caerulomycin H | 1315331-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: caerulomycin H
• 英文别名: (E)-4-hydroxy-2,2'-bipyridine-6-carbaldehyde oxime；2-[(E)-hydroxyiminomethyl]-6-pyridin-2-yl-1H-pyridin-4-one
• CAS: 1315331-79-3
• 化学式: C₁₁H₉N₃O₂
• 分子量: 215.211
• InChiKey: XLFYSDMKBLTHTJ-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  caerulomycin H 在 乙醛酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 4-hydroxy-2,2'-bipyridine-6-carbaldehyde
  参考文献：
  名称：

  Acyclic Congeners from Actinoalloteichus cyanogriseus Provide Insights into Cyclic Bipyridine Glycoside Formation

  摘要：

  Inactivation of the O-methyltransferase gene crmM of Actinoalloteichus cyanogriseus WH1-2216-6 led to a mutant that produced three new acyclic bipyridine glycosides, cyanogrisides E-G (1-3). Further chemical analysis of the wild strain yielded 1 and another new analogue, cyanogriside H (4). Compounds 1-4 possess a skeleton consisting of a 2,2'-bipyridine and a d-quinovose or l-rhamnose sugar moiety. Cyanogriside G (3) was considered to be a key biosynthetic intermediate of the cyclic bipyridine glycosides cyanogrisides A-D. Compounds 2 and 3 showed cytotoxicities against HCT116 and HL-60 cells, and compounds 1 and 4 were cytotoxic on K562 cells.

  DOI：

  10.1021/ol5019757

文献信息

• DIPYRIDYL ALKALOID, PREPARATION METHOD THEREFOR AND USE THEREOF
  申请人：OCEAN UNIVERSITY OF CHINA

  公开号：US20190322638A1

  公开（公告）日：2019-10-24

  Disclosed are dipyridyl alkaloid, a preparation method therefor and use thereof. The structure of the dipyridyl alkaloid is as shown in formula I. The dipyridyl alkaloid has a tumor cell proliferation inhibitory activity and can be used as a tumor cell proliferation inhibitor or for developing an anti-tumor drug.

  本发明涉及二吡啶类生物碱、其制备方法及其用途。所述二吡啶类生物碱的结构如公式I所示。该二吡啶类生物碱具有抑制肿瘤细胞增殖的活性，可用作肿瘤细胞增殖抑制剂或用于开发抗肿瘤药物。
• Cytotoxic Bipyridines from the Marine-Derived Actinomycete <i>Actinoalloteichus cyanogriseus</i> WH1-2216-6
  作者：Peng Fu、Shuxia Wang、Kui Hong、Xia Li、Peipei Liu、Yi Wang、Weiming Zhu

  DOI：10.1021/np200258h

  日期：2011.8.26

  Five new bipyridine alkaloids (1-5) and a new phenylpyridine alkaloid (6), which we name caerulomycins F-K, along with five known analogues (7-11), were isolated from the marine-derived actinomycete Actinoalloteichus cyanogriseus WH1-2216-6. The structures of 1-6 were established on the basis of spectroscopic analyses and chemical methods. Compounds 1-10 showed cytotoxicity against the HL-60, K562, KB, and A549 cell lines, with IC50 values of 0.26 to 15.7 mu M. Compounds 7 and 8 also showed antimicrobial activities against Escherichia coli, Aerobacter aerogenes, Pseudomonas aeruginosa, and Candida albicans, with MIC values of 9.7 to 38.6 mu M.
• Acyclic Congeners from <i>Actinoalloteichus cyanogriseus</i> Provide Insights into Cyclic Bipyridine Glycoside Formation
  作者：Peng Fu、Yiguang Zhu、Xiangui Mei、Yi Wang、Haijian Jia、Changsheng Zhang、Weiming Zhu

  DOI：10.1021/ol5019757

  日期：2014.8.15

  Inactivation of the O-methyltransferase gene crmM of Actinoalloteichus cyanogriseus WH1-2216-6 led to a mutant that produced three new acyclic bipyridine glycosides, cyanogrisides E-G (1-3). Further chemical analysis of the wild strain yielded 1 and another new analogue, cyanogriside H (4). Compounds 1-4 possess a skeleton consisting of a 2,2'-bipyridine and a d-quinovose or l-rhamnose sugar moiety. Cyanogriside G (3) was considered to be a key biosynthetic intermediate of the cyclic bipyridine glycosides cyanogrisides A-D. Compounds 2 and 3 showed cytotoxicities against HCT116 and HL-60 cells, and compounds 1 and 4 were cytotoxic on K562 cells.