25-deacetylrifabutin N-oxide | 122144-02-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 25-deacetylrifabutin N-oxide
• 英文别名: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E,21Z)-2,13,15,17-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-1'-oxidospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(31),2,4,9,19,21,25,29-octaene-28,4'-piperidin-1-ium]-6,23,32-trione
• CAS: 122144-02-9
• 化学式: C₄₄H₆₀N₄O₁₁
• 分子量: 820.981
• InChiKey: WDXSTPUXTMPWES-XGGSAYMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  59
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  214
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  25-O-desacetylrifabutin 在 Oxone 、 苄基三乙基氯化铵 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 以19.1%的产率得到25-deacetylrifabutin N-oxide
  参考文献：
  名称：

  Synthesis and evaluation of rifabutin analogs against Mycobacterium avium and H37Rv, MDR and NRP Mycobacterium tuberculosis

  摘要：

  Clinical utility of rifabutin 1 (RBT), a potent antibiotic used in multidrug regimens for tuberculosis (TB) as well as for infections caused by Mycobacterium avium complex (MAC), has been hampered due to dose-limiting toxicity. RBT analogs 2-11 were synthesized and evaluated against M. avium 1581 and Mycobacterium tuberculosis susceptible and resistant strains in vitro. A selection of candidates were also assayed against non-replicating persistent (NRP) M. tuberculosis. Subsequent in vivo studies with the best preclinical candidate drugs 5 and 8, in a model of progressive pulmonary tuberculosis of Balb/C mice infected either with H(37)Rv drug-sensible strain or with multidrug resistant (MDR) clinical isolates, resistant to all primary antibiotics including rifampicin, were performed. The results disclosed here suggest that 5 and 8 have potential for clinical application. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.006