Orn-5-benzyloxymulundocandin | 321660-96-2

• 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
• 英文名称: Orn-5-benzyloxymulundocandin
• CAS: 321660-96-2
• 化学式: C₅₅H₈₃N₇O₁₆
• 分子量: 1098.3
• InChiKey: VTFWAVBTSWUOLP-YRTJWVAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.36
• 重原子数：
  78.0
• 可旋转键数：
  21.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  357.19
• 氢给体数：
  13.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  4-哌啶基哌啶 、 聚合甲醛 、 Orn-5-benzyloxymulundocandin 以 1,4-二氧六环 为溶剂， 生成 N1-[(6S,9S,14aS,15S,16S,20S,23S,25aS,2R,11R)-23-((1S,2S)-2-(3-(4-(1-azinanyl)-1-azinanylmethyl)-4-hydroxyphenyl)-1,2-dihydroxyethyl)-12-benzyloxy-2,11,15-trihydroxy-6-((1R)-1-hydroxyethyl)-20-hydroxymethyl-16-methyl-5,8,14,19,22,25-hexaoxoperhydrodiazolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-12-methyltetradecanamide
  参考文献：
  名称：

  Mannich reaction: an approach for the synthesis of water soluble mulundocandin analogues

  摘要：

  Semisynthetic modifications at Hydroxy tyrosine (Htyr) unit of mulundocandin (1) were carried out to improve its aqueous solubility. A single step introduction of substituted aminomethyl groups at the ortho position(s) of phenolic hydroxyl of HTyr unit of mulundocandin has been achieved in 7-85% yield. The in vitro screening of Mannich products against Candida albicans and Aspergillus fumigatus, retained the in vivo activity of parent by oral and intraperitoneal route. Compound 20, showed significant improvement in activity over mulundocandin (1) and activity compares well with that of fluconazole. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.015
• 作为产物：
  描述：

  苯甲醇 、 mulundocandin 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以67.1%的产率得到Orn-5-benzyloxymulundocandin
  参考文献：
  名称：

  Semisynthetic modifications of hemiaminal function at ornithine unit of mulundocandin, towards chemical stability and antifungal activity

  摘要：

  Mulundocandin (1), is an echinocandin class of lipopeptide. It has wide spectrum of antifungal activity against Candida and Aspergillus species. Semisynthetic modification at Ornithine-5-hydroxyl (hemiaminal function) of 1 was carried out to improve solution stability and hence in vivo activity. Synthesis of ether (C-OR), thioether (C-SR) and C-N linkage at hemiaminal function have been described. All synthetic analogues were evaluated for their stability in aqueous solution and found to be more stable than mulundocandin. Antifungal activity of Orn-5 analogues was evaluated both in vitro against Candida albicans and Aspergillus famigatus by agar well method and in vivo (oral and intraperitoneal) in C. albicans infected Swiss mice. Results of in vivo assays of analogues 2-9 by the oral route suggests that the introduction of either oxygen nucleophiles (-OR) or sulphur nucleophiles (-SR), at either Orn-5 or at both Orn-5 and HTyr-4 positions, results in retaining the activity of the parent compound with improved aqueous stability in most cases. Compound 9 has shown improved antifungal activity in comparison to mulundocandin by oral application in Swiss mice. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.003

文献信息

• Approaches towards the stabilization of hemiaminal function at ornithine unit of mulundocandin
  作者：Bansi Lal、Vitthal Genbhau Gund

  DOI：10.1016/j.bmcl.2003.12.084

  日期：2004.3

  Semisynthetic modifications at position-12 (ornithine-5-position, hemiaminal function) of mulundocandin were carried out to improve its chemical stability. New carbon-carbon (C-C) and carbon-hydrogen (C-H) linkage at hemiaminal function -12 has been achieved. Lewis acid catalyzed introduction of electron rich aryl group at position-12 of mulundocandin is developed. Synthesized mulundocandin analogues were evaluated for their chemical stability and antifungal activity against C. albicans and A. fumigatus. (C) 2004 Elsevier Ltd. All rights reserved.