2-(2-cyclohexyl-5-methyl-4-oxazolyl)ethanol | 132646-47-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-cyclohexyl-5-methyl-4-oxazolyl)ethanol
• 英文别名: 2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethanol；2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethanol
• CAS: 132646-47-0
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: GDHMDXZIPQXVCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-cyclohexyl-5-methyl-4-oxazolyl)ethanol 在 lithium hydroxide 、 三苯基膦 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-(5-{2-[2-cyclohexyl-5-methyl-1,3-oxazol-4-yl]ethoxy}-2,3-dihydro-1H-inden-1-yl)butanoic acid
  参考文献：
  名称：

  Substituted indanylacetic acids as PPAR-α–γ activators

  摘要：

  A series of oxazole-substituted indanylacetic acids were prepared which show a spectrum of activity as ligands for PPAR nuclear receptor subtypes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.008
• 作为产物：
  描述：

  3-(cyclohexanecarbonyl-amino)-4-oxo-pentanoic acid benzyl ester 在 氢氧化钾 、 硼烷四氢呋喃络合物 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 2-(2-cyclohexyl-5-methyl-4-oxazolyl)ethanol
  参考文献：
  名称：

  Application of the Dakin−West Reaction for the Synthesis of Oxazole-Containing Dual PPARα/γ Agonists

  摘要：

  An improved method for the preparation of a series of oxazole-containing dual PPARalpha/gamma agonists is described. A synthetic sequence utilizing a Dakin-West reaction was devised that allows for the introduction of the oxazole ring either late in the synthetic sequence via aminomalonate-derived chemistry or in pivotal SAR intermediates derived from aspartic acid.

  DOI：

  10.1021/jo026655v

文献信息

• [EN] SUBSTITUTED 4-ALKOXYOXAZOL DERIVATIVES AS PPAR AGONISTS<br/>[FR] DERIVES DE 4-ALCOXYOXAZOLE SUBSTITUES EN TANT QU'AGONISTES DES RECEPTEURS PPAR
  申请人：HOFFMANN LA ROCHE

  公开号：WO2004041275A1

  公开（公告）日：2004-05-21

  The present invention relates to compounds of formula (I) wherein R1 to R8 and n are as defined in the description and claims, and pharmaceutically acceptable salts and esters thereof. The compounds are useful for the treatment of diseases such as diabetes.

  本发明涉及式（I）的化合物，其中R1至R8和n如描述和权利要求中所定义，并且其药学上可接受的盐和酯。这些化合物可用于治疗疾病，如糖尿病。
• [EN] HETEROCYCLIC COMPOUNDS AS MODULATORS OF PEROXISOME PROLIFERATOR ACTIVATED RECEPTORS, USEFUL FOR THE TREATMENT AND/OR PREVENTION OF DISORDERS MODULATED BY A PPAR<br/>[FR] COMPOSES HETEROCYCLIQUES UTILISES COMME MODULATEURS DES RECEPTEURS ACTIVES PROLIFERATEURS DU PEROXYSOME (PPAR), UTILES DANS LE TRAITEMENT ET/OU LA PREVENTION DE TROUBLES MODULES PAR UN PPAR
  申请人：LILLY CO ELI

  公开号：WO2005051945A1

  公开（公告）日：2005-06-09

  The present invention is directed to a compound of formula (I), or a pharmaceutically acceptable salt, solvate, hydrate or stereoisomer thereof, which is useful in treating or preventing disorders mediated by a peroxisome proliferator activated receptor (PPAR) such as syndrome X, type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to syndrome X and cardiovascular diseases.

