4442-59-5

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dihydro-1,4-benzodioxin-2-ylmethylamine is used as a key intermediate in the synthesis of N-substituted (dihydrobenzodioxinyl)methylamine derivatives. These derivatives have potential applications as atypical antipsychotic agents, particularly due to their affinity for α1 adrenoceptors. 2,3-DIHYDRO-1,4-BENZODIOXIN-2-YLMETHYLAMINE's unique structure allows for the development of D2 antagonists and 5-HT1A partial agonists, which can be beneficial in treating various psychiatric disorders.

InChI:InChI=1/C9H11NO2/c10-5-7-6-11-8-3-1-2-4-9(8)12-7/h1-4,7H,5-6,10H2/p+1/t7-/m1/s1

Upstream product

• 2164-33-2 2-chloromethyl-1,4-benzodioxane 
• 1008-92-0 2-cyano-1,4-benzodioxane 
• 128318-80-9 2-azidomethyl-2,3-dihydro-1,4-benzodioxine 
• 3663-82-9 2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin 
• 1094-91-3 2-(toluene-4-sulfonyloxymethyl)-2,3-dihydro-benzo[1,4]dioxine 

Downstream Products

• 101997-49-3 1-[N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-glycyl]-piperidine 
• 3562-90-1 4-[N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-glycyl]-morpholine 
• 102071-89-6 1-[N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-β-alanyl]-piperidine 
• 110356-88-2 N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-β-alanine-cyclohexylamide 
• 119750-12-8 PCM-0102881 
• 74398-46-2 3-[(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-amino]-propan-1-ol 

Relevant academic research and scientific papers

Efficient conversion of primary and secondary alcohols to primary amines

A convenient single-vessel conversion of primary and secondary alcohols to primary amines is reported. Use of this method results in substantially cleaner crude products than similar procedures reported in the literature. A simple work-up also makes this procedure ideal for parallel synthesis.

Versatile solid-phase synthesis of secondary amines from alcohols. Development of an N-Boc-(o-nitrobenzene)sulfonamide linker

The development of a versatile amine releasing linker based on the modified o-nitrobenzene sulfonamide protective group is described. This new N-Boc-o-nitrobenzenesulfonamide (Boc-ONBS) linker enables the elaboration on resin of primary and secondary amines by sequential substitution of the sulfonamide moiety using the Mitsunobu reaction. A 16-member array of secondary and Boc protected primary amines was then prepared using this linker.

N-Hydroxyl derivatives of guanidine based drugs as enzymatic NO donors

Recent research suggests that NO may play a role in the physiological effects of some guanidine-containing drugs. In this report, three guanidine-containing drugs (guanadrel, guanoxan, and guanethidine) together with their N-hydroxyl derivatives were synthesized and their NO-releasing abilities catalyzed by nitric oxide synthases (NOSs) and horseradish peroxidase were evaluated. The guanidine containing compounds could not release NO in the presence of NOS or peroxidase. The corresponding N-hydroxyl compounds exhibited weak NO-releasing ability under the catalyzed of NOS and good NO-releasing ability under the oxidation by horseradish peroxidase in the presence of H2O2. These compounds also displayed vasodilatory activity. Elsevier Science Ltd. All rights reserved.

Design and synthesis of substituted compounds containing the 1,4- benzodioxin subunit. New potential calcium antagonists

New compounds possessing 1,4-benzodioxin or its saturated analogous heterocyclic system were synthesized and tested for calcium antagonist activity. Biological differences were seen between the different modifications applied. These compounds have been shown to be representative of a novel series of calcium channel antagonists. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

N-substituted (2,3-dihydro-1,4-benzodioxin-2-yl)methylamine derivatives as 92 antagonists/5-HT(1A) partial agonists with potential as atypical antipsychotic agents

A series of N-substituted 1-(2,3-dihydro-1,4-benzodioxin-2- yl)methylamine derivatives with D2 antagonist/5-HT(1A) partial agonist activity has been prepared as potential atypical antipsychotic agents. Optimization of in vitro receptor binding activity and in vivo activity in rodent models of psychosis has led to compound 24, which showed good affinities for human D2, D3, and 5-HT(1A) receptors but significantly less affinity for human α1 adrenoceptors and rat H1 and muscarinic receptors. In rodents, 24 showed functional D2-like antagonism and 5-HT(1A) partial agonism. After oral dosing, 24 showed good activity in rodent antipsychotic tests and very little potential to cause extrapyramidal side effects (EPS), as measured by its ability to induce catalepsy in rats only at very high doses. In the light of this promising profile of activity, 24 has been selected for clinical investigation as a novel antipsychotic agent with a predicted low propensity to cause EPS.

BENZODIOXANE DERIVATIVES

Compounds represented by the general formula (I): STR1 (where R. sub.1 is an admantyl group; R 2 is a hydrogen atom, a lower alkyl group, a lower alkenyl group or an aralkyl group; R 3 is a 1,4-benzodioxane ring that may optionally have 1-4 substituents selected from among a lower alkyl group, a lower alkoxy group, a halogen atom, an amino group, a hydroxyl group and a lower alkylcarbonyl group; n is an integer of 1-4) or a salt thereof. These compounds have both antianxiety and antidepressant actions and yet they cause less side effects. Therefore, they can be used as excellent drugs that are highly effective in the prevention and treatment of various diseases such as neurosis. psychosomatic diseases, autonomic imbalance and depression.