119448-27-0

Basic information

• Product Name: IMIDAZO[1,2-A]PYRIDINE-2-CARBOHYDRAZIDE
• Synonyms: IMIDAZO[1,2-A]PYRIDINE-2-CARBOHYDRAZIDE;IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID HYDRAZIDE
• CAS NO: 119448-27-0
• Molecular Formula: C₈H₈N₄O
• Molecular Weight: 176.18
• Mol File: 119448-27-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: IMIDAZO[1,2-A]PYRIDINE-2-CARBOHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: IMIDAZO[1,2-A]PYRIDINE-2-CARBOHYDRAZIDE(119448-27-0)
• EPA Substance Registry System: IMIDAZO[1,2-A]PYRIDINE-2-CARBOHYDRAZIDE(119448-27-0)

Safety Data

• Hazardous Substances Data: 119448-27-0(Hazardous Substances Data)

Upstream product

• 38922-77-9 ethyl imidazo[1,2-a]pyridine-2-carboxylate hydrobromide 
• 504-29-0 2-aminopyridine 
• 832099-51-1 2-amino-1-(3-ethoxy-2,3-dioxopropyl)pyridinium bromide 
• 38922-77-9 ethyl 3-imidazo[1,2-a]pyridine-2-carboxylate 

Downstream Products

• 1637480-48-8 N-benzyl-2-(imidazo[1,2-a]pyridin-2-ylcarbonyl)hydrazinecarbothioamide 
• 1637480-49-9 2-(imidazo[1,2-a]pyridin-2-ylcarbonyl)-N-(2-phenylethyl)hydrazinecarbothioamide 
• 1637480-50-2 2-(imidazo[1,2-a]pyridin-2-ylcarbonyl)-N-phenylhydrazinecarbothioamide 
• 1637480-51-3 2-(imidazo[1,2-a]pyridin-2-ylcarbonyl)-N-(4-methylphenyl)hydrazinecarbothioamide 
• 1637480-52-4 N-(4-chlorophenyl)-2-(imidazo[1,2-a]pyridin-2-ylcarbonyl)hydrazinecarbothioamide 
• 1637480-53-5 N-(4-bromophenyl)-2-(imidazo[1,2-a]pyridin-2-ylcarbonyl)hydrazinecarbothioamide 
• 1637480-54-6 N-(4-fluorophenyl)-2-(imidazo[1,2-a]pyridin-2-ylcarbonyl)hydrazinecarbothioamide 
• 1637480-58-0 N'-(3-benzyl-4-oxo-1,3-thiazolidin-2-ylidene)imidazo[1,2-a]pyridine-2-carbohydrazide 
• 1637480-59-1 N'-[4-oxo-3-(2-phenylethyl)-1,3-thiazolidin-2-ylidene]imidazo[1,2-a]pyridine-2-carbohydrazide 
• 1637480-60-4 N'-[3-(4-methylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]imidazo[1,2-a]pyridine-2-carbohydrazide 
• 1637480-62-6 N-(4-chlorophenyl)-5-(imidazo[1,2-a]pyridin-2-yl)-1,3,4-oxadiazol-2-amine 
• 1637480-63-7 N-(4-bromophenyl)-5-(imidazo[1,2-a]pyridin-2-yl)-1,3,4-oxadiazol-2-amine 
• 1637480-64-8 N-(4-fluorophenyl)-5-(imidazo[1,2-a]pyridin-2-yl)-1,3,4-oxadiazol-2-amine 

Relevant articles and documents

Synthesis and biological evaluation of novel imidazo[1,2-a]pyridine-oxadiazole hybrids as anti-proliferative agents: Study of microtubule polymerization inhibition and DNA binding

Efforts towards the development of potential anticancer agents, a new series of imidazo[1,2-a]pyridine-oxadiazole hybrids were synthesized and evaluated for their in vitro anticancer activity against lung cancer (A549) and prostate cancer (PC-3, DU-145) cell lines. Amongst the compounds tested, 6d showed the highest potency on A549 cells with an IC50 value of 2.8 ± 0.02 μM. Flow cytometric analysis of compound 6d treated A549 cells showed apoptosis induction by annexin-v/PI dual staining assay and the effect of 6d on different phases of cell cycle was also analyzed. Target based studies demonstrated the inhibition of tubulin polymerization by 6d at an IC50 value of 3.45 ± 0.51 μM and its effective binding with CT-DNA. Further, the molecular modelling studies revealed that 6d has a prominent binding affinity towards α/β-tubulin receptor with admirable physico-chemical properties.

Design, synthesis, in vitro evaluation and molecular docking study of N'-Arylidene imidazo [1,2-a] pyridine -2-carbohydrazide derivatives as novel Tyrosinase inhibitors

A novel series of imidazo[1,2-a]pyridine 2-carbohudrazide derivatives bearing different arylidene pendantrs were designed, synthesized and evaluated for their inhibitory activity against mushroom Tyrosinase. It was found that compounds bearing 3-nitro (6j) and 4?hydroxy (6g) moieties on the arylidene pendant exhibited the best Tyrosinase inhibitory activity with IC50 values of 7.19 and 8.11 μM, respectively. These results were comparable to that of kojic acid as the reference drug (IC50 = 9.64±0.5 μM). Additionally, molecular docking analysis was performed to study the interactions and binding modes of compounds 6j, 6h and 6g which are showing the potential of two critical pi-pi interactions with His263 and Phe264 in the active site of Tyrosinase. The results indicated that 6j and 6g could be introduced as potent Tyrosinase inhibitors that might serve as promising candidates in medicine, cosmetics or food industry.

Synthesis of novel imidazo[l,2-a]pyridines and evaluation of their antifungal activities

New 2-(imidazo[1,2-a]pyridin-2-ylcarbonyl)-N-substituted hydrazinecarbothioamides (4a-j), N'-(3-substitu-ted-4-oxo-1,3-thiazolidin-2- ylidene)imidazo[1,2-a]pyridine-2-carbohydrazides (5a-f ), and N-(nonsubstituted/4-substitu-ted phenyl)-5-(imidazo[1,2-a]p

Aminoimidazo[1,2-a]pyridines: Regioselective synthesis of substituted imidazonaphthyridines, azacarbolines and cyclazines

In order to study the regioselectivity of thermal cyclocondensation, aminoimidazo[1,2-a]pyridines (AIP) 5a-e were prepared, further converted into iminophosphoranes 7a-e, and ultimately converted regioselectively in angular annulated imidazonaphthyridines (IN) 8a, 10a, 11a, 12a or linear annulated dipyridoimidazole (DPI) 17a. From 2-substituted derivative 23, the peri annulated product 24a was obtained. The starting amines 5a-f reacted with aldehydes to yield regioselectively IN 8a-c, 10a-c, 11a-c, 12a,b, DPI 16a-e, 17a-d and TIBO like structures (±)-13 and 24a-c, as proved by X-ray analysis. The 1,2- or 1,4-addition between amines and α,β-unsaturated aldehydes concerning the pyridine and imidazole moieties is discussed in the light of these results.

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.