73794-59-9

Usage

Uses

Used in Organic Synthesis:
2-(3-methylphenyl)-1H-pyrrole is used as a building block for the synthesis of various organic compounds, including pharmaceuticals and agrochemicals. Its unique structural features make it a valuable component in the development of new molecules with desired properties.
Used in Medicinal Chemistry:
2-(3-methylphenyl)-1H-pyrrole is used as a starting material in the design and synthesis of new pharmaceutical agents. Its potential biological activities make it a promising candidate for drug discovery and development.
Used in Drug Discovery:
2-(3-methylphenyl)-1H-pyrrole may exhibit interesting biological activities, making it a valuable target for further research and development in the field of drug discovery. Its unique structure and potential interactions with biological targets can lead to the development of new therapeutic agents.
Used in Material Science:
2-(3-methylphenyl)-1H-pyrrole can also be used in material science for the development of new materials with specific properties. Its unique structure and potential for modification make it a promising candidate for the creation of novel materials with applications in various industries.

Upstream product

• 620-22-4 3-Methylbenzonitrile 
• 109-97-7 pyrrole 
• 17933-03-8 m-tolylboronic acid 
• 1439921-55-7 1-(m-tolyl)but-3-en-1-one oxime 
• 1250909-95-5 1-(m-tolyl)but-3-en-1-one 
• 24165-64-8 1-(3-methylphenyl)but-3-en-1-ol 
• 1616603-18-9 C₁₃H₁₅NO₂ 
• 620-23-5 m-tolyl aldehyde 
• 73794-65-7 2-Methyl-4-(2-pyrrolyl)-2,5-cyclohexadien-1-carbonsaeure 

Downstream Products

• 1604834-08-3 C₂₃H₂₂N₂O 

Relevant academic research and scientific papers

GRP94 SELECTIVE INHIBITORS AND USES THEREOF

The present technology provides compounds according to Formula I or Formula III as well as compositions including such compounds useful for the treatment of metastatic cancer and/or glaucoma.

Transformation of the non-selective aminocyclohexanol-based Hsp90 inhibitor into a Grp94-seletive scaffold

Glucose regulated protein 94 kDa, Grp94, is the endoplasmic reticulum (ER) localized isoform of heat shock protein 90 (Hsp90) that is responsible for the trafficking and maturation of toll-like receptors, immunoglobulins, and integrins. As a result, Grp94 has emerged as a therapeutic target to disrupt cellular communication, adhesion, and tumor proliferation, potentially with fewer side effects compared to pan-inhibitors of all Hsp90 isoforms. Although, the N-terminal ATP binding site is highly conserved among all four Hsp90 isoforms, recent cocrystal structures of Grp94 have revealed subtle differences between Grp94 and other Hsp90 isoforms that has been exploited for the development of Grp94-selective inhibitors. In the current study, a structure-based approach has been applied to a Grp94 nonselective compound, SNX 2112, which led to the development of 8j (ACO1), a Grp94-selective inhibitor that manifests -440 nM affinity and ≥200-fold selectivity against cytosolic Hsp90 isoforms.

Copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates: A facile synthesis of 2-arylpyrroles

A novel and facile copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates for the synthesis of 2-arylpyrroles has been developed. The reaction tolerates a range of functional groups and is a practical procedure for rapid synthesis of 2-arylpyrroles in high yields under mild conditions. the Partner Organisations 2014.

Iron-mediated direct suzuki-miyaura reaction: A new method for the ortho -arylation of pyrrole and pyridine

(Figure presented) The first example of an iron-mediated direct Suzuki-Miyaura reaction between N-heterocyclic compounds and arylboronic acids is described, and both electron-rich and electron-deficient heteroarenes can be successfully used for the coupling reaction.

Aryl-substituted C3-bridged oligopyrroles as anion receptors for formation of supramolecular organogels

BF2 complexes of aryl-substituted dipyrrolyldiketones (3a-c, 5a-d) have been synthesized by the condensation of arylpyrroles obtained by Suzuki cross-coupling reactions with malonyl chloride, followed by treatment with BF3·OEt2. The binding constants (K a11) of the BF2 complexes (3a-c) for various anions (Cl-, Br-, CH3CO2-, H2PO4-, and HSO4-) in CH2Cl2 decrease in the order Ph (3a) > o-tolyl (3b) > 2,6-Me2Ph (3c), possibly because of differences in the planarity and the number of interacting o-CH units at the binding sites. Aryl-substituted receptors exhibit a [1+1] binding mode with Cl- as well as a [2+1] binding mode under conditions of high concentration and low temperature, as suggested by 1H NMR studies in CD2Cl2. These receptors, especially phenyl-substituted (3a) and o-tolyl (3b), exhibit drastic colorimetric and fluorescent changes in the presence of F- due to extended π-conjugation, as compared to 2,6-dimethylphenyl (3c) and the previously reported derivatives (1a-c). Aryl-substitution at the α-positions of pyrrole is an excellent means for the introduction of various substituents at the periphery of the anion receptors. For example, derivatives with long alkoxy chains at 3,4,5-positions of the substituent aryl rings (5b-d) afford emissive gel structures in hydrocarbon solvents, such as octane, based on the stacking of slipped H- and J-aggregates at the core π-plane. The structural organization of the supramolecular gels was investigated by AFM, SEM, and XRD measurements as well as by considering the solid-state packing of crystalline derivatives. The slow transformation of the gel to the solution phase by the addition of various anions, possibly except for F-, is correlated with the unique properties of these acyclic receptors where inversions of pyrrole rings are required for anion binding. Boron complexes of 1,3-dipyrrolyl-1,3-propanediones with aryl-substituents, as a new class of acyclic anion receptors, have shown efficient binding due to the interacting o-CH units and, in the case of the derivative with long aliphatic chains, afforded the emissive supramolecular organogels using stacking of core π-planes controlled by external chemical stimuli.

Convenient access to 2-arylpyrroles from 2-lithio-N,N- dibenzylcyclopropylamine and nitriles

N,N-Dibenzylaminocyclopropyl ketimines formed as intermediates upon treatment of 2-lithiated N,N-dibenzylcyclopropylamines with nitriles, being donor-acceptor-substituted cyclopropanes, immediately underwent ring-enlarging rearrangement and 1,2-elimination of dibenzylamine to produce 2-substituted pyrroles in good yields (14 examples, 55-80%). Georg Thieme Verlag Stuttgart.

Reactions of Electron Deficient Dienes with (Acylmethylene)triphenylphosphoranes: One-Pot-Three-Step-Reactions

3a-Azaazulenes (1, 7) react with (acylmethylene)triphenylphosphoranes (2) in a one-pot-three-step-synthesis (Michael addition, intramolecular addition, Wittig elimination) to form cyclohexadiene 1,4-derivatives (3, 8).The course of the reaction is determined by steric requirements which is shown by ethyl 3-isopropylbenzoate (11) formation from ethyl 1,3-cyclohexadiene-1-carboxylate (9) and phosphorane 2b.