26279-89-0

Basic information

• Product Name: 2-chloro-N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
• Synonyms: 2-Chloro-N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide; acetamide, 2-chloro-N-[(7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]-
• CAS NO: 26279-89-0
• Molecular Formula: C₂₂H₂₄ClNO₆
• Molecular Weight: 433.8821
• Mol File: 26279-89-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 746.3°C at 760 mmHg
• Flash Point: 405.1°C
• Density: 1.31g/cm³
• Vapor Pressure: 3.8E-22mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 2-chloro-N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide(26279-89-0)
• EPA Substance Registry System: 2-chloro-N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide(26279-89-0)

Safety Data

• Hazardous Substances Data: 26279-89-0(Hazardous Substances Data)

Upstream product

• 64-86-8 colchicine 
• 1415695-51-0 N-deacetylcolchicine trifluoroacetate 
• 79-11-8 chloroacetic acid 
• 3476-50-4 deacetylcolchicine 
• 541-88-8 Chloroacetic anhydride 
• 186374-94-7 (S)-tert-butyl-N-acetyl(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalene-7-yl)carbamate 
• 186374-95-8 (S)-tert-butyl N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalene-7-yl)carbamate 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 1252803-32-9 C₁₀₇H₁₄₅N₁₇O₄₂S₃ 
• 1252803-35-2 C₁₀₇H₁₄₇N₁₉O₄₀S₃ 
• 1252803-45-4 C₁₁₀H₁₆₂N₂₂O₄₉S₄ 
• 1252803-47-6 C₁₁₀H₁₆₄N₂₄O₄₇S₄ 

Relevant articles and documents

Effects on tubulin polymerization and down-regulation of c-Myc, hTERT and VEGF genes by colchicine haloacetyl and haloaroyl derivatives

Several colchicine analogues in which the N-acetyl residue has been replaced by haloacetyl, cyclohexylacetyl, phenylacetyl and various aroyl moieties have been synthesized. The cytotoxic activities of the synthesized compounds have been measured on three tumor cell lines (HT-29, MCF-7 and A549) and on one non-tumor cell line (HEK-293). These compounds exhibit high antiproliferative activities at the nanomolar level, in many cases with a higher potency than colchicine itself. Some of the compounds, particularly the haloacetyl derivatives, inhibit the polymerization of tubulin in a similar manner as colchicine. As regards the cell cycle, the most active compounds are the chlorobenzoyl and bromobenzoyl derivatives, which cause cell cycle arrest at the G2/M phase when tested at 20 nM, and the bromoacetyl derivative, which arrests the cell cycle at 15 nM. In addition, these colchicine derivatives have shown fairly active downregulating the expression of the c-Myc, hTERT and VEGF genes, as well as VEGF protein secretion, at very low concentrations.

Inhibition of mitosis by glycopeptide dendrimer conjugates of colchicine

Glycopeptide dendrimers have been prepared bearing four or eight identical glycoside moieties at their surface (β-glucose, α-galactose, α-N-acetyl-galactose, or lactose), natural amino acids within the branches (Ser, Thr, His, Asp, Glu, Leu, Val, Phe), 2,3-diaminopropionic acid as the branching unit, and a cysteine residue at the core. These dendrimers have been used as drug-delivery devices for colchicine. Colchicine was attached to the dendrimers at the cysteine thiol group through a disulfide or thioether linkage. The biological activities of the glycopeptide dendrimer conjugates were evaluated in HeLa tumor cells and non-transformed mouse embryonic fibroblasts (MEFs). The concentrations of glycopeptide dendrimer drug conjugates required to achieve inhibition of cell proliferation by interference with the tubulin system were found to be higher (IC50 > 1 μm) compared to the required colchicine concentration. On the other hand, the glycopeptide dendrimer conjugates inhibited the proliferation of HeLa cells 20-100 times more effectively than the proliferation of MEFs. In comparison, non-glycosylated dendrimers and colchicine itself showed a selectivity of 10-fold or less for HeLa cells.