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metacridamides A | 1356937-10-4

中文名称
——
中文别名
——
英文名称
metacridamides A
英文别名
[(3S,6E,8S,9R,10E,12S,13S,14E,16S,17R)-3-benzyl-9-hydroxy-6,8,10,12,14,16-hexamethyl-17-[(2S,4S)-4-methylhexan-2-yl]-2,5-dioxo-1-oxa-4-azacycloheptadeca-6,10,14-trien-13-yl] acetate
metacridamides A化学式
CAS
1356937-10-4
化学式
C37H55NO6
mdl
——
分子量
609.847
InChiKey
WIRRTALUVUQONX-HVCDBQLESA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    7.4
  • 重原子数:
    44
  • 可旋转键数:
    8
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.59
  • 拓扑面积:
    102
  • 氢给体数:
    2
  • 氢受体数:
    6

反应信息

  • 作为反应物:
    描述:
    metacridamides A盐酸 作用下, 以 丙酸 为溶剂, 反应 15.0h, 生成 L-苯丙氨酸
    参考文献:
    名称:
    Metacridamides A and B, Macrocycles from Conidia of the Entomopathogenic Fungus Metarhizium acridum
    摘要:
    Metarhizium acridum, an entomopathogenic fungus, has been commercialized and used successfully for biocontrol of grasshopper pests in Africa and Australia. Its conidia produce two novel 17-membered macrocycles, metacridamides A (1) and B (2), which consist of a Phe unit condensed with a nonaketide. Planar structures were elucidated by a combination of mass spectrometric and NMR techniques. Following hydrolysis of 1, chiral amino acid analysis assigned the L-configuration to the Phe unit. A crystal structure established the absolute configuration of the eight remaining stereogenic centers in 1. Metacridamide A (1) showed cytotoxicity to three cancer lines with IC50's of 6.2, 11.0, and 10.8 mu M against Caco-2 (epithelial colorectal adenocarcinoma), MCF-7 (breast cancer), and HepG2/C3A (hepatoma) cell lines, respectively. In addition, metacridamide B (2) had an IC50 of 18.2 mu M against HepG2/C3A, although it was inactive at 100 mu M against Caco-2 and MCF-7. Neither analogue showed antimicrobial, phytotoxic, or insecticidal activity.
    DOI:
    10.1021/np2007044
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文献信息

  • Metacridamides A and B, Macrocycles from Conidia of the Entomopathogenic Fungus <i>Metarhizium acridum</i>
    作者:Stuart B. Krasnoff、Ulrich Englich、Paula G. Miller、Michael L. Shuler、Raymond P. Glahn、Bruno G. G. Donzelli、Donna M. Gibson
    DOI:10.1021/np2007044
    日期:2012.2.24
    Metarhizium acridum, an entomopathogenic fungus, has been commercialized and used successfully for biocontrol of grasshopper pests in Africa and Australia. Its conidia produce two novel 17-membered macrocycles, metacridamides A (1) and B (2), which consist of a Phe unit condensed with a nonaketide. Planar structures were elucidated by a combination of mass spectrometric and NMR techniques. Following hydrolysis of 1, chiral amino acid analysis assigned the L-configuration to the Phe unit. A crystal structure established the absolute configuration of the eight remaining stereogenic centers in 1. Metacridamide A (1) showed cytotoxicity to three cancer lines with IC50's of 6.2, 11.0, and 10.8 mu M against Caco-2 (epithelial colorectal adenocarcinoma), MCF-7 (breast cancer), and HepG2/C3A (hepatoma) cell lines, respectively. In addition, metacridamide B (2) had an IC50 of 18.2 mu M against HepG2/C3A, although it was inactive at 100 mu M against Caco-2 and MCF-7. Neither analogue showed antimicrobial, phytotoxic, or insecticidal activity.
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