2,6-二氨基烟醛 | 151510-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2,6-二氨基烟醛
• 英文名称: 2,6-diaminopyridine-3-carboxaldehyde
• 英文别名: 2,6-diamino-pyridine-3-carbaldehyde；2,6-diaminopyridine-3-carbaldehyde；2,6-Diaminonicotinaldehyde
• CAS: 151510-21-3
• 化学式: C₆H₇N₃O
• mdl: MFCD18818974
• 分子量: 137.141
• InChiKey: YDVDHHVHCIAGAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-二氨基烟醛 在 哌啶 、 吡啶 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 N-{3-cyano-7-[(2,2-dimethylpropanoyl)amino]-1,8-naphthyridin-2-yl}-2,2-dimethylpropanamide
  参考文献：
  名称：

  通过四重氢键进行分子识别的异二聚体

  摘要：

  合成DAAD氢键供体（D）和受体（A）阵列1，并通过1 H NMR滴定测量互补的ADDA底物2的识别和通过四个氢键形成的异二聚体。空间上不拥挤的二聚体的结合能与根据增量计算的值一致。

  DOI：

  10.1016/s0040-4039(98)01200-3
• 作为产物：
  描述：

  2,6-二氨基吡啶 在 氢氧化钾 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 2,6-二氨基烟醛
  参考文献：
  名称：

  Convenient synthesis of 2-amino-1,8-naphthyridines, building blocks for host-guest and self-assembling systems

  摘要：

  Application of the Reimer-Tiemann reaction to 2,6-diaminopyridine afforded a 26% yield of 2,6-diaminopyridine-3-carboxaldehyde (4) and a small amount (4%) of 2,6-diaminopyridine-3,5-dicarboxaldehyde. Alternatively, conversion of 2,6-diaminopyridine to 2,6-bis(pivaloylamino)pyridine (6), directed lithiation with n-butyllithium, treatment with N-formylmorpholine, and hydrolysis produced 4 in 67% overall yield. The Friedlander condensation of 4 with a variety of activated and unactivated ketones afforded 2-amino-1,8-naphthyridines and bis(2-amino-1,8-naphthyridines) in moderate to good yields, providing a convenient synthesis of useful building blocks for new host-guest and self-assembling systems.

  DOI：

  10.1021/jo00076a021

文献信息

• [EN] NAPHTHYRIDINONE DERIVATIVES AS INHIBITORS OF CYTOMEGALOVIRUS DNA POLYMERASE<br/>[FR] DÉRIVÉS DE NAPHTHYRIDINONE EN TANT QU'INHIBITEURS D'ADN POLYMÉRASE DU CYTOMÉGALOVIRUS
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2013152063A1

  公开（公告）日：2013-10-10

  Compounds of Formula (I) wherein n, m, R1, R2, R3, R4, R5 and R6 are defined herein, are useful for the treatment of cytomegalovirus disease and/or infection.

  式（I）中n、m、R1、R2、R3、R4、R5和R6的化合物，适用于巨细胞病毒疾病和/或感染的治疗。
• Synthesis of heterocyclic compounds containing three contiguous hydrogen bonding sites in all possible arrangements
  作者：Thomas J. Murray、Steven C. Zimmerman、Sergei V. Kolotuchin

  DOI：10.1016/0040-4020(94)00922-h

  日期：1995.1

  The synthesis of compounds containing three contiguous hydrogen bond sites is reported. There are six ways of arranging three adjacent hydrogen bond donor (D) and acceptor (A) sites. General synthetic routes to heterocyclic compounds with each arrangement is reported.
• 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.
• Four Hydrogen Bonds − DDAA, DADA, DAAD and ADDA Hydrogen Bond Motifs
  作者：Ulrich Lüning、Christine Kühl、Andreas Uphoff

  DOI：10.1002/1099-0690(200212)2002:23<4063::aid-ejoc4063>3.0.co;2-l

  日期：2002.12
• Supramolecular Polymer Chemistry:  Self-Assembling Dendrimers Using the DDA·AAD (GC-like) Hydrogen Bonding Motif
  作者：Yuguo Ma、Sergei V. Kolotuchin、Steven C. Zimmerman

  DOI：10.1021/ja0202006

  日期：2002.11.1

  Heterocyclic unit 2 containing complementary donor-donor-acceptor (DDA) and acceptor-acceptor-donor (AAD) hydrogen bonding arrays at an angle of about 601 Was designed to self-assemble into a hexamer. To investigate whether this unit could self-assemble dendrimers, the 2,8-diamino-2-N-ethylpyrimido-(4,5-b)(1, 8)naphthyridine-3H-4-one subunit was synthesized with a first (2a), second (2b), and third generation (2c) Frechet-type dendron attached to the 8-amino group. The synthesis of 2a-c was accomplished in 11 steps beginning with 2,6-diaminopyridine and the corresponding dendron bromide. Studies using H-1 NMR, size exclusion chromatography (SEC), and dynamic light scattering (DLS) support the cooperative formation of cyclic hexamers in apolar solvents. The stability of the self-assembled dendrimers is dependent on the size of the attached dendron, and mixing studies with 2a-c indicate their usefulness in constructing dynamic combinatorial libraries.