3-(5-methyl-[1,3,4]oxadiazol-2-yl)-propionic acid | 1023812-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(5-methyl-[1,3,4]oxadiazol-2-yl)-propionic acid
• 英文别名: (5-methyl-[1,3,4]oxadiazol-2-yl)-propionic acid；3-(5-methyl-1,3,4-oxadiazol-2-yl)propanoic acid；(5-methyl-1,3,4-oxadiazol-2-yl)propanoic acid
• CAS: 1023812-48-7
• 化学式: C₆H₈N₂O₃
• mdl: MFCD09880437
• 分子量: 156.141
• InChiKey: CXFLYPMEODYQPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  349.0±44.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  succinic acid acetylhydrazide 在 四磷十氧化物 、 硫酸 作用下， 以20%的产率得到3-(5-methyl-[1,3,4]oxadiazol-2-yl)-propionic acid
  参考文献：
  名称：

  1,3,4-Oxadiazoles for Crystal Engineering. Convenient Synthesis and Self-Assembly: Nonchiral Chains versus Chiral Helices

  摘要：

  A series of new 1,3,4-oxadiazoles containing carboxylic and halogen groups and a double bond have been synthesized in good yields and a multigram scale. This was achieved at room temperature from readily available 1,2-diacylhydrazines using a cheap condensation reagent (the solution of P2O5 in H2SO4). Single-crystal X-ray diffraction analysis has shown that all studied 1,3,4-oxadiazole-containing acids are self-assembled by intermolecular H-bonds into supramolecular zigzag chains or helices, depending on the tecton molecular structure and the type of H-bonding. Factors affecting helix formation have been found, and a Cambridge Structural Database (CSD) survey has been performed to support these findings. Moreover, it has been demonstrated that the tuning of the crystal structure leading to spontaneous symmetry breaking for supramolecular helices based on nonchiral molecules is possible even by as little change in molecular structure as a shift from an isopropyl substituent to a cyclopropyl. Subsequently, the studied 1,3,4-oxadiazole-containing acids and related compounds are found to be easily accessible building blocks for crystal engineering of new chiral materials with tunable supramolecular arrangement.

  DOI：

  10.1021/cg400649h

文献信息

• [EN] BIARYL-PROPIONIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICALS<br/>[FR] DÉRIVÉS D'ACIDE BIARYL-PROPIONIQUE ET LEUR UTILISATION EN TANT QUE PRODUITS PHARMACEUTIQUES
  申请人：SANOFI SA

  公开号：WO2014154727A1

  公开（公告）日：2014-10-02

  The present invention relates to compounds of the formula (I), wherein X, R, R1, R2, D, E1, E2, E3, E4, G1, G2, G3 and G4 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. They are inhibitors of the protease cathepsin A, and are useful for the treatment of diseases such as atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula (I), their use and pharmaceutical compositions comprising them.

  本发明涉及式(I)的化合物，其中X、R、R1、R2、D、E1、E2、E3、E4、G1、G2、G3和G4在权利要求中所示的含义，这些化合物是有价值的药用活性化合物。它们是蛋白酶卡特普辛A的抑制剂，可用于治疗动脉粥样硬化、心力衰竭、肾脏疾病、肝脏疾病或炎症性疾病等疾病。此外，本发明还涉及制备式(I)化合物的方法，它们的用途以及包含它们的药物组合物。
• BIARYL-PROPIONIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICALS
  申请人：SANOFI

  公开号：EP2978754A1

  公开（公告）日：2016-02-03