2-二甲氨基-5-碘嘧啶 | 1083329-41-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-二甲氨基-5-碘嘧啶
• 英文名称: 5-iodo-N,N-dimethylpyrimidin-2-amine
• 英文别名: N,N-Dimethyl-5-iodopyrimidine-2-amine
• CAS: 1083329-41-2
• 化学式: C₆H₈IN₃
• 分子量: 249.054
• InChiKey: HOLFICYUXUVXQP-UHFFFAOYSA-N

物化性质

• 沸点：
  297.4±32.0 °C(Predicted)
• 密度：
  1.831±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-二甲氨基-5-碘嘧啶 在 copper(l) iodide 、 1,10-菲罗啉 、 三溴化硼 、 potassium carbonate 、 caesium carbonate 作用下， 以 二氯甲烷 、 甲苯 、 丁酮 为溶剂， 反应 38.0h， 生成 1-(3-((2-(dimethylamino)pyrimidin-5-yl)oxy)-2-hydroxy-2-methylpropanoyl)indoline-4-carbonitrile
  参考文献：
  名称：

  1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators

  摘要：

  We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.

  DOI：

  10.1021/jm401625b
• 作为产物：
  描述：

  2-氨基-5-碘嘧啶, 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以96%的产率得到2-二甲氨基-5-碘嘧啶
  参考文献：
  名称：

  A Simple Cu-Catalyzed Coupling Approach to Substituted 3-Pyridinol and 5-Pyrimidinol Antioxidants

  摘要：

  A convenient approach to 3-pyridinols and 5-pyrimidinols via a two-step Cu-catalyzed benzyloxylation/catalytic hydrogenation sequence is presented. The corresponding 3-pyridinamines and 5-pyrimidinamines can be prepared in an analogous sequence utilizing benzylamine in lieu of benzyl alcohol. The radical-scavenging ability of these derivatives are preliminarily explored and reveal that the increased acidities of the pyridinols and pyrimidinols render them susceptible to more significant kinetic solvent effects when compared to phenols.

  DOI：

  10.1021/jo801501e

文献信息

• Enantio‐ and Regioselective NiH‐Catalyzed Reductive Hydroarylation of Vinylarenes with Aryl Iodides
  作者：Yuli He、Chuang Liu、Lei Yu、Shaolin Zhu

  DOI：10.1002/anie.202010386

  日期：2020.11.23

  A highly enantio‐ and regioselective hydroarylation process of vinylarenes with aryl halides has been developed using a NiH catalyst and a new chiral bis imidazoline ligand. A broad range of structurally diverse, enantioenriched 1,1‐diarylalkanes, a structure found in a number of biologically active molecules, have been obtained with excellent yields and enantioselectivities under extremely mild conditions

  使用NiH催化剂和新型手性双咪唑啉配体开发了乙烯基芳烃与芳基卤化物的高度对映和区域选择性加氢芳基化方法。在极其温和的条件下，以优异的收率和对映选择性获得了多种结构多样的，对映体富集的1,1-二芳基烷烃，该结构存在于许多生物活性分子中。
• Compounds and compositions for inducing chondrogenesis
  申请人：NOVARTIS AG

  公开号：US10188638B2

  公开（公告）日：2019-01-29

  The present invention provides compounds of formula I: or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof, wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds, and methods of using such compounds for treatment of joint damage or joint injury in a mammal, and for inducing differentiation of mesenchymal stem cells into chondrocytes.

  本发明提供了式 I 的化合物： 或其药学上可接受的盐、同系物或立体异构体，其中变量如本文所定义。本发明进一步提供了包含此类化合物的药物组合物，以及使用此类化合物治疗哺乳动物关节损伤或关节损伤和诱导间充质干细胞分化为软骨细胞的方法。
• Terminal-Selective C(sp³)–H Arylation: NiH-Catalyzed Remote Hydroarylation of Unactivated Internal Olefins
  作者：Yuli He、Bo Han、Shaolin Zhu

  DOI：10.1021/acs.organomet.0c00819

  日期：2021.7.26
• A Simple Cu-Catalyzed Coupling Approach to Substituted 3-Pyridinol and 5-Pyrimidinol Antioxidants
  作者：Susheel J. Nara、Mukund Jha、Johan Brinkhorst、Tony J. Zemanek、Derek A. Pratt

  DOI：10.1021/jo801501e

  日期：2008.12.5

  A convenient approach to 3-pyridinols and 5-pyrimidinols via a two-step Cu-catalyzed benzyloxylation/catalytic hydrogenation sequence is presented. The corresponding 3-pyridinamines and 5-pyrimidinamines can be prepared in an analogous sequence utilizing benzylamine in lieu of benzyl alcohol. The radical-scavenging ability of these derivatives are preliminarily explored and reveal that the increased acidities of the pyridinols and pyrimidinols render them susceptible to more significant kinetic solvent effects when compared to phenols.
• COMPOUNDS AND COMPOSITIONS FOR INDUCING CHONDROGENESIS
  申请人：NOVARTIS AG

  公开号：US20170239227A1

  公开（公告）日：2017-08-24

  The present invention provides compounds of formula I: or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof, wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds, and methods of using such compounds for treatment of joint damage or joint injury in a mammal, and for inducing differentiation of mesenchymal stem cells into chondrocytes.