(2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-on)-2-spiro-1'-(4'-methoxy-6'-methylcyclohex-3'-ene-2'-one) | 469-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-on)-2-spiro-1'-(4'-methoxy-6'-methylcyclohex-3'-ene-2'-one)
• 英文别名: d-isogriseofulvin；isogriseofulvin；(2S,6'R)-7-chloro-4,6,4'-trimethoxy-6'-methyl-spiro[benzofuran-2,1'-cyclohex-3'-ene]-3,2'-dione；(2S,6'R)-7-Chlor-4,6,4'-trimethoxy-6'-methyl-spiro[benzofuran-2,1'-cyclohex-3'-en]-3,2'-dion；7-Chlor-4,6,4'-trimethoxy-6'-methyl-3,2'-dioxo-spiro-cyclohexen>；(2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,6'-cyclohex-2-ene]-1',3-dione
• CAS: 469-52-3
• 化学式: C₁₇H₁₇ClO₆
• 分子量: 352.771
• InChiKey: FFKRWPQQTGWKIH-RBHXEPJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  乙酸乙酯 、 (2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-on)-2-spiro-1'-(4'-methoxy-6'-methylcyclohex-3'-ene-2'-one) 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (2S,2'Ξ,4'Ξ,6'R)-7-chloro-2'-hydroxy-4,6,4'-trimethoxy-6'-methyl-spiro[benzofuran-2,1'-cyclohexan]-3-one
  参考文献：
  名称：

  764.灰黄霉素。第六部分 还原产物的化学

  摘要：

  DOI：

  10.1039/jr9520003994
• 作为产物：
  描述：

  灰黄霉素 在 sodium methylate 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.33h， 生成 (2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-on)-2-spiro-1'-(4'-methoxy-6'-methylcyclohex-3'-ene-2'-one)
  参考文献：
  名称：

  Syntheses and Antifungal Activity of dl-Griseofulvin and Its Congeners. II.

  摘要：

  我们采用我们开发的一种合成方法，制备了灰黄霉素衍生物，dl-6'-去甲基-6'-乙基灰黄霉素（dl-5）和dl-6'-去甲基-6'-苯基灰黄霉素（dl-6）。这些衍生物的抗真菌活性顺序为dl-灰黄霉素（dl-1）>dl-5»dl-6（无活性）。这些衍生物与乙硫醇反应得到了两种类型的化合物，2'-(乙硫基)灰黄霉素（15）和4'-(乙硫基)异灰黄霉素（16）。讨论了分离产率比值15和16与灰黄霉素衍生物抗真菌活性之间的关系。

  DOI：

  10.1248/cpb.45.327

文献信息

• Disparate SAR Data of Griseofulvin Analogues for the Dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 Cancer Cells
  作者：Mads H. Rønnest、Marc S. Raab、Simon Anderhub、Sven Boesen、Alwin Krämer、Thomas O. Larsen、Mads H. Clausen

  DOI：10.1021/jm200835c

  日期：2012.1.26

  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.
• Grove et al., Journal of the Chemical Society, 1952, p. 3949,3957
  作者：Grove et al.

  DOI：——

  日期：——
• Oxford et al., Biochemical Journal, 1939, vol. 33, p. 240,246
  作者：Oxford et al.

  DOI：——

  日期：——
• Syntheses and Antifungal Activity of dl-Griseofulvin and Its Congeners. II.
  作者：Yasuo TAKEUCHI、Hideo TOMOZANE、Keiji MISUMI、Kuniko YATA、Teruyuki KAWATA、Yoshiko NIINO、Masatoshi YAMATO、Takashi HARAYAMA

  DOI：10.1248/cpb.45.327

  日期：——

  Griseofulvin derivatives, dl-6'-demethyl-6'-ethylgriseofulvin (dl-5) and dl-6'-demethyl-6'-phenylgriseofulvin (dl-6) were prepared by application of a synthetic method developed by us. Antifungal activity of these derivatives decreased in the order of dl-griseofulvin (dl-1)>dl-5»dl-6 (inactive). The reaction of these derivatives with ethanethiol gave two types of compounds, 2'-(ethylthio)griseofulvin (15) and 4'-(ethylthio)isogriseofulvin (16). The relationship between the ratios of isolated yield of 15 and 16 and antifungal the activity of griseofulvin derivatives is discussed.

  我们采用我们开发的一种合成方法，制备了灰黄霉素衍生物，dl-6'-去甲基-6'-乙基灰黄霉素（dl-5）和dl-6'-去甲基-6'-苯基灰黄霉素（dl-6）。这些衍生物的抗真菌活性顺序为dl-灰黄霉素（dl-1）>dl-5»dl-6（无活性）。这些衍生物与乙硫醇反应得到了两种类型的化合物，2'-(乙硫基)灰黄霉素（15）和4'-(乙硫基)异灰黄霉素（16）。讨论了分离产率比值15和16与灰黄霉素衍生物抗真菌活性之间的关系。
• 764. Griseofulvin. Part VI. Chemistry of the reduction products
  作者：T. P. C. Mulholland

  DOI：10.1039/jr9520003994

  日期：——