1-amino-3-(aminooxy)-2-propanol dihydrochloride

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-amino-3-(aminooxy)-2-propanol dihydrochloride
• 英文别名: 2-hydroxy APA dihydrochloride；O-(3-Amino-2-hydroxypropyl)-hydroxylamine dihydrochloride；1-Amino-3-aminooxypropan-2-ol;hydrochloride
• 化学式: C₃H₁₀N₂O₂*2ClH
• 分子量: 179.046
• InChiKey: CDNYZQKHCXXBPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.38
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  81.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-amino-3-(aminooxy)-2-propanol dihydrochloride 在 sulfur tetrafluoride 、 氢氟酸 作用下， 生成 3-aminooxy-2-fluoro-1-propanamine
  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：

  O-(2,3-epoxypropyl)-acetohydroximic acid ethyl ester 在 ammonium hydroxide 、 氨 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 1-amino-3-(aminooxy)-2-propanol dihydrochloride
  参考文献：
  名称：

  O-[3-(4-Substituted-piperazin-1-yl)-2-hydroxypropyl]-hydroxylamines

  摘要：

  一种通式为##STR1##的化合物，其中X代表从以下公式组中选择的基团之一：##STR2## 其中R.sup.1代表从以下组中选择的基团之一：(a)氢原子，(b)氨基，当X代表--OR.sup.1基团时，(c)碳数为1至6的烷基基团，(d)最多为双核的芳基基团，未取代或取代有最多3个卤素原子、烷基、烷氧基、卤代烷基基团，每个碳数最多为4个碳原子，有3至6个碳原子的环烷基基团，硝基和氰基；R.sup.2和R.sup.3可以相同也可以不同，每个代表从以下组中选择的基团之一：(a)氢原子，(b)碳数为1至6的烷基基团，碳数为3至7的未取代环烷基基团，该环烷基基团被最多3个羟基基团和碳数为1至4的烷氧羰基基团取代，(c)芳基烷基基团，二芳基基团，每个烷基基团中的碳数为1至4，并且在烷基基团中的至少一个基团和芳基基团中的最多3个取代基中被羟基基团取代，或被从以下组中选择的最多3个取代基团之一取代：碳数为1至4的烷氧基基团和卤素原子；(d)最多为双核的芳基基团，未取代或取代有最多3个碳数为1至4的烷基、烷氧基、卤代烷基基团和卤素原子的取代基团；(e)羟基，当R.sup.2和R.sup.3中的另一个基团为氢时，(f)R.sup.2和R.sup.3与它们连接的氮原子一起，代表从以下组中选择的5至7元环：未取代的环，被碳数为1至4的烷基取代的环，以及被氧、硫和进一步的氮原子所选择的杂原子中断的环；(g)R.sup.2和R.sup.3与它们连接的氮原子一起，代表从以下组中选择的环：一个含有最多4个氮原子的5元杂芳环，这样的环连接到苯环或尿嘧啶环上，以及其生理上可接受的酸加盐，以及制备它们的方法和含有它们的制药组合物。

  公开号：

  US04404384A1

文献信息

• Selective delivery of 2-hydroxy APA to Trypanosoma brucei using the melamine motif
  作者：Nina Klee、Pui Ee Wong、Beatriz Baragaña、Farah El Mazouni、Margaret A. Phillips、Michael P. Barrett、Ian H. Gilbert

  DOI：10.1016/j.bmcl.2010.06.070

  日期：2010.8

  Trypanosoma brucei, the parasite that causes human African trypanosomiasis, is auxotrophic for purines and has specialist nucleoside transporters to import these metabolites. In particular, the P2 aminopurine transporter can also selectively accumulate melamine derivatives. In this Letter, we report the coupling of the melamine moiety to 2-hydroxy APA, a potent ornithine decarboxylase inhibitor, with the aim of selectively delivering this compound to the parasite. The best compound described here shows an increased in vitro trypanocidal activity compared with the parent. (C) 2010 Elsevier Ltd. All rights reserved.
• 2-Substituted 3-(aminooxy)propanamines as inhibitors of ornithine decarboxylase: synthesis and biological activity
  作者：Jaroslav Stanek、Joerg Frei、Helmut Mett、Peter Schneider、Urs Regenass

