474956-06-4

Basic information

• Product Name: IMidazo[1,2-a]pyridine-2-carboxylic acid, 6-broMo-, hydrazide
• Synonyms: IMidazo[1,2-a]pyridine-2-carboxylic acid, 6-broMo-, hydrazide;6-BroMo-iMidazo[1,2-a]pyridine-2-carbohydrazide
• CAS NO: 474956-06-4
• Molecular Formula: C₈H₇BrN₄O
• Molecular Weight: 255.07138
• Mol File: 474956-06-4.mol

Chemical Properties

• Appearance: /
• Density: 1.94±0.1 g/cm3(Predicted)
• PKA: 8.98±0.20(Predicted)
• CAS DataBase Reference: IMidazo[1,2-a]pyridine-2-carboxylic acid, 6-broMo-, hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: IMidazo[1,2-a]pyridine-2-carboxylic acid, 6-broMo-, hydrazide(474956-06-4)
• EPA Substance Registry System: IMidazo[1,2-a]pyridine-2-carboxylic acid, 6-broMo-, hydrazide(474956-06-4)

Safety Data

• Hazardous Substances Data: 474956-06-4(Hazardous Substances Data)

Upstream product

• 1072-97-5 5-bromo-2-pyridylamine 
• 67625-37-0 ethyl 6-bromoimidazo<1,2-a>pyridine-2-carboxylate 

Downstream Products

• 1516888-18-8 4-(4-methylbenzylideneamino)-5-(6-bromo-imidazo[1,2-a]pyridin-2-yl)-4H-1,2,4-triazole-3-thiol 
• 1516888-22-4 4-(4-nitrobenzylideneamino)-5-(6-bromo-imidazo[1,2-a]pyridin-2-yl)-4H-1,2,4-triazole-3-thiol 
• 1516888-26-8 4-(4-fluorobenzylideneamino)-5-(6-bromo-imidazo[1,2-a]pyridin-2-yl)-4H-1,2,4-triazole-3-thiol 
• 1516887-96-9 5-(6-bromoimidazo[1,2-a]pyridin-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol 
• 1516888-30-4 6-bromo-2-(4-phenyl-5-(propylthio)-4H-1,2,4-triazol-3-yl)-imidazo[1,2-a]pyridine 
• 1516888-33-7 2-(5-(benzylthio)-4-phenyl-4H-1,2,4-triazol-3-yl)-6-bromoimidazo[1,2-a]pyridine 
• 1516888-37-1 2-(5-(4-methoxybenzylthio)-4-phenyl-4H-1,2,4-triazol-3-yl)-6-bromo-imidazo[1,2-a]pyridine 
• 1516888-40-6 2-(5-(4-nitrobenzylthio)-4-phenyl-4H-1,2,4-triazol-3-yl)-6-bromo-imidazo[1,2-a]pyridine 
• 1083201-46-0 N'-(4-fluorobenzylidene)-6-bromo-imidazo[1,2-a]pyridine-2-carbohydrazide 
• 1185237-05-1 N'-(4-hydroxy-3-methoxybenzylidene)-6-bromo-imidazo[1,2-a]pyridine-2-carbohydrazide 
• 957757-07-2 6-bromo-imidazo[1,2-a]pyridine-2-carbohydrazide 

Relevant articles and documents

Effective inhibition of mild steel corrosion by 6-bromo-(2,4-dimethoxyphenyl)methylidene]imidazo [1,2-a]pyridine-2-carbohydrazide in 0.5 M HCl: Insights from experimental and computational study

A new inhibitor, 6-bromo-(2,4-dimethoxyphenyl)methylidene]imidazo [1,2-a]pyridine-2-carbohydrazide (DMPIP) was evaluated as a corrosion inhibitor for Mild Steel (MS) in 0.5 M HCl solution at 303–323 K using potentiodynamic polarization and electrochemical impedance spectroscopic (EIS) techniques. Both the techniques confirmed an increase in inhibition efficiency with the concentration of DMPIP but decrease with temperature. The highest inhibitive action (96.7%) was registered at 303 K for 500 ppm of DMPIP concentration. Polarization study revealed mixed inhibition action by DMPIP. Nyquist plot obtained for MS using EIS technique showed two capacitive loops on addition of inhibitor to HCl solution confirmed the inhibitory action of DMPIP via adsorption at the metal/solution interface. The surface morphology analysis was carried out by SEM, EDX and FTIR techniques. The adsorption process was demonstrated using Langmuir's adsorption isotherm model. The thermodynamic parameters (?Goads, ?Hoads) indicated that the adsorption was spontaneous and done by physisorption. Further, quantum chemical studies using Density Functional Theory (DFT) elucidated that the formation of Fe-DMPIP complex presumably due to the interaction of protonated form of DMPIP with the empty d orbitals of the iron atom.

Design, Synthesis, and Biological Evaluation of Imidazo[1,2- a]pyridine Derivatives as Novel PI3K/mTOR Dual Inhibitors

PI3K-Akt-mTOR signaling pathway has been validated as an effective targeting pathway for cancer therapy. However, no PI3K/mTOR dual inhibitor has been approved by the FDA yet. Therefore, it is still essential to discover a candidate with good efficacy and low toxicity. In our design, a series of imidazo[1,2-a]pyridine derivatives had been synthesized and subjected to activity assessment in vitro and in vivo. 15a was proved to be a potent PI3K/mTOR dual inhibitor with excellent kinase selectivity, modest plasma clearance, and acceptable oral bioavailability. Besides, 15a displayed significant inhibition of tumor growth in HCT116 and HT-29 xenografts without obvious effect on body weight.

New 6-bromoimidazo[1,2-A]pyridine-2-carbohydrazide derivatives: Synthesis and anticonvulsant studies

In the present work, we report the facile synthesis and anticonvulsant study of new imidazo[1,2-A]pyridines carrying biologically active hydrazone functionality (3a-3e) and suitably substituted 1,2,4-triazole moieties (4, 5a-5d, 6, and 7a-7d). The newly synthesized intermediates and final compounds were characterized by various spectral techniques such as FTIR, 1H NMR, 13C NMR, and mass spectral and elemental analysis studies. The in vivo anticonvulsant study of the target compounds were carried out following maximal electroshock seizure and subcutaneous pentylene tetrazole methods, while their toxicity study was performed following rotarod method by taking 20, 40, and 100 mg/kg dose levels. Most of the new compounds displayed remarkable anticonvulsant properties at these doses. Particularly, compounds 3b and 4 carrying hydrogen bond donor groups, viz. hydroxyl and amine moieties respectively, exhibited complete protection against seizure and their results are comparable to that of standard drug diazepam. Further, the motor impairment study revealed that all the compounds are nontoxic upto 100 mg/kg.

Synthesis and antimicrobial activity of some imidazo-[1,2-a]pyridine-2-carboxylic acid arylidenehydrazide derivatives

Imidazo[1,2-a]pyridine-2-carboxylic acid, ethyl esters were reacted with hydrazine hydrate to furnish imidazo[1,2-a]pyridine-2-carboxylic acid hydrazide. The hydrazides formed were treated with various aldehydes to obtain 28 imidazo[1,2-a]pyrldine-2-carboxylic acid arylidenehydrazides. Antimicrobial activity of the compounds were examined.