114772-19-9

Basic information

• Product Name: 4-HYDROXYMETHYL-3-(4-NITRO-BENZYL)-2-MERCAPTO-3H-IMIDAZOLE
• Synonyms: (2-mercapto-1-(4-nitrobenzyl)-1H-imidazol-5-yl)methanol;REF DUPL: 4-Hydroxymethyl-3-(4-nitro-benzyl)-2-mercapto-3H-imidazole;2H-Imidazole-2-thione, 1,3-dihydro-5-(hydroxymethyl)-1-[(4-nitrophenyl)methyl]-
• CAS NO: 114772-19-9
• Molecular Formula: C₁₁H₁₁N₃O₃S
• Molecular Weight: 265.29
• Mol File: 114772-19-9.mol

Chemical Properties

• Boiling Point: 479.4°Cat760mmHg
• Flash Point: 243.8°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.727
• PKA: 11.49±0.70(Predicted)
• CAS DataBase Reference: 4-HYDROXYMETHYL-3-(4-NITRO-BENZYL)-2-MERCAPTO-3H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXYMETHYL-3-(4-NITRO-BENZYL)-2-MERCAPTO-3H-IMIDAZOLE(114772-19-9)
• EPA Substance Registry System: 4-HYDROXYMETHYL-3-(4-NITRO-BENZYL)-2-MERCAPTO-3H-IMIDAZOLE(114772-19-9)

Safety Data

• Hazardous Substances Data: 114772-19-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-HYDROXYMETHYL-3-(4-NITRO-BENZYL)-2-MERCAPTO-3H-IMIDAZOLE is used as a potential therapeutic agent for various applications due to its antimicrobial, antifungal, and antiparasitic properties inherent to imidazoles. The specific modifications in its structure may enhance these activities or provide new therapeutic avenues.
Used in Drug Development Research:
In the field of drug development, 4-HYDROXYMETHYL-3-(4-NITRO-BENZYL)-2-MERCAPTO-3H-IMIDAZOLE serves as a subject of study to understand how the addition of hydroxymethyl and nitro-benzyl groups can influence the compound's pharmacokinetics and pharmacodynamics, potentially leading to the discovery of novel drugs with improved efficacy and safety profiles.

InChI:InChI=1/C11H11N3O3S/c15-7-10-5-12-11(18)13(10)6-8-1-3-9(4-2-8)14(16)17/h1-5,15H,6-7H2,(H,12,18)

Upstream product

• 96-26-4 dihydroxyacetone 
• 333-20-0 potassium thioacyanate 
• 18600-42-5 4-nitrobenzylamine hydrochloride 
• 62147-49-3 1,3-dihydroxyacetone dimer 
• 7409-30-5 p-nitrobenzylamine 
• 62147-49-3 dihydroxyacetone-dimer 

Downstream Products

• 309254-11-3 2-ethylthio-5-hydroxymethyl-1-[(4-nitropehnyl)methyl]imidazole 
• 114772-20-2 5-hydroxymethyl-2-methylthio-1-[(4-nitropehnyl)methyl]imidazole 
• 309254-12-4 5-hydroxymethyl-1-[(4-nitropehnyl)methyl]-2-propylthioimidazole 
• 125665-53-4 N-[4-(5-Hydroxymethyl-imidazol-1-ylmethyl)-phenyl]-phthalamic acid 
• 309254-14-6 1-[(4-aminophenyl)methyl]-5-hydroxymethyl-2-propylthioimidazole 
• 309254-13-5 1-[(4-aminophenyl)methyl]-2-ethylthio-5-hydroxymethylimidazole 
• 114772-21-3 1-[(4-aminophenyl)methyl]-5-hydroxymethyl-2-methylthioimidazole 
• 85102-92-7 2-(hydroxymethyl)-1-<(4-nitrophenyl)methyl>imidazole 

Relevant articles and documents

Synthesis and calcium channel blocker activity of alkyl 1,4-dihydro-2,6-dimethyl-4-nitrobenzyl thioimidazolyl-3,5-pyridinedicarboxylates

New alkyl ester analogues of nifedipine, in which the orthonitrophenyl group of position 4 is replaced by 1-methyl 2-(p-nitrobenzyl)thio-5-imidazolyl substituent, were synthesized and evaluated as calcium-channel antagonists using the high K+ contraction of guinea-pig ileal longitudinal smooth muscle. The results for the symmetrical esters showed that increasing the length of methylen chain in C3 and C5 ester substituents decreased activity. When the presence of bulky lipophilic esters increased activity. In ztnsymmetrical diester series, the results showed when R1 is a small substituent (R1=Me), increasing of the lipophilic property in R2 substituent increased the activity if this high lipophilicity don't accompany with steric hinderance. Our results demonstrate that the most active compound was diphenyl ester derivative and it was almost seven times more active than the reference drug nifedipine.

Preparation of a clinically investigated ras farnesyl transferase inhibitor

The synthesis of ras farnesyl-protein transferase inhibitor 1 is described on a multi-kilogram scale. Retrosynthetic analysis reveals chloromethylimidazole 2 and a piperazinone 3 as viable precursors. The 1,5-disubstituted imidazole system was regioselectively assembled via an improved Marckwald imidazole synthesis. A new imidazole dethionation procedure has been developed to convert the Marckwald mercaptoimidazole product to the desired imidazole. This methodology was found to be tolerant of a variety of functional groups providing good to excellent yields of 1,5-disubstituted imidazoles. A new Mitsunobu cyclization strategy was developed to prepare the arylpiperazinone fragment 3.

Synthesis and calcium antagonist activity of new 1,4-dihydropyridines containing nitrobenzylimidazolyl substituent in ginea-pig ileal smooth muscle

New alkyl ester analogues of nifedipine, in which the ortho-nitrophenyl group of position 4 is replaced by 1-(4-nitrobenzyl)-5-imidazolyl or 2-methylthio-1-(4-nitrobenzyl)-5-imidazolyl substituent, were synthesized and evaluated as calcium-channel antagonists using the electrically induced contraction of guinea-pig ileal longitudinal smooth muscle. Our results demonstrate that all compounds inhibited the contractile response of guinea-pig ileum to electrical stimulation and the IC50 value of the most potent compounds 6a and 6f were significantly lower than that of nifedipine. Therefore, they are more potent than nifedipine.

Process for making 1,5-disubstituted imidazoles

The present invention is directed to a process for synthesizing 1,5-disubstituted imidazoles, which are useful in the preparation of farnesyl-protein transferase inhibitors.

ANGIOTENSIN II RECEPTOR BLOCKING IMIDAZOLES

Substituted imidazoles such as STR1 are useful as angiotensin II blockers. These compounds have activity in treating hypertension and congestive heart failure.

Treatment of congestive heart failure with angiotensin 11 receptor blocking imidazoles

Substituted imidazoles such as STR1 are useful as angiotensin II blockers. These compounds have activity in treating hypertension and congestive heart failure.

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.