78238-94-5

Usage

InChI:InChI=1/C17H19NO2.ClH/c1-19-16-8-13-10-18-11-15(12-6-4-3-5-7-12)14(13)9-17(16)20-2;/h3-9,15,18H,10-11H2,1-2H3;1H

Upstream product

• 78238-92-3 6,7-dimethoxy-1-phenyl-3,4-dihydronaphthalene 
• 221158-41-4 4-(3,4-dimethoxyphenyl)-1-phenylbutan-1-one 
• 78238-93-4 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-1-ol 
• 13575-75-2 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydronaphthalene 
• 5333-34-6 3-(3,4-dimethoxybenzoyl)propionic acid 
• 91-16-7 1,2-dimethoxybenzene 
• 52417-29-5 4-(3,4-dimethoxyphenyl)butanal 
• 56880-86-5 4-(3,4-dimethoxyphenyl)butan-1-ol 
• 946412-69-7 4-(3,4-dimethoxyphenyl)-1-phenylbutan-1-ol 
• 13575-74-1 4-(3,4-dimethoxyphenyl)butanoic acid 

Downstream Products

• 78239-01-7 2,5-dibromo-6,7-dimethoxy-1-phenylnaphthalene 
• 78239-00-6 5-bromo-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene 
• 78239-03-9 5-bromo-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene-1-ol 
• 78239-02-8 4-bromo-2,3-dimethoxy-8-phenyl-5,6,7,8-tetrahydronaphthalen-1-yl acetate 

Relevant academic research and scientific papers

Inhibition of IGF-1R and lipoxygenase by nordihydroguaiaretic acid (NDGA) analogs

Herein, we pursue the hypothesis that the structure of nordihydroguaiaretic acid (NDGA) can be refined for selective potency against the insulin-like growth factor 1 receptor (IGF-1R) as a potential therapeutic target for breast cancer while diminishing its action against other cellular targets. Thus, a set of NDGA analogs (7a-7h) was prepared and examined for inhibitory potency against IGF-1R kinase and an alternative target, 15-lipoxygenase (15 LOX). The anti-cancer effects of these compounds were determined by their ability to inhibit IGF-1 mediated cell growth of MCF-7 breast cancer cells. The design of the analogs was based upon a cursory Topliss approach in which one of NDGA's aromatic rings was modified with various substituents. Structural modification of one of the two catechol rings of NDGA was found to have little effect upon the inhibitory potency against both kinase activity of the IGF-1R and IGF-1 mediated cell growth of MCF-7 cells. 15-LOX was found to be most sensitive to structural modifications of NDGA. From the limited series of NDGA analogs examined, the compound that exhibited the greatest selectivity for IGF-1 mediated growth compared to 15-LOX inhibition was a cyclic analog 7h with a framework similar to a natural product isolated from Larrea divaricata. The results for 7h are significant because while NDGA displays biological promiscuity, 7h exhibits greater specificity toward the breast cancer target IGF-1R with that added benefit of possessing a 10-fold weaker potency against 15-LOX, an enzyme which has a purported tumor suppressing role in breast cancer. With increased specificity and potency, 7h may serve as a new lead in developing novel therapeutic agents for breast cancer.

Anomalous Acetoxylation of Aromatic Nuclei: Some Structural Requirements in the Substrate

For certain aromatic nuclei, bromination in acetic acid in the presence of pyridine is accompanied by nuclear acetoxylation.As first observed with galbulin, when two alkoxyl groups, one meta and one para to a benzylic centre of the substrate are present, acetoxylation occurs at the intervening ortho position.Under the given conditions, acetoxylation occurs at position 8 of 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene, and at position 2 of 3,4-dimethoxy diphenyl and triphenyl-methanes.Acetoxylation does not occur in the absence of either of the alkoxy groups or in the absence of pyridine, not does it occur in the pendant ring of 1-(3',4'-dimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene.These results are consistent with the earlier suggestion that the reaction occurs by way of initial oxidative formation of a doubly benzylic cation