3117-67-7

Usage

Uses

Used in Pharmaceutical Industry:
2-[(E)-(4-methoxyphenyl)methylidene]aminophenol is used as an anthelmintic agent for the treatment of parasitic worm infections in humans and animals. It is effective against various types of parasitic worms, including roundworms, whipworms, and hookworms, due to its ability to inhibit the formation of microtubules in the worms, disrupting their normal cellular function and leading to their death. Mebendazole is considered a broad-spectrum anthelmintic and is typically administered orally, making it a safe and effective treatment option for parasitic infections.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 95-55-6 2-amino-phenol 
• 35388-38-6 2-(4-methoxyphenyl)-1-nitro-1-ethoxycarbonylethene 
• 123-08-0 4-hydroxy-benzaldehyde 
• 1624-53-9 2-(benzylideneamino)phenol 
• 117649-25-9 2-(4-nitro-benzylidenamino)-phenol 
• 1707159-25-8 2-(4-cyanobenzylideneamino)phenol 
• 1761-56-4 2-[[(2-hydroxyphenyl)imino]methyl]phenol 
• 1624-49-3 2-(4-dimethylamino-benzylidenamino)-phenol 

Downstream Products

• 838-34-6 2-(p-methoxyphenyl)benzoxazole 
• 3117-67-7 cis-N-(p-Methoxybenzylidene)-o-aminophenol 
• 673435-36-4 2-(4-Methoxy-phenyl)-2,3-dihydro-benzooxazole 
• 1005495-42-0 (2S)-1-(2-hydroxyphenyl)-2-(4-methoxyphenyl)-5-methyl-2,3-dihydro-1H-pyridin-4-one 
• 1000026-14-1 (R,R)-2-[1-(4-methoxy-phenyl)-2-phenyl-but-3-enylamino]-phenol 
• 248609-59-8 RuCl(P(C₆H₅)3)(OC₆H₄CHNC₆H₄OCH₃)2 
• 248609-76-9 Ru(OC₆H₄CHNC₆H₃OCH₃)(P(C₆H₅)3)(CH₃OH)Cl 
• 221456-57-1 [PdCl(P(CH₂CH₃)3)(C₁₄H₁₂NO₂)] 
• 221456-54-8 [PtCl(P(CH₂CH₃)3)(C₁₄H₁₂NO₂)] 
• 199464-01-2 Ru((C₅H₄N)2)2(OC₆H₄NCHC₆H₄OCH₃)⁽¹⁺⁾*ClO₄^(1-)=[Ru((C₅H₄N)2)2(OC₆H₄NCHC₆H₄OCH₃)]ClO₄ 

Relevant academic research and scientific papers

A DFT and experimental study of the spectroscopic and hydrolytic degradation behaviour of some benzylideneanilines

The spectroscopic and hydrolytic degradation behaviour of some N-benzylideneanilines are investigated experimentally and theoretically via high quality density function theoretical (DFT) modelling techniques. Their absorption and vibrational spectra, accurately predicted by DFT calculations, are highly dependent on the nature of the substituents on the aromatic rings, hence, though some of their spectroscopic features are similar, energetic differences exist due to differences in their electronic structures. Whereas the o-hydroxy aniline derived adducts undergo hydrolysis via two pathways, the most energetically economical of which is initiated by a fast enthalpy driven hydration, over a conservative free energy (ΔG?) barrier of 53 kJ mol?1, prior to the rate limiting entropy controlled lysis step which occurs via a conservative barrier of ca.132 kJ mol?1, all other compounds hydrolyse via a slower two-step pathway, limited by the hydration step. Barriers heights for both pathways are controlled primarily by the structure and hence, stability of the transition states, all of which are cyclic for both pathways.

2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms

The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 μg/ml; MIC(LORA) 2.06 and 1.59 μg/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 μM respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 μM respectively) followed by the Vit-K2 rescue study and ATP production assay.

Hemoglobin: A New Biocatalyst for the Synthesis of 2-substituted Benzoxazoles via Oxidative Cyclization

Efficient and mild synthesis of a series of 2-substituted benzoxazoles via oxidative cyclization catalyzed by hemoglobins reported here for the first time. Satisfactory yields (84 %–97 %) and mild reaction conditions make this method highly viable for practical applications.

