3-(1,3-苯并噁唑-2-基)丙酸 | 78757-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 3-(1,3-苯并噁唑-2-基)丙酸
• 英文名称: 2-benzoxazolyl propanoic acid
• 英文别名: 3-(benzo[d]oxazol-2-yl)propanoic acid；β-(2-Benzoxazolyl)propionsaeure；2-(2-Carboxy-aethyl)-benzoxazol；3-benzoxazol-2-yl-propionic acid；3-benzooxazol-2-yl-propionic acid；3-Benzoxazol-2-yl-propionsaeure；2-Benzoxazolepropionic acid；3-(1,3-Benzoxazol-2-yl)propanoic acid
• CAS: 78757-00-3
• 化学式: C₁₀H₉NO₃
• mdl: MFCD01925019
• 分子量: 191.186
• InChiKey: FUPQHVOTDIAYLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(1,3-苯并噁唑-2-基)丙酸 在 正丁基锂 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (S)-3-(3-(benzo[d]oxazol-2-yl)propanoyl)-4-benzyl-5,5-dimethyloxazolidin-2-one
  参考文献：
  名称：

  一种通过Ru催化自由基加成对烯醇化锆进行N-酰基恶唑烷酮不对称三氟甲基化的简单方法

  摘要：

  已经开发了 Ru 催化的 N-酰基恶唑烷酮的直接热三氟甲基化和全氟烷基化。该反应在实验上很简单，需要廉价的试剂，同时提供良好的立体控制水平的产品收率。初步研究表明，与官能团、芳烃和某些杂芳烃取代基具有显着的相容性。所描述的方法为以实验方便的方式合成氟化材料提供了一种有用的替代方法。

  DOI：

  10.1021/ja302552e
• 作为产物：
  描述：

  2-甲基苯并唑 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 3-(1,3-苯并噁唑-2-基)丙酸
  参考文献：
  名称：

  Cycloaddition reactions of pyridinium and related azomethine ylides

  摘要：

  The Rh(H)-catalyzed reaction of alpha-diazoacetophenone in the presence of 2-(methylthio)pyridine and dimethyl acetylenedicarboxylate gave 3-benzoyl-1,2-dicarbomethoxy-3,5-dihydro-5-(methylthio)-indolizine. The formation of the cycloadduct proceeds via a pyridinium ylide formed by attack of the nitrogen lone pair on the electrophilic keto carbenoid. A related cyclization occurred using 1-diazo-3-[(2-pyridyl)thio]-2-propanone. The Rh(II)-catalyzed reaction of 1-(3'-diazoacetonyl)-2-pyridone with DMAD was also found to give cycloadducts derived from an azomethine ylide. The initial reaction involves generation of the expected carbonyl ylide dipole by intramolecular cyclization of the keto carbenoid onto the oxygen atom of the amide group. A subsequent proton exchange generates the thermodynamically more stable azomethine ylide which is trapped by DMAD. Azomethine ylide cycloadducts derived from keto carbenoid cyclization onto a thiobenzoxazole are also formed. When 1-diazo-3-[(2-benzoxazolyl)thio]-2-propanone was used, the initially formed cycloadduct underwent a subsequent 1,3-sigmatropic thio shift. An analogous cyclization occurred using 2-(4-diazo-3-oxobutyl)benzoxazole. In addition to undergoing dipolar cycloaddition, the highly stabilized dipole formed from this benzoxazole loses a proton to produce a cyclic ketene N,O-acetal. This compound reacts further with DMAD to eventually produce a novel phenolic lactam whose structure was established by an X-ray crystal structure analysis.

  DOI：

  10.1021/jo00057a029

文献信息

• [EN] 3-(5-CHLORO-2-OXOBENZO[D]OXAZOL-3(2H)-YL)PROPANOIC ACID DERIVATIVES AS KMO INHIBITORS<br/>[FR] DÉRIVÉS D'ACIDE 3-(5-CHLORO-2-OXOBENZO[D]OXAZOL-3(2H)-YL)PROPANOÏQUE EN TANT QU'INHIBITEURS DE LA KMO
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2015091647A1

  公开（公告）日：2015-06-25

  A compound of formula (I) or a salt thereof are provided wherein R1, X and R3 are defined in the specification, useful in the treatment of disorders mediated by KMO such as acute pancreatitis, chronic kidney disease, other conditions associated with systemic inflammatory response syndrome (SIRS), Huntington's disease, Alzheimer's disease, spinocerebellar ataxias, Parkinson's disease, AIDS-dementia complex, amylotrophic lateral sclerosis (ALS), depression, schizophrenia, sepsis, cardiovascular shock, severe trauma, acute lung injury, acute respiratory distress syndrome, acute cholecystitis, severe burns, pneumonia, extensive surgical procedures, ischemic bowel, severe acute hepatic disease, severe acute hepatic encephalopathy or acute renal failure.

