3-丙基异噁唑-5-胺 | 747411-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-丙基异噁唑-5-胺
• 中文别名: 3-丙基-5-氨基异噁唑
• 英文名称: 3-propylisoxazol-5-amine
• 英文别名: 3-propyl-1,2-oxazol-5-amine
• CAS: 747411-47-8
• 化学式: C₆H₁₀N₂O
• mdl: MFCD05270911
• 分子量: 126.158
• InChiKey: NORVABBMTGHGCF-UHFFFAOYSA-N

物化性质

• 沸点：
  255.0±20.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  52
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-丙基异噁唑-5-胺 、 1-溴-3-苯基丙烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以42%的产率得到N-(3-phenylpropyl)-3-propylisoxazol-5-amine
  参考文献：
  名称：

  Identification of diphenylalkylisoxazol-5-amine scaffold as novel activator of cardiac myosin

  摘要：

  To identify novel potent cardiac myosin activator, a series of diphenylalkylisoxazol-5-amine compounds 4-7 have been synthesized and evaluated for cardiac myosin ATPase activation. Among the 37 compounds, 4a (CMA at 10 µM = 81.6%), 4w (CMA at 10 µM = 71.2%) and 6b (CMA at 10 µM = 67.4%) showed potent cardiac myosin activation at a single concentration of 10 µM. These results suggested that the introduction of the amino-isoxazole ring as a bioisostere for urea group is acceptable for the cardiac myosin activation. Additional structure-activity relationship (SAR) studies were conducted. Para substitution (-Cl, -OCH₃, -SO₂N(CH₃)₂) to the phenyl rings or replacement of a phenyl ring with a heterocycle (pyridine, piperidine and tetrahydropyran) appeared to attenuate cardiac myosin activation at 10 µM. Additional hydrogen bonding acceptor next to the amino group of the isoxazoles did not enhance the activity. The potent isoxazole compounds showed selectivity for cardiac myosin activation over skeletal and smooth muscle myosin, and therefore these potent and selective isoxazole compounds could be considered as a new series of cardiac myosin ATPase activators for the treatment of systolic heart failure.

  DOI：

  10.1016/j.bmc.2020.115742
• 作为产物：
  描述：

  3-氧代己腈 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 水 为溶剂， 以75%的产率得到3-丙基异噁唑-5-胺
  参考文献：
  名称：

  Identification of diphenylalkylisoxazol-5-amine scaffold as novel activator of cardiac myosin

  摘要：

  To identify novel potent cardiac myosin activator, a series of diphenylalkylisoxazol-5-amine compounds 4-7 have been synthesized and evaluated for cardiac myosin ATPase activation. Among the 37 compounds, 4a (CMA at 10 µM = 81.6%), 4w (CMA at 10 µM = 71.2%) and 6b (CMA at 10 µM = 67.4%) showed potent cardiac myosin activation at a single concentration of 10 µM. These results suggested that the introduction of the amino-isoxazole ring as a bioisostere for urea group is acceptable for the cardiac myosin activation. Additional structure-activity relationship (SAR) studies were conducted. Para substitution (-Cl, -OCH₃, -SO₂N(CH₃)₂) to the phenyl rings or replacement of a phenyl ring with a heterocycle (pyridine, piperidine and tetrahydropyran) appeared to attenuate cardiac myosin activation at 10 µM. Additional hydrogen bonding acceptor next to the amino group of the isoxazoles did not enhance the activity. The potent isoxazole compounds showed selectivity for cardiac myosin activation over skeletal and smooth muscle myosin, and therefore these potent and selective isoxazole compounds could be considered as a new series of cardiac myosin ATPase activators for the treatment of systolic heart failure.

  DOI：

  10.1016/j.bmc.2020.115742

文献信息

• Pyrrolidine Compounds Which Modulate The CB2 Receptor
  申请人：Berry Angela

  公开号：US20120142677A1

  公开（公告）日：2012-06-07

  Compounds which modulate the CB2 receptor are disclosed. Compounds according to the invention bind to and are agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain. (I)

  本发明揭示了调节CB2受体的化合物。本发明的化合物结合并激动CB2受体，并且可用于治疗炎症。那些是激动剂的化合物还可用于治疗疼痛。 (I)
• Approach to the Library of Fused Pyridine-4-carboxylic Acids by Combes-Type Reaction of Acyl Pyruvates and Electron-Rich Amino Heterocycles
  作者：Dmitriy M. Volochnyuk、Sergey V. Ryabukhin、Andrey S. Plaskon、Yuri V. Dmytriv、Oleksandr O. Grygorenko、Pavel K. Mykhailiuk、Dmitriy G. Krotko、Alexei Pushechnikov、Andrey A. Tolmachev

  DOI：10.1021/cc100040q

  日期：2010.7.12

  A library of fused pyridine-4-carboxylic acids (including pyrazolo[3,4-b]pyridines, isoxazolo[5,4-b]pyridines, furo[2,3-b]pyridines, thieno[2,3-b]pyridines, and pyrido[2,3-d]pyrimidines) was generated by Combes-type reaction of acyl pyruvates and electron-rich amino heterocycles followed by hydrolysis of the ester. The library members were also demonstrated to undergo the standard combinatorial transformations including amide coupling and esterification, as well as less common heterocyclizations to 1,2,4-triazoles and 1,2,4-oxadiazoles.
• PYRROLIDINE COMPOUNDS WHICH MODULATE THE CB2 RECEPTOR
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2384320B1

  公开（公告）日：2015-03-04
• US8629157B2
  申请人：——

  公开号：US8629157B2

  公开（公告）日：2014-01-14