5-[(pyridin-2-ylthio)methyl]isoxazole-4-carboxylic acid | 1027781-92-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-[(pyridin-2-ylthio)methyl]isoxazole-4-carboxylic acid
• 英文别名: 5-(Pyridin-2-ylsulfanylmethyl)-1,2-oxazole-4-carboxylic acid；5-(pyridin-2-ylsulfanylmethyl)-1,2-oxazole-4-carboxylic acid
• CAS: 1027781-92-5
• 化学式: C₁₀H₈N₂O₃S
• 分子量: 236.251
• InChiKey: CLWVGBDRXTXJDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[(pyridin-2-ylthio)methyl]isoxazole-4-carboxylic acid 、 五氟苯酚 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以69%的产率得到pentafluorophenyl 5-[(pyridin-2-ylthio)methyl]isoxazole-4-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of Novel Uracil Polyoxin C Conjugates as Substrate Analogues of Chitin Synthase

  摘要：

  Stereoselective syntheses of both the natural (C5'-S) and unnatural (C5'-R) diastereoisomers of uracil polyoxin C methyl ester have been developed. The key stereocontrolled step involves nucleophilic addition of trimethylsilyl cyanide to the appropriate chiral sulfinimine derived from 2',3'-protected 5'-formyluridine and (S)-(-)-tert-butanesulfinamide or (R)-(+)-tert-butanesulfinamide, respectively. A variety of substrate mimics designed to function as inhibitors of chitin synthase have been synthesized by conjugation of the methyl ester of uracil polyoxin C (UPOC) with activated isoxazole carboxylic acids. Amide bond formation was accomplished via coupling of the amino functionality of UPOC methyl ester with a free isoxazole acid using HBTU or alternatively an isoxazole pentafluorophenyl ester. The substrate mimics incorporate features of the nucleoside-peptide antibiotics, the polyoxins and the nikkomycins, as well as features of the transition state structure expected during polymerization of the natural chitin synthase substrate uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc), namely, a metal-binding site and glycosyl oxocarbenium ion mimic.

  DOI：

  10.1021/jo702564y
• 作为产物：
  描述：

  methyl 5-[(pyridin-2-ylthio)methyl]isoxazole-4-carboxylate 在 盐酸 、 溶剂黄146 作用下， 反应 24.0h， 以2.02 g的产率得到5-[(pyridin-2-ylthio)methyl]isoxazole-4-carboxylic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Novel Uracil Polyoxin C Conjugates as Substrate Analogues of Chitin Synthase

  摘要：

  Stereoselective syntheses of both the natural (C5'-S) and unnatural (C5'-R) diastereoisomers of uracil polyoxin C methyl ester have been developed. The key stereocontrolled step involves nucleophilic addition of trimethylsilyl cyanide to the appropriate chiral sulfinimine derived from 2',3'-protected 5'-formyluridine and (S)-(-)-tert-butanesulfinamide or (R)-(+)-tert-butanesulfinamide, respectively. A variety of substrate mimics designed to function as inhibitors of chitin synthase have been synthesized by conjugation of the methyl ester of uracil polyoxin C (UPOC) with activated isoxazole carboxylic acids. Amide bond formation was accomplished via coupling of the amino functionality of UPOC methyl ester with a free isoxazole acid using HBTU or alternatively an isoxazole pentafluorophenyl ester. The substrate mimics incorporate features of the nucleoside-peptide antibiotics, the polyoxins and the nikkomycins, as well as features of the transition state structure expected during polymerization of the natural chitin synthase substrate uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc), namely, a metal-binding site and glycosyl oxocarbenium ion mimic.

  DOI：

  10.1021/jo702564y

文献信息

• Application of the Ugi Reaction for the One-Pot Synthesis of Uracil Polyoxin C Analogues
  作者：Andrew Plant、Peter Thompson、David M. Williams

  DOI：10.1021/jo900244m

  日期：2009.7.3

  of uracil polyoxin C (UPOC) methyl ester using the Ugi reaction is described. The four components employed in the Ugi reaction are 2′,3′-isopropylidine-protected uridine-5′-aldehyde, 2,4-dimethoxybenzylamine, an isoxazolecarboxylic acid, and the convertible isonitrile N-(2-[(tert-butyldimethylsilyl)oxy]methyl}phenyl)carbonitrile. Following the Ugi reaction, treatment with HCl in MeOH achieves deprotection

  描述了使用Ugi反应简单，两步合成尿嘧啶多氧合酶C（UPOC）甲酯的酰胺衍生物的方法。Ugi反应中使用的四个组分是2'，3'-异丙基吡啶保护的尿苷5'-醛，2,4-二甲氧基苄胺，异恶唑羧酸和可转换的异腈N-（2-[（叔丁基二甲基甲硅烷基）氧基]甲基}苯基）腈。在Ugi反应之后，用HCl在MeOH中的溶液处理可实现异亚丙基和N-苄基的脱保护，并将异腈衍生的酰胺（Ugi产物）转化为相应的甲酯。该程序适用于与多恶英和尼克霉素核苷肽抗生素相关的新型化合物的自动多平行合成。
• Stereoselective Synthesis of Novel Uracil Polyoxin C Conjugates as Substrate Analogues of Chitin Synthase
  作者：Andrew Plant、Peter Thompson、David M. Williams

  DOI：10.1021/jo702564y

  日期：2008.5.1

  Stereoselective syntheses of both the natural (C5'-S) and unnatural (C5'-R) diastereoisomers of uracil polyoxin C methyl ester have been developed. The key stereocontrolled step involves nucleophilic addition of trimethylsilyl cyanide to the appropriate chiral sulfinimine derived from 2',3'-protected 5'-formyluridine and (S)-(-)-tert-butanesulfinamide or (R)-(+)-tert-butanesulfinamide, respectively. A variety of substrate mimics designed to function as inhibitors of chitin synthase have been synthesized by conjugation of the methyl ester of uracil polyoxin C (UPOC) with activated isoxazole carboxylic acids. Amide bond formation was accomplished via coupling of the amino functionality of UPOC methyl ester with a free isoxazole acid using HBTU or alternatively an isoxazole pentafluorophenyl ester. The substrate mimics incorporate features of the nucleoside-peptide antibiotics, the polyoxins and the nikkomycins, as well as features of the transition state structure expected during polymerization of the natural chitin synthase substrate uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc), namely, a metal-binding site and glycosyl oxocarbenium ion mimic.