(3S,4S)-4-(羟甲基)吡咯烷-3-醇 | 397883-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (3S,4S)-4-(羟甲基)吡咯烷-3-醇
• 英文名称: (3S,4S)-3-hydroxy-4-hydroxymethylpyrrolidine
• 英文别名: (3S,4S)-4-(hydroxymethyl)pyrrolidin-3-ol
• CAS: 397883-77-1
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: BSQXZHMREYHKOM-CRCLSJGQSA-N

物化性质

• 沸点：
  268.1±15.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-(羟甲基)吡咯烷-3-醇 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 tert-butyl (3S,4S)-3-hydroxy-4-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Tight binding enantiomers of pre-clinical drug candidates

  摘要：

  MTDIA is a picomolar transition state analogue inhibitor of human methylthioadenosine phosphorylase and a femtomolar inhibitor of Escherichia coli methylthioadenosine nucleosidase. MTDIA has proven to be a non-toxic, orally available pre-clinical drug candidate with remarkable anti-tumour activity against a variety of human cancers in mouse xenografts. The structurally similar compound MTDIH is a potent inhibitor of human and malarial purine nucleoside phosphorylase (PNP) as well as the newly discovered enzyme, methylthioinosine phosphorylase, isolated from Pseudomonas aeruginosa. Since the enantiomers of some pharmaceuticals have revealed surprising biological activities, the enantiomers of MTDIH and MTDIA, compounds 1 and 2, respectively, were prepared and their enzyme binding properties studied. Despite binding less tightly to their target enzymes than their enantiomers compounds 1 and 2 are nanomolar inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.059
• 作为产物：
  描述：

  ethyl (3R,4S)-4-(acetyloxy)-1-benzylpyrrolidine-3-carboxylate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 0.5h， 生成 (3S,4S)-4-(羟甲基)吡咯烷-3-醇
  参考文献：
  名称：

  嘌呤核苷磷酸化酶的两种有效过渡态类似物抑制剂的L对映体的合成和生物活性。

  摘要：

  （1R）-1-（9-脱氮杂黄嘌呤-9-基）-1,4-二脱氧-1,4-亚氨基-L-核糖醇[（+）-5]和（3S，4S）-1-[[9 -脱氮杂黄嘌呤-9-基）甲基] -4-（羟甲基）吡咯烷-3-醇[（-）-6]是Immucillin-H（D-ImmH）和DADMe-immucillin-H（D-这些D-异构体分别是嘌呤核苷磷酸化酶（PNPases）的高亲和力过渡态类似物抑制剂，被开发为针对涉及T细胞异常活化的疾病的潜在药物。盐酸C-核苷D-ImmH [（-）-5）x HCl，现在作为抗T细胞白血病剂正在“ Fodosine”处于II期临床试验，而D-DADMe-ImmH是第二代抑制剂与目标酶具有极强的结合力，并已作为抗银屑病药物进入临床第一阶段测试。由于某些药物的对映异构体显示出令人惊讶的生物学活性，因此分别制备了D-ImmH和D-DADMe-ImmH的L-核苷类似物（+）-5 x HCl和（

  DOI：

  10.1039/b517883e

文献信息

• [EN] METHOD FOR PREPARING 3-HYDROXY-4-HYDROXYMETHYL-PYRROLIDINE COMPOUNDS<br/>[FR] PROCEDE DE PREPARATION DE COMPOSES DE 3-HYDROXY-4-HYDROXYMETHYL-PYRROLIDINE
  申请人：IND RES LTD

  公开号：WO2005033076A1

  公开（公告）日：2005-04-14

  This invention relates to a method of preparing (3R,4R)-3-hydroxy-4-hydroxymethylpyrrolidine, a key intermediate compound for the synthesis of certain inhibitor compounds, including the step of enzyme catalysed enantioselective esterification of an hydroxy group of an hydroxypyrrolidine. The invention further relates to a method for preparing (3S,4S)-3-hydroxy-4-hydroxymethylpyrrolidine, which is the enantiomer of (3R,4R)-3-hydroxy-4-hydroxymethylpyrrolidine.

  这项发明涉及一种制备(3R,4R)-3-羟基-4-羟甲基吡咯烷的方法，这是合成某些抑制剂化合物的关键中间体化合物，包括酶催化的对羟基吡咯烷的对映选择性酯化步骤。该发明还涉及一种制备(3S,4S)-3-羟基-4-羟甲基吡咯烷的方法，这是(3R,4R)-3-羟基-4-羟甲基吡咯烷的对映体。
• COMPOUNDS AND COMPOSITIONS FOR INHIBITING THE ACTIVITY OF ABL1, ABL2 AND BCR-ABL1
  申请人：Furet Pascal

  公开号：US20150183801A1

  公开（公告）日：2015-07-02

  The present invention relates to compounds of formula (I): in which Y, Y, R, R 2, R 3 and R 4 are defined in the Summary of the Invention; capable of inhibiting the activity of BCR-ABL1 and mutants thereof. The invention further provides a process for the preparation of compounds of the invention, pharmaceutical preparations comprising such compounds and methods of using such compounds in the treatment of cancers.

  本发明涉及式(I)的化合物：其中Y，Y，R，R2，R3和R4在发明摘要中定义; 能够抑制BCR-ABL1及其突变体的活性。本发明还提供了一种制备本发明化合物的方法，包括这些化合物的制药制剂以及使用这些化合物治疗癌症的方法。
• Compounds and compositions for inhibiting the activity of ABL1, ABL2 and BCR-ABL1
  申请人：Furet Pascal

  公开号：US09278981B2

  公开（公告）日：2016-03-08

  The present invention relates to compounds of formula (I): in which Y, Y, R, R 2, R 3 and R 4 are defined in the Summary of the Invention; capable of inhibiting the activity of BCR-ABL1 and mutants thereof. The invention further provides a process for the preparation of compounds of the invention, pharmaceutical preparations comprising such compounds and methods of using such compounds in the treatment of cancers.

  本发明涉及公式(I)的化合物：其中Y，Y，R，R2，R3和R4在本发明摘要中定义；能够抑制BCR-ABL1及其突变体的活性。 本发明还提供了一种制备本发明化合物的方法，包括这些化合物的制药制剂以及使用这些化合物治疗癌症的方法。
• Synthesis of enantiomerically pure 4-substituted pyrrolidin-3-ols via asymmetric 1,3-dipolar cycloaddition
  作者：Staffan Karlsson、Hans-Erik Högberg

  DOI：10.1016/s0957-4166(01)00367-6

  日期：2001.8

  Asymmetric 1,3-dipolar cycloadditions of chiral azomethine ylides to 3-benzyloxy-substituted alkenoyleamphorsultams are described. trans-3,4-Disubstituted pyrrolidines containing a protected hydroxyl group at C(4) of the pyrrolidine ring are obtained in high diastereomeric ratios. Such compound can serve as chiral building blocks for the syntheses of enantiopure bioactive pyrrolidines. This is exemplified by a short synthetic route to a known glycosidase inhibitor, (3R,4R)-4-(hydroxy- methyl)pyrrolidin-3-ol and its enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.
• WO2007/69923
  申请人：——

  公开号：——

  公开（公告）日：——