5-methyl-3-(N,N-dimethylaminomethyl) isoxazole | 60148-37-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-methyl-3-(N,N-dimethylaminomethyl) isoxazole
• 英文别名: dimethyl-(5-methyl-isoxazol-3-ylmethyl)-amine；N,N-dimethyl-1-(5-methyl-1,2-oxazol-3-yl)methanamine
• CAS: 60148-37-0
• 化学式: C₇H₁₂N₂O
• 分子量: 140.185
• InChiKey: XUHIUDURJIWDGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-3-(N,N-dimethylaminomethyl) isoxazole 、 碘甲烷 以 乙醇 为溶剂， 反应 0.33h， 以89%的产率得到5-methyl-3-(N,N,N-trimethylammoniummethyl) isoxazole iodide
  参考文献：
  名称：

  Regioisomeric 3-, 4- and 5-aminomethyl isoxazoles: synthesis and muscarinic activity

  摘要：

  A series of 3-, 4- and 5-aminomethyl isoxazoles and isoxazoles with one or two additional methyl groups at the heterocycle were synthesized in order to investigate the structural requirements, ie heterocyclic moiety, regiochemistry and length of an aminoalkyl unit, for muscarinic activity. This was assayed on isolated rabbit vas deferens (M(1) receptor subtype) and isolated guinea-pig atrium (M(2) receptor subtype) and ileum (M(3) receptor subtype). The isoxazoles tested are one to three orders of magnitude less active than furane or oxadiazole derivatives, having similar structural characteristics except for the heterocycle. Thus, the differences in molecular point charges and charge distribution contribute to the muscarinic activity of these compounds more than small differences in molecular shape and conformational energies.

  DOI：

  10.1016/0223-5234(96)88303-6
• 作为产物：
  描述：

  乙酰丙酮酸甲酯 在 dimethyl sulfide borane 、 硫酸 、 盐酸羟胺 、 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 5-methyl-3-(N,N-dimethylaminomethyl) isoxazole
  参考文献：
  名称：

  Regioisomeric 3-, 4- and 5-aminomethyl isoxazoles: synthesis and muscarinic activity

  摘要：

  A series of 3-, 4- and 5-aminomethyl isoxazoles and isoxazoles with one or two additional methyl groups at the heterocycle were synthesized in order to investigate the structural requirements, ie heterocyclic moiety, regiochemistry and length of an aminoalkyl unit, for muscarinic activity. This was assayed on isolated rabbit vas deferens (M(1) receptor subtype) and isolated guinea-pig atrium (M(2) receptor subtype) and ileum (M(3) receptor subtype). The isoxazoles tested are one to three orders of magnitude less active than furane or oxadiazole derivatives, having similar structural characteristics except for the heterocycle. Thus, the differences in molecular point charges and charge distribution contribute to the muscarinic activity of these compounds more than small differences in molecular shape and conformational energies.

  DOI：

  10.1016/0223-5234(96)88303-6

文献信息

• [EN] 1H-PYRAZOLO[4,3-d]PYRIMIDINE COMPOUNDS AS TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS<br/>[FR] COMPOSÉS DE 1H-PYRAZOLO[4,3-D]PYRIMIDINE EN TANT QU'AGONISTES DU RÉCEPTEUR 7 DE TYPE TOLL (TLR7)
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2021154669A1

  公开（公告）日：2021-08-05

  Compounds according to formula I or II are useful as agonists of Toll-like receptor 7 (TLR7). Such compounds can be used in cancer treatment, especially in combination with an anti-cancer immunotherapy agent, or as a vaccine adjuvant.

  根据公式I或II合成的化合物可用作Toll样受体7（TLR7）的激动剂。这些化合物可用于癌症治疗，特别是与抗癌免疫疗法药物联合使用，或作为疫苗佐剂。
• Gainer,J. et al., Journal of the Chemical Society. Perkin transactions I, 1976, p. 994 - 997
  作者：Gainer,J. et al.

  DOI：——

  日期：——
• GAINER J.; HOWARTH G. A.; HOYLE W.; ROBERTS S. M.; SUSCHITZKY H., J. CHEM. SOC. PERKIN TRANS, PART 1 <JCPK-BH>, 1976, NO 9, 994-997
  作者：GAINER J.、 HOWARTH G. A.、 HOYLE W.、 ROBERTS S. M.、 SUSCHITZKY H.

  DOI：——

  日期：——
• BENZAMIDE AND NICOTINAMIDE COMPOUNDS AND METHODS OF USING SAME
  申请人：Oncotartis Inc.

  公开号：EP3087051B1

  公开（公告）日：2020-07-15
• AMINO PYRIDINE DERIVATIVES AS PHOSPHATIDYLINOSITOL 3-KINASE INHIBITORS
  申请人：Novartis AG

  公开号：EP3134396B1

  公开（公告）日：2019-09-18