![molecular formula C31H33ClN6O B8540554 1H-Imidazole-5-methanol, 2-butyl-4-chloro-1-[[2'-[2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-](/img/structure/B8540554.png)
1H-Imidazole-5-methanol, 2-butyl-4-chloro-1-[[2'-[2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-
Overview
Description
The compound (2-butyl-5-chloro-3-{2’-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-biphenyl-4-ylmethyl}-3H-imidazol-4-yl)-methanol is a complex organic molecule that features a combination of imidazole and tetrazole rings
Preparation Methods
Synthetic Routes and Reaction Conditions
The synthesis of (2-butyl-5-chloro-3-{2’-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-biphenyl-4-ylmethyl}-3H-imidazol-4-yl)-methanol typically involves multi-step organic synthesis. The process begins with the preparation of the imidazole and tetrazole precursors, followed by their coupling to form the final compound. Common reagents used in these reactions include various chlorinating agents, alkylating agents, and catalysts to facilitate the formation of the desired bonds .
Industrial Production Methods
Industrial production of this compound may involve the use of continuous flow reactors to optimize reaction conditions and improve yield. The use of microwave-assisted synthesis has also been explored to enhance reaction rates and achieve higher yields .
Chemical Reactions Analysis
Types of Reactions
The compound (2-butyl-5-chloro-3-{2’-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-biphenyl-4-ylmethyl}-3H-imidazol-4-yl)-methanol undergoes various chemical reactions, including:
Oxidation: The hydroxyl group can be oxidized to form a ketone or aldehyde.
Reduction: The compound can be reduced to modify the imidazole or tetrazole rings.
Substitution: Halogen atoms can be substituted with other functional groups using nucleophilic substitution reactions
Common Reagents and Conditions
Common reagents used in these reactions include oxidizing agents like potassium permanganate, reducing agents like lithium aluminum hydride, and nucleophiles like sodium azide for substitution reactions .
Major Products
The major products formed from these reactions depend on the specific conditions and reagents used. For example, oxidation of the hydroxyl group may yield a ketone, while substitution reactions can introduce various functional groups to the molecule .
Scientific Research Applications
Chemistry
In chemistry, this compound is used as a building block for the synthesis of more complex molecules. Its unique structure allows for the exploration of new synthetic pathways and the development of novel materials .
Biology
In biological research, the compound is studied for its potential as a pharmacophore. Its imidazole and tetrazole rings are known to interact with various biological targets, making it a candidate for drug development .
Medicine
The compound has shown promise in medicinal chemistry for its potential therapeutic applications. It is being investigated for its anti-inflammatory, antimicrobial, and anticancer properties .
Industry
In the industrial sector, the compound is used in the development of advanced materials, including polymers and coatings. Its unique chemical properties make it suitable for various applications .
Mechanism of Action
The mechanism of action of (2-butyl-5-chloro-3-{2’-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-biphenyl-4-ylmethyl}-3H-imidazol-4-yl)-methanol involves its interaction with specific molecular targets. The imidazole and tetrazole rings can bind to enzymes and receptors, modulating their activity. This interaction can lead to various biological effects, such as inhibition of enzyme activity or modulation of receptor signaling pathways .
Comparison with Similar Compounds
Similar Compounds
(2-butyl-5-chloro-3-{2’-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-biphenyl-4-ylmethyl}-3H-imidazol-4-yl)-methanol: This compound is unique due to its specific combination of functional groups and rings.
Imidazole derivatives: Compounds like metronidazole and clotrimazole share the imidazole ring but differ in their overall structure and applications.
Tetrazole derivatives: Compounds like losartan and valsartan contain the tetrazole ring and are used as antihypertensive agents.
Uniqueness
The uniqueness of (2-butyl-5-chloro-3-{2’-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-biphenyl-4-ylmethyl}-3H-imidazol-4-yl)-methanol lies in its combination of imidazole and tetrazole rings, which confer distinct chemical and biological properties. This makes it a versatile compound for various applications in research and industry .
Properties
Molecular Formula |
C31H33ClN6O |
|---|---|
Molecular Weight |
541.1 g/mol |
IUPAC Name |
[2-butyl-5-chloro-3-[[4-[2-[2-(2-phenylpropan-2-yl)tetrazol-5-yl]phenyl]phenyl]methyl]imidazol-4-yl]methanol |
InChI |
InChI=1S/C31H33ClN6O/c1-4-5-15-28-33-29(32)27(21-39)37(28)20-22-16-18-23(19-17-22)25-13-9-10-14-26(25)30-34-36-38(35-30)31(2,3)24-11-7-6-8-12-24/h6-14,16-19,39H,4-5,15,20-21H2,1-3H3 |
InChI Key |
OMOPLAPBVQZYJL-UHFFFAOYSA-N |
Canonical SMILES |
CCCCC1=NC(=C(N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NN(N=N4)C(C)(C)C5=CC=CC=C5)CO)Cl |
Origin of Product |
United States |
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