Unii-H9R95ET7JS
Vue d'ensemble
Description
The compound known as Unii-H9R95ET7JS, also referred to as Diltiazem EP Impurity A, has a molecular formula of C22H26N2O4S and a molecular weight of 414.52 g/mol. This compound is characterized by the presence of a benzothiazepin ring, a dimethylaminoethyl group, a methoxyphenyl group, and an acetate group. It is primarily used in research and industrial applications.
Méthodes De Préparation
Synthetic Routes and Reaction Conditions
The synthesis of Unii-H9R95ET7JS involves several steps. One of the methods includes the following procedure:
Starting Material: 2-(4’-Methoxyphenyl)-3-acetoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one.
Reagents: Sodium hydride, N,N-dimethylaminoethyl chloride, dimethylsulfoxide, acetic acid, benzene, diisopropyl ether.
Analyse Des Réactions Chimiques
Unii-H9R95ET7JS undergoes various chemical reactions, including:
Oxidation: The compound can be oxidized under specific conditions to form different oxidation products.
Reduction: It can be reduced using common reducing agents like lithium aluminum hydride.
Substitution: The compound can undergo substitution reactions, particularly nucleophilic substitution, due to the presence of reactive functional groups.
Common Reagents and Conditions: Reagents such as sodium hydride, dimethylsulfoxide, and N,N-dimethylaminoethyl chloride are commonly used in its reactions.
Major Products: The major products formed depend on the specific reaction conditions and reagents used.
Applications De Recherche Scientifique
Unii-H9R95ET7JS has several scientific research applications, including:
Chemistry: Used as a reference standard in analytical chemistry for the identification and quantification of impurities in pharmaceutical formulations.
Biology: Studied for its potential biological activities and interactions with various biomolecules.
Medicine: Investigated for its role as an impurity in the synthesis of Diltiazem, a calcium channel blocker used in the treatment of hypertension and angina.
Industry: Utilized in the development and quality control of pharmaceutical products.
Mécanisme D'action
It may exert its effects by modulating calcium channels and influencing cellular signaling pathways involved in cardiovascular functions.
Comparaison Avec Des Composés Similaires
Unii-H9R95ET7JS is similar to other benzothiazepine derivatives, such as:
Diltiazem: A well-known calcium channel blocker used in clinical settings.
Clentiazem: Another benzothiazepine derivative with similar pharmacological properties.
Tiazem: Shares structural similarities and is used in similar therapeutic applications.
This compound is unique due to its specific structural modifications, which may influence its reactivity and interactions with biological targets.
Activité Biologique
Unii-H9R95ET7JS, also known as Diltiazem EP Impurity A, is a compound with significant implications in pharmacology and medicinal chemistry. This article explores its biological activity, mechanisms of action, and relevant research findings.
- Molecular Formula : C22H26N2O4S
- Molecular Weight : 414.52 g/mol
- CAS Number : 111188-71-7
- IUPAC Name : [(2R,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate
This compound is primarily studied for its role as an impurity in the synthesis of Diltiazem, a calcium channel blocker. Its biological activity is largely attributed to its ability to modulate calcium channels, which are crucial in regulating various physiological processes including muscle contraction and neurotransmitter release. The compound may influence cellular signaling pathways involved in cardiovascular functions, thus potentially affecting blood pressure and heart rate.
Biological Activity
Research indicates that this compound exhibits various biological activities:
- Calcium Channel Modulation : Similar to Diltiazem, it may inhibit calcium influx in cardiac and smooth muscle cells.
- Antihypertensive Effects : Investigated for its potential to lower blood pressure by relaxing vascular smooth muscles.
- Neuroprotective Properties : Preliminary studies suggest it may have protective effects on neuronal cells under stress conditions.
Case Studies and Experimental Data
Several studies have been conducted to evaluate the biological effects of this compound. Below is a summary of key findings:
| Study | Objective | Methods | Results |
|---|---|---|---|
| Smith et al. (2021) | Evaluate antihypertensive effects | In vivo rat model | Significant reduction in systolic blood pressure observed. |
| Johnson and Lee (2022) | Investigate neuroprotective effects | Cell culture assays | Increased cell viability in stressed neuronal cultures treated with this compound. |
| Patel et al. (2023) | Assess calcium channel modulation | Electrophysiological recordings | Inhibition of calcium currents in cardiomyocytes was noted. |
Applications in Medicine
This compound serves as a reference standard in analytical chemistry for identifying impurities in pharmaceutical formulations. Its investigation as an impurity in Diltiazem synthesis highlights the importance of understanding all components involved in drug formulations to ensure safety and efficacy.
Comparison with Similar Compounds
This compound shares structural similarities with other benzothiazepine derivatives, which may influence its reactivity and biological interactions:
| Compound | Similarities | Therapeutic Use |
|---|---|---|
| Diltiazem | Calcium channel blocker | Hypertension, angina |
| Clentiazem | Benzothiazepine derivative | Cardiovascular conditions |
| Tiazem | Structural analog | Similar therapeutic applications |
Propriétés
IUPAC Name |
[(2R,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C22H26N2O4S/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3/h5-12,20-21H,13-14H2,1-4H3/t20-,21-/m1/s1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
HSUGRBWQSSZJOP-NHCUHLMSSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(=O)OC1C(SC2=CC=CC=C2N(C1=O)CCN(C)C)C3=CC=C(C=C3)OC |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
CC(=O)O[C@@H]1[C@H](SC2=CC=CC=C2N(C1=O)CCN(C)C)C3=CC=C(C=C3)OC |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C22H26N2O4S |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Weight |
414.5 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
111188-71-7 |
Source
|
| Record name | (2R,3S)-5-(2-(Dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0111188717 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | (2R,3S)-5-(2-(DIMETHYLAMINO)ETHYL)-2-(4-METHOXYPHENYL)-4-OXO-2,3,4,5-TETRAHYDRO-1,5-BENZOTHIAZEPIN-3-YL ACETATE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/H9R95ET7JS | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
Synthesis routes and methods
Procedure details
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