2-(2-苯基-1,3-恶唑-4-基)乙酸乙酯 | 84446-03-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(2-苯基-1,3-恶唑-4-基)乙酸乙酯
• 英文名称: ethyl 2-(2-phenyl-oxazol-4-yl)acetate
• 英文别名: ethyl 2-(2-phenyl-4-oxazolyl)acetate；ethyl (2-phenyl-4-oxazolyl)acetate；ethyl 2-phenyl-4-oxazolylacetata；(2-phenyloxazol-4-yl)acetic acid ethyl ester；ethyl 2-phenyl-4-oxazoleacetate；Ethyl (2-phenyl-1,3-oxazol-4-yl)acetate；ethyl 2-(2-phenyl-1,3-oxazol-4-yl)acetate
• CAS: 84446-03-7
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: WDASBQYNHGLIKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  352.8±34.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-苯基-1,3-恶唑-4-基)乙酸乙酯 在 LiAlH4 作用下， 以 乙醚 、 水 、 乙酸乙酯 为溶剂， 以81%的产率得到2-(2-phenyloxazol-4-yl)ethan-1-ol
  参考文献：
  名称：

  Hypoglycemic and hypolipidemic compounds

  摘要：

  这项发明提供了化合物及其药用盐，所述化合物的药用制剂，以及治疗与非胰岛素依赖型糖尿病相关的高血糖和治疗高脂血症的方法。

  公开号：

  US06194446B1
• 作为产物：
  描述：

  (Z)-5-ethoxycarbonylmethylene-3-phenyl-5,6-dihydro-4H-1,2,4-oxadiazine 以5%的产率得到
  参考文献：
  名称：

  TABEI, KATSUMI;KAWASHIMA, ETSUKO;TAKADA, TOYOZO;KATO, TETSUZO, HETEROCYCLES, 1982, 19, N 11, 2061-2066

  摘要：

  DOI：

文献信息

• Ramoplanin derivatives possessing antibacterial activity
  申请人：Raju G. Bore

  公开号：US20060211603A1

  公开（公告）日：2006-09-21

  Novel ramoplanin derivatives are disclosed. These ramoplanin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against gram positive bacteria, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.

  新型拉莫普兰衍生物已被披露。这些拉莫普兰衍生物表现出抗菌活性。由于本发明的化合物对革兰氏阳性细菌表现出强效活性，它们是有用的抗微生物药剂。该化合物的合成方法和使用方法也已被披露。
• Studies on antidiabetic agents. 11. Novel thiazolidinedione derivatives as potent hypoglycemic and hypolipidemic agents
  作者：Takashi Sohda、Katsutoshi Mizuno、Yu Momose、Hitoshi Ikeda、Takeshi Fujita、Kanji Meguro

  DOI：10.1021/jm00092a012

  日期：1992.7

  antidiabetic pioglitazone (AD-4833, U-72,107), a series of 5-[4-(2- or 4-azolylalkoxy)benzyl- or -benzylidene]-2,4-thiazolidinediones was prepared and evaluated for hypoglycemic and hypolipidemic activities in insulin-resistant, genetically obese, and diabetic KKA(y) mice. Replacement of the 2-pyridyl moiety of pioglitazone by a 2- or 4-oxazolyl or a 2- or 4-thiazolyl moiety greatly enhanced in vivo potency

  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。
• Thiazolidinedione derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04725610A1

  公开（公告）日：1988-02-16

  Thiazolidinedione derivatives of the general formula: ##STR1## [wherein R.sup.1 is hydrogen or a hydrocarbon residue or heterocyclic residue which may each be substituted; R.sup.2 is hydrogen or lower alkyl which may be substituted by hydroxyl group; X is an oxygen or sulfur atom; Z is a hydroxylated methylene or carbonyl; m is 0 or 1; n is an integer of 1 to 3; L and M represent independently a hydrogen atom or L and M combine with each other to cooperate jointly to form a linkage] and their salts, which are novel compounds, possess blood-glucose and blood-lipid lowering actions in mammals, and are of value as a therapeutic agent for diabetes and therapeutic agent for hyperlipemia.

  通用公式的噻唑烷二酮衍生物：##STR1## [其中R.sup.1为氢或可被取代的碳氢残基或杂环残基；R.sup.2为氢或可被羟基取代的低碳基；X为氧或硫原子；Z为羟基化的亚甲基或羰基；m为0或1；n为1到3的整数；L和M分别代表氢原子或L和M结合以共同形成连接]及其盐，这些是新颖的化合物，在哺乳动物体内具有降低血糖和血脂的作用，并且对于糖尿病的治疗剂和高脂血症的治疗剂具有价值。
• Oral hypoglycemic agents
  申请人：Eli Lilly and Company

  公开号：US05641796A1

  公开（公告）日：1997-06-24

  Antihyperglycemic compounds selected from the group consisting of C-substituted pentacycloazoles and N-alkyl-substituted pentacycloazoles.

  从C取代的五环氮唑和N烷基取代的五环氮唑中选择的抗高血糖化合物。
• Acetic Acid Aldose Reductase Inhibitors Bearing a Five-Membered Heterocyclic Core with Potent Topical Activity in a Visual Impairment Rat Model
  作者：Concettina La Motta、Stefania Sartini、Silvia Salerno、Francesca Simorini、Sabrina Taliani、Anna Maria Marini、Federico Da Settimo、Luciana Marinelli、Vittorio Limongelli、Ettore Novellino

  DOI：10.1021/jm701613h

  日期：2008.6.1

  A number of 1,2,4-oxadiazol-5-yl-acetic acids and oxazol-4-yl-acetic acids were synthesized and tested for their ability to inhibit aldose reductase (ALR2). The oxadiazole derivatives, 7c, 7f, 7i, and 8h, 8i, proved to be the most active compounds, exhibiting inhibitory levels in the submicromolar range. In this series, the phenyl group turned out to be the preferred substitution pattern, as its lengthening to a benzyl moiety determined a general reduction of the inhibitory potency. The lead compound, 2-[3-(4-methoxyphenyl)1,2,4-oxadiazol-5-yl] acetic acid, 7c, showed an excellent in vivo activity, proving to prevent cataract development in severely galactosemic rats when administered as an eye-drop solution in the precorneal region of the animals. Computational studies on the ALR2 inhibitors were performed to rationalize the structure-activity relationships observed and to provide the basis for further structure-guided design of novel ALR2 inhibitors.