(S)-1-(1-methyl-1H-pyrazol-5-yl)ethanamine | 1535165-96-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-1-(1-methyl-1H-pyrazol-5-yl)ethanamine
• 英文别名: (S)-1-(1-Methyl-1H-pyrazol-5-yl)ethan-1-amine；(1S)-1-(2-methylpyrazol-3-yl)ethanamine
• CAS: 1535165-96-8
• 化学式: C₆H₁₁N₃
• mdl: MFCD27756434
• 分子量: 125.173
• InChiKey: RRQYXOXCBVYWMU-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Cytidine, 2',5'-dideoxy-2',2'-difluoro-5'-iodo- 、 (S)-1-(1-methyl-1H-pyrazol-5-yl)ethanamine 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-[[[(1S)-1-(2-methylpyrazol-3-yl)ethyl]amino]methyl]oxolan-2-yl]pyrimidin-2-one
  参考文献：
  名称：

  5'-氨基-2'，5'-二脱氧-2'，2'-二氟胞苷衍生物的合成作为新型抗癌核苷类似物

  摘要：

  为了鉴定抗癌核苷类似物，已经合成了新型的5'-氨基-2'，5'-二脱氧-2'，2'-二氟胞苷衍生物。设计并实施了几种合成路线，这些路线依靠S N 2置换或还原胺化来提供所需的衍生物。

  DOI：

  10.1016/j.tetlet.2013.11.018

文献信息

• Syntheses of 5′-amino-2′,5′-dideoxy-2′,2′-difluorocytidine derivatives as novel anticancer nucleoside analogs
  作者：Marc A. Labroli、Michael P. Dwyer、Ruichao Shen、Janeta Popovici-Muller、Qinglin Pu、Judson Richard、Kristen Rosner、Kamil Paruch、Timothy J. Guzi

  DOI：10.1016/j.tetlet.2013.11.018

  日期：2014.1

  A novel class of 5′-amino-2′,5′-dideoxy-2′,2′-difluorocytidine derivatives has been synthesized in order to identify anticancer nucleoside analogs. Several synthetic routes were devised and implemented which relied upon either SN2 displacement or reductive amination to provide the desired derivatives.

  为了鉴定抗癌核苷类似物，已经合成了新型的5'-氨基-2'，5'-二脱氧-2'，2'-二氟胞苷衍生物。设计并实施了几种合成路线，这些路线依靠S N 2置换或还原胺化来提供所需的衍生物。
• WO2023/86638
  申请人：——

  公开号：——

  公开（公告）日：——
• The identification of novel 5′-amino gemcitabine analogs as potent RRM1 inhibitors
  作者：Marc A. Labroli、Michael P. Dwyer、Ruichao Shen、Janeta Popovici-Muller、Qinglin Pu、Daniel Wyss、Mark McCoy、Dianah Barrett、Nicole Davis、Wolfgang Seghezzi、Frances Shanahan、Lorena Taricani、Maribel Beaumont、Maria-Christina Malinao、David Parry、Timothy J. Guzi

  DOI：10.1016/j.bmc.2014.02.007

  日期：2014.4

  The ribonucleotide reductase (RNR) enzyme is a heteromer of RRM1 and RRM2 subunits. The active enzyme catalyzes de novo reduction of ribonucleotides to generate deoxyribonucleotides (dNTPs), which are required for DNA replication and DNA repair processes. Complexity in the generation of physiologically relevant, active RRM1/RRM2 heterodimers was perceived as limiting to the identification of selective RRM1 inhibitors by high-throughput screening of compound libraries and led us to seek alternative methods to identify lead series. In short, we found that gemcitabine, as its diphosphate metabolite, represents one of the few described active site inhibitors of RRM1. We herein describe the identification of novel 5'-amino gemcitabine analogs as potent RRM1 inhibitors through in-cell phenotypic screening. (c) 2014 Elsevier Ltd. All rights reserved.