6-甲基-8-喹啉胺 | 68420-93-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 6-甲基-8-喹啉胺
• 英文名称: 6-methylquinolin-8-amine
• 英文别名: 8-amino-6-methylquinoline；8-Amino-6-methyl-chinolin
• CAS: 68420-93-9
• 化学式: C₁₀H₁₀N₂
• mdl: MFCD06408350
• 分子量: 158.203
• InChiKey: ZAKYERLVLCYWJN-UHFFFAOYSA-N

物化性质

• 熔点：
  73°C
• 沸点：
  333.29°C (estimate)
• 密度：
  1.1606 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  6-甲基-8-喹啉胺 在 iron(III) chloride 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 30.0h， 生成 (E)-N-(5-cinnamyl-6-methylquinolin-8-yl)pivalamide
  参考文献：
  名称：

  Iron-Catalyzed, Chelation-Induced Remote C–H Allylation of Quinolines via 8-Amido Assistance

  摘要：

  An iron-catalyzed, 8-amido-enabled regiodivergent C-H allylation of quinolines is described. This reaction represents a rare example of chelation-induced geometrically inaccessible C-H functionalization, allowing for the highly regio- and stereoselective preparation of either the C5- or the C4-allylated quinoline scaffolds regiocontrolled by the catalytic systems.

  DOI：

  10.1021/ol501534z
• 作为产物：
  描述：

  4-溴-2-硝基苯胺 在 四(三苯基膦)钯 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.75h， 生成 6-甲基-8-喹啉胺
  参考文献：
  名称：

  Synthesis and in vitro evaluation of novel 8-aminoquinoline–pyrazolopyrimidine hybrids as potent antimalarial agents

  摘要：

  In the search of novel chemotherapeutic agents for emerging drug resistant parasites, the hybridization approaches have successfully emerged as an efficient tool in malarial chemotherapy. Herein, a rational design and synthesis of novel 8-aminoquinoline and pyrazolopyrimidine hybrids and their antimalarial activity against wild type Plasmodium falciparum (Pf_NF54) and resistant strain (Pf_K1) is reported. The medicinal chemistry approach to expand the scope of this series resulted in an identification of potent compounds with nanomolar potency (best IC50 5-10 nM). Systematic structure activity relationship (SAR) studies revealed that pyrazolopyrimidine and 8-aminoquinoline ring are essential for achieving good P. falciparum potency. The docking study revealed that the compound 6 can retain some of the critical interactions within pfDHODH drug target. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.01.003

文献信息

• (8-Amino)quinoline and (4-amino)phenanthridine complexes of Re(CO)3 halides
  作者：Sanjay Gaire、Robert J. Ortiz、Briana R. Schrage、Issiah B. Lozada、Pavan Mandapati、Allen J. Osinski、David E. Herbert、Christopher J. Ziegler

  DOI：10.1016/j.jorganchem.2020.121338

  日期：2020.8

  present a study on the synthesis, structure and electronics of a series of (8-amino)quinoline and (4-amino)phenanthridine complexes of Re(CO)3X, where X = Cl and Br. In all cases, the (amino)heterocycles bind as bidentate ligands, with surprisingly symmetric modes of binding based on Re–N bond lengths. Between the complexes of (8-amino)quinolines and (4-amino)phenanthridines studied in this report, we do

  在本报告中，我们对 Re(CO) 3 X的一系列（8-氨基）喹啉和（4-氨基）菲啶配合物的合成、结构和电子学进行了研究，其中 X = Cl 和 Br。在所有情况下，（氨基）杂环作为双齿配体结合，具有基于 Re-N 键长的令人惊讶的对称结合模式。在本报告中研究的（8-氨基）喹啉和（4-氨基）菲啶的复合物之间，我们没有观察到太多的结构变化和非常相似的紫外-可见吸收光谱。(4-氨基)菲啶复合物中 π 系统的扩展确实导致最低能量跃迁强度的增加 ( λ max)，计算模型表明，与较小的 (8-氨基) 喹啉支持的复合物中这些跃迁的混合 π-π∗/MLCT 特征相比，其更纯粹的 MLCT 特征。DFT 和 TDDFT 建模进一步表明，考虑自旋轨道耦合 (SOC) 是必不可少的；省略 SOC 会错过 π-π∗ 对λ max 的贡献，并且无法准确模拟观察到的电子吸收光谱。
• Transition-Metal-Free Regioselective C-H Bond Fluorination of 8-Amidoquinolines with Selectfluor
  作者：Hao Chen、Pinhua Li、Min Wang、Lei Wang

