CJ-14,877

• 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: CJ-14,877
• 英文别名: Methyl 5-[(1S,2S)-1,2-dihydroxypropyl]pyridine-2-carboxylate
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: XZXCYBBAXJQLFQ-IMTBSYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  79.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  CJ-14,877 在 lithium hydroxide 作用下， 反应 1.0h， 以5 mg的产率得到5-((1S,2S)-1,2-Dihydroxy-propyl)-pyridine-2-carboxylic acid
  参考文献：
  名称：

  Novel Cytokine Production Inhibitors Produced by a Basidiomycete, Marasmiellus sp.

  摘要：

  新的细胞因子产生抑制剂 CJ-14, 877 (I) 和 CJ-14, 897 (II) 是从担子菌 Marasmiellus sp. 的发酵液中分离出来的。 CL21624。其结构确定为甲基-(7R,8S)-5-(7,8-二羟丙基)吡啶-2-羧酸酯和甲基(7R,8S)-5-(8-乙酰氧基-7-羟丙基)吡啶-2 -羧酸盐，分别通过光谱分析。这些化合物对人全血中脂多糖诱导的白介素-1β和肿瘤坏死因子-a的产生具有抑制活性，IC50值范围为0.059至2.6 JUM。

  DOI：

  10.7164/antibiotics.54.703
• 作为产物：
  描述：

  (E)-methyl 5-(prop-1-en-1-yl)picolinate 在 乙酰胺 、 asymmetric dihydroxylation-mix-α 作用下， 以 水 、 叔丁醇 为溶剂， 反应 6.0h， 以100%的产率得到CJ-14,877
  参考文献：
  名称：

  First asymmetric synthesis of CJ-14877 and its enantiomer and their interleukin-1β inhibitory activities

  摘要：

  A potent antiinflammatory methyl picolinate alkaloid CJ-14877 [(+)-1] and its enantiomer (-)-1 were synthesized in two steps starting from commercially available methyl 5-bromopicolinate. The synthesis includes microwave-assisted Suzuki coupling reaction and Sharpless asymmetric dihydroxylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.064

文献信息

• Novel Cytokine Production Inhibitors Produced by a Basidiomycete, Marasmiellus sp.
  作者：KATSUOMI ICHIKAWA、HIDEO HIRAI、MASARU ISHIGURO、TAKAHITO KAMBARA、YOSHINAO KATO、YOON JEONG KIM、YASUHIRO KOJIMA、YASUE MATSUNAGA、HLROYUKI NLSHIDA、YUKIO SHIOMI、NOBUJI YOSHIKAWA、NAKAO KOJIMA

  DOI：10.7164/antibiotics.54.703

  日期：——

  New cytokine production inhibitors, CJ-14, 877 (I) and CJ-14, 897 (II), were isolated from the fermentation broth of a basidiomycete, Marasmiellus sp. CL21624. Their structures were determined to be methyl-(7R, 8S)-5-(7, 8-dihydroxypropyl)pyridine-2-carboxylate and methyl(7R, 8S)-5-(8-acetoxy-7-hydroxypropyl)pyridme-2-carboxylate, respectively, by spectroscopic analyses. These compounds showed inhibitory activities for lipopolysaccharide-induced production of interleukin-1β and tumor necrosis factor-a in human whole blood with IC50 values of the range from 0.059 to 2.6 JUM.

  新的细胞因子产生抑制剂 CJ-14, 877 (I) 和 CJ-14, 897 (II) 是从担子菌 Marasmiellus sp. 的发酵液中分离出来的。 CL21624。其结构确定为甲基-(7R,8S)-5-(7,8-二羟丙基)吡啶-2-羧酸酯和甲基(7R,8S)-5-(8-乙酰氧基-7-羟丙基)吡啶-2 -羧酸盐，分别通过光谱分析。这些化合物对人全血中脂多糖诱导的白介素-1β和肿瘤坏死因子-a的产生具有抑制活性，IC50值范围为0.059至2.6 JUM。
• First asymmetric synthesis of CJ-14877 and its enantiomer and their interleukin-1β inhibitory activities
  作者：Yutaka Aoyagi、Yoshiyuki Adachi、Shunta Akagi、Naohito Ohno、Koichi Takeya

  DOI：10.1016/j.bmcl.2009.02.064

  日期：2009.4

  A potent antiinflammatory methyl picolinate alkaloid CJ-14877 [(+)-1] and its enantiomer (-)-1 were synthesized in two steps starting from commercially available methyl 5-bromopicolinate. The synthesis includes microwave-assisted Suzuki coupling reaction and Sharpless asymmetric dihydroxylation. (C) 2009 Elsevier Ltd. All rights reserved.