4-噁唑烷羧酸

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4-噁唑烷羧酸
• 中文别名: 恶唑烷-4-羧酸
• 英文名称: oxazolidine-4-carboxylic acid
• 英文别名: 1,3-oxazolidine-4-carboxylic acid；oxaproline；1,3-oxazolidin-3-ium-4-carboxylate
• 化学式: C₄H₇NO₃
• 分子量: 117.104
• InChiKey: XFZIPCXDWCWTCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-二硫二苯甲酰氯 、 4-噁唑烷羧酸 在 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 3-[2-[[2-(4-Carboxy-1,3-oxazolidine-3-carbonyl)phenyl]disulfanyl]benzoyl]-1,3-oxazolidine-4-carboxylic acid
  参考文献：
  名称：

  Thiazolothiazepine Inhibitors of HIV-1 Integrase

  摘要：

  A series of thiazolothiazepines were prepared and tested against purified human immunodeficiency virus type-1 integrase (HIV-1 IN) and viral replication. Structure-activity studies reveal that the compounds possessing the pentatomic moiety SC(O)CNC(O) with two carbonyl groups are in general more potent against purified IN than those containing only one carbonyl group. Substitution with electron-donating or -withdrawing groups did not enhance nor abolish potency against purified IN. By contrast, compounds with a naphthalene ring system showed enhanced potency, suggesting that a hydrophobic pocket in the IN active site might accommodate an aromatic system rather than a halogen. The position of sulfur in the thiazole ring appears important for potency against IN, as its replacement with an oxygen or carbon abolished activity. Further extension of the thiazole ring diminished potency. Compounds 1, 19, and 20 showed antiviral activity and inhibited IN within similar concentrations. These compounds inhibited IN when Mn2+ or Mg2+ was used as cofactor. None of these compounds showed detectable activities against HIV-1 reverse transcriptase, protease, virus attachment, or nucleocapsid protein zinc fingers. Therefore, thiazolothiazepines are potentially important lead compounds for development as inhibitors of IN and HIV replication.

  DOI：

  10.1021/jm990047z
• 作为产物：
  描述：

  聚合甲醛 、 DL-丝氨酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 4-噁唑烷羧酸
  参考文献：
  名称：

  制备3,4-二取代的1,3-恶唑烷和1,2,5-三取代的咪唑啉丁-4-酮的简便方法

  摘要：

  轻便，可替代的合成路线6，（R）-6-，和（S）-6- -3-苄基- ñ - （2,6-二甲基苯基）-1,3-恶唑烷-4-甲酰胺（6），手性报道了托卡尼的恶唑烷衍生物。本文所述的合成路线还提供了11 -，（R）-11-和12，它们具有咪唑啉丁-4-酮核心，属于一类对其生物学活性感兴趣的化合物。所有最终化合物和中间体均得到了充分表征。对映体过量的同型手性6和11用2-羟丙基-β-环糊精或高度硫酸化的γ-环糊精作为手性选择剂，通过毛细管电泳分析确定。J.杂环化​​学。（2010）

  DOI：

  10.1002/jhet.536

文献信息

• Facile routes for the preparation of 3,4-disubstituted 1,3-oxazolidines and 1,2,5-trisubstituted imidazolidin-4-ones
  作者：Alessia Catalano、Alessia Carocci、Giovanni Lentini、Antonia Di Mola、Claudio Bruno、Carlo Franchini

  DOI：10.1002/jhet.536

  日期：2011.3

  Facile, alternative synthetic routes to 6, (R)‐6, and (S)‐6‐3‐benzyl‐N‐(2,6‐dimethylphenyl)‐1,3‐oxazolidine‐4‐carboxamides (6), a chiral oxazolidine derivative of tocainide, are reported. The synthetic routes described herein also afforded 11‐, (R)‐11‐, and 12, which present the imidazolidin‐4‐one core and belong to a class of compounds interesting for their biological activities. All the final compounds

  轻便，可替代的合成路线6，（R）-6-，和（S）-6- -3-苄基- ñ - （2,6-二甲基苯基）-1,3-恶唑烷-4-甲酰胺（6），手性报道了托卡尼的恶唑烷衍生物。本文所述的合成路线还提供了11 -，（R）-11-和12，它们具有咪唑啉丁-4-酮核心，属于一类对其生物学活性感兴趣的化合物。所有最终化合物和中间体均得到了充分表征。对映体过量的同型手性6和11用2-羟丙基-β-环糊精或高度硫酸化的γ-环糊精作为手性选择剂，通过毛细管电泳分析确定。J.杂环化​​学。（2010）
• Thiazolothiazepine Inhibitors of HIV-1 Integrase
  作者：Nouri Neamati、Jim A. Turpin、Heather E. Winslow、John L. Christensen、Karen Williamson、Ann Orr、William G. Rice、Yves Pommier、Antonio Garofalo、Antonella Brizzi、Giuseppe Campiani、Isabella Fiorini、Vito Nacci

  DOI：10.1021/jm990047z

  日期：1999.8.1

  A series of thiazolothiazepines were prepared and tested against purified human immunodeficiency virus type-1 integrase (HIV-1 IN) and viral replication. Structure-activity studies reveal that the compounds possessing the pentatomic moiety SC(O)CNC(O) with two carbonyl groups are in general more potent against purified IN than those containing only one carbonyl group. Substitution with electron-donating or -withdrawing groups did not enhance nor abolish potency against purified IN. By contrast, compounds with a naphthalene ring system showed enhanced potency, suggesting that a hydrophobic pocket in the IN active site might accommodate an aromatic system rather than a halogen. The position of sulfur in the thiazole ring appears important for potency against IN, as its replacement with an oxygen or carbon abolished activity. Further extension of the thiazole ring diminished potency. Compounds 1, 19, and 20 showed antiviral activity and inhibited IN within similar concentrations. These compounds inhibited IN when Mn2+ or Mg2+ was used as cofactor. None of these compounds showed detectable activities against HIV-1 reverse transcriptase, protease, virus attachment, or nucleocapsid protein zinc fingers. Therefore, thiazolothiazepines are potentially important lead compounds for development as inhibitors of IN and HIV replication.