73790-19-9

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-2,2-dimethyl-1,3-benzodioxole is used as a reactant in the preparation of phenanthridine-based Bcl-XL inhibitors. Bcl-XL is an anti-apoptotic protein that plays a crucial role in regulating cell death, and its inhibition can lead to the development of potential therapeutic agents for the treatment of various diseases, including cancer.
In the synthesis of phenanthridine-based Bcl-XL inhibitors, 5-bromo-2,2-dimethyl-1,3-benzodioxole serves as a key building block, providing the necessary structural features and reactivity for the formation of the desired inhibitory compounds. The bromine atom at the 5-position can be further functionalized or replaced with other functional groups, allowing for the exploration of structure-activity relationships and the optimization of inhibitory potency.
Furthermore, the presence of the benzodioxole ring in 5-bromo-2,2-dimethyl-1,3-benzodioxole contributes to the overall stability and lipophilicity of the resulting phenanthridine-based Bcl-XL inhibitors, which can be critical factors in determining their pharmacokinetic properties and bioavailability.

Upstream product

• 14005-14-2 2,2-dimethyl-1,3-benzodioxole 
• 2859-78-1 4-Bromoveratrole 
• 77-76-9 2,2-dimethoxy-propane 
• 17345-77-6 1-bromo-3,4-dihydroxybenzene 
• 120-80-9 benzene-1,2-diol 
• 67-64-1 acetone 

Downstream Products

• 56011-75-7 2,2-dimethyl-1,3-benzodioxole-5-carboxylic acid 
• 1391976-76-3 (C₅H₄N)N(CH₃)(CH₂)6(C₆H₃O₂B)(2,4,6-C₆H₂iPr₃) 
• 1391976-75-2 C₂₄H₂₇BN₂O₂ 
• 1391976-74-1 (C₅H₄N)N(CH₃)(CH₂)6(C₆H₃O₂B)(2,4,6-C₆H₂F₃) 
• 1391976-73-0 4-(6-(methyl(pyridin-4-yl)amino)hexyl)benzene-1,2-diol 
• 369354-51-8 4-bromo-5-chloropyrocatechol 
• 103028-36-0 1,2-diacetoxy-4-bromo-5-nitro-benzene 
• 52864-93-4 4-bromo-5-nitro-pyrocatechol 
• 122850-27-5 E-4-(heptadec-8'-enyl)benzene-1,2-diol 
• 122850-26-4 Z-4-(heptadec-8'-enyl)benzene-1,2-diol 
• 122850-20-8 2,2-dimethyl-1,3-benzodioxol-5-ylmethyltriphenylphosphonium chloride 
• 105419-12-3 4-<8'Z,11'Z-heptadecadienyl>catechol 
• 765312-54-7 (2,2,2',2'-tetramethyl[4,4'-bibenzo[d][1,3]dioxole]-5,5'-diyl)bis(diphenylphosphine) 

Relevant academic research and scientific papers

Rotational energy barrier around the C1-C11 single bond in lamellarins: A study by variable-temperature NMR

In order to estimate the free energy barrier to rotation around the C1-C11 single bond in lamellarins, new lamellarin analogues (1a), (1b), (2a), and (2b) possessing diastereotopic protons or carbons at the C1 aryl moiety were synthesized. Variable-temperature 1H and 13C NMR measurements of these analogues revealed that the free energy barriers to rotation around the C1-C11 axis in 5,6-saturated and 5,6-unsaturated lamellarins were around 72-74 and 83-87 kJ/mol, respectively.

N-{[2-(PIPERIDIN-1-YL)PHENYL](PHENYL)METHYL}-2-(3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXA ZIN-7-YL)ACETAMIDE DERIVATIVES AND RELATED COMPOUNDS AS ROR-GAMMA MODULATORS FOR TREATING AUTOIMMUNE DISEASES

The present invention provides e.g. N-{[2-(piperidin-1-yl)phenyl] (phenyl)methyl}-2-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)acetamide derivatives and related compounds as ROR-gamma modulators for treating e.g. autoimmune diseases, autoimmune-related diseases, inflammatory diseases, metabolic diseases, fibrotic diseases or cholestatic diseases, such as e.g. arthitis and asthma.

