2-(3-phenyl-1,2,4-oxadiazol-5-yl)acetic acid | 27349-43-5

• 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-(3-phenyl-1,2,4-oxadiazol-5-yl)acetic acid
• 英文别名: (3-phenyl-[1,2,4]oxadiazol-5-yl)-acetic acid
• CAS: 27349-43-5
• 化学式: C₁₀H₈N₂O₃
• mdl: MFCD04969977
• 分子量: 204.185
• InChiKey: FTUATJKDOQCWME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二正丁胺 、 2-(3-phenyl-1,2,4-oxadiazol-5-yl)acetic acid 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 以38%的产率得到N,N-di-n-butyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)acetamide
  参考文献：
  名称：

  具有五元杂芳族环的叔酰胺作为转运蛋白的新探针

  摘要：

  在这项研究中，使用先前设计的新型转运蛋白（TSPO）的配体，其特征在于五元芳族杂环（即恶唑，异恶唑，恶二唑），苯环和羧基或乙酸型酰胺侧链。报告的药效团/拓扑模型。大多数化合物显示显著TSPO结合亲和力（K我在纳摩尔/亚微摩尔范围内的值），最高被显示通过oxazolacetamides 6。测试了许多化合物抑制人胶质母细胞瘤细胞系U87MG增殖/活力的能力。剂量-时间依赖性细胞对6d治疗的反应证明了所观察到的效应的特异性。6d的能力诱导线粒体膜耗散（Δm）证实了配体结合TSPO激活的细胞内促凋亡机制。

  DOI：

  10.1016/j.ejmech.2011.07.025
• 作为产物：
  描述：

  2-(3-苯基-1,2,4-噁二唑-5-基)乙酸乙酯 在 乙醇 、 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以74%的产率得到2-(3-phenyl-1,2,4-oxadiazol-5-yl)acetic acid
  参考文献：
  名称：

  New non-hydroxamic ADAMTS-5 inhibitors based on the 1,2,4-triazole-3-thiol scaffold

  摘要：

  In this Letter we describe the design, synthesis, screening, and optimization of a new family of ADAMTS-5 inhibitors. These inhibitors display an original 1,2,4-triazole-3-thiol scaffold as a putative zinc binding-group. In vitro results are rationalized by in silico docking of the compounds in ADAMTS-5's crystal structure. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.108

文献信息

• Lithiation of five-membered heteroaromatic compounds. The methyl substituted 1,2-azoles, oxadiazoles, and thiadiazoles
  作者：R. G. Micetich

  DOI：10.1139/v70-334

  日期：1970.7.1

  The lithiation of various methyl substituted isoxazoles, isothiazoles, pyrazoles, oxadiazoles, and thiadiazoles using n-butyllithium has been studied. Three types of reactions, namely, lateral lithiation, ring cleavage, and addition of butyllithium to the ring, have been found. 3,5-Dimethylisoxazole, 3-phenyl-5-methylisoxazole, 3,4-dimethyl-1,2,5-oxadiazole, 2,5-dimethyl-1,3,4-thiadiazole, 3-phenyl-5-methyl-1,2,4-oxadiazole, and 3,5-dimethyl-1,2,4-thiadiazole all undergo lateral lithiation to give the respective acetic acids after carboxylation. 1-Methyl-3,5-disubstituted pyrazoles form the 1-lithiomethyl derivatives, while 1-phenyl-3,5-disubstituted pyrazoles are converted to the 1-ortholithiophenyl-3,5-disubstituted pyrazoles. 4-Methylisothiazole is lithiated mainly at C-5, but also suffers ring cleavage to form 1-n-butylthio-2-cyanoprop-1-ene. Heteroaromatic compounds containing an N—S bond, such as 3,4-dimeth yl-1,2,5-thiadiazole, 4-methyl-5-phenyl-1,2,3-thiadiazole, and 3,5-dimethylisothiazole, undergo nucleophilic attack at sulfur with resulting ring cleavage. 3,5-Dimethylisothiazole produces 2-n-butylthiopent-2-en-4-one. 3-Methyl-5-phenyl-1,2,4-oxadiazole gave 3-methyl-5-phenyl-5-n-butyl-1,2,4-dihydroöxadiazole by addition to the azomethine bond. The results of these lithiations are discussed. 3-Methyl-5-lithiomethylisoxazole was converted to various derivatives. Nuclear magnetic resonance spectral analysis was used to establish the identity of the products.

