(2S,6'R)-(7-chloro-4,6-dimethoxybenzofuran-3-one)-2-spiro-1'-(6'-methyl-2'-(4-hydroxymethylbenzyloxy)cyclohex-2'-ene-4'-one) | 1233215-69-4

• 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-dimethoxybenzofuran-3-one)-2-spiro-1'-(6'-methyl-2'-(4-hydroxymethylbenzyloxy)cyclohex-2'-ene-4'-one)
• 英文别名: (2S,5'R)-7-chloro-3'-[[4-(hydroxymethyl)phenyl]methoxy]-4,6-dimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
• CAS: 1233215-69-4
• 化学式: C₂₄H₂₃ClO₇
• 分子量: 458.895
• InChiKey: SMBQHXSDCMUAIA-OZAJXLCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 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,6'R)-(7-chloro-4,6-dimethoxybenzofuran-3-one)-2-spiro-1'-(6'-methyl-2'-(4-hydroxymethylbenzyloxy)cyclohex-2'-ene-4'-one)
  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

文献信息

• Griseofulvin analogues for the treatment of cancer by inhibition of centrosomal clustering
  申请人：Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts

  公开号：EP2204367A1

  公开（公告）日：2010-07-07

  The present invention relates to uses of compounds having a structure as shown by formula (I) for the manufacture of a pharmaceutical composition for the treatment of cancer. Moreover, the present invention encompasses methods of treatment for said diseases.

  本发明涉及具有式（I）所示结构的化合物在制造治疗癌症的药物组合物中的用途。此外，本发明还包括上述疾病的治疗方法。
• GRISEOFULVIN ANALOGUES FOR THE TREATMENT OF CANCER BY INHIBITION OF CENTROSOMAL CLUSTERING
  申请人：Kraemer Alwin

  公开号：US20120035200A1

  公开（公告）日：2012-02-09

  The invention relates to compounds of the formula (I), where the symbols have the meaning given in the specification, for use in a method for treating cancer, to use of these compounds for the manufacture of a pharmaceutical composition for the treatment of cancer, and to methods of treatment for said diseases employing a compound of formula (I).
• US9108941B2
  申请人：——

  公开号：US9108941B2

  公开（公告）日：2015-08-18
• 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.