  提供了一种公式(I)的化合物或其盐，其中R1、X和R3如说明书中所定义，用于治疗由KMO介导的疾病，如急性胰腺炎、慢性肾病、与其他系统性炎症反应综合征(SIRS)相关的条件、亨廷顿病、阿尔茨海默病、脊髓小脑共济失调、帕金森病、艾滋病痴呆复合体、肌萎缩侧索硬化(ALS)、抑郁症、精神分裂症、败血症、心血管休克、严重创伤、急性肺损伤、急性呼吸窘迫综合征、急性胆囊炎、严重烧伤、肺炎、大手术程序、缺血性肠病、严重急性肝病、严重急性肝性脑病或急性肾衰竭。
• Microwave-Assisted Direct Synthesis of 2-Substituted Benzoxazoles from Carboxylic Acids under Catalyst and Solvent-Free Conditions
  作者：Asit K. Chakraborti、Raj Kumar、C. Selvam、Gurmeet Kaur

  DOI：10.1055/s-2005-868509

  日期：——

  A direct coupling of carboxylic acids with 2-aminophenol under microwave irradiation has been achieved leading to the synthesis of 2-substituted benzoxazoles under metal and solvent-free conditions. Aliphatic, aromatic and heteroaromatic carboxylic acids provide good yields. Benzoxazole formation takes place in the presence of chloro, methoxy, phenoxy, thiophenoxy, and α,β-unsaturated functionalities. In the case of dicarboxylic acids, the reaction proceeds via the formation of the corresponding anhydride with predominant formation of the mono-benzoxazole.

  在微波辐射下，羧酸与2-氨基苯酚直接耦合，实现了无金属和溶剂条件下的2-取代苯并恶唑合成。脂肪族、芳香族和杂芳香族羧酸均可提供良好的产率。苯并恶唑的形成在氯、甲氧基、苯氧基、噻吩氧基和α,β-不饱和功能团的存在下发生。对于二元羧酸，反应通过形成相应的酸酐进行，主要生成单苯并恶唑。
• Pyrimidine derivatives as ALK-5 inhibitors
  申请人：Novartis AG

  公开号：EP1878733A1

  公开（公告）日：2008-01-16

  Compounds of formula I in free or salt or solvate form, where T1, T2, K, Ra and Rb have the meanings as indicated in the specification, are useful for treating diseases mediated by the ALK-5 and/or ALK-4 receptor. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

  公式I中的化合物以自由形式、盐或溶剂形式存在，其中T1、T2、K、Ra和Rb的含义如规范中所示，可用于治疗由ALK-5和/或ALK-4受体介导的疾病。还描述了含有这些化合物的药物组合物以及制备这些化合物的过程。
• An efficient synthesis of novel di-heterocyclic benzazole derivatives and evaluation of their antiproliferative activities
  作者：Oztekin Algul、Ronak Haj Ersan、Mehmet Abdullah Alagoz、Nizami Duran、Serdar Burmaoglu

  DOI：10.1080/07391102.2020.1803966

  日期：2021.12.12

  di-heterocyclic compounds of benzazole derivatives were synthesized at one step via cyclization reaction. The compounds evaluated for in vitro cytotoxic activity against A549, A498, HeLa, and HepG2 cancer cell lines. The biological evaluation results show that 23, 26 and 29 exhibit better activity against HepG2 and HeLa cancer cell lines. Compound 23 also showed good activity against A549, and A498 cancer cell

  摘要 通过环化反应一步合成了一系列苯并唑衍生物的不对称九杂环化合物。评估了化合物对 A549、A498、HeLa 和 HepG2 癌细胞系的体外细胞毒活性。生物学评价结果表明，23、26和29对HepG2和HeLa癌细胞系表现出更好的活性。化合物23还对 A549 和 A498 癌细胞系显示出良好的活性。类似物进一步针对人细胞色素 P450 2C8 单加氧酶进行了分子对接研究，计算了一些理论量子参数、ADMET 描述符和分子静电势分析。在这项研究工作中应用的策略可以作为合理设计潜在抗癌药物的一个视角。 由 Ramaswamy H. Sarma 交流
• New amino-alkyl-amide derivatives as CCR3 receptor ligands
  申请人：PAPPNE BEHR Agnes

  公开号：US20080287434A1

  公开（公告）日：2008-11-20

  The invention relates to a compound of the general formula (I), as defined herein which is useful for the treatment of a pathology in a patient wherein a CCR3 receptor plays a role in the development of the pathology, and pharmaceutical preparations containing such compound. The invention is also directed to a process for preparing the compound of the general formula (I), and intermediate useful in the preparation.

  本发明涉及一种通式（I）所定义的化合物，其对治疗患者中CCR3受体在病理发展中发挥作用的疾病有用，并且包含这种化合物的制药制剂。本发明还涉及一种制备通式（I）所定义的化合物的方法，以及在制备中有用的中间体。