35854-46-7

Usage

Uses

Used in Organic Synthesis:
3-phenylimidazo[1,5-a]pyridine is used as a building block in the production of pharmaceuticals and agrochemicals. Its unique structure allows for the creation of a wide range of compounds with potential therapeutic and pesticidal properties.
Used in Medicinal Chemistry Research:
Due to its potential biological activity, 3-phenylimidazo[1,5-a]pyridine is of interest in medicinal chemistry research. Scientists are exploring its interactions with biological targets to develop new drugs and therapies.
Used in Advanced Materials Development:
3-phenylimidazo[1,5-a]pyridine has been studied for its potential use in the development of advanced materials with unique electronic and optical properties. Its aromatic and heteroaromatic nature makes it a promising candidate for applications in materials science.

InChI:InChI=1/C13H10N2/c1-2-6-11(7-3-1)13-14-10-12-8-4-5-9-15(12)13/h1-10H

Upstream product

• 35854-47-8 N-((pyridin-2-yl)methyl)benzamide 
• 18904-38-6 N-benzyl-2-pyridinecarboxamide 
• 2524-52-9 ethyl-2-picolinate 
• 906668-42-6 1-iodo-3-phenylimidazo[1,5-a]pyridine 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 3731-51-9 2-(Aminomethyl)pyridine 
• 65-85-0 benzoic acid 
• 274-47-5 imidazo[1,5-a]pyridine 
• 108-86-1 bromobenzene 
• 1121-60-4 pyridine-2-carbaldehyde 
• 2935-35-5 (S)-2-phenylglycine 
• 100-52-7 benzaldehyde 
• 622-42-4 1-nitro-1-phenylmethane 
• 614-21-1 2-nitroacetophenone 

Downstream Products

• 13389-61-2 3-(2’-pyridyl)-5-phenyl-1,2,4-oxadiazole 
• 72315-49-2 1-nitro-3-phenyl-imidazo[1,5-a]pyridine 
• 849797-69-9 2-isopropyl-3-phenylimidazo[1,5-a]pyridinium iodide 
• 1173922-98-9 1-chloro-3-phenylimidazo[1,5-a]pyridine 
• 906668-42-6 1-iodo-3-phenylimidazo[1,5-a]pyridine 
• 1173923-05-1 1-fluoro-3-phenylimidazo[1,5-a]pyridine 
• 104202-15-5 1-bromo-3-phenylimidazo[1,5-a]pyridine 
• 79159-65-2 1-phenyl-3-phenylimidazo[1,5-a]pyridine 
• 906668-43-7 1-(4-methoxylphenyl)-3-phenylimidazo[1,5-a]pyridine 
• 1146973-47-8 3-phenyl-1-(4-(trifluoromethyl)phenyl)imidazo[1,5-a]pyridine 
• 52095-67-7 bis(3-phenylimidazo[1,5-a]pyridine-1-yl)sulfide 

Relevant academic research and scientific papers

Synthesis and biological evaluation of imidazo[1,5-a]pyridine-benzimidazole hybrids as inhibitors of both tubulin polymerization and PI3K/Akt pathway

A series of imidazo[1,5-a]pyridine-benzimidazole hybrids (5a-aa) were prepared and evaluated for their cytotoxic activity against a panel of sixty human tumor cell lines. Among them compounds 5d and 5l showed significant cytotoxic activity with GI50

Halogenated imidazo[1,5-a]pyridines: chemical structure and optical properties of a promising luminescent scaffold

A series of halogenated imidazo[1,5-a]pyridines was prepared and their structural and optical properties investigated. The products were characterized by spectroscopic techniques and their optical properties discussed in relation to their chemical structu

Tandem approach for the synthesis of 3-sulfenylimidazo[1,5-: A] pyridines from dithioesters

Iodine-mediated synthesis of 3-sulfenylimidazo[1,5-a]pyridines via C-H functionalization has been achieved using dithioesters, 2-methylaminopyridines and sulfonyl hydrazides. A library of 3-sulfanylimidazopyridines and imidazopyridines with broad function

Syntheses and optical properties of BODIPY derivatives based on imidazo[1,5-a]pyridine

