macbecin II | 73341-73-8

• 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: macbecin II
• 英文别名: [(4E,6Z,8S,9R,10E,12S,13R,14S,16S,17R)-20,22-dihydroxy-13,14,17-trimethoxy-4,8,10,12,16-pentamethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl] carbamate
• CAS: 73341-73-8
• 化学式: C₃₀H₄₄N₂O₈
• 分子量: 560.688
• InChiKey: SVSFCSOFEPJFSF-BMJWZTMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  150
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  macbecin II 在 吡啶 、 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 生成 Acetic acid (4E,6Z,9E)-(8S,11S,12S,13R,14S,16S,17R)-20-acetoxy-11,13,14,17-tetramethoxy-4,8,10,12,16-pentamethyl-3-oxo-2-aza-bicyclo[16.3.1]docosa-1(22),4,6,9,18,20-hexaen-22-yl ester
  参考文献：
  名称：

  Macbecin I和II的结构：新型抗肿瘤抗生素

  摘要：

  通过氧化-还原关系UV显示，Macbecin I 1，C 30 H 42 N 2 O 8和Macbecin II 2，C 30 H 44 N 2 O 8是2，6-二取代的苯醌和对苯二酚衍生物。1 H和13 C NMR谱。的碱性甲醇分解1，得到2-氨基苯醌衍生物5，这意味着一个柄型结构为1，和的酸水解1得到decarbamoyl产品9，10和图11表示氨基甲酰氧基在烯丙基位置的位置。旋上解耦研究1，3和5阐明了部分结构[甲]，[乙]，[ C ^ ]和[ d ]。从它们的相互配置中，提出了两个结构1a和1b，其中根据氧化降解产物12的结构从1a中选择了1a作为结构1。对1的溴乙酰基衍生物进行X射线分析证实了上述结构，并确定了1的绝对立体化学。1和2。

  DOI：

  10.1016/s0040-4020(01)92041-1
• 作为产物：
  描述：

  [(2R,3S,6S,7R,8E,11S,12Z,14E)-2,5,6-三甲氧基-3,7,9,11,15-五甲基-16,20,22-三氧代-17-氮杂双环[16.3.1]二十二-1(21),8,12,14,18-五烯-10-基]氨基甲酸酯 在 sodium dithionite 作用下， 生成 macbecin II
  参考文献：
  名称：

  Macbecin I和II的结构：新型抗肿瘤抗生素

  摘要：

  通过氧化-还原关系UV显示，Macbecin I 1，C 30 H 42 N 2 O 8和Macbecin II 2，C 30 H 44 N 2 O 8是2，6-二取代的苯醌和对苯二酚衍生物。1 H和13 C NMR谱。的碱性甲醇分解1，得到2-氨基苯醌衍生物5，这意味着一个柄型结构为1，和的酸水解1得到decarbamoyl产品9，10和图11表示氨基甲酰氧基在烯丙基位置的位置。旋上解耦研究1，3和5阐明了部分结构[甲]，[乙]，[ C ^ ]和[ d ]。从它们的相互配置中，提出了两个结构1a和1b，其中根据氧化降解产物12的结构从1a中选择了1a作为结构1。对1的溴乙酰基衍生物进行X射线分析证实了上述结构，并确定了1的绝对立体化学。1和2。

  DOI：

  10.1016/s0040-4020(01)92041-1

文献信息

• Macrolactams by engineered biosynthesis
  申请人：Ashley Gary W.

  公开号：US20080188450A1

  公开（公告）日：2008-08-07

  Macrolactams are made by feeding aromatic amino acids as replacement starter units to a mutant strain of the geldanamycin-producing microorganism Streptomyces hygroscopicus var. geldanus NRRL 3602, wherein the gene cluster encoding enzymes for the biosynthesis of the natural starter unit 3-amino-5-hydroxybenzoic acid has been deleted.

  大环内酰胺是通过将芳香族氨基酸作为替代起始单元供应给生产格尔达霉素的微生物链霉菌属湿生链霉菌格尔达努斯NRRL 3602的突变菌株制备的，其中编码天然起始单元3-氨基-5-羟基苯甲酸生物合成酶的基因簇已被删除。
• Novel Compounds and Methods for Their Production
  申请人：Gaisser Sabine

  公开号：US20090117127A1

  公开（公告）日：2009-05-07

  The present invention relates to 11-O-desmethylmacbecin analogues that are useful, e.g. in the treatment of cancer, B-cell malignancies, malaria, fungal infection, diseases of the central nervous system and neurodegenerative diseases, diseases dependent on angiogenesis, autoimmune diseases and/or as a prophylactic pretreatment for cancer. The present invention also provides methods for the production of these compounds and their use in medicine, in particular in the treatment and/or prophylaxis of cancer or B-cell malignancies.
• 21-DEOXYMACBECIN ANALOGUES USEFUL AS ANTITUMOR AGENTS
  申请人：Martin Christine Janet

  公开号：US20090209494A1

  公开（公告）日：2009-08-20

  The present invention relates to 21-deoxymacbecin analogues that are useful, e.g. in the treatment of cancer, B-cell malignancies, malaria, fungal infection, diseases of the central nervous system and neurodegenerative diseases, diseases dependent on angiogenesis, autoimmune diseases or as a prophylactic pretreatment for cancer. The present invention also provides methods for the production of these compounds and their use in medicine, in particular in the treatment and or prophylaxis of cancer or B-cell malignancies.
• 15-O-Desmethylmacbecin Derivatives and Their Use in the Treatment of Cancer or B-Cell Malignancies
  申请人：Gaisser Sabine

  公开号：US20090209507A1

  公开（公告）日：2009-08-20

  The present invention relates to 15-O-desmethylmacbecin analogues according to the formula (IA) or (IB) herein, or a pharmaceutically acceptable salt thereof: wherein: R 1 and R 2 either both represent H or together they represent a bond (i.e. C4 to C5 is a double bond); and R 3 represents H or CONH 2 that are useful, e.g. in the treatment of cancer, B-cell malignancies, malaria, fungal infection, diseases of the central nervous system and neurodegenerative diseases, diseases dependent on angiogenesis, autoimmune diseases and/or as a prophylactic pretreatment for cancer. The present invention also provides methods for the production of these compounds and their use in medicine, in particular in the treatment and/or prophylaxis of cancer or B-cell malignancies.
• 18 ,21-Didesoxymacbecin Derivatives for the Treatment of Cancer
  申请人：Martin Christine

  公开号：US20090253667A1

  公开（公告）日：2009-10-08

  The present invention relates to 18,21-didesoxymacbecin analogues that are useful, e.g. in the treatment of cancer, B-cell malignancies, malaria, fungal infection, diseases of the central nervous system and neurodegenerative diseases, diseases dependent on angiogenesis, autoimmune diseases and/or as a prophylactic pre-treatment for cancer. The present invention also provides methods for the production of these compounds and their use in medicine, in particular in the treatment and/or prophylaxis of cancer or B-cell malignancies.