1011718-33-4

Basic information

• Product Name: C₂₀H₂₉NO₂
• CAS NO: 1011718-33-4
• Molecular Weight: 315.456
• Mol File: 1011718-33-4.mol

Chemical Properties

• CAS DataBase Reference: C₂₀H₂₉NO₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₀H₂₉NO₂(1011718-33-4)
• EPA Substance Registry System: C₂₀H₂₉NO₂(1011718-33-4)

Safety Data

• Hazardous Substances Data: 1011718-33-4(Hazardous Substances Data)

Upstream product

• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 18022-81-6 (3-chloropropylidene)cyclohexane 

Relevant articles and documents

Small P-gp modulating molecules: SAR studies on tetrahydroisoquinoline derivatives

The development of small molecules as P-gp modulating agents and SAR studies on these ligands represented the aim of the present work. A series of 6,7-dimethoxytetrahydroisoquinoline derivatives was prepared and their ability to inhibit P-gp activity has been evaluated. The basic nucleus of these compounds, common to the best P-gp inhibitors such as Tariquidar and Elacridar, has been functionalized with no-basic moiety from our studied sigma receptor ligands displaying potent P-gp inhibition. The best results were obtained for compounds 3c and 3a (EC50 = 1.64 and 4.86 μM, respectively) and these results were remarkable because Elacridar showed in the same biological evaluation similar inhibitory activity (EC50 = 2 μM). SAR studies displayed that the removal of double bond on the spacer or its shifting into tetraline ring decreased the P-gp inhibiting activity. Moreover, the P-gp inhibition mechanism of tested compounds was investigated by three selected biological experiments. The results displayed that only compound 3c was P-gp inhibitor as Elacridar, while compound 3a and reference compounds Cyclosporin A and Verapamil modulated P-gp activity saturating the efflux pump as substrates. Flow cytometry studies carried out in Doxorubicin resistant breast cancer cell line (MCF7/Adr) confirmed that compound 3c increased Doxorubicin cell accumulation 5.7-fold. In addition, in MCF7/Adr, antiproliferative effect of 5 μM Doxorubicin shifted from 5% to 95% when co-administered with compound 3c (20 μM). The present study suggested a new class of small molecules displaying P-gp inhibitor activity differing from reference compounds Elacridar and Tariquidar for a simplified, and in the meantime, efficacious no-basic moiety.