1-Propanamine, 3-(aminooxy)-2-fluoro-, dihydrochloride | 130545-04-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1-Propanamine, 3-(aminooxy)-2-fluoro-, dihydrochloride
• 英文别名: 3-(aminooxy)-2-fluoropropanamine dihydrochloride；3-aminoxy-2-fluoropropylamine dihydrochloride
• CAS: 130545-04-9；139526-94-6
• 化学式: C₃H₉FN₂O*2ClH
• 分子量: 181.038
• InChiKey: BJBJJZONWWPTEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.27
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  磷酸吡哆醛 、 1-Propanamine, 3-(aminooxy)-2-fluoro-, dihydrochloride 在 sodium hydroxide 作用下， 反应 1.0h， 以99%的产率得到2-fluoro-3-<<<<3-hydroxy-2-methyl-5-<(phosphonooxy)methyl>-4-pyridyl>methylidene>amino>oxy>propanamine hydrochloride
  参考文献：
  名称：

  2-Substituted 3-(aminooxy)propanamines as inhibitors of ornithine decarboxylase: synthesis and biological activity

  摘要：

  1-Amino-3-(aminooxy)-2-propanol (6a) has been synthesized and found to inhibit rat liver ornithine decarboxylase (ODC) with an IC50 in the nanomolar range. Compound 6a served as a basis for the design of new enzyme inhibitors, which led to the identification of 3-(aminooxy)-2-fluoropropanamine (15) as a new powerful enzyme blocker. Compound 15 inhibited ODC at 3 times lower concentrations than 6a and 3-(aminooxy)propanamine (APA), and it was superior to APA as an antiproliferative agent in inhibiting the growth of human T24 bladder carcinoma cells in vitro.

  DOI：

  10.1021/jm00086a003
• 作为产物：
  描述：

  N,N'-bis<(tert-butyloxy)carbonyl>-3-(aminooxy)-2-fluoropropanamine 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以42%的产率得到1-Propanamine, 3-(aminooxy)-2-fluoro-, dihydrochloride
  参考文献：
  名称：

  2-Substituted 3-(aminooxy)propanamines as inhibitors of ornithine decarboxylase: synthesis and biological activity

  摘要：

  1-Amino-3-(aminooxy)-2-propanol (6a) has been synthesized and found to inhibit rat liver ornithine decarboxylase (ODC) with an IC50 in the nanomolar range. Compound 6a served as a basis for the design of new enzyme inhibitors, which led to the identification of 3-(aminooxy)-2-fluoropropanamine (15) as a new powerful enzyme blocker. Compound 15 inhibited ODC at 3 times lower concentrations than 6a and 3-(aminooxy)propanamine (APA), and it was superior to APA as an antiproliferative agent in inhibiting the growth of human T24 bladder carcinoma cells in vitro.

  DOI：

  10.1021/jm00086a003

文献信息

• Hydroxylamine compounds
  申请人：Ciba-Geigy Corporation

  公开号：US05169867A1

  公开（公告）日：1992-12-08

  Compounds of formula ##STR1## wherein R.sub.1 is amino or is a radical ##STR2## wherein R.sub.3 is lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, carboxy, lower alkoxycarbonyl, phenyl, phenyl substituted by lower alkyl, halo-lower alkyl, hydroxy-lower alkyl, halogen, hydroxy, lower alkoxy, lower alkanoyloxy and/or by nitro, pyridyl, pyridyl substituted by lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, phosphonooxy-lower alkyl, lower alkanoyl, carboxy, lower alkoxycarbonyl, hydroxy, lower alkoxy, lower alkanoyloxy, nitro and/or by oxido, or quinolyl, R.sub.4 is hydrogen, lower alkyl, hydroxy-lower alkyl or halo-lower alkyl, or R.sub.3 and R.sub.4 together are C.sub.4 -C.sub.6 alkylene or benzo-C.sub.4 -C.sub.6 alkylene, and R.sub.2 is straight-chain C.sub.1 -C.sub.4 alkyl, and salts thereof, have a strong specific inhibitory action on the enzyme ornithine decarboxylase. The compounds of Formula I are prepared according to processes known per se.

  式为##STR1##的化合物中，其中R.sub.1是氨基或是基团##STR2##其中R.sub.3是低碳基，羟基-低碳基，低氧基-低碳基，羧基，低氧基羰基，苯基，被低碳基，卤代-低碳基，羟基-低碳基，卤素，羟基，低氧基，低脂肪酰氧基和/或硝基，吡啶基，被低碳基，羟基-低碳基，低氧基-低碳基，膦酸氧-低碳基，低脂肪酰基，羧基，低氧基羰基，羟基，低氧基，低脂肪酰氧基，硝基和/或氧化物，或喹啉基，R.sub.4是氢，低碳基，羟基-低碳基或卤代-低碳基，或R.sub.3和R.sub.4一起是C.sub.4-C.sub.6烷基或苯并C.sub.4-C.sub.6烷基，R.sub.2是直链C.sub.1-C.sub.4烷基，及其盐，在鸟氨酸脱羧酶酶上具有强烈的特异性抑制作用。式I的化合物可按已知的方法制备。