5-cyclohexylmethyl-4-hydroxy-2-oxo-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester | 1005188-03-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 5-cyclohexylmethyl-4-hydroxy-2-oxo-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
• 英文别名: methyl 3-(cyclohexylmethyl)-4-hydroxy-6-oxo-2,3-dihydro-1H-pyridine-5-carboxylate
• CAS: 1005188-03-3
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: NNJZDAWMBHHEFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-cyclohexylmethyl-4-hydroxy-2-oxo-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester 、 4-(1H-咪唑-1-基)苯胺 以 四氢呋喃 为溶剂， 生成 3-(cyclohexylmethyl)-4-hydroxy-N-(4-imidazol-1-ylphenyl)-6-oxo-2,3-dihydro-1H-pyridine-5-carboxamide
  参考文献：
  名称：

  Design and structure–activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): Tetramic, tetronic acids and dihydropyridin-2-ones

  摘要：

  Based on a pharmacophore hypothesis substituted tetramic and tetronic acid 3-carboxamides as well as dihydropyridin-2-one- 3-carboxamides were investigated as inhibitors of undecaprenyl pyrophosphate synthase (UPPS) for use as novel antimicrobial agents. Synthesis and structure - activity relationship patterns for this class of compounds are discussed. Selectivity data and antibacterial activities for selected compounds are provided. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.009
• 作为产物：
  描述：

  3-cyclohexyl-2-[(2-methoxycarbonyl-acetylamino)-methyl]-propionic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 5-cyclohexylmethyl-4-hydroxy-2-oxo-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Design and structure–activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): Tetramic, tetronic acids and dihydropyridin-2-ones

  摘要：

  Based on a pharmacophore hypothesis substituted tetramic and tetronic acid 3-carboxamides as well as dihydropyridin-2-one- 3-carboxamides were investigated as inhibitors of undecaprenyl pyrophosphate synthase (UPPS) for use as novel antimicrobial agents. Synthesis and structure - activity relationship patterns for this class of compounds are discussed. Selectivity data and antibacterial activities for selected compounds are provided. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.009

文献信息

• INHIBITORS OF UNDECAPRENYL PYROPHOSPHATE SYNTHASE
  申请人：Hurley Timothy Brian

  公开号：US20090203694A1

  公开（公告）日：2009-08-13

  The present invention relates to compounds that are selective and/or potent inhibitors of UPPS. In addition to compounds which inhibit UPPS, the invention also provides pharmaceutical compositions comprising these compounds and methods of using these compounds for treating bacterial disease, such as bacterial infection.

  本发明涉及一种选择性和/或强效抑制UPPS的化合物。除了抑制UPPS的化合物外，本发明还提供包含这些化合物的药物组合物以及使用这些化合物治疗细菌性疾病（如细菌感染）的方法。
• WO2008/14311
  申请人：——

  公开号：——

  公开（公告）日：——
• Design and structure–activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): Tetramic, tetronic acids and dihydropyridin-2-ones
  作者：Stefan Peukert、Yingchuan Sun、Rui Zhang、Brian Hurley、Mike Sabio、Xiaoyu Shen、Christen Gray、JoAnn Dzink-Fox、Jianshi Tao、Regina Cebula、Sompong Wattanasin

  DOI：10.1016/j.bmcl.2008.02.009

  日期：2008.3

  Based on a pharmacophore hypothesis substituted tetramic and tetronic acid 3-carboxamides as well as dihydropyridin-2-one- 3-carboxamides were investigated as inhibitors of undecaprenyl pyrophosphate synthase (UPPS) for use as novel antimicrobial agents. Synthesis and structure - activity relationship patterns for this class of compounds are discussed. Selectivity data and antibacterial activities for selected compounds are provided. (C) 2008 Elsevier Ltd. All rights reserved.