N'-palmitoyl-rifabutin | 1134783-46-2

• 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: N'-palmitoyl-rifabutin
• 英文别名: N-palmitoylrifabutin；[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-27-hexadecanoyl-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23,32-trioxospiro[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'-piperidine]-13-yl] acetate
• CAS: 1134783-46-2
• 化学式: C₆₂H₉₂N₄O₁₂
• 分子量: 1085.43
• InChiKey: XFWLKISFKGKUTB-ZZOVXKQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  78
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  214
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  rifabutin 、 棕榈酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到N'-palmitoyl-rifabutin
  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

文献信息

• Synthesis and evaluation of rifabutin analogs against Mycobacterium avium and H37Rv, MDR and NRP Mycobacterium tuberculosis
  作者：Ricardo Figueiredo、Cristina Moiteiro、M. Augusta Medeiros、P. Almeida da Silva、D. Ramos、F. Spies、M.O. Ribeiro、M. Cristina S. Lourenço、I.N. Júnior、M. Manuela Gaspar、M. Eugénia M. Cruz、M. João Marcelo Curto、S.G. Franzblau、H. Orozco、D. Aguilar、R. Hernandez-Pando、M. Céu Costa

  DOI：10.1016/j.bmc.2008.12.006

  日期：2009.1

  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.