clitidine | 63592-84-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: clitidine
• 英文别名: Clitidin；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyridine-3-carboxylic acid
• CAS: 63592-84-7
• 化学式: C₁₁H₁₄N₂O₆
• 分子量: 270.242
• InChiKey: FYEBWHCXONMZDU-ZYUZMQFOSA-N

物化性质

• 沸点：
  549.3±50.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  134
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  clitidine 在 吡啶 、 水 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以40%的产率得到clitidine 5'-mononucleotide
  参考文献：
  名称：

  Clitidine 5′-mononucleotide, a toxic pyridine nucleotide from Clitocybe acromelalga

  摘要：

  A new toxic pyridine nucleotide, clitidine 5'-mononucleotide, was isolated from the toadstool Clitocybe acromelalga and its structure was deduced from spectral data and confirmed by chemical conversions. Its occurrence helps to elucidate the biogenesis of clitidine.

  DOI：

  10.1016/s0031-9422(00)90634-4
• 作为产物：
  描述：

  β-烟酰胺腺嘌呤二核苷酸 在 ammonium hydroxide 、 5'-nucleotidase 、 p-g-Grain NADase 、 三羟甲基氨基甲烷盐酸盐 、 magnesium chloride 作用下， 反应 42.0h， 生成 clitidine
  参考文献：
  名称：

  Enzymatic Synthesis of New Pyridine Nucleosides. Clitidine and Its Amide Derivative

  摘要：

  两种β-NAD类似物是通过猪脑NAD酶催化的碱基交换反应制备的。这些类似物被证实含有甲基1,4-二氢-4-亚氮喹啉酸盐和1,4-二氢-4-亚氮喹啉胺基团。通过对这些类似物进行连续的水解降解，获得了具有3-羧基和3-氨基甲酰基的1,4-二氢-4-亚氮吡啶β-核糖苷，产率很好。前一种化合物与最近从毒蘑菇分离出的毒性吡啶核苷克利替定相同。本次合成确认了克利替定的1,4-二氢-4-亚氮β-核糖苷结构。初步生物测试表明，3-氨基甲酰基化合物的毒性高于克利替定，这表明克利替定的酰胺衍生物是在毒蘑菇中的一种重要毒性物质。

  DOI：

  10.1246/bcsj.54.212

文献信息

• Clitidine, a new toxic pyridine nucleoside from clitocybe acromelalga
  作者：K. Konno、K. Hayano、H. Shirahama、H. Saito、T. Matsumoto

  DOI：10.1016/0040-4020(82)80107-5

  日期：1982.1

  From a poisonous mushroom, Clitocybe acromelalga, a new nucleoside clitidine (1) was isolated as a toxic principle. The structure was deduced to be 1 from spectral data and chemical degradation studies. Synthesis of 1 through condensation of methyl 4-aminonicotinate with 3, 5-di-O-benzoyl-D-ribofuranosyl chloride confirmed the structure, including absolute configuration.

  从有毒蘑菇Clitocybe acromelalga中分离出一种新的核苷可力丁（1）作为有毒成分。根据光谱数据和化学降解研究推导该结构为1。通过4-氨基烟酸甲酯与3，5-二-O-苯甲酰基-D-呋喃呋喃糖基氯的缩合反应合成1，证实了其结构，包括绝对构型。
• Enzymatic Synthesis of New Pyridine Nucleosides. Clitidine and Its Amide Derivative
  作者：Shuichi Tono-oka、Yasuhiko Sasahara、Akio Sasaki、Haruhisa Shirahama、Takeshi Matsumoto、Shichiro Kakimoto

  DOI：10.1246/bcsj.54.212

  日期：1981.1

  Two β-NAD-analogs were prepared utilizing a base-exchange reaction catalyzed by pig-brain NADase. These analogs were proved to contain a methyl 1,4-dihydro-4-iminonicotinate and a 1,4-dihydro-4-iminonicotinamide moiety. By successive hydrolytic degradations of these analogs, 1,4-dihydro-4-iminopyridine β-ribosides with 3-carboxyl and 3-carbamoyl groups were prepared in good yields. The former compound was identical with clitidine, a toxic pyridine nucleoside recently isolated from a toadstool. The present synthesis confirmed the 1,4-dihydro-4-imino β-riboside structure of clitidine. Preliminary biological tests showed that the 3-carbamoyl compound was more toxic than clitidine, suggesting that the amide derivative of clitidine is an essential toxic substance in the toadstool.

  两种β-NAD类似物是通过猪脑NAD酶催化的碱基交换反应制备的。这些类似物被证实含有甲基1,4-二氢-4-亚氮喹啉酸盐和1,4-二氢-4-亚氮喹啉胺基团。通过对这些类似物进行连续的水解降解，获得了具有3-羧基和3-氨基甲酰基的1,4-二氢-4-亚氮吡啶β-核糖苷，产率很好。前一种化合物与最近从毒蘑菇分离出的毒性吡啶核苷克利替定相同。本次合成确认了克利替定的1,4-二氢-4-亚氮β-核糖苷结构。初步生物测试表明，3-氨基甲酰基化合物的毒性高于克利替定，这表明克利替定的酰胺衍生物是在毒蘑菇中的一种重要毒性物质。
• Clitidine 5′-mononucleotide, a toxic pyridine nucleotide from Clitocybe acromelalga
  作者：Kimiaki Yamano、Haruhisa Shirahama

  DOI：10.1016/s0031-9422(00)90634-4

  日期：1994.3

  A new toxic pyridine nucleotide, clitidine 5'-mononucleotide, was isolated from the toadstool Clitocybe acromelalga and its structure was deduced from spectral data and confirmed by chemical conversions. Its occurrence helps to elucidate the biogenesis of clitidine.