  DOI：10.1002/ejoc.201800389

  日期：2018.5.15

  A simple and efficient transition‐metal‐free protocol was developed for the fluorination of the 5‐position of 8‐aminoquinolines with Selectfluor. Numerous substituted 8‐aminoquinoline amides were tolerated under the reaction conditions to give the corresponding products in good yields.

  开发了一种简单高效的无过渡金属方案，用于使用Selectfluor氟化8位氨基喹啉的5位。在反应条件下可耐受多种取代的8-氨基喹啉酰胺，从而以高收率得到相应的产物。
• Novel Sulfonaminoquinoline Hepcidin Antagonists
  申请人：Buhr Wilm

  公开号：US20120214803A1

  公开（公告）日：2012-08-23

  The present invention relates to novel hepcidin antagonists, pharmaceutical compositions comprising them and the use thereof as medicaments for the use in the treatment of iron metabolism disorders, such as, in particular, iron deficiency diseases and anemias, in particular anemias in connection with chronic inflammatory diseases.

  本发明涉及新型肝铁蛋白拮抗剂，包括它们的药物组合物以及将其用作药物治疗铁代谢紊乱，特别是铁缺乏病和贫血等疾病，特别是与慢性炎症性疾病相关的贫血。
• Copper-Catalyzed C5–H Sulfenylation of Unprotected 8-Aminoquinolines Using Sulfonyl Hydrazides
  作者：Qing Yu、Yiming Yang、Jie-Ping Wan、Yunyun Liu

  DOI：10.1021/acs.joc.8b01658

  日期：2018.9.21

  unprotected 8-aminoquinolines and sulfonyl hydrazides is achieved via the catalysis of CuI. The reactions are hypothesized to proceed via the Cu(I)–Cu(II)–Cu(I) catalytic processes induced by aerobic oxidation and single-electron transfer on the Cu(II)–8-aminoquinoline complex. This work discloses an unprecedented step-efficient method for the synthesis of C5-sulfenylated 8-aminoquinolines bearing a useful free

  使用未保护的8-氨基喹啉和磺酰基酰肼合成C5-亚磺酰基化的8-氨基喹啉是通过CuI的催化来实现的。假设反应是通过有氧氧化和单电子转移在Cu（II）-8-氨基喹啉络合物上诱导的Cu（I）-Cu（II）-Cu（I）催化过程进行的。这项工作公开了一种空前的步骤高效的方法，用于合成带有有用的游离NH 2基团的C5-亚磺酰基化的8-氨基喹啉。
• [EN] QUINOLINYL-PYRAZINE-CARBOXAMIDE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE QUINOLINYL-PYRAZINE-CARBOXAMIDE ET UTILISATIONS ASSOCIÉES
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2020132459A1

  公开（公告）日：2020-06-25

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a quinolinyl-pyrazine-carboxamide (or similar) structure which function as activators of the cholesterol biosynthesis pathway within cancer cells and/or immune cells, which function as activators of the cell cycle regulation pathway within cancer cells and/or immune cells, and which function as up-regulators of HMGCS1 protein expression within cancer cells and/or immune cells, and which function as effective therapeutic agents for treating, ameliorating, and preventing various forms of cancer and other inflammatory disease.

  这项发明属于药物化学领域。具体来说，该发明涉及一类新型小分子，其具有喹啉基-吡嗪-羧酰胺（或类似）结构，其在癌细胞和/或免疫细胞内作为胆固醇生物合成途径的激活剂，作为癌细胞和/或免疫细胞内细胞周期调控途径的激活剂，作为癌细胞和/或免疫细胞内HMGCS1蛋白表达的上调剂，以及作为治疗、改善和预防各种癌症和其他炎症性疾病的有效治疗剂。