A series of covalently linked dyads 3a-3e incorporating imidazo[1,5-a]pyridine derivatives with boron dipyrromethene (BODIPY) fragment have been synthesized by a concise procedure. The absorptions with high molar extinction coefficient for 3a-3e have been

A new synthetic route for synthesis of 3-substituted imidazo[1,5-a]pyridines

A new convenient route for the synthesis of 3-substituted-imidazo[1,5-a]pyridines has been described as well as the scope and limitations of the method are evaluated. By reacting 2-picolylamine and different aldehydes in presence of selenium dioxide as the oxidant, a series of 3-substituted imidazo[1,5-a]pyridines was isolated in good yields. Different kinds of aldehydes such as aliphatic, aromatic, heterocyclic as well as aromatic ring carrying some substituents have been used.

Synthesis of 3-aryl-1-phosphinoimidazo[1,5-a]pyridine ligands for use in Suzuki-Miyaura cross-coupling reactions

3-Aryl-1-phosphinoimidazo[1,5-a]pyridine ligands were synthesized from 2-aminomethylpyridine as the initial substrateviatwo complementary routes. The first synthetic pathway underwent the coupling of 2-aminomethylpyridine with substituted benzoyl chlorides, followed by cyclization, iodination and palladium-catalyzed cross-coupling phosphination reactions sequence to give our phosphorus ligands. In the second route, 2-aminomethylpyridine was cyclized with aryl aldehydes, followed by the iodination and palladium-catalyzed cross-coupling phosphination reactions to yield our phosphorus ligands. The 3-aryl-1-phosphinoimidazo[1,5-a]pyridine ligands were evaluated in palladium-catalyzed sterically-hindered biaryl and heterobiaryl Suzuki-Miyaura cross-coupling reactions.

Regioselective C-H Phosphorothiolation of (Hetero)arenes Enabled by the Synergy of Electrooxidation and Ultrasonic Irradiation

An electrochemically regioselective C-H phosphorothiolation of (hetero)arenes with thiocyanate as the S source under ultrasonic irradiation has been developed. The synergistic cooperation of electrooxidation and ultrasonication markedly accelerated the C-H phosphorothiolation reaction. This mechanistically different method is distinguished by its wide substrate scope and transition-metal-free and external-oxidant-free conditions, thus complementing the existing metal-catalyzed or peroxide-mediated protocols for the green synthesis of S-(hetero)aryl phosphorothioates.

Thionyl chloride-mediated synthesis of 2-azaindolizine sulfur-bridged dimers by C-H bond direct chalcogenation of imidazo[1,5-a]pyridines

Thionyl chloride-mediated chalcogenation of imidazo[1,5-a]pyridine serves as a new protocol for the synthesis of rare bisimidazopyridyl sulfides. This method provides the new route to synthesis of 2-azaindolizine sulfur-bridged dimers called chalcogenide

Synthesis of (Z)-3-(arylamino)-1-(3-phenylimidazo[1,5-a]pyridin-1-yl)prop-2-en-1-ones as potential cytotoxic agents

The new derivatives based on (Z)-3-(arylamino)-1-(3-phenylimidazo[1,5-a]pyridin-1-yl)prop-2-en-1-one scaffold was synthesized and evaluated for their in vitro cytotoxic potential against a panel of cancer cell lines, viz., A549 (human lung cancer), HCT-116 (human colorectal cancer), B16F10 (murine melanoma cancer), BT-474 (human breast cancer), and MDA-MB-231 (human triple-negative breast cancer). Among them, many of the synthesized compounds exhibited promising cytotoxic potential against the panel of tested cancer cell lines with IC50 50 value of 1.21 ± 0.14 μM. Flow cytometric analysis revealed that compound 15i arrested the G0/G1 phase of the cell cycle. Moreover, increased reactive oxygen species (ROS) generation, clonogenic assay, acridine orange staining, DAPI nuclear staining, measurement of mitochondrial membrane potential (ΔΨm), and annexin V-FITC assays revealed that compound 15i promoted cell death through apoptosis.

Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

Imidazo[1,5-a]pyridines were efficiently prepared via the cyclization of 2-picolylamines with nitroalkanes electrophilically activated in the presence of phosphorous acid in polyphosphoric acid (PPA) medium.