Synthesis, Antiviral Activity, and Structure–Activity Relationship of 1,3-Benzodioxolyl Pyrrole-Based Entry Inhibitors Targeting the Phe43 Cavity in HIV-1 gp120

The pathway by which HIV-1 enters host cells is a prime target for novel drug discovery because of its critical role in the life cycle of HIV-1. The HIV-1 envelope glycoprotein gp120 plays an important role in initiating virus entry by targeting the primary cell receptor CD4. We explored the substitution of bulky molecular groups in region I in the NBD class of entry inhibitors. Previous attempts at bulky substituents in that region abolished antiviral activity, even though the binding site is hydrophobic. We synthesized a series of entry inhibitors containing the 1,3-benzodioxolyl moiety or its bioisostere, 2,1,3-benzothiadiazole. The introduction of the bulkier groups was well tolerated, and despite only minor improvements in antiviral activity, the selectivity index of these compounds improved significantly.

Synthesis of a functionalized benzofuran as a synthon for salvianolic acid C analogues as potential LDL Antioxidants

A palladium mediated synthesis of a common synthon for the syntheses of antioxidant analogues of naturally occurring salvianolic acids is presented. The synthetic route may be used to obtain analogues with a balanced lipophilicity/hydrophilicity which may

4-AMINO-6-(HETEROCYCLIC)PICOLINATES AND 6-AMINO-2-(HETEROCYCLIC)PYRIMIDINE-4-CARBOXYLATES AND THEIR USE AS HERBICIDES

Novel 4-amino-6-(heterocyclic)picolinic acids and their derivatives and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their derivatives are useful to control undesirable vegetation.

PROCESS FOR PRODUCTION OF HYDROXYTYROSOL USING ORGANOMETALLIC COMPOUNDS

Disclosed is a process for the production of a 4-(2-hydroxyalkyl)-1,2-benzenediol, comprising the steps of (a) providing protected 1,2-benzenediol having the 1,2-hydroxyl groups protected, (b) halogenating the protected 1,2-benzenediol to obtain a protected 4-halo-1,2-benzenediol having the 1,2-hydroxyl groups protected, (c) reacting, in the presence of a metal or organometallic compound, the protected 4-halo-1,2-benzenediol to protected 4-(2-hydroxyalkyl)-1,2-benzenediol having the 1,2-hydroxyl groups protected, and (d) deprotecting the protected 4-(2-hydroxyalkyl)-1,2-benzenediol to obtain the 4-(2-hydroxyalkyl)-1,2-benzenediol. Also disclosed is the use of 1,2-benzenediol for the production of hydroxytyrosol.

NOVEL BIPHENYL COMPOUNDS AND THEIR USE

The invention is directed to certain biphenyl compounds. Specifically, the invention is directed to compounds according to Formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, and Y are as defined below, and to pharmaceutically-acceptable salts thereo

Synthesis and biological activity of 2-carbomethoxy-3-catechol-8- azabicyclo[3.2.1]octanes

Cocaine inhibits the dopamine transporter and the consequent elevation of dopamine is thought to contribute to the addictive properties of cocaine. Tropane analogues of cocaine, targeted to the dopamine transporter (DAT), are a significant focus of drug d

NO-CARRIER ADDED (NCA) ARYL FLUORIDES VIA THE NUCLEOPHILIC AROMATIC SUBSTITUTION OF ELECTRON-RICH AROMATIC RINGS

Nucleophilic aromatic substitution by fluoride ion has been demonstrated on rings containing electron donating groups in addition to the necessary electron withdrawing and leaving groups.The reaction of (18)F- with a series of aromatic nitro aldehydes having protected hydroxyl substituents on the ring was studied.The reactivity of the aromatic ring towards nucleophilic substitution to give (18)F-labeled aromatic fluoroaldehyde derivatives is correlated with electron density at the reaction center.The effect of a number of protected hydroxyl substituents is reported. 13C-NMR was used as a sensitive probe for the changes in electron distribution at the ring carbon atoms.Radiochemical yield correlated with ppm values at the reaction center.This methodology has been applied to the synthesis of no-carrier-added(NCA) 6-fluoro-L-DOPA.The extension of this strategy to the syntheses of other labeled pharmaceuticals appears promising.

Diphenyl ether derivatives and their use as insecticides

A compound of formula: STR1 wherein W represents one or more substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Y is a group of formula STR2 wherein X is a group of formula --(CF2)n R3, where R3 is selected from hydrogen, chloro and fluoro, and n is one or two, R1 is selected from hydrogen, chloro, fluoro and hydroxy and R2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.