Effect of substituents on the UV spectra of supermolecular system: Silver nanoparticles with bi-aryl Schiff bases containing hydroxyl

Effect of substituents on the ultraviolet (UV) spectra of supermolecular system involving silver nanoparticles (AgNPs) and Schiff bases was investigated. AgNPs and 49 samples of model compounds (MC), bi-aryl Schiff bases containing hydroxyl (XBAY, involving 4-OHArCH?NArY, 2-OHArCH?NArY, XArCH?NAr-4′-OH, and XArCH?NAr-2′-OH), were synthesized. The size of AgNPs was characterized by transmission electron microscopy (TEM), and the UV absorption spectra of AgNPs, XBAYs, and MC-AgNPs mixed solutions were measured, respectively. The results show that (1) the size of AgNPs is larger in MC-AgNPs solutions than that in AgNPs solution due to the distribution of MC molecules on the surface of AgNPs; (2) the UV absorption wavelength of XBAYs changes in the action of AgNPs and their wavelength shift exists limitation between XBAY and MC-AgNPs solutions; and (3) the wavelength shift limit of MC-AgNPs (λWSL) is influenced by the substituents X and Y and the position of hydroxyl OH. The wavenumber ΔνWSL of λWSL can be quantified by employing the excited-state substituent constant σexCC and Hammett constant σ of substituents X and Y. Comparing with the 4-OH, the 4′-OH makes the ΔνWSL a red shift, whereas the 2′-OH, comparing with the 2-OH, makes the ΔνWSL a blue shift.

Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions

Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yi

In vitro and in vivo anti-inflammatory properties of imine resveratrol analogues

Resveratrol is a natural polyphenol found mainly on red grapes and in red wine, pointed as an important anti-inflammatory/immunomodulatory molecule. However, its bioavailability problems have limited its use encouraging the search for new alternatives agents. Thus, in this study, we synthetize 12 resveratrol analogues (6 imines, 1 thioimine and 5 hydrazones) and investigated its cytotoxicity, antioxidant activity and in vitro anti-inflammatory/immunomodulatory properties. The most promising compounds were also evaluated in vivo. The results showed that imines presented less cytotoxicity, were more effective than resveratrol on DPPH scavenger and exhibited an anti-inflammatory profile. Among them, the imines with a radical in the para position, on the ring B, not engaged in an intramolecular hydrogen-interaction, showed more prominent anti-inflammatory activity modulating, in vivo, the edema formation, the inflammatory infiltration and cytokine levels. An immunomodulatory activity also was observed in these molecules. Thus, our results suggest that imines with these characteristics presents potential to control inflammatory disorders.

Oxidative NHC Catalysis for the Generation of Imidoyl Azoliums: Synthesis of Benzoxazoles

N-Heterocyclic carbene (NHC)-catalyzed intramolecular cyclization of aldimines generated from 2-amino phenols and aromatic aldehydes leading to the synthesis of 2-arylbenzoxazoles under mild conditions is presented. The reaction proceeds via the generation of the aza-Breslow intermediates from imines and NHC, which under oxidative conditions form the key imidoyl azoliums and a subsequent intramolecular cyclization furnishes the product. The reaction tolerates a broad range of functional groups, and the products are formed in generally good yields.

Remarkable difference between five- and six- number-membered ring transition states for intramolecular proton transfer in excited state

In this study, a range of organic dyes were prepared to investigate difference between five- and six- number-membered ring transition states for internal proton transfer in excited state. Different strength intramolecular hydrogen bond in the target dyes

Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine

The indirect ("ex-cell") electrochemical synthesis of benzoxazoles from imines using a redox mediator based on the iodine(I)/iodine(III) redox couple is reported. Tethering the redox-active iodophenyl subunit to a tetra-alkylammonium moiety allowed for anodic oxidation to be performed without supporting electrolyte. The mediator salt can be easily recovered and reused. Our "ex-cell" approach toward the electrosynthesis of benzoxazoles is compatible with a range of redox-sensitive functional groups. An unprecedented concerted reductive elimination mechanism for benzoxazole formation is proposed on the basis of control experiments and DFT calculations.

Base-Free and Catalyst-Free Synthesis of Functionalized Dihydrobenzoxazoles via Vinylogous Carbonate to Carbamate Rearrangement

An unexpected, catalyst-free, and base-free intramolecular cyclization of N-aryloxyacrylate aldimines, under thermal conditions leading to the synthesis of functionalized dihydrobenzoxazoles, is reported. The reaction features a unique rearrangement of vi