40174-10-5

Basic information

• Product Name: 2-(3,4,5-trimethoxyphenyl)ethyl methanesulfonate
• Synonyms: 2-(3,4,5-trimethoxyphenyl)ethyl methanesulfonate
• CAS NO: 40174-10-5
• Molecular Weight: 290.337
• Mol File: 40174-10-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(3,4,5-trimethoxyphenyl)ethyl methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4,5-trimethoxyphenyl)ethyl methanesulfonate(40174-10-5)
• EPA Substance Registry System: 2-(3,4,5-trimethoxyphenyl)ethyl methanesulfonate(40174-10-5)

Safety Data

• Hazardous Substances Data: 40174-10-5(Hazardous Substances Data)

Upstream product

• 37785-48-1 2-(3,4,5-trimethoxyphenyl)ethanol 
• 124-63-0 methanesulfonyl chloride 
• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 13400-02-7 3,4,5-trimethoxy styrene 
• 951-82-6 3,4,5-trimethoxyphenyl acetic acid 

Downstream Products

• 54-04-6 mescaline 
• 910866-99-8 5-(2-azidoethyl)-1,2,3-trimethoxybenzene 
• 1621065-36-8 1-[2-(3,4,5-trimethoxyphenyl)ethyl]-1,2,3,4-tetrahydropyrimidino[1,2-b][1,2,4]benzothiadiazine 6,6-dioxide 
• 733047-91-1 11-[2-(3,4,5-trimethoxyphenyl)ethyl]-11H-benzo[f]pyrido[3,2-c][1,2,5]oxathiazepine 5,5-dioxide 
• 204510-70-3 (R,S)-1-methoxy-2-cyano-3-[2-(3,4,5-trimethoxyphenyl)ethyl]cyclopentene 
• 204510-66-7 2-Oxo-5-[2-(3,4,5-trimethoxy-phenyl)-ethyl]-cyclopentanecarbonitrile 
• 204510-65-6 5-(2-iodoethyl)-1,2,3-trimethoxybenzene 
• 91216-68-1 (3,4,5-trimethoxy-phenethyl)-hydrazine 

Relevant articles and documents

Synthesis and Biological Evaluation of N-[2-(4-Hydroxyphenylamino)-pyridin-3-yl]-4-methoxy-benzenesulfonamide (ABT-751) Tricyclic Analogues as Antimitotic and Antivascular Agents with Potent in Vivo Antitumor Activity

Benzopyridothiadiazepine (2a) and benzopyridooxathiazepine (2b) were modified to produce tricyclic quinazolinone 15-18 or benzothiadiazine 26-27 derivatives. These compounds were evaluated in cytotoxicity and tubulin inhibition assays and led to potent inhibitors of tubulin polymerization. N-[2(4-Methoxyphenyl)ethyl]-1,2-dihydro-pyrimidino[2,1-b]quinazolin-6-one (16a) exhibited the best in vitro cytotoxic activity (GI50 10-66.9 nM) against the NCI 60 human tumor cell line and significant potency against tubulin assembly (IC50 0.812 μM). In mechanism studies, 16a was shown to block cell cycle in G2/M phase and to disrupt microtubule formation and displayed good antivascular properties as inhibition of cell migration, invasion, and endothelial tube formation. Compound 16a was evaluated in C57BL/6 mouse melanoma B16F10 xenograft model to validate its antitumor activity, in comparison with reference ABT-751 (1). Compound 16a displayed strong in vivo antitumor and antivascular activities at a dose of 5 mg/kg without obvious toxicity, whereas 1 needed a 10-fold higher concentration to reach similar effects.

Novel benzopyridothiadiazepines as potential active antitumor agents

The synthesis of novel thiadiazepine derivatives, that could be considered as constraint analogues of E-7010, are reported. These molecules were evaluated for their antiproliferative activity toward the murine L1210 leukemia cell line. Flow cytometric studies performed on L1210 cells with the most cytotoxic compounds showed an accumulation of the cells in the G2/M phases of the cell cycle with a significant percentage of tetraploid cells (8N DNA content). Submicromolar cytotoxicities were observed with compounds 2b, 4b, 4e, 4g, and 4i. Two of them, compounds 2b and 4b, were found to be potent inhibitors of tubulin polymerization with IC50 of respectively 3.8 and 2.4 μM compared to 2.4 μM for desoxypodophyllotoxin. A 4-methoxyphenylethyl substitution on the pyridinyl nitrogen of the benzopyridothiadiazepine was found to be essential for the antiproliferative activity. The in vitro activities of compounds 2b and 4b make benzopyridothiadiazepine dioxides a promising new class of tubulin binders which warrant further in vivo evaluation.