144835-67-6

Basic information

• Product Name: 2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID HYDRAZIDE
• Synonyms: 2-methylimidazo[1,2-a]pyridine-3-carbohydrazide(SALTDATA: FREE);2-Methylimidazo[1,2-a]pyridine-3-carboxylic acid hydrazide, 3-(Hydrazinocarbonyl)-2-methylimidazo[1,2-a]pyridine
• CAS NO: 144835-67-6
• Molecular Formula: C₉H₁₀N₄O
• Molecular Weight: 190.2
• Mol File: 144835-67-6.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.42g/cm³
• Refractive Index: 1.697
• CAS DataBase Reference: 2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID HYDRAZIDE(144835-67-6)
• EPA Substance Registry System: 2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID HYDRAZIDE(144835-67-6)

Safety Data

• Hazardous Substances Data: 144835-67-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID HYDRAZIDE is used as an intermediate in the synthesis of various pharmaceutical agents, particularly for the development of antiviral and antitumor drugs. Its unique structural features contribute to the effectiveness of these medications.
Used in Industrial Processes:
In the industrial sector, 2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID HYDRAZIDE is utilized as a reagent for the production of agrochemicals and dyes. Its versatility in these applications highlights its importance in the development of various products in the agricultural and dye industries.

InChI:InChI=1/C9H10N4O/c1-6-8(9(14)12-10)13-5-3-2-4-7(13)11-6/h2-5H,10H2,1H3,(H,12,14)

Upstream product

• 2549-19-1 ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate 
• 504-29-0 2-aminopyridine 

Downstream Products

• 155699-17-5 2-methyl-N'-(4-methylbenzylidene)imidazo[1,2-a]pyridine-3-carbohydrazide 
• 144835-73-4 C₁₆H₁₅N₅OS 
• 144835-70-1 C₁₃H₁₅N₅OS 

Relevant articles and documents

Synthesis and antinociceptive properties of new structurally planned imidazo[1,2-a]pyridine 3-acylarylhydrazone derivatives

This paper describes recent results of a research program aiming at the synthesis and pharmacological evaluation of new N-heterocyclic functionalized acylarylhydrazone compounds, belonging to 3-acyl-(2-methyl-imidazo[1,2-a]pyridinyl)-arylhydrazone 2 series. These compounds were structurally planned applying classical ring bioisosterism strategies on previously described 4-acyl-(N-phenylpyrazolyl)-arylhydrazone 1, which presented important analgesic properties, in order to identify the pharmacophore contribution of the acylarylhydrazone moiety and investigate the structure-activity relationship (SAR) in these series. The results herein disclosed indicate that this strategy of molecular modification gave rise to a new series of analgesic and anti-inflammatory agents, where the activity seems to be more dependent on the nature of the para-substituent at the pharmacophore acylarylhydrazone (AAH) moiety, than the N-heterocyclic acyl-ring pattern.

Microwave-assisted synthesis and photophysical studies of novel fluorescent N-acylhydrazone and semicarbazone-7-OH-coumarin dyes

A microwave-assisted synthesis of novel N-acylhydrazone and semicacarbazone-7-hidroxy-coumarins derivatives, starting from 3-acetyl-7-hydroxy-2H-chromen-2-one, is described. This optimized protocol led to higher yields and considerable reduction in reaction time from ～24 to ～1 hour. Aqueous solutions of these compounds showed bright blue to cyan emission and maximum quantum yields of 0.244. The stereoelectronic effects of the attached groups led to modulation of the spectral characteristics by favoring syn or anti amide conformers. The synthesized compounds showed pH dependent luminescence and a strong batochromic shift up to 65 nm in a low polarity medium (methanol) due to a better stabilization of the syn-conformer promoting this redshifted emission. These characteristics can be exploited for designing new luminescent probes for pH as well as polar microenvironments.

Identification and development of 2-methylimidazo[1,2-a]pyridine-3- carboxamides as Mycobacterium tuberculosis pantothenate synthetase inhibitors

In the present study, we used crystal structure of mycobacterial pantothenate synthetase (PS) bound with 2-(2-(benzofuran-2-ylsulfonylcarbamoyl)- 5-methoxy-1H-indol-1-yl) acetic acid inhibitor for virtual screening of antitubercular compound database to identify new scaffolds. One of the identified lead was modified synthetically to obtain thirty novel analogues. These synthesized compounds were evaluated for Mycobacterium tuberculosis (MTB) PS inhibition study, in vitro antimycobacterial activities and cytotoxicity against RAW 264.7 cell line. Among the compounds tested, N′-(1-naphthoyl)- 2-methylimidazo[1,2-a]pyridine-3-carbohydrazide (5b) was found to be the most active compound with IC50 of 1.90 ± 0.12 μM against MTB PS, MIC of 4.53 μM against MTB with no cytotoxicity at 50 μM. The binding affinity of the most potent inhibitor 5b was further confirmed biophysically through differential scanning fluorimetry.

Design, synthesis, and pharmacological evaluation of N-acylhydrazones and novel conformationally constrained compounds as selective and potent orally active phosphodiesterase-4 inhibitors

Among a small series of tested N-acylhydrazones (NAHs), the compound 8a was selected as a selective submicromolar phosphodiesterase-4 (PDE4) inhibitor associated with anti-TNF-α properties measured both in vitro and in vivo. The recognition pattern of compound 8a was elucidated through molecular modeling studies based on the knowledge of the 3D-structure of zardaverine, a PDE4 inhibitor resembling the structure of 8a, cocrystallized with the PDE4. Based on further conformational analysis dealing with N-methyl-NAHs, a quinazoline derivative (19) was designed as a conformationally constrained NAH analogue and showed similar in vitro pharmacological profile, compared with 8a. In addition 19 was found active when tested orally in LPS-evoked airway hyperreactivity and fully confirmed the working hypothesis supporting this work.