241. Griseofulvin analogues. Part I. Modification of the aromatic ring

Arkley, Vincent; Attenburrow, J.; Gregory, G. I.; Walker, T.

doi:10.1039/jr9620001260

Cited by 45 publications

(32 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…27 The syntheses of 9 and 10 have already been described. 22,28 For the preparation of 11, 12, and 13, see Rønnest et al 29 and Arkley et al 27 Compound 12 was alkylated using Ag 2 O and EtBr followed by repeated solvolysis in MeOH with camphor sulfonic acid (CSA) to afford 14. The dichloro analogues 15 and 16 were synthesized using 2, 30 POCl 3 , LiCl, and dioxane, a modification of a known method (Scheme 2).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The 4-phenol (4) was synthesized from 1 by treatment with freshly prepared MgI 2 , procured by sonication of Mg and I 2 in Et 2 O/toluene, affording 4 in 99% yield, an improvement on prior methods (Scheme 1). 22,27 Alkylation of 4 to synthesize 5 and 6 has previously been described. 22,27 Position 4 analogues 7 and 8 were prepared from 4 with Ag 2 O and the appropriate alkyl bromide in dioxane as solvent.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…22,27 Alkylation of 4 to synthesize 5 and 6 has previously been described. 22,27 Position 4 analogues 7 and 8 were prepared from 4 with Ag 2 O and the appropriate alkyl bromide in dioxane as solvent. 27 The syntheses of 9 and 10 have already been described.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…22,27 Position 4 analogues 7 and 8 were prepared from 4 with Ag 2 O and the appropriate alkyl bromide in dioxane as solvent. 27 The syntheses of 9 and 10 have already been described. 22,28 For the preparation of 11, 12, and 13, see Rønnest et al 29 and Arkley et al 27 Compound 12 was alkylated using Ag 2 O and EtBr followed by repeated solvolysis in MeOH with camphor sulfonic acid (CSA) to afford 14.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

See 3 more Smart Citations

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

et al. 2012

View full text Add to dashboard Cite

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 and 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.

show abstract