  各种甲基取代异噁唑、异硫唑、吡唑、噁二唑和噻二唑的锂化反应已经被研究。发现了三种类型的反应，即侧链锂化、环裂解和丁基锂加入环中。3,5-二甲基异噁唑、3-苯基-5-甲基异噁唑、3,4-二甲基-1,2,5-噁二唑、2,5-二甲基-1,3,4-噻二唑、3-苯基-5-甲基-1,2,4-噁二唑和3,5-二甲基-1,2,4-噻二唑都经历侧链锂化，在羧化后生成相应的乙酸。1-甲基-3,5-二取代吡唑形成1-锂甲基衍生物，而1-苯基-3,5-二取代吡唑转化为1-邻锂苯基-3,5-二取代吡唑。4-甲基异硫唑主要在C-5处发生锂化，但也发生环裂解形成1-正丁硫基-2-氰基丙-1-烯。含有N—S键的杂环化合物，如3,4-二甲基-1,2,5-噻二唑、4-甲基-5-苯基-1,2,3-噻二唑和3,5-二甲基异硫唑，在硫原子上发生亲核攻击，导致环裂解。3,5-二甲基异硫唑产生2-正丁硫代戊-2-烯-4-酮。3-甲基-5-苯基-1,2,4-噁二唑通过加成到偶氮亚胺键生成3-甲基-5-苯基-5-正丁基-1,2,4-二氢噁二唑。讨论了这些锂化的结果。3-甲基-5-锂甲基异噁唑被转化为各种衍生物。核磁共振光谱分析用于确定产物的身份。
• Coumarin derivatives, their preparation and their use as optical
  申请人：Produits Chimiques Ugine Kuhlmann

  公开号：US03994907A1

  公开（公告）日：1976-11-30

  Coumarin of the formula: ##SPC1## In which R.sub.1 represents an alkyl group having 1 to 5 carbon atoms, and either unsubstituted or substituted by a non-ionic and non-chromophoric group, R.sub.2 represents a benzene, styryl or heterocyclic residue such residue being unsubstituted or substituted by one or two non-ionic and non-chromophoric groups; process for the preparation of a coumarin of the above formula which comprises reacting an orthohydroxy-benzaldehyde of formula (II) upon an acid of formula (III) or one of its functional derivatives: ##SPC2## Wherein R.sub.1 and R.sub.2 have the same definitions as in claim 1; process for the fluorescent brightening of fibrous material of synthetic origin which comprises treating the material with a coumarin of the above formula; fluorescent brightening composition containing a coumarin of the above formula and a dispersing agent resulting from the condensation of naphthalene-sulphonic acids with formaldehyde in the presence of or absence of phenol compounds, said dispersing agent comprising 30% to 50% monosulphonated condensates, 30% to 50% disulphonated condensates and 10% to 40% trisulphonated or higher polysulphonated condensates; fibres of synthetic origin treated with a coumarin of the above formula or with a brightening composition as set out above.

  公式为：##SPC1## 其中R.sub.1表示1至5个碳原子的烷基，可以是未取代的或被非离子和非色团基团取代的；R.sub.2表示苯基，亚基或杂环残基，该残基可以是未取代的或被一或两个非离子和非色团基团取代的；制备上述公式的香豆素的过程包括将公式（II）的邻羟基苯甲醛与公式（III）或其官能衍生物之一发生反应：##SPC2## 其中R.sub.1和R.sub.2的定义与权利要求1中相同；用上述公式的香豆素处理合成纤维材料的荧光增白过程；荧光增白组合物包括上述公式的香豆素和萘磺酸与甲醛在酚类化合物的存在或不存在下缩聚而成的分散剂，所述分散剂包括30％至50％的单磺酸缩聚物，30％至50％的双磺酸缩聚物和10％至40％的三磺酸或更高磺酸缩聚物；用上述公式的香豆素或上述增白组合物处理的合成纤维。
• Compounds, Methods and Formulations for the Oral Delivery of a Glucagon-Like Peptide (Glp)-1 Compound or a Melanocortin-4 Receptor (Mc4) Agonist Peptide
  申请人：Herr Robert Jason

  公开号：US20080214448A1

  公开（公告）日：2008-09-04

  The present invention relates to novel compounds, methods, and formulations useful for the oral delivery of a GLP-1 compound or an MC4 agonist peptide.

  本发明涉及一种新型化合物、方法和配方，用于口服给药GLP-1化合物或MC4激动剂肽。
• COMPOUNDS, METHODS AND FORMULATIONS FOR THE ORAL DELIVERY OF A GLUCAGON-LIKE PEPTIDE (GLP-1) COMPOUND OR A MELANOCORTIN-4 RECEPTOR (MC4) AGONIST PEPTIDE
  申请人：HERR Robert Jason

  公开号：US20100120876A1

  公开（公告）日：2010-05-13

  The present invention relates to novel compounds, methods, and formulations useful for the oral delivery of a GLP-1 compound or an MC4 agonist peptide.

  本发明涉及一种新型化合物、方法和配方，用于口服给药GLP-1化合物或MC4激动剂肽。
• COMPOUNDS, METHODS AND FORMULATIONS FOR THE ORAL DELIVERY OF A GLUCAGON-LIKE PEPTIDE (GLP-1) COMPOUND OR A MELANOCORTIN-4 RECEPTOR (MIC4) AGONIST PEPTIDE
  申请人：Emisphere Technologies, Inc.

  公开号：US20140031287A1

  公开（公告）日：2014-01-30

  The present invention relates to novel compounds, methods, and formulations useful for the oral delivery of a GLP-1 compound or an MC4 agonist peptide.

  本发明涉及新型化合物、方法和配方，用于口服给药GLP-1化合物或MC4激动剂肽。