benzoxazinorifamycin | 7483-61-6

• 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: benzoxazinorifamycin
• 英文别名: (1²S,3E,5S,13E,15Z)-7t-acetoxy-1⁵,9c,11t-trihydroxy-5r-methoxy-1^2,4,6t,8c,10c,12t,16-heptamethyl-2-oxa-18-aza-1(2,7)-furo[2',3':5,6]benzo[1,2-a]phenoxazina-cyclooctadecaphane-3,13,15-triene-1^1,6,17-trione；4',O¹-didehydro-4'H-benzo[5',6'][1,4]oxazino[2',3':3,4]-4-deoxy-rifamycin；1',O¹-didehydro-rifamycin-VIII
• CAS: 7483-61-6
• 化学式: C₄₃H₄₈N₂O₁₂
• 分子量: 784.86
• InChiKey: VLTKOPTVHDUCOR-NBASAYNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  57.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  203.95
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  benzoxazinorifamycin 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (12S,5S)-7t-acetoxy-15,9c,11t-trihydroxy-5r-methoxy-12,4,6t,8c,10c,12t,16ξ-heptamethyl-2-oxa-18-aza-1(2,7)-furo[2',3':5,6]benzo[1,2-a]phenoxazina-cyclooctadecaphan-3t-ene-11,6,17-trione
  参考文献：
  名称：

  Zur Kenntnis von Rifamycin-S. Reaktionen des chinoiden Nucleus. Modifikationen von Antibiotica, 9. Mitteilung [1]

  摘要：

  AbstractThe reactivity of rifamycin‐S (1) with respect to nucleophilic reagents has been studied. Several new classes of derivatives, some of which show interesting biological activities, are described.

  DOI：

  10.1002/hlca.19730560720
• 作为产物：
  描述：

  利福霉素 、 2-氨基苯酚 以 苯 为溶剂， 生成 benzoxazinorifamycin
  参考文献：
  名称：

  Zur Kenntnis von Rifamycin-S. Reaktionen des chinoiden Nucleus. Modifikationen von Antibiotica, 9. Mitteilung [1]

  摘要：

  AbstractThe reactivity of rifamycin‐S (1) with respect to nucleophilic reagents has been studied. Several new classes of derivatives, some of which show interesting biological activities, are described.

  DOI：

  10.1002/hlca.19730560720

文献信息

• Synthesis and Biological Activity of 5'-Aminobenzoxazinorifamycin Derivatives.
  作者：Takehiko YAMANE、Takuji HASHIZUME、Katsuji YAMASHITA、Kazunori HOSOE、Takayoshi HIDAKA、Kiyoshi WATANABE、Hajime KAWAHARADA、Sukeyoshi KUDOH

  DOI：10.1248/cpb.40.2707

  日期：——

  Benzoxazinorifamycin reacted with various secondary amines to yield various 5'-substituted aminobenzoxazinorifamycin derivatives. The derivatives exhibited potent acitvities against gram-positive bacteria and mycobacteria. The antimicrobial activities of these compounds against Mycobacterium tuberculosis and Mycobacterium intracellulare were superior to those of rifampicin. Some of these compounds showed good plasma levels after oral administration in rats.

  苯并恶嗪orifamycin 与各种仲胺反应生成了各种 5'- 取代的氨基苯并恶嗪orifamycin 衍生物。这些衍生物对革兰氏阳性菌和分枝杆菌具有很强的抗菌活性。这些化合物对结核分枝杆菌和细胞内分枝杆菌的抗菌活性优于利福平。其中一些化合物在大鼠口服后显示出良好的血浆水平。
• Preparation and in vitro anti-staphylococcal activity of novel 11-deoxy-11-hydroxyiminorifamycins
  作者：Jing Li、Zhenkun Ma、Katrina Chapo、Dalai Yan、A. Simon Lynch、Charles Z. Ding

  DOI：10.1016/j.bmcl.2007.08.048

  日期：2007.10

  We report herein the preparation and anti-staphylococcal activity of a series of novel 11-deoxy-11-hydroxyiminorifamycins. Many of the compounds synthesized exhibit potent activity against wild-type Staphylococcus aureus with MICs equivalent to, or better than, rifamycin reference agents. In addition, some of the compounds retain potent activity against an intermediate rifamycin-resistant strain of Staphylococcus aureus. For instance, compound 5k exhibits an MIC of 0.12 mu g/mL against an intermediate rifamycin-resistant strain, while the rifamycin reference agents, rifampin and rifalazil, exhibit MICs of 16 mu g/mL and 2 mu g/mL, respectively, against the same strain. (c) 2007 Elsevier Ltd. All rights reserved.
• KONDO, XIDEHO;XASIDZUMEH, TAKUO;YAMANEH, TAKEHXIKO;YAMASITA, KATSUDZI;VAT+
  作者：KONDO, XIDEHO、XASIDZUMEH, TAKUO、YAMANEH, TAKEHXIKO、YAMASITA, KATSUDZI、VAT+

  DOI：——

  日期：——
• YAMANE, TAKEHIKO;HASHIZUME, TAKUJI;YAMASHITA, KATSUJI;WATANABE, KIYOSHI
  作者：YAMANE, TAKEHIKO、HASHIZUME, TAKUJI、YAMASHITA, KATSUJI、WATANABE, KIYOSHI

  DOI：——

  日期：——