72744-56-0

Usage

InChI:InChI=1/C8H5BrO4/c9-4-1-2-5-7(13-3-12-5)6(4)8(10)11/h1-2H,3H2,(H,10,11)

Upstream product

• 72744-54-8 5-bromo-benzo[1,3]dioxole-4-carbaldehyde 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 124-38-9 carbon dioxide 
• 83983-71-5 6-bromo-2,3-dihydroxybenzaldehyde 
• 20035-45-4 6-bromo-3-ethoxy-2-hydroxybenzaldehyde 
• 492-88-6 3-ethoxysalicylaldehyde 

Downstream Products

• 401811-77-6 N-(5-bromo-1,3-benzodioxol-4-yl)carbamic acid 1,1-dimethylethyl ester 
• 78987-02-7 cis-13-hydroxymethyl-9,10-methylenedioxy-2,3-dimethoxytetrahydroprotoberberine 
• 1235872-06-6 C₃₄H₃₁NO₄ 
• 548-30-1 oxysanguinarine 
• 1429504-68-6 (4-benzyl-4-hydroxypiperidin-1-yl)(5-(pyridin-4-yl)-1,3-benzodioxol-4-yl)methanone 
• 1429505-72-5 (4-benzyl-4-hydroxypiperidin-1-yl)(5-bromo-1,3-benzodioxol-4-yl)methanone 
• 1235871-75-6 7-(biphenyl-4-yl)-9,10-dimethoxy-12-methylbenzo[1,3]dioxolo[4,5]phenanthridin-13(12H)-one 
• 1235871-74-5 N-(4-(biphenyl-4-yl)-6,7-dimethoxynaphthalen-1-yl)-5-bromo-N-methylbenzo[1,3]dioxole-4-carboxamide 
• 1235871-33-6 8-biphenyl-4-yl-9,10-dimethoxy-12-methyl-12H-1,3-dioxa-12-azacyclopenta[a]chrysene-13-one 
• 1235871-38-1 C₂₇H₂₁NO₅ 
• 1235871-32-5 N-(5-([1,1'-biphenyl]-4-yl)-6,7-dimethoxynaphthalen-1-yl)-5-bromo-N-methylbenzo[1,3]dioxole-4-carboxamide; 
• 1235871-37-0 C₂₇H₂₂BrNO₅ 
• 1235871-14-3 C₃₃H₂₆NO₄⁽¹⁺⁾*Cl^(1-) 
• 1235871-05-2 8-biphenyl-4-yl-9,10-dimethoxy-12-methyl-1,3-dioxa-12-azoniacyclopenta[a]chrysene chloride 

Relevant academic research and scientific papers

Enantioselective Divergent Syntheses of (+)-Bulleyanaline and Related Isoquinoline Alkaloids from the Genus Corydalis

The isoquinoline alkaloids isolated from the genus Corydalis possess potent and diverse biological activities. Herein, a concise, divergent, and enantioselective route to access these natural products is disclosed. Key transformations of our approach incl

Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis

A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).

Structure-activity relationship studies of phenanthridine-based Bcl-X L inhibitors

Despite their structural similarities, the natural products chelerythrine (5) and sanguinarine (6) target different binding sites on the pro-survival Bcl-XL protein. This paper details the synthesis of phenanthridine-based analogues of the natu

Synthesis and SAR exploration of dinapsoline analogues

Dinapsoline is a full D1 dopamine receptor agonist that produces robust rotational activity in the unilateral 6-OHDA rat model. This compound is orally active, and shows a low tendency to cause tolerance in rat models. The active enantiomer was determined to have the S-(+) configuration, and the opposite enantiomer is essentially devoid of biological activity. Taken together, dinapsoline has significant metabolic and pharmacological advantages over previous D1 agonists. In an attempt to define the structure-activity relationships (SARs) and to map out the key elements surrounding the unique structure of dinapsoline, core analogues and substitution analogues of the parent tetracyclic condensed ring structure were prepared. Based on a recently developed synthesis of dinapsoline and its enantiomers, both core and substitution analogues on all four rings (A, B′, C and D ring) of dinapsoline were synthesized. It was found that affinity for both D1and D2 receptors was decreased by most substituents on the A, B′, and C rings, whereas D ring substitutions preserved much of the dopamine receptor binding activity.

Discovery of a New Class of Anilinoquinazoline Inhibitors with High Affinity and Specificity for the Tyrosine Kinase Domain of c-Src

Deregulated activity of the nonreceptor tyrosine kinase c-Src is believed to result in signal transduction, cytoskeletal and adhesion changes, ultimately promoting a tumor-invasive phenotype. We report here the discovery of a new class of anilinoquinazoline inhibitors with high affinity and specificity for the tyrosine kinase domain of the c-Src enzyme. Special attention was directed toward finding inhibitors selective against KDR tyrosine kinase in order to ensure that the in vivo profile of a specific Src inhibitor could be determined. The 4-aminobenzodioxole quinazoline series gave compounds with excellent potency and selectivity. The most interesting compounds were evaluated in vivo and displayed good pharmacokinetics following oral dosing. Compounds such as the aminobenzodioxoles were shown to be potent inhibitors of tumor growth in a c-Src-transformed 3T3 xenograft model in vivo, resulting in more than 90% growth inhibition at doses as low as 6 mg/kg po once daily. Src tyrosine kinase inhibitors such as these may provide a novel therapeutic modality for targeting cancer invasion and metastasis.

Ligand conformation has a definitive effect on 5-HT1A and serotonin reuptake affinity

Conformationally constrained cyclohexanes and cyclohexenes were prepared and tested for 5-HT1A and SSRI activity. The conformation of the dioxyaryl ring with respect to the cyclohexane ring is a key factor for selecting the relative potency of the compounds at the two receptors studied. Conformationally constrained aryl cyclohexanes and cyclohexenes based on aryl cyclohexanols 1 were prepared. Locking the aryl ring in plane with the cyclohexane moiety provided potent SSRIs 3. Conversely, fixing the aryl ring perpendicular to the cyclohexane ring via a spiro lactone provided balanced 5-HT1A antagonists with mid-nanomolar range SSRI potency (compounds 2).

3-ETHOXY-2-HYDROXYBENZALDEHYDE AS A STARTING COMPOUND FOR SYNTHESIS OF ISOQUINOLINE ALKALOIDS

3-Ethoxy-2-hydroxybenzaldehyde (I) was used to prepare 6-bromo-2,3-dihydroxybenzaldehyde (V), 6-bromo-2,3-methylenedioxybenzaldehyde (VIa), 6-bromo-2,3-methylenedioxybenzoic acid (VIIa), and for new synthesis of compounds II, IIIa, IIIb, IV, VIb, VIIb, VIIIa, VIIIb, IXa and IXb.