55511-34-7

Basic information

• Product Name: N-[10-(ethylsulfanyl)-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
• CAS NO: 55511-34-7
• Molecular Formula: C₂₃H₂₇NO₅S
• Molecular Weight: 429.5292
• Mol File: 55511-34-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 731.9°C at 760 mmHg
• Flash Point: 396.5°C
• Density: 1.25g/cm³
• Vapor Pressure: 2.78E-21mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: N-[10-(ethylsulfanyl)-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[10-(ethylsulfanyl)-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide(55511-34-7)
• EPA Substance Registry System: N-[10-(ethylsulfanyl)-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide(55511-34-7)

Safety Data

• Hazardous Substances Data: 55511-34-7(Hazardous Substances Data)

Upstream product

• 64-86-8 colchicine 
• 811-51-8 sodium thioethylate 
• 75-08-1 ethanethiol 

Downstream Products

• 55511-31-4 (S)-10-ethylsulfanyl-7-amino-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one 

Relevant articles and documents

7-Deacetyl-10-alkylthiocolchicine derivatives-new compounds with potent anticancer and fungicidal activity

A series of new semi-synthetic 7-deacetyl-10-alkylthiocolchicne derivatives with ethyl, n-propyl, i-propyl and n-butyl substituents were synthesised and characterised by spectroscopic methods, elemental analysis, DFT calculations and molecular docking simulations. All the synthesized compounds have been tested for fungicidal and anticancer activities against SKOV-3, LoVo, MCF-7, MDA-MB-231 and the lung-derived fibroblast CCD39Lu. All the new colchicine derivatives exhibit significantly higher cytotoxicity towards the SKOV-3 tumour cell line than the natural product-colchicine. The most effective cytotoxic agents were 7-deacetyl-10-n-buthylthiocolchicine and 7-deacetyl-10-i-propylthiocolchicine. Among all the compounds tested, 7-deacetyl-10-n-buthylthiocolchicine exhibited the highest fungicidal activity. Molecular modeling indicated that several mutations found in the β-tubulin unit of the tested fungal strains are crucial for antifungal activity and selectivity of 7-deacetyl-10-n-buthylthiocolchicine. The obtained results may be useful for the development of selective colchicine derivatives as effective fungicidal and/or anticancer drugs.

Alkylthiocolchicines and N deacetyl alkylthiocolchicines and their antileukemic activity

A series of alkylthiocolchicines (methyl, ethyl, n butyl, n hexyl, n octyl and pinanyl) was prepared from cholchicine by treatment with the appropriate alkyl mercaptan and p toluene sulfonic acid. Some of these compounds (methyl, ethyl, and n butylthiocolchicines) were deacetylated in good yields with 2 N hydrochloric acid in methanol. These compounds were tested for their antileukemic activity in an in vitro assay against L 1210 (mouse leukemia). Preliminary results showed that methylthiocolchicine is more active and the other alkylthiocolchicines are much less active than colchicine. N deacetyl methylthiocolchicine is as active as colchicine.