(2-hydroxypyridin-3-yl)(1H-imidazol-1-yl)methanone | 211425-43-3

• 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
• 英文名称: (2-hydroxypyridin-3-yl)(1H-imidazol-1-yl)methanone
• CAS: 211425-43-3
• 化学式: C₉H₇N₃O₂
• 分子量: 189.173
• InChiKey: NKBAJBWKXRUMCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.01
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2-hydroxypyridin-3-yl)(1H-imidazol-1-yl)methanone 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 1-methyl-5-(2-oxo-1H-pyridin-3-yl)-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one
  参考文献：
  名称：

  Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 1. Sildenafil analogs

  摘要：

  Parasitic diseases, such as African sleeping sickness, have a significant impact on the health and wellbeing in the poorest regions of the world. Pragmatic drug discovery efforts are needed to find new therapeutic agents. In this Letter we describe target repurposing efforts focused on trypanosomal phosphodiesterases. We outline the synthesis and biological evaluation of analogs of sildenafil (1), a human PDE5 inhibitor, for activities against trypanosomal PDEB1 (TbrPDEB1). We find that, while low potency analogs can be prepared, this chemical class is a sub-optimal starting point for further development of TbrPDE inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.119
• 作为产物：
  描述：

  2-羟基烟酸 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 反应 19.0h， 以98%的产率得到(2-hydroxypyridin-3-yl)(1H-imidazol-1-yl)methanone
  参考文献：
  名称：

  Tripodal trisamides based on nicotinic and picolinic acid derivatives

  摘要：

  一些多齿芳胺配体已通过将各种无环三脚架或线性多胺与烟酸和吡啶甲酸衍生物偶联而制备。本研究采用了两种合成方法；三{[(2-羟基烟酰基)羰基]-2-氨基乙基}胺（H₃NICTREN）通过方法A，即HOSu/DCC方法制备，而本研究中的其他芳胺通过方法B，即CDI方法制备。方法A涉及N-羟基琥珀酰亚胺与2-羟基烟酸（在二环己基碳二亚胺（DCC）存在下作为脱水偶联试剂）反应形成琥珀酰亚胺酯，然后与TREN反应生成H₃NICTREN。方法B涉及羧酸（2-羟基烟酸、3-羟基吡啶甲酸、烟酸或吡啶甲酸）与羰基二咪唑（CDI）反应形成N-酰基咪唑，然后与胺（TREN、TAME、精胺或TRPN）反应生成所需的芳胺。确定了1,1,1-三{[(3-羟基吡啶基)羰基]-2-氨基甲基}乙烷（H₃PICTAME）的X射线结构；H₃PICTAME的晶体为单斜晶系，a = 10.257(2)，b = 15.572(3)，c = 15.208(2) Å，β = 96.124(15)°，Z = 4，空间群P2₁/a。该结构通过直接方法解决，并通过全矩阵最小二乘法精化至R = 0.041和R_w = 0.038，对于I >= 3 sigma (I)的2506个反射。在固态中，H₃PICTAME包含广泛的氢键网络，每个分子有八个分子内和一个分子间氢键；配体部分预组织以供金属离子螯合。已确定了H₃NICTREN和1,1,1-三{[(2-羟基烟酰基)羰基]-2-氨基甲基}乙烷（H₃NICTAME）的酸解离常数；H₃NICTREN（H₃NICTAME）的pK_a1 = 11.2（10.68），pK_a2 = 10.7（10.58），pK_a3 = 10.0（9.71），pK_a4 = 6.25；高酚pK_a值与固态中观察到的氢键结合一致。关键词：芳胺，氢键，预组织。

  DOI：

  10.1139/v98-030

文献信息

• Hydrotropic Polymers:  Synthesis and Characterization of Polymers Containing Picolylnicotinamide Moieties
  作者：Sang Cheon Lee、Ghanashyam Acharya、Jaehwi Lee、Kinam Park

  DOI：10.1021/ma021629k

  日期：2003.4.1

  Our previous studies on low molecular weight hydrotropes showed that nicotinamide derivatives increased the aqueous solubility of paclitaxel by several orders of magnitude. We were interested in knowing whether the polymeric forms of those low molecular weight hydrotropes could maintain hydrotropic properties. N-Picolylnicotinamide (PNA) was one of the best hydrotropes identified for paclitaxel, and polymers based on PNA were synthesized and tested for their hydrotropic properties. The pendent hydrotropic PNA moieties were attached to the polymer backbone through either an oligo(ethylene glycol) or a phenyl group as a spacer. The PNA moiety was bound to the polymer backbone either at the 2-position or at the 6-position of the pyridine ring of nicotinamide to result in poly(2-(4-vinylbenzyloxy)-N-picolylnicotinamide) (P(2-VBOPNA)) or poly(6-(4-vinylbenzyloxy)-N-picolylnicotinamide) (P(6-VBOPNA)), respectively. The ability of PNA-containing polymers to increase the aqueous solubility of paclitaxel was examined by measuring the concentration of dissolved paclitaxel in various polymer concentrations. The PNA-containing polymers increased the water solubility of paclitaxel by more than 3 orders of magnitude, and the hydrotropic property of the polymers was pronounced even at low polymer concentrations. P(2-VBOPNA) showed a higher hydrotropic property than P(6-VBOPNA). At the polymer concentration of 40 mg/mL, the water solubility of paclitaxel was enhanced up to 700-fold, depending on the type of polymer used. On the other hand, PNA displayed an efficient solubilizing ability at above 100 mg/mL. Fluorescence study indicated that the hydrotropic polymers formed noncovalent molecular assemblies through the self-association of pendent hydrotropic PNA moieties at much lower concentration range ((2.1-4.6) x 10(-2) mg/mL) than PNA (22 mg/mL). This observation supports the high solubilization abilities of hydrotropic polymers for paclitaxel. These results suggest a hydrotropic property of the PNA-based polymers operates under the same mechanism as PNA itself. The cross-linked networks of PNA-based hydrotropic polymers (i.e., hydrotropic hydrogels) were as effective as water-soluble polymers in solubilizing paclitaxel. This study shows that hydrotropic polymers and hydrogels that are prepared based on low molecular weight hydrotropic agent are as effective as the low molecular weight counterpart.
• Domagala, John M., Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1705 - 1707
  作者：Domagala, John M.

  DOI：——

  日期：——