  DOI：10.1021/jm00086a003

  日期：1992.4

  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.
• O-[3-(4-Substituted-piperazin-1-yl)-2-hydroxypropyl]-hydroxylamines
  申请人：Hoechst Aktiengesellschaft

  公开号：US04404384A1

  公开（公告）日：1983-09-13

  A compound of general formula ##STR1## wherein X represents a radical selected from the group consisting of one of the formulae ##STR2## in which R.sup.1 represents a radical selected from the group (a) a hydrogen atom, (b) an amino group, when X represents an --OR.sup.1 moiety, (c) an alkyl group having from 1 to 6 carbon atoms (d) an at most binuclear aryl group being unsubstituted or substituted by at most 3 substituents of the group halogen atoms, alkyl, alkoxy, halogenalkyl groups each having up to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, nitro and cyano groups; and R.sup.2 and R.sup.3, which may be the same or different, each represents a radical selected from the group (a) a hydrogen atom, (b) an alkyl group having from 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having from 3 to 7 carbon atoms, such cycloalkyl group substituted by at most 3 substituents of the group hydroxy groups and alkoxycarbonyl groups having 1 to 4 carbon atoms, (c) an aralkyl group, a diaralkyl group each having 1 to 4 carbon atoms in the alkyl moiety and being unsubstituted or substituted in at least one of the radicals in the alkyl moiety by hydroxy groups, and in the aryl moieties by at most 3 substituents selected from the group consisting of alkoxy groups having from 1 to 4 carbon atoms and halogen atoms, (d) an at most binuclear aryl group being unsubstituted or substituted by at most 3 substituents selected from the group consisting of alkyl, alkoxy, halogenoalkyl groups each having up to 4 carbon atoms and halogen atoms, (e) a hydroxy group when the other of R.sup.2 and R.sup.3 is hydrogen, (f) R.sup.2 and R.sup.3, together with the nitrogen atom to which they are attached, represent a 5- to 7-membered ring selected from the group consisting of an unsubstituted ring, a ring being substituted by an alkyl group having from 1 to 4 carbon atoms, and a ring being interrupted by a heteroatom selected from the group consisting of oxygen, sulphur and further nitrogen atom, and (g) R.sup.2 and R.sup.3 together with the nitrogen atom to which they are attached, represent a ring from the group a 5-membered heteroaromatic ring containing up to 4 nitrogen atoms and such a ring being anelled to a benzene- or uracil-ring, and physiologically acceptable acid addition salts thereof, a process for their preparation and a pharmaceutical composition containing them.

  一种通式为##STR1##的化合物，其中X代表从以下公式组中选择的基团之一：##STR2## 其中R.sup.1代表从以下组中选择的基团之一：(a)氢原子，(b)氨基，当X代表--OR.sup.1基团时，(c)碳数为1至6的烷基基团，(d)最多为双核的芳基基团，未取代或取代有最多3个卤素原子、烷基、烷氧基、卤代烷基基团，每个碳数最多为4个碳原子，有3至6个碳原子的环烷基基团，硝基和氰基；R.sup.2和R.sup.3可以相同也可以不同，每个代表从以下组中选择的基团之一：(a)氢原子，(b)碳数为1至6的烷基基团，碳数为3至7的未取代环烷基基团，该环烷基基团被最多3个羟基基团和碳数为1至4的烷氧羰基基团取代，(c)芳基烷基基团，二芳基基团，每个烷基基团中的碳数为1至4，并且在烷基基团中的至少一个基团和芳基基团中的最多3个取代基中被羟基基团取代，或被从以下组中选择的最多3个取代基团之一取代：碳数为1至4的烷氧基基团和卤素原子；(d)最多为双核的芳基基团，未取代或取代有最多3个碳数为1至4的烷基、烷氧基、卤代烷基基团和卤素原子的取代基团；(e)羟基，当R.sup.2和R.sup.3中的另一个基团为氢时，(f)R.sup.2和R.sup.3与它们连接的氮原子一起，代表从以下组中选择的5至7元环：未取代的环，被碳数为1至4的烷基取代的环，以及被氧、硫和进一步的氮原子所选择的杂原子中断的环；(g)R.sup.2和R.sup.3与它们连接的氮原子一起，代表从以下组中选择的环：一个含有最多4个氮原子的5元杂芳环，这样的环连接到苯环或尿嘧啶环上，以及其生理上可接受的酸加盐，以及制备它们的方法和含有它们的制药组合物。