N-hydroxy-1,3-thiazole-2-carboximidoyl chloride | 119496-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-hydroxy-1,3-thiazole-2-carboximidoyl chloride
• CAS: 119496-35-4
• 化学式: C₄H₃ClN₂OS
• 分子量: 162.6
• InChiKey: FOJSJCQTNBBOQB-UHFFFAOYSA-N

物化性质

• 沸点：
  320.5±25.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-hydroxy-1,3-thiazole-2-carboximidoyl chloride 、 3-丁炔-2-酮 在 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 1-(3-(thiazol-2-yl)isoxazol-5-yl)ethanone
  参考文献：
  名称：

  Substituted N-Phenyl-5-(2-(phenylamino)thiazol-4-yl)isoxazole-3-carboxamides Are Valuable Antitubercular Candidates that Evade Innate Efflux Machinery

  摘要：

  Tuberculosis remains one of the deadliest infectious diseases in the world, and the increased number of multidrug-resistant and extremely drug-resistant strains is a significant reason for concern. This makes the discovery of novel antitubercular agents a cogent priority. We have previously addressed this need by reporting a series of substituted 2-aminothiazoles capable to inhibit the growth of actively replicating, nonreplicating persistent, and resistant Mycobacterium tuberculosis strains. Clues from the structureactivity relationships lining up the antitubercular activity were exploited for the rational design of improved analogues. Two compounds, namely N-phenyl-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 7a and N-(pyridin-2-yl)-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 8a, were found to show high inhibitory activity toward susceptible M. tuberculosis strains, with an MIC90 of 0.1250.25 mu g/mL (0.330.66 mu M) and 0.060.125 mu g/mL (0.160.32 mu M), respectively. Moreover, they maintained good activity also toward resistant strains, and they were selective over other bacterial species and eukaryotic cells, metabolically stable, and apparently not susceptible to the action of efflux pumps.

  DOI：

  10.1021/acs.jmedchem.7b00793
• 作为产物：
  描述：

  thiazole-2-carbaldehyde oxime 在 N-氯代丁二酰亚胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-hydroxy-1,3-thiazole-2-carboximidoyl chloride
  参考文献：
  名称：

  Substituted N-Phenyl-5-(2-(phenylamino)thiazol-4-yl)isoxazole-3-carboxamides Are Valuable Antitubercular Candidates that Evade Innate Efflux Machinery

  摘要：

  Tuberculosis remains one of the deadliest infectious diseases in the world, and the increased number of multidrug-resistant and extremely drug-resistant strains is a significant reason for concern. This makes the discovery of novel antitubercular agents a cogent priority. We have previously addressed this need by reporting a series of substituted 2-aminothiazoles capable to inhibit the growth of actively replicating, nonreplicating persistent, and resistant Mycobacterium tuberculosis strains. Clues from the structureactivity relationships lining up the antitubercular activity were exploited for the rational design of improved analogues. Two compounds, namely N-phenyl-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 7a and N-(pyridin-2-yl)-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 8a, were found to show high inhibitory activity toward susceptible M. tuberculosis strains, with an MIC90 of 0.1250.25 mu g/mL (0.330.66 mu M) and 0.060.125 mu g/mL (0.160.32 mu M), respectively. Moreover, they maintained good activity also toward resistant strains, and they were selective over other bacterial species and eukaryotic cells, metabolically stable, and apparently not susceptible to the action of efflux pumps.

  DOI：

  10.1021/acs.jmedchem.7b00793

文献信息

• Diastereoselective nitrile oxide cycloadditions to chiral allyl ethers derived from 1,1-dithio-3-buten-2-ols
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1016/s0040-4020(01)86167-6

  日期：1988.1

  Highly diastereoselective cycloaddition of nitrile oxides to the title compounds gives masked polyfunctional products amenable to a variety of synthetic elaboration; an entry to enantiomerically pure derivatives is described.

  标题化合物对氮氧化物的高度非对映选择性环加成反应可得到适合各种合成工艺的掩盖多官能团产物。描述了对映体纯衍生物的条目。
• WO2006/109026
  申请人：——

  公开号：——

  公开（公告）日：——