56643-86-8

Usage

Uses

Used in Pharmaceutical Research and Development:
2-METHYL-1-(4-NITROBENZYL)-1H-IMIDAZOLE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 2-METHYL-1-(4-NITROBENZYL)-1H-IMIDAZOLE serves as a building block for creating more complex chemical structures. Its presence of the 4-nitrobenzyl group makes it suitable for use in organic synthesis, contributing to the advancement of chemical science.
Used in Organic Synthesis:
2-METHYL-1-(4-NITROBENZYL)-1H-IMIDAZOLE is used as a key component in organic synthesis processes. Its 4-nitrobenzyl group provides a reactive site for further chemical reactions, enabling the formation of a wide range of organic compounds.
It is crucial to handle and use 2-METHYL-1-(4-NITROBENZYL)-1H-IMIDAZOLE with care, as it may present hazards if not managed properly. Proper safety measures should be taken to ensure the safe use of 2-METHYL-1-(4-NITROBENZYL)-1H-IMIDAZOLE in various applications.

InChI:InChI=1/C11H11N3O2/c1-9-12-6-7-13(9)8-10-2-4-11(5-3-10)14(15)16/h2-7H,8H2,1H3

Upstream product

• 693-98-1 2-methylimidazole 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 18994-90-6 1-(4-nitrobenzyl)-1H-imidazole 
• 100-14-1 4-nitrobenzyl chloride 

Downstream Products

• 125665-48-7 N-[4-(2-Methyl-imidazol-1-ylmethyl)-phenyl]-phthalamic acid 
• 152537-12-7 [4-(2-Methyl-imidazol-1-ylmethyl)-phenyl]-hydrazine 
• 772311-98-5 4-(2-methyl-imidazol-1-ylmethyl)-phenylamine 

Relevant academic research and scientific papers

Synthesis and biological activity of imidazole group-substituted arylaminopyrimidines (IAAPs) as potent BTK inhibitors against B-cell lymphoma and AML

Bruton's tyrosine kinase (BTK) is a member of the Tec kinase family and plays a key role in the modulation of the B-cell receptor (BCR)-mediated signaling pathway. Inhibition of BTK has been proven to be an effective therapeutic approach for various hemat

Azolo pyrimidine derivative, pharmaceutical composition thereof and application of azolopyrimidine derivative in tumor resistance

The invention discloses an azolopyrimidine derivative, a pharmaceutical composition thereof and an application of the azolopyrimidine derivative in tumor resistance, and relates to the field of medicines and chemical engineering. The azolopyrimidine deriv

Synthesis and investigation of inhibitory activities of imidazole derivatives against the metallo-β-lactamase IMP-1

Mutations in bacteria can result in antibiotic resistance due to the overuse or abuse of β-lactam antibiotics. One strategy which bacteria can become resistance toward antibiotics is secreting of metallo β-lactamase enzymes that can open the lactam ring of the β-lactam antibiotic and inactivate them. This issue is a threat for human health and one strategy to overcome this situation is co-administration of β-lactam antibiotics with an inhibitor. So far, no clinically available inhibitors of metallo β-lactamases (MBLs) reported and the clinically inhibitors of serine β-lactamase are useless for MBLs. Accordingly, finding a potent inhibitor of the MBLs being very important. In this study, imidazole derivatives primarily were synthesized and their inhibitory activity were measured. Later in silico binding model was used to predict the configuration and conformation of the ligands into the active site of enzyme. Two molecules demonstrated with IC50 of 39 μM and 46 μM against MBL (IMP-1).

Amide derivatives and medicinal compositions thereof

PCT No. PCT/JP98/00237 Sec. 371 Date May 7, 1999 Sec. 102(e) Date May 7, 1999 PCT Filed Jan. 22, 1998 PCT Pub. No. WO98/32742 PCT Pub. Date Jul. 30, 1998An amide derivative represented by the following general formula (I) or a salt thereof and a pharmaceutical composition containing the amide derivative and a pharmaceutically acceptable vehicle. (The symbols in the formula have the following meanings. (wherein A: heteroarylene; X: bond, O, S, -NR5-, -NR5CO-, -NR5CONH-, -NR5SO2- or -NR5C(=NH)NH-; R1: -H, -optionally substituted lower alkyl, -optionally substituted aryl, -optionally substituted heteroaryl or -optionally substituted cycloalkyl; R2a, R2b: -H or -lower alkyl, which may be the same or different; R3: -H or -lower alkyl; R4a, R4b: -H or -OH, which may be the same different, or R4a and R4b are taken together to form =O or =N DIFFERENCE O-lower alkyl; and R5: -H or -lower alkyl.

