tert-butyl (R)-(4-((2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methoxy)phenyl)carbamate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (R)-(4-((2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methoxy)phenyl)carbamate
• 英文别名: [(2R)-2-[[4-(tert-butoxycarbonylamino)phenoxy]methyl]-2-methyl-3H-imidazo[2,1-b]oxazol-6-yl]azinic acid；tert-butyl N-[4-[[(2R)-2-methyl-6-nitro-3H-imidazo[2,1-b][1,3]oxazol-2-yl]methoxy]phenyl]carbamate
• 化学式: C₁₈H₂₂N₄O₆
• 分子量: 390.396
• InChiKey: CBNKLXGVVATWPF-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-(4-((2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methoxy)phenyl)carbamate 、 对甲苯异硫氰酸酯 在 三氟乙酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-1-(4-((2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methoxy)phenyl)-3-(p-tolyl)thiourea
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Polar Functionalities Containing Nitrodihydroimidazooxazoles as Anti-TB Agents

  摘要：

  Novel polar functionalities containing 6-nitro-2,3-dihydroimidazooxazole (NHIO) analogues were synthesized to produce a compound with enhanced solubility. Polar functionalities including sulfonyl, uridyl, and thiouridyl-bearing NHIO analogues were synthesized and evaluated against Mycobacterium tuberculosis (MTB) H(37)Rv. The aqueous solubility of compounds with MIC values <= 0.5 mu g/mL were tested, and six compounds showed enhanced aqueous solubility. The best six compounds were further tested against resistant (Rif(R) and MDR) and dormant strains of MTB and tested for cytotoxicity in HepG2 cell line. Based on its overall in vitro characteristics and solubility profile, compound 6d was further shown to possess high microsomal stability, solubility under all tested biological conditions (PBS, SGF and SIF), and favorable oral in vivo pharmacokinetics and in vivo efficacy.

  DOI：

  10.1021/acsmedchemlett.5b00202
• 作为产物：
  描述：

  (R)-2-氯-1-(2-甲基环氧乙烷-2-基甲基)-4-硝基咪唑 、 4-(BOC-氨基)酚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以35%的产率得到tert-butyl (R)-(4-((2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methoxy)phenyl)carbamate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Polar Functionalities Containing Nitrodihydroimidazooxazoles as Anti-TB Agents

  摘要：

  Novel polar functionalities containing 6-nitro-2,3-dihydroimidazooxazole (NHIO) analogues were synthesized to produce a compound with enhanced solubility. Polar functionalities including sulfonyl, uridyl, and thiouridyl-bearing NHIO analogues were synthesized and evaluated against Mycobacterium tuberculosis (MTB) H(37)Rv. The aqueous solubility of compounds with MIC values <= 0.5 mu g/mL were tested, and six compounds showed enhanced aqueous solubility. The best six compounds were further tested against resistant (Rif(R) and MDR) and dormant strains of MTB and tested for cytotoxicity in HepG2 cell line. Based on its overall in vitro characteristics and solubility profile, compound 6d was further shown to possess high microsomal stability, solubility under all tested biological conditions (PBS, SGF and SIF), and favorable oral in vivo pharmacokinetics and in vivo efficacy.

  DOI：

  10.1021/acsmedchemlett.5b00202