5-propyl-isoxazol-3-one | 10004-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-propyl-isoxazol-3-one
• 英文别名: 5-Propylisoxazol-3(2H)-one；5-propyl-1,2-oxazol-3-one
• CAS: 10004-46-3
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: VBZVFEACZQOVTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-propyl-isoxazol-3-one 在 氢溴酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 4-(Bromomethyl)-2-(methoxymethyl)-5-propyl-1,2-oxazol-3-one
  参考文献：
  名称：

  Excitatory amino-acid receptor agonists. Synthesis and pharmacology of analogues of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid

  摘要：

  We have previously proposed the existence of a lipophilic cavity of the 2-amino-3-(3-hydroxy-5-methylisoxazol4-yl)propionic acid (AMPA) receptor recognition site capable of accommodating alkyl substituents of limited size in the 5-position of the isoxazole ring. In order to indirectly elucidate the approximate extent of this proposed cavity we have synthesized and pharmacologically characterized a number of AMPA analogues. For most of these AMPA analogues, a positive correlation between AMPA receptor affinity and agonist effect was observed. The only exception was demethyl-AMPA (8a), which showed relatively high AMPA receptor affinity (IC50 = 0.27 mu M) but remarkably weak agonist potency (EC50 = 900 mu M). Whereas the ethyl analogue of AMPA (Et-AMPA) (IC50 = 0.030 mu M; EC50 = 2.3 mu M) has previously been shown to be slightly more potent than AMPA (IC50 = 0.040 mu M; EC50 = 3.5 mu M), substitutions of a propyl or a butyl group for the methyl group of AMPA to give 8b (IC50 = 0.090 mu M; EC50 = 5.0 mu M) or 8f (IC50 = 1.0 mu M; EC50 = 32 mu M), respectively, result in progressive loss of the AMPA agonist effect. Analogues containing larger groups, such as isopentyl (8e), 1-propylbutyl (8g), 2,2-dimethylpropyl (8h), or benzyl (14) groups, were very weak or totally inactive as AMPA receptor ligands.

  DOI：

  10.1016/s0223-5234(97)89085-x
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 sodium hydroxide 、 盐酸羟胺 作用下， 反应 1.0h， 以59%的产率得到5-propyl-isoxazol-3-one
  参考文献：
  名称：

  Synthesis of 3-isoxazolols revisited. Diketene and (β-ketoesters as starting materials

  摘要：

  3-异噁唑醇可以通过β-酮酸酯或二酮乙烯和羟胺在良好收率下制备，前提是在整个反应过程中保持pH值约为10，并且用过量的强矿酸淬灭反应混合物。这样可以抑制5-异噁唑酮的形成，否则这些通常是反应的主要产物。

  DOI：

  10.1139/v84-333

文献信息

• [EN] BICYCLIC COMPOUNDS AS AUTOTAXIN (ATX) AND LYSOPHOSPHATIDIC ACID (LPA) PRODUCTION INHIBITORS<br/>[FR] COMPOSÉS BICYCLIQUES EN TANT QU'INHIBITEURS DE PRODUCTION D'AUTOTAXINE (ATX) ET D'ACIDE LYSOPHOSPHATIDIQUE (LPA)
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015144605A1

  公开（公告）日：2015-10-01

  The invention provides novel compounds having the general formula (I) wherein R1, R2, A, W, m, n, p and q are as described herein, compositions including the compounds. The compounds of formula (I) are useful as autotaxin (ATX) inhibitors which are inhibitors of lysophosphatidic acid (LPA) production and thus modulators of LPA levels and associated signaling; in particular they are useful for the treatment or prophylaxis of renal conditions, liver conditions, inflammatory conditions, conditions of the nervous system, conditions of the respiratory system, vascular and cardiovascular conditions, fibrotic diseases, cancer, ocular conditions, metabolic conditions, cholestatic and other forms of chronic pruritus and acute and chronic organ transplant rejection.

  该发明提供了具有通式（I）的新化合物，其中R1、R2、A、W、m、n、p和q如本文所述，包括这些化合物的组合物。通式（I）的化合物可用作自体税肽酶（ATX）抑制剂，这些抑制剂是溶磷脂酸（LPA）产生的抑制剂，从而调节LPA水平和相关信号传导；特别是它们可用于治疗或预防肾脏疾病、肝脏疾病、炎症性疾病、神经系统疾病、呼吸系统疾病、血管和心血管疾病、纤维化疾病、癌症、眼部疾病、代谢性疾病、胆汁淤积和其他形式的慢性瘙痒以及急性和慢性器官移植排斥反应的治疗。
• AZETIDINE POLYSUBSTITUTED COMPOUNDS, PREPARATION THEREOF, AND THERAPEUTIC APPLICATION THEREOF
  申请人：Bernardelli Patrick

  公开号：US20110152236A1

  公开（公告）日：2011-06-23

  The invention relates to compounds of the formula (I) where: R is a (C 1 -C 6 )alkyl group, a halo(C 1 -C 6 )alkyl group; R1 is a hydrogen atom; R2 is a heteroaromatic group or a heteroaromatic(C 1 -C 4 )alkyl group, said groups being optionally substituted; R3 and R4 represent independently from each other an optionally substituted phenyl group; Y is a hydrogen atom, a halogen, a cyano, a (C 1 -C 6 )alkyl group, a halo(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a halo(C 1 -C 6 )alkoxy group or a (C 1 -C 6 )alkylS(O) p group; and p is 0 to 2. Said compounds can be in the form — of a base or a salt for addition to an acid. The invention also relates to a method for preparing same and to the therapeutic application thereof.

  该发明涉及化合物的结构式（I），其中：R是（C1-C6）烷基基团，卤代（C1-C6）烷基基团；R1是氢原子；R2是杂环芳基团或杂环芳基（C1-C4）烷基基团，这些基团可以选择性地被取代；R3和R4分别独立地表示一个可以选择性取代的苯基团；Y是氢原子、卤素、氰基、（C1-C6）烷基基团、卤代（C1-C6）烷基基团、（C1-C6）烷氧基、卤代（C1-C6）烷氧基或（C1-C6）烷基S（O）p基团；p为0至2。所述化合物可以以盐的形式存在，用于与酸发生加成反应。该发明还涉及制备该化合物的方法及其治疗应用。
• ESTROGEN RECEPTOR MODULATORS AND USES THEREOF
  申请人：Smith Nicholas D.

  公开号：US20130231333A1

  公开（公告）日：2013-09-05

  Described herein are compounds that are estrogen receptor modulators. Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well methods of using such estrogen receptor modulators, alone and in combination with other compounds, for treating diseases or conditions that are mediated or dependent upon estrogen receptors.

  本文描述了一些雌激素受体调节剂化合物。还描述了包括所述化合物的制药组合物和药物，以及使用这些雌激素受体调节剂，单独或与其他化合物结合，治疗与雌激素受体介导或依赖的疾病或症状的方法。
• Sato, Kazuo; Sugai, Soji; Tomita, Kazuo, Agricultural and Biological Chemistry, 1986, vol. 50, # 7, p. 1831 - 1838
  作者：Sato, Kazuo、Sugai, Soji、Tomita, Kazuo

  DOI：——

  日期：——
• [EN] ESTROGEN RECEPTOR MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DES RÉCEPTEURS DES OESTROGÈNES ET LEURS UTILISATIONS
  申请人：ARAGON PHARMACEUTICALS INC

  公开号：WO2012037411A9

  公开（公告）日：2012-05-18