N-(6-氨基-5-甲酰基-吡啶-2-基)-乙酰胺 | 1026039-22-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(6-氨基-5-甲酰基-吡啶-2-基)-乙酰胺
• 英文名称: N-(6-amino-5-formyl-pyridin-2-yl)-acetamide
• 英文别名: N-(6-amino-5-formylpyridin-2-yl)acetamide
• CAS: 1026039-22-4
• 化学式: C₈H₉N₃O₂
• 分子量: 179.178
• InChiKey: SZNPVEDZADBWFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(6-氨基-5-甲酰基-吡啶-2-基)-乙酰胺 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以48%的产率得到N-(6-amino-5-hydroxymethyl-pyridin-2-yl)-acetamide
  参考文献：
  名称：

  Synthesis, in vitro and in vivo activity of thiamine antagonist transketolase inhibitors

  摘要：

  Tumor cells extensively utilize the pentose phosphate pathway for the synthesis of ribose. Transketolase is a key enzyme in this pathway and has been suggested as a target for inhibition in the treatment of cancer. In a pharmacodynamic study, nude mice with xenografted HCT-116 tumors were dosed with 1 ('N3'-pyridyl thiamine'; 3-(6-methyl-2-amino-pyridin-3-ylmethyl)-5-(2-hydroxyethyl)-4-methyl-thiazol-3-ium chloride hydrochloride), an analog of thiamine, the co-factor of transketolase. Transketolase activity was almost completely suppressed in blood, spleen, and tumor cells, but there was little effect on the activity of the other thiamine-utilizing enzymes alpha-ketoglutarate dehydrogenase or glucose-6-phosphate dehydrogenase. Synthesis and SAR of transketolase inhibitors is described. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.101
• 作为产物：
  描述：

  乙酸酐 、 2,6-二氨基烟醛 以 甲苯 为溶剂， 反应 18.0h， 以66%的产率得到N-(6-氨基-5-甲酰基-吡啶-2-基)-乙酰胺
  参考文献：
  名称：

  Synthesis, in vitro and in vivo activity of thiamine antagonist transketolase inhibitors

  摘要：

  Tumor cells extensively utilize the pentose phosphate pathway for the synthesis of ribose. Transketolase is a key enzyme in this pathway and has been suggested as a target for inhibition in the treatment of cancer. In a pharmacodynamic study, nude mice with xenografted HCT-116 tumors were dosed with 1 ('N3'-pyridyl thiamine'; 3-(6-methyl-2-amino-pyridin-3-ylmethyl)-5-(2-hydroxyethyl)-4-methyl-thiazol-3-ium chloride hydrochloride), an analog of thiamine, the co-factor of transketolase. Transketolase activity was almost completely suppressed in blood, spleen, and tumor cells, but there was little effect on the activity of the other thiamine-utilizing enzymes alpha-ketoglutarate dehydrogenase or glucose-6-phosphate dehydrogenase. Synthesis and SAR of transketolase inhibitors is described. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.101

文献信息

• Synthesis, in vitro and in vivo activity of thiamine antagonist transketolase inhibitors
  作者：Allen A. Thomas、Y. Le Huerou、J. De Meese、Indrani Gunawardana、Tomas Kaplan、Todd T. Romoff、Stephen S. Gonzales、Kevin Condroski、Steven A. Boyd、Josh Ballard、Bryan Bernat、Walter DeWolf、May Han、Patrice Lee、Christine Lemieux、Robin Pedersen、Jed Pheneger、Greg Poch、Darin Smith、Francis Sullivan、Solly Weiler、S. Kirk Wright、Jie Lin、Barb Brandhuber、Guy Vigers

  DOI：10.1016/j.bmcl.2007.11.101

  日期：2008.3

  Tumor cells extensively utilize the pentose phosphate pathway for the synthesis of ribose. Transketolase is a key enzyme in this pathway and has been suggested as a target for inhibition in the treatment of cancer. In a pharmacodynamic study, nude mice with xenografted HCT-116 tumors were dosed with 1 ('N3'-pyridyl thiamine'; 3-(6-methyl-2-amino-pyridin-3-ylmethyl)-5-(2-hydroxyethyl)-4-methyl-thiazol-3-ium chloride hydrochloride), an analog of thiamine, the co-factor of transketolase. Transketolase activity was almost completely suppressed in blood, spleen, and tumor cells, but there was little effect on the activity of the other thiamine-utilizing enzymes alpha-ketoglutarate dehydrogenase or glucose-6-phosphate dehydrogenase. Synthesis and SAR of transketolase inhibitors is described. (C) 2007 Elsevier Ltd. All rights reserved.