Imidazole, triazole and tetrazole derivatives

A class of substituted imidazole, triazole and tetrazole derivatives of formula (I), wherein the broken circle represents two non-adjacent double bonds in any position in the five-membered ring; two, three or four of V,W,X,Y and Z represent nitrogen and the remainder represent carbon provided that, when two of V,W,X,Y and Z represent nitrogen and the remainder represent carbon, then the said nitrogen atoms are in non-adjacent positions within the five-membered ring; E represents a bond or a straight or branched alkylene chain containing from 1 to 4 carbon atoms; F represents a group of formula (lI); U represents nitrogen or C--R2 ; B represents oxygen, sulphur or N--R3 ; are selective agonists of 5--HT1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.

Synthesis and serotonergic activity of N,N-dimethyl-2-[5-(1,2,4-triazol- 1-ylmethyl)-1H-indol-3-yl]ethylamine and analogues: Potent agonists for 5- HT(1D) receptors

The synthesis and the 5-HT receptor activity of a novel series of N,N- dimethyltryptamines substituted in the 5-position with an imidazole, triazole, or tetrazole ring are described. The objective of this work was to identify potent and selective 5-HT(1D) receptor agonists with high oral bioavailability and low central nervous system penetration. Compounds have been prepared in which the azole ring is attached through either nitrogen or carbon to the indole. Conjugated and methylene-bridged derivatives have been studied (n = 0 or 1). Substitution of the azole ring has been explored either α or β to the point of attachment to indole. In a series of N-linked azoles (X = N), simple unsubstituted compounds have high affinity and selectivity for 5-HT(1D) receptors. It is proposed that for good affinity and selectivity a hydrogen bond acceptor interaction with the 5-HT(1D) receptor, through a β-nitrogen in the azole ring, is required. In a series of C-linked triazoles and tetrazoles (X = C), optimal affinity and selectivity for the 5-HT(1D) receptor was observed when the azole ring is substituted at the 1-position with a methyl or ethyl group. This study has led to the discovery of the 1,2,4-triazole 10a (MK-462) as a potent and selective 5-HT(1D) receptor agonist which has high oral bioavailability and rapid oral absorption. The in vitro activity and the preliminary pharmacokinetics of compounds in this series are presented.

Triazole containing indole derivatives

A class of substituted imidazole, triazole and tetrazole derivatives are selective agonists of 5-HT 1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.

The Discovery of Potent Nonpeptide Angiotensin II Receptor Antagonists: A New Class of Potent Antihypertensives

A new class of potent antihypertensives has been discovered that exert their effect through blockade of the angiotensin II (AII) receptor.Most AII antagonists reported so far are peptide mimics of the endogenous vasoconstrictor octapeptide angiotensin II.The compounds of this paper are nonpeptides and therefore constitute a new class of potent AII receptor antagonists.Based on the overlap of a conformation of AII with literature lead 3, a hypothesis was developed suggesting the need for an additional acidic functionality to increase the lead's potency.The substitution of an additional carboxylic acid resulted in a 10-fold increase in binding affinity observed for diacid 4.The binding affinities for subsequent compounds were eventually increased 1000-fold over that of the literature leads through a systematic SAR study.Thus the AII receptor binding affinity 50 (μM)> of 15 μM for literature lead 1, for example, was increased to 0.018 and 0.012 μM for compounds 33 and 53.A structure-affinity relationship has been found requiring the presence of four key elements for good activity: (1) an additional phenyl ring at the N-benzyl para position of the benzylimidazole nucleus, (2) an acidic functionality at the ortho position of the terminal aromatic ring, (3) a lipophilic side chain at the imidazole 2-position of three to five carbon atoms in length, and (4) a group at the imidazole 5-position capable of hydrogen bonding.The synthesis as well as the pharmacological activity of the compounds in this new series of AII receptor antagonists are presented.