R为氢或1-6个碳原子的烷基；A为R1，R2，R3分别独立地为氢，1-6个碳原子的烷氧基，1-6个碳原子的硫代烷基，三氟甲基，R4为氢，1-6个碳原子的烷基，卤素或1-6个碳原子的烷氧基；R5为苯基，萘基，噻吩基，呋喃基，其中R5可以选择性地单取代，二取代或三取代，取代基选自1-6个碳原子的烷基，1-6个碳原子的烷氧基，三氟甲基，卤素，2-7个碳原子的烷氧羰基，1-6个碳原子的烷基氨基和两个烷基均为1-6个碳原子，硝基，氰基，-CO2H，2-7个碳原子的烷基羧氧基和2-7个碳原子的烷基羰基；m=1-4；n=1-4；X=O，S，或其药用盐，这些化合物在治疗与胰岛素抵抗或高血糖相关的代谢紊乱方面具有用途。
• 3-aryl-2-hydroxypropionic acid derivatives and analogs as hypoglycemic
  申请人：Pfizer Inc.

  公开号：US05438074A1

  公开（公告）日：1995-08-01

  Certain 3-(phenyl, chroman-2-yl, benzofuran-5-yl or benzoxazol-5-yl)-2-(hydroxy or mercapto)propionic acid derivatives and analogs are useful as hypoglycemic and hypocholesterolemic agents.

  某些3-(苯基、色满-2-基、苯并呋喃-5-基或苯并噁唑-5-基)-2-(羟基或巯基)丙酸衍生物和类似物可用作降血糖和降胆固醇剂。
• 3-aryl-2-hydroxypropionic acid derivatives and analogs as
  申请人：Pfizer Inc.

  公开号：US05232945A1

  公开（公告）日：1993-08-03

  A method of using certain 3-aryl-2-hydroxypropionic acid derivatives and analogs in the treatment of hypertension.

  使用某些3-芳基-2-羟基丙酸衍生物和类似物治疗高血压的方法。
• 3-coxazolyl [phenyl, chromanyl or benzofuranyl]-2-hydroxypropionic acid
  申请人：Pfizer Inc.

  公开号：US05089514A1

  公开（公告）日：1992-02-18

  Certain 3-(phenyl, chroman-2-yl, benzofuran-5-yl, or benzoxazol-5-yl)-2-(hydroxy or mercapto)propionic acid derivatives and analogs are useful as hypoglycemic and hypocholesterolemic agents.

  某些3-(苯基，色满-2-基，苯并呋喃-5-基或苯并噁唑-5-基)-2-(羟基或巯基)丙酸衍生物和类似物可用作降血糖和降胆固醇剂。