26881-56-1

Basic information

• Product Name: 2',7-Dichloro-4,6-dimethoxy-6'-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione
• Synonyms: 2',7-Dichloro-4,6-dimethoxy-6'-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione
• CAS NO: 26881-56-1
• Molecular Formula: C₁₆H₁₄Cl₂O₅
• Molecular Weight: 357.19
• Mol File: 26881-56-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 558.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.46±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2',7-Dichloro-4,6-dimethoxy-6'-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2',7-Dichloro-4,6-dimethoxy-6'-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione(26881-56-1)
• EPA Substance Registry System: 2',7-Dichloro-4,6-dimethoxy-6'-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione(26881-56-1)

Safety Data

• Hazardous Substances Data: 26881-56-1(Hazardous Substances Data)

Upstream product

• 1158186-19-6 griseofulvic acid 
• 126-07-8 griseofulvin 

Downstream Products

• 1158186-23-2 (2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-one)-2-spiro-1'-(6'-methyl-2'-(4-methylbenzyloxy)-cyclohex-2'-en-4'-one) 
• 1094369-64-8 (2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-one)-2-spiro-1'-(6'-methyl-2'-(2-phenylethoxy)-cyclohex-2'-en-4'-one) 
• 1158186-24-3 (2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-one)-2-spiro-1'-(2'-(4-biphenylmethoxy)-6'-methyl-cyclohex-2'-en-4'-one) 
• 1094369-60-4 (1'R,6'R)-2'-(benzylsulfanyl)-7-chloro-4,6-dimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione 
• 888042-13-5 (2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-one)-2-spiro-1'-(2'-benzyloxy-6'-methyl-cyclohex-2'-en-4'-one) 
• 888042-12-4 (2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-one)-2-spiro-1'-(6'-methyl-2'-phenoxy-cyclohex-2'-en-4'-one) 
• 1233215-74-1 (2S,6'R)-(7-chloro-4,6-dimethoxybenzofuran-3-one)-2-spiro-1'-(2'-(4-fluorobenzyloxy)-6'-methylcyclohex-2'-ene-4'-one) 
• 1233215-81-0 (2S,6'R)-(7-chloro-4,6-dimethoxybenzofuran-3-one)-2-spiro-1'-(2'-(4-trifluoromethylbenzyloxy)-6'-methylcyclohex-2'-ene-4'-one) 
• 1354716-62-3 C₂₄H₂₃ClO₇ 
• 1233215-69-4 (2S,6'R)-(7-chloro-4,6-dimethoxybenzofuran-3-one)-2-spiro-1'-(6'-methyl-2'-(4-hydroxymethylbenzyloxy)cyclohex-2'-ene-4'-one) 
• 1354716-61-2 C₂₄H₂₃ClO₇ 
• 1354716-63-4 C₂₄H₂₃ClO₇ 
• 1279033-22-5 (2S,6'R)-7-chloro-4,6-dimethoxy-2'-(methoxy-d3)-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione 
• 1233215-66-1 (2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-one)-2-spiro-1'-(2'-(4-iodobenzyloxy)-6'-methylcyclohex-2'-ene-4'-one) 

Relevant articles and documents

Synthesis and formulation studies of griseofulvin analogues with improved solubility and metabolic stability

Griseofulvin (1) is an important antifungal agent that has recently received attention due to its antiproliferative activity in mammalian cancer cells. Comprehensive SAR studies have led to the identification of 2′-benzyloxy griseofulvin 2, a more potent analogue with low micromolar anticancer potency in?vitro. Analogue 2 was also shown to retard tumor growth through inhibition of centrosomal clustering in murine xenograft models of colon cancer and multiple myeloma. However, similar to griseofulvin, compound 2 exhibited poor metabolic stability and aqueous solubility. In order to improve the poor pharmacokinetic properties, 11 griseofulvin analogues were synthesized and evaluated for biological activity and physiological stabilities including SGF, plasma, and metabolic stability. Finally, the most promising compounds were investigated in respect to thermodynamic solubility and formulation studies. The 2′-benzylamine analogue 10 proved to be the most promising compound with low μM in?vitro anticancer potency, a 200-fold increase in PBS solubility over compound 2, and with improved metabolic stability. Furthermore, this analogue proved compatible with formulations suitable for both oral and intravenous administration. Finally, 2′-benzylamine analogue 10 was confirmed to induce G2/M cell cycle arrest in?vitro.

Synthesis and structure-activity relationship of griseofulvin analogues as inhibitors of centrosomal clustering in cancer cells

Griseofulvin was identified as an inhibitor of centrosomal clustering in a recently developed assay. Centrosomal clustering is an important cellular event that enables bipolar mitosis for cancer cell lines harboring supernumerary centrosomes. We report he