3534-05-2

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLORO-1-(10,11-DIHYDRO-DIBENZO[B,F]AZEPIN-5-YL)-ETHANONE is used as a key intermediate compound for the development of pharmaceuticals, specifically for the synthesis of selective M2 muscarinic receptor antagonists. These antagonists have potential applications in the treatment of various conditions, including chronic obstructive pulmonary disease (COPD) and other respiratory disorders.
Used in Cancer Treatment:
In the field of oncology, 2-CHLORO-1-(10,11-DIHYDRO-DIBENZO[B,F]AZEPIN-5-YL)-ETHANONE is utilized as an anticancer agent due to its inhibitory effects on cancer cell growth and proliferation. Its potential to treat cancer makes it a valuable compound in the development of novel therapeutic strategies against various types of cancer.

InChI:InChI=1/C16H14ClNO/c17-11-16(19)18-14-7-3-1-5-12(14)9-10-13-6-2-4-8-15(13)18/h1-8H,9-11H2

Upstream product

• 494-19-9 9,10-dihydrodibenzazepine 
• 79-04-9 chloroacetyl chloride 

Relevant academic research and scientific papers

Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on Leishmania major growth and Trypanosoma brucei trypanothione reductase

A number of phenothiazine-, phenoxazine- and related tricyclics-derived chloroacetamides were synthesized and evaluated in vitro for antiprotozoal activities against Leishmania major (L. major) promastigotes. Several analogs were remarkably potent inhibitors, with antileishmanial activities being comparable or superior to those of the reference antiprotozoal drugs. Furthermore, we explored the structure-activity relationships of N-10 haloacetamides that influence the potency of such analogs toward inhibition of L. major promastigote growth in vitro. With respect to the mechanism of action, selected compounds were evaluated for time-dependent inactivation of Trypanosoma brucei trypanothione reductase. Our results are indicative of a covalent interaction which could account for potent antiprotozoal activities.

N-Homolupinanoyl and N-(ω-lupinylthio)alkanoyl derivatives of some tricyclic systems as ligands for muscarinic M1 and M2 receptor subtypes

A set of N-homolupinanoyl- and N-(ω-lupinylthio)alkanoyl derivatives of tricyclic systems (as phenothiazine, iminodibenzyl and dihydropyridobenzodiazepinone) has been prepared and tested for affinity for rat muscarinic M1 and M2 receptor subtypes labeled with [3H]pirenzepine and [3H]AF-DX 384. Good affinity for both M1 and M2 subtypes was displayed by most compounds, often with nanomolar Ki values, which for lupinylthiopropionyl- and lupinylthiobutyryl-phenothiazines (13-16) were comparable to those of pirenzepine and methoctramine, respectively. However, only moderate selectivity for one or the other subtype was seen.

Tricyclic compounds as selective antimuscarinics. 1. Structural requirements for selectivity toward the muscarinic acetylcholine receptor in a series of pirenzepine and imipramine analogues

The M1-selective antiulcer drug pirenzepine (1) is a tricyclic compound with close resemblance to tricyclic psychotropic agents such as imipramine (2). Despite this fact, pirenzepine is devoid of any psychotropic effects, exhibiting measurable antagonistic effects in biochemical assays and receptor binding studies only toward the muscarinic receptor system. To understand how different groups in these tricyclic molecules affect binding affinities, a set of nine compounds structurally related to pirenzepine (1) and imipramine (2) has been selected for analysis, comprising three different tricycles and three different side chains. The compounds were tested for their affinity to the imipramine and muscarinic receptors in homogenized rat cortex tissue. The result of these studies suggests that it is the nature and placement of accessory groups that determine the differences in receptor recognition and the binding process. In the case of pirenzepine (1), preferential binding toward the muscarinic receptor is brought about by the endocyclic amide group, by the positioning of the protonated N atom of the side chain, and to a minor extent by the exocyclic amide group. From these findings a putative model for the explanation of selective binding of pirenzepine (1) to the muscarinic receptor has been derived.

The synthesis of non-exchangeable deuterated internal standards for imipramine and its metabolites

The synthesis of 10,11-dihydro-5-(3-dimethylaminopropyl)-5H-dibenz[b,f]azepine (imipramine) and its 3-methylamino analogue (desipramine) labelled with deuterium in either the 1- or the 3-position of the side chain in high isotopic purity is described. The 3,3-d2 compounds are obtained from the common precursor 5-(2-cyanoethyl)-10, 11-dihydro-5H-dibenz[b,f]azepine by reduction and alkylation, while the 1,1-d2 products are accessible from the 5-(3-chloropropionyl) derivative by amination and reduction. These compounds are required for use as non-exchangeable mass spectrometric stable isotope internal standards for the simultaneous determination of imipramine and desipramine in biological fluids.