(2-苯基-1,3-噁唑-4-基)乙酸 | 22086-89-1

• 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-苯基-1,3-噁唑-4-基)乙酸
• 英文名称: (2-phenyloxazol-4-yl)acetic acid
• 英文别名: 2-(2-phenyl-oxazol-4-yl)acetic acid；2-phenyl-4-oxazoleacetic acid；(2-phenyl-oxazol-4-yl)-acetic acid；(2-Phenyl-1,3-oxazol-4-yl)acetic acid；2-(2-phenyl-1,3-oxazol-4-yl)acetic acid
• CAS: 22086-89-1
• 化学式: C₁₁H₉NO₃
• mdl: MFCD07838437
• 分子量: 203.197
• InChiKey: GHGUBEHGXLMGTM-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C
• 沸点：
  399.0±34.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (2-苯基-1,3-噁唑-4-基)乙酸 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到2-(2-phenyloxazol-4-yl)ethan-1-ol
  参考文献：
  名称：

  Faul, Margaret M.; Winneroski, Leonard L.; York, Jeremy S., Heterocycles, 2001, vol. 55, # 4, p. 689 - 704

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-苯基-1,3-恶唑-4-基)乙酸乙酯 在 sodium hydroxide 、 水 作用下， 反应 1.0h， 以60%的产率得到(2-苯基-1,3-噁唑-4-基)乙酸
  参考文献：
  名称：

  Acetic Acid Aldose Reductase Inhibitors Bearing a Five-Membered Heterocyclic Core with Potent Topical Activity in a Visual Impairment Rat Model

  摘要：

  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.

  DOI：

  10.1021/jm701613h

文献信息

• Tertiary amides with a five-membered heteroaromatic ring as new probes for the translocator protein
  作者：Barbara Cosimelli、Francesca Simorini、Sabrina Taliani、Concettina La Motta、Federico Da Settimo、Elda Severi、Giovanni Greco、Ettore Novellino、Barbara Costa、Eleonora Da Pozzo、Sara Bendinelli、Claudia Martini

  DOI：10.1016/j.ejmech.2011.07.025

  日期：2011.9

  In this study novel ligands of the translocator protein (TSPO), characterized by a five-membered aromatic heterocycle (i.e. oxazole, isoxazole, oxadiazole), a phenyl ring, and an amide side chain of carboxy or acetic type, were designed using a previously reported pharmacophore/topological model. Most of compounds showed significant TSPO binding affinity (Ki values in the nanomolar/submicromolar range)

  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。
• Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds
  申请人：——

  公开号：US20020045747A1

  公开（公告）日：2002-04-18

  Disclosed are compounds which inhibit &bgr;-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits &bgr;-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

  公开了抑制β-淀粉样肽释放和/或其合成的化合物，因此可用于治疗阿尔茨海默病。还公开了包含抑制β-淀粉样肽释放和/或其合成的化合物的药物组合物，以及使用这些药物组合物预防性和治疗性治疗阿尔茨海默病的方法。
• 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。
• N-(aryl/heteroarylacetyl) amino acid esters, pharmaceutical compositions
  申请人：Athena Neurosciences, Inc.

  公开号：US06117901A1

  公开（公告）日：2000-09-12

  Disclosed are compounds which inhibit .beta.-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed pharmaceutical compositions comprising a compound which inhibits .beta.-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

  揭示了一种抑制β-淀粉样蛋白释放和/或合成的化合物，因此在治疗阿尔茨海默病方面具有用途。还披露了包括抑制β-淀粉样蛋白释放和/或合成的化合物的药物组合物，以及使用这种药物组合物预防性和治疗性治疗阿尔茨海默病的方法。
• Novel Benzoxazole 2,4-Thiazolidinediones as Potent Hypoglycemic Agents. Synthesis and Structure-Activity Relationships.
  作者：Kenji ARAKAWA、Masanori INAMASU、Mamoru MATSUMOTO、Kunihito OKUMURA、Kosuke YASUDA、Hidenori AKATSUKA、Saburo KAWANAMI、Akishige WATANABE、Koichi HOMMA、Yutaka SAIGA、Masakatsu OZEKI、Ikuo IIJIMA

  DOI：10.1248/cpb.45.1984

  日期：——

  benzoxazole 2,4-thiazolidinediones was synthesized and evaluated for hypoglycemic activity in genetically obese and diabetic yellow KK mice. 2-Arylmethyl- and 2-(heteroarylmethyl)benzoxazole derivatives showed far more potent activity than known 2,4-thiazolidinedione derivatives such as ciglitazone, troglitazone and pioglitazone. A facile synthesis of benzoxazole 2,4-thiazolidinediones was also established using

  合成了一系列新的苯并恶唑2，4-噻唑烷二酮，并评估了遗传性肥胖和糖尿病黄色KK小鼠的降血糖活性。2-芳基甲基-和2-（杂芳基甲基）苯并恶唑衍生物显示出比已知的2,4-噻唑烷二酮衍生物例如西格列酮，曲格列酮和吡格列酮强得多的活性。还使用氨基苯酚2,4-噻唑烷二酮（11）作为关键中间体，建立了苯并恶唑2,4-噻唑烷二酮的简便合成方法。描述了该系列的合成和构效关系的细节。