2,3-dimethylquinoxaline-6-carbaldehyde | 108763-28-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-dimethylquinoxaline-6-carbaldehyde
• 英文别名: 2,3-Dimethylquinoxaline-6-carboxaldehyde
• CAS: 108763-28-6
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: BYLBWMINSPCQKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2,3-dimethylquinoxaline-6-carbaldehyde 在 劳森试剂 、 双氧水 、 sodium hydride 、 caesium carbonate 、 溶剂黄146 、 sodium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 41.0h， 生成 3-{2-[4-(2,3-dimethylquinoxalin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl]acetamido}benzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles as transforming growth factor-β type 1 receptor kinase inhibitors

  摘要：

  A series of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles 14a-d, 15a-d, 17a, 17b, 18a-d, 19a, and 19b has been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in a cell-based luciferase reporter assay. The 2-[3-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl]-N-phenylethanethioamide (18a) inhibited ALK5 phosphorylation with an IC50 value of 0.013 mu M and showed 80% inhibition at 0.1 mu M in a luciferase reporter assay using HaCaT cells permanently transfected with p3TP-luc reporter construct. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.063
• 作为产物：
  描述：

  2,3- 二甲基-喹喔啉-6-羧酸 在 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2,3-dimethylquinoxaline-6-carbaldehyde
  参考文献：
  名称：

  A new family of quinoline and quinoxaline analogues of combretastatins

  摘要：

  The 3-hydroxy-4-methoxyphenyl ring of combretastatin A-4 can be replaced by a 2-naphthyl moiety without significant loss of cytotoxicity and inhibition of tubulin polymerization potency. In this paper we show that the 6- or 7-quinolyl systems can in turn replace both cyclic moieties, keeping in the first case most of the potency as cytotoxic agent and in the second case as inhibitor of tubulin polymerization, related to the activities displayed by model compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.098

文献信息

• Alpha-aminoacyl-penicillins and cephalosporins
  申请人：Bayer Aktiengesellschaft

  公开号：US04734407A1

  公开（公告）日：1988-03-29

  Antibacterially active and animal growth-regulating novel .beta.-lactam compounds of the formula ##STR1## in which R.sup.1 represents an optionally substituted radical of the formula ##STR2## Z represents oxygen, sulphur or --N--R.sup.13, and A represents the group ##STR3##

  具有抗菌活性和动物生长调节作用的新型β-内酰胺化合物的化学式为##STR1##其中R.sup.1表示化学式##STR2##的可选择取代基团，Z表示氧、硫或--N--R.sup.13，A表示基团##STR3##
• Beta-Lactam-Antibiotika, Verfahren zur Herstellung und ihre Verwendung als Arzneimittel
  申请人：BAYER AG

  公开号：EP0197294A2

  公开（公告）日：1986-10-15

  Die Erfindung betrifft β-Lactamantibiotika der allgemeinen Formel (I) in welcher X, R', R2, R3 und R4 die in der Beschreibung angegebene Bedeutung haben, Verfahren zu ihrer Herstellung sowie ihre Verwendung in Arzneimitteln, insbesondere als oral wirksame Antibiotika.

  本发明涉及通式（I）的β-内酰胺类抗生素。 中 X、R'、R2、R3 和 R4 的含义，以及它们的制备工艺和在药物中的用途，特别是作为口服活性抗生素。
• US4734407A
  申请人：——

  公开号：US4734407A

  公开（公告）日：1988-03-29
• Synthesis and biological evaluation of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles as transforming growth factor-β type 1 receptor kinase inhibitors
  作者：Cheng Hua Jin、Domalapally Sreenu、Maddeboina Krishnaiah、Vura Bala Subrahmanyam、Kota Sudhakar Rao、Annaji Venkata Nagendra Mohan、Chul-Yong Park、Jee-Yeon Son、Do-Hyun Son、Hyun-Ju Park、Yhun Yhong Sheen、Dae-Kee Kim

  DOI：10.1016/j.ejmech.2011.05.063

  日期：2011.9

  A series of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles 14a-d, 15a-d, 17a, 17b, 18a-d, 19a, and 19b has been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in a cell-based luciferase reporter assay. The 2-[3-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl]-N-phenylethanethioamide (18a) inhibited ALK5 phosphorylation with an IC50 value of 0.013 mu M and showed 80% inhibition at 0.1 mu M in a luciferase reporter assay using HaCaT cells permanently transfected with p3TP-luc reporter construct. (C) 2011 Elsevier Masson SAS. All rights reserved.
• A new family of quinoline and quinoxaline analogues of combretastatins
  作者：Concepción Pérez-Melero、Ana B.S Maya、Benedicto del Rey、Rafael Peláez、Esther Caballero、Manuel Medarde

  DOI：10.1016/j.bmcl.2004.04.098

  日期：2004.7

  The 3-hydroxy-4-methoxyphenyl ring of combretastatin A-4 can be replaced by a 2-naphthyl moiety without significant loss of cytotoxicity and inhibition of tubulin polymerization potency. In this paper we show that the 6- or 7-quinolyl systems can in turn replace both cyclic moieties, keeping in the first case most of the potency as cytotoxic agent and in the second case as inhibitor of tubulin polymerization, related to the activities displayed by model compounds. (C) 2004 Elsevier Ltd. All rights reserved.