N-pyrrolidino-3-hydroxyazetidinium chloride | 52900-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-pyrrolidino-3-hydroxyazetidinium chloride
• 英文别名: 4-azoniaspiro[3.4]octan-2-ol;chloride
• CAS: 52900-08-0
• 化学式: C₇H₁₄NO*Cl
• 分子量: 163.647
• InChiKey: SIIFMZPYYHWIHR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.02
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-pyrrolidino-3-hydroxyazetidinium chloride 在 氢氧化钾 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 diethyl γ-N-pyrrolidino-β-benzyloxypropyl phosphonate
  参考文献：
  名称：

  Convenient synthesis of propane aminophosphonic acids, aminodiphosphonic acids and their structural analogues, mediated by azetidinium salts

  摘要：

  The reactions of azetidinium salts with phosphorus nucleophiles R2P(O)H have been investigated. Treatment of O-benzyl-N,N-diethyl-3-hydroxyazetidinium salt 2 with R2P(O)H in the presence of sodium hydride gave the corresponding gamma-N,N-diethylamino-beta-benzyloxypropylphosphonate 6a or phosphine oxide 6b. After debenzylation gamma-N,N-diethylamino-beta-hydroxypropylphosphonate 3a and phosphine oxide 3b were obtained. The compound 6a was converted into its sulfonate ester 8 which underwent elimination to yield 4. The structure 4 has been employed in Michael addition of R2P(O)H to form compounds 5 containing two phosphorus centers. Further compounds of type 3 have been transformed into compounds 5 by reaction with R2P(O)H in the presence of 1.1 equivalents of NaH in boiling toluene. Finally, azetidinium salts 1 have been converted into compounds 5a by reaction with two equivalents of R2P(O)H in the presence of 2.1 equivalents of NaH. Molecular mechanics with implementation of the Allinger MM2 force field and semiempirical AM1 and PM3 methods were used to investigate structures 5d and 5f. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00698-5
• 作为产物：
  描述：

  四氢吡咯 、 环氧氯丙烷 以 乙醇 为溶剂， 生成 N-pyrrolidino-3-hydroxyazetidinium chloride
  参考文献：
  名称：

  Sladowska, Helena; Sabiniarz, Aleksandra; Sapa, Jacek, Acta poloniae pharmaceutica, 2009, vol. 66, # 1, p. 57 - 63

  摘要：

  DOI：

文献信息

• Synthesis of Polyfunctional Organosulfur Compounds Mediated by Azetidinium­ Salts
  作者：Bożena Krawiecka、Agata Jeziorna、Jan Heliński

  DOI：10.1055/s-2003-36825

  日期：——

  Ring-opening of N,N-dialkyl-3-hydroxyazetidinium chlorides la-d with sulfur nucleophiles leads to C-S bond formation furnishing polyfunctional sulfides, sulfonates and thiosulfonates.

  N,N-二烷基-3-羟基氮杂环丁烷氯化物la-d与硫亲核试剂的开环导致CS键形成，提供多官能硫化物、磺酸盐和硫代磺酸盐。
• Rational drug design based synthesis of novel arylquinolines as anti-tuberculosis agents
  作者：Puneet P. Jain、Mariam S. Degani、Archana Raju、Muktikanta Ray、M.G.R. Rajan

  DOI：10.1016/j.bmcl.2013.09.027

  日期：2013.11

  A series of novel arylquinoline derivatives was designed retaining significant pharmacophoric features and three dimensional geometry of bedaquiline. In silico ADME study was performed to assess drug likeness and toxicity profiles of the designed molecules. The compounds were evaluated for activity against Mycobacterium tuberculosis H(37)Rv using Resazurin Microtitre Assay (REMA) plate method and cytotoxicity in VERO C1008 cell line. Several of the synthesized compounds exhibited good antituberculosis activity and selectivity, especially compounds, 12i (MIC: 5.18 mu M and MIC/CC50: 152.86) and 12l (MIC: 5.59 mu M and MIC/CC50: 160.57). The study opens up a new platform for the development of arylquinoline based drugs for treating tuberculosis. (c) 2013 Elsevier Ltd. All rights reserved.