(2S,5'R)-7-chloro-4,6-dimethoxy-5'-methyl-3'-(naphthalen-1-ylmethoxy)spiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione | 1094369-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,5'R)-7-chloro-4,6-dimethoxy-5'-methyl-3'-(naphthalen-1-ylmethoxy)spiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
• CAS: 1094369-52-4
• 化学式: C₂₇H₂₃ClO₆
• 分子量: 478.929
• InChiKey: YPFXDKRKCZYIIC-RXAIFQJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,5'R)-7-chloro-4,6-dimethoxy-5'-methyl-3'-(naphthalen-1-ylmethoxy)spiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 18.0h， 以96%的产率得到(2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-one)-2-spiro-1'-(2'-(naphthalen-1-ylmethoxy)-6'-methylcyclohex-2'-ene-4'-one-4'-oxime)
  参考文献：
  名称：

  Disparate SAR Data of Griseofulvin Analogues for the Dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 Cancer Cells

  摘要：

  Griseofulvin and 53 analogues of this compound have been tested against the pathogenic dermatophytes Trichophyton rubrum and Trichophyton mentagrophytes as well as against the breast cancer cell line MDA-MB-231. The modifications to griseofulvin include the 4, 5, 6, 2', 3', and 4' positions. The SAR of the griseofulvin analogues toward the two fungi followed the same trend with the majority being less active than griseofulvin and none had more than twice the potency of the parent compound. A comparison of the antifungal the anticancer SAR revealed distinct differences, as the majority of analogues showed increased activity against the cancer cell line MDA-MB-231, highlighted by 2'-benzyloxy-2'-demethoxy-griseofulvin, which showed low activity against both fungi but was among the most potent compounds against MDA-MB-231 cancer cells. Tubulin has been proposed as the target of griseofulvin in both fungal and mammalian cells, but the differences revealed by this SAR study strongly suggest that the mode-of-action of the compound class toward fungi and mammalian cancer cells is different.

  DOI：

  10.1021/jm200835c
• 作为产物：
  描述：

  灰黄霉素 在 硫酸 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.5h， 生成 (2S,5'R)-7-chloro-4,6-dimethoxy-5'-methyl-3'-(naphthalen-1-ylmethoxy)spiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
  参考文献：
  名称：

  Disparate SAR Data of Griseofulvin Analogues for the Dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 Cancer Cells

  摘要：

  Griseofulvin and 53 analogues of this compound have been tested against the pathogenic dermatophytes Trichophyton rubrum and Trichophyton mentagrophytes as well as against the breast cancer cell line MDA-MB-231. The modifications to griseofulvin include the 4, 5, 6, 2', 3', and 4' positions. The SAR of the griseofulvin analogues toward the two fungi followed the same trend with the majority being less active than griseofulvin and none had more than twice the potency of the parent compound. A comparison of the antifungal the anticancer SAR revealed distinct differences, as the majority of analogues showed increased activity against the cancer cell line MDA-MB-231, highlighted by 2'-benzyloxy-2'-demethoxy-griseofulvin, which showed low activity against both fungi but was among the most potent compounds against MDA-MB-231 cancer cells. Tubulin has been proposed as the target of griseofulvin in both fungal and mammalian cells, but the differences revealed by this SAR study strongly suggest that the mode-of-action of the compound class toward fungi and mammalian cancer cells is different.

  DOI：

  10.1021/jm200835c