2-[4-(2-hydroxyethyl)piperazin-1-yl]nicotinic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-[4-(2-hydroxyethyl)piperazin-1-yl]nicotinic acid
• 英文别名: 2-[4-(2-Hydroxyethyl)-1-piperazinyl]nicotinic acid；2-[4-(2-hydroxyethyl)piperazin-1-yl]pyridine-3-carboxylic acid
• 化学式: C₁₂H₁₇N₃O₃
• mdl: MFCD11107299
• 分子量: 251.285
• InChiKey: CQRGFILLDOIDOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氨基-6-乙基-4-甲氧基-苯甲酸 、 2-[4-(2-hydroxyethyl)piperazin-1-yl]nicotinic acid 在 二-1H-吡咯-1-基甲酮 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis and optimization of 2-pyridin-3-yl-benzo[d][1,3]oxazin-4-one based inhibitors of human neutrophil elastase

  摘要：

  The hit-to-lead optimization of the HNE inhibitor 5-methyl-2-(2-phenoxy-pyridin-3-yl)-benzo[d][1,3]oxazin-4-one is described. A structure-activity relationship study that focused on the 5 and 7 benzoxazinone positions yielded the optimized 5-ethyl-7-methoxy-benzo[d][1,3]oxazin-4-one core structure. 2-[2-(4Methyl-piperazin-1-yl)-pyridin-3-yl] derivatives of this core were shown to yield HNE inhibitors of similar potency with significantly different stabilities in rat plasma. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.053
• 作为产物：
  描述：

  N-羟乙基哌嗪 、 2-氯烟酸 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以Grams 3.9 of 2-[4-(2-hydroxyethyl)piperazin-1-yl]nicotinic acid, melting at 148°-171° C. (with decomposition), were obtained的产率得到2-[4-(2-hydroxyethyl)piperazin-1-yl]nicotinic acid
  参考文献：
  名称：

  Pharmacologically active alkylol derivatives

  摘要：

  描述了一种新的烷基醇衍生物，其属于具有结构式 ##STR1## 的类，其中 R 代表从吡啶，嘧啶，吡嗪，吡嗪啉，噻吩，呋喃，噻唑中选择的5或6元杂环环，其可以选择性地被取代为一种或多种从烷基，烷氧基，卤素，酰胺，羟基，甲硫基，三氟甲基，氰基，羧基和相应的烷基酯和碱金属盐所选择的基团；n为2X，X'分别代表氢原子或羟基，但两者都是氢原子的除外，X'可以是羟乙氧基；m为0或1；以及相应的无毒药用可接受的酸加合盐。式I的化合物具有有趣的镇咳活性，并且在其活性剂量下，几乎没有不良副作用。

  公开号：

  US04849422A1

文献信息

• US4849422A
  申请人：——

  公开号：US4849422A

  公开（公告）日：1989-07-18
• Synthesis and optimization of 2-pyridin-3-yl-benzo[d][1,3]oxazin-4-one based inhibitors of human neutrophil elastase
  作者：Kevin R. Shreder、Julia Cajica、Lingling Du、Allister Fraser、Yi Hu、Yasushi Kohno、Emme C.K. Lin、Steve J. Liu、Eric Okerberg、Lan Pham、Jiangyue Wu、John W. Kozarich

  DOI：10.1016/j.bmcl.2009.06.053

  日期：2009.8

  The hit-to-lead optimization of the HNE inhibitor 5-methyl-2-(2-phenoxy-pyridin-3-yl)-benzo[d][1,3]oxazin-4-one is described. A structure-activity relationship study that focused on the 5 and 7 benzoxazinone positions yielded the optimized 5-ethyl-7-methoxy-benzo[d][1,3]oxazin-4-one core structure. 2-[2-(4Methyl-piperazin-1-yl)-pyridin-3-yl] derivatives of this core were shown to yield HNE inhibitors of similar potency with significantly different stabilities in rat plasma. (C) 2009 Elsevier Ltd. All rights reserved.
• Pharmacologically active alkylol derivatives
  申请人：Dompe' Farmaceutici S.p.A.

  公开号：US04849422A1

  公开（公告）日：1989-07-18

  New alkylol derivatives are described, which belong to the class having the structure formula ##STR1## where R represents a 5 or 6 membered heterocyclic ring selected among pyridine, pyrimidine, pyrazine, pyridazine, thiophene, furan, thiazole which optionally may be substituted with one or more groups selected among alkyl, alkoxy, halogen, amide, hydroxy, methylthio, trifluoromethyl, cyano, carboxy and the corresponding alkyl esters and salts with alkali metals n is 2 X and X' represent each a hydrogen atom or hydroxy group with the exception of both being hydrogen atom, and X' may be hydroxyethoxy moiety m is 0 or 1 and the corresponding non-toxic pharmaceutically acceptable acid addition salts. The compounds of the formula I are endowed with an interesting antitussive activity and, at their active dose, practically they are free of undesired side effects.

  描述了新的烷基醇衍生物，属于具有结构式的类别 ##STR1## 其中 R 代表在吡啶、嘧啶、吡嗪、吡啶二氮杂环、噻吩、呋喃、噻唑中选择的5或6元杂环，该环可选择地用烷基、烷氧基、卤素、酰胺、羟基、甲硫基、三氟甲基、氰基、羧基和相应的烷基酯及碱金属盐取代，n 为 2，X 和 X' 分别代表氢原子或羟基，但两者不能同时为氢原子，X' 可能是羟乙氧基基团，m 为 0 或 1，以及相应的无毒药用酸盐。公式 I 的化合物具有有趣的镇咳活性，在其有效剂量下，几乎没有不良副作用。