  本发明涉及一种式(I)的化合物，或其药学上可接受的盐、溶剂合物、水合物或立体异构体，该化合物在治疗或预防由过氧化物酶体增殖激活受体（PPAR）介导的疾病中具有用途，如X综合征、2型糖尿病、高血糖、高脂血症、肥胖、凝血障碍、高血压、动脉硬化以及与X综合征和心血管疾病相关的其他疾病。
• 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。
• Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists
  申请人：——

  公开号：US20040097590A1

  公开（公告）日：2004-05-20

  Compounds represented by the following structural formula (I), and pharmaceutically acceptable salts, solvates and hydrates thereof, wherein: n is 2, 3, or 4 and W is CH 2 , CH(OH), C(O) or O; R1 is an unsubstituted or substituted aryl, heteroaryl, cycloalkyl, heterocycloalkyl, aryl-alkyl, heteroaryl-alkyl, cycloalkyl-alkyl, or t-butyl; R2 is H, alkyl, haloalkyl or phenyl; Y is an unsubstituted or substituted thiophen-2,5-diyl or phenylene; R3 is alkyl or haloalkyl; R4 is a substituted or unsubstituted phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, quinolyl, pyridyl or benzo[1,3]dioxol-5-yl group; and R5 is H, alkyl, or aminoalkyl; are useful for modulating a peroxisome proliferator activated receptor, particularly in the treatment of diabetes mellitus. 1

  由以下结构式（I）表示的化合物及其药用可接受的盐、溶剂合物和水合物，其中：n为2、3或4，W为CH2、CH（OH）、C（O）或O；R1为未取代或取代的芳基、杂环芳基、环烷基、杂环烷基、芳基-烷基、杂环芳基-烷基、环烷基-烷基或叔丁基；R2为H、烷基、卤代烷基或苯基；Y为未取代或取代的噻吩-2,5-二基或苯基；R3为烷基或卤代烷基；R4为取代或未取代的苯基、萘基、1,2,3,4-四氢萘基、喹啉基、吡啶基或苯并[1,3]二氧杂环-5-基团；R5为H、烷基或氨基烷基；用于调节过氧化物酶增殖物激活受体，特别是在糖尿病治疗中。
• [EN] OXAZOLYL-ARYLPROPIONIC ACID DERIVATIVES AND THEIR USE AS PPAR AGONISTS<br/>[FR] DÉRIVÉS D'ACIDE OXAZOLYL-ARYLPROPIONIQUE ET LEUR UTILISATION COMME AGONISTES DES PPAR
  申请人：LILLY CO ELI

  公开号：WO2002016331A1

  公开（公告）日：2002-02-28

  Compounds represented by the following structural formula (I), and pharmaceutically acceptable salts, solvates and hydrates thereof, wherein: n is 2, 3, or 4 and W is CH2, CH(OH), C(O) or O; R1 is an unsubstituted or substituted aryl, heteroaryl, cycloalkyl, heterocycloalkyl, aryl-alkyl, heteroaryl-alkyl, cycloalkyl-alkyl, or t-butyl; R2 is H, alkyl, haloalkyl or phenyl; Y is an unsubstituted or substituted thiophen-2,5-diyl or phenylene; R3 is alkyl or haloalkyl; R4 is a substituted or unsubstituted phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, quinolyl, pyridyl or benzo[1,3]dioxol-5-yl group; and R5 is H, alkyl, or aminoalkyl; are useful for modulating a peroxisome proliferator activated receptor, particularly in the treatment of diabetes mellitus.

  以下结构式(I)所代表的化合物及其药学上可接受的盐、溶剂化物和水合物，其中：n为2、3或4，W为CH2、CH(OH)、C(O)或O；R1为未取代或取代的芳基、杂环芳基、环烷基、杂环烷基、芳基烷基、杂环芳基烷基、环烷基烷基或叔丁基；R2为H、烷基、卤代烷基或苯基；Y为未取代或取代的噻吩-2,5-二基或苯基；R3为烷基或卤代烷基；R4为取代或未取代的苯基、萘基、1,2,3,4-四氢萘基、喹啉基、吡啶基或苯并[1,3]二噁烷-5-基团；R5为H、烷基或氨基烷基；在调节过氧化物酶体增殖物激活受体方面有用，特别是在糖尿病治疗中。