704-13-2

Usage

Uses

Used in Chemical Research:
3-Hydroxy-4-nitrobenzaldehyde is used as a key intermediate in the synthesis of various organic compounds, particularly in the study of enantioselective thioester aldol reactions. This reaction is catalyzed by copper(II) triflate in the presence of a chiral bisoxazoline ligand, highlighting its importance in asymmetric synthesis.
Used in Pharmaceutical Research:
In the field of pharmaceuticals, 3-Hydroxy-4-nitrobenzaldehyde serves as a chromophoric substrate for probing the catalytic mechanism of horse liver alcohol dehydrogenase. This application is crucial for understanding enzyme mechanisms and can potentially lead to the development of new drugs and therapies.
Used in Analytical Chemistry:
3-Hydroxy-4-nitrobenzaldehyde can be employed as a reagent in analytical chemistry for the detection and quantification of specific compounds due to its chromophoric properties. Its ability to change color upon interaction with certain substances makes it a valuable tool in analytical assays and methods.
Used in Material Science:
3-Hydroxy-4-nitrobenzaldehyde may also find applications in material science, particularly in the development of new materials with unique optical, electronic, or catalytic properties. Its structural features and reactivity make it a candidate for creating novel materials with specific functions.

InChI:InChI=1/C7H5NO4/c9-4-5-1-2-6(8(11)12)7(10)3-5/h1-4,10H

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 61161-83-9 5-(hydroxymethyl)-2-nitrophenol 
• 619-14-7 3-hydroxy-4-nitro-benzoic acid 
• 116496-11-8 3-hydroxy-4-nitro-benzaldehyde-oxime 

Downstream Products

• 90729-86-5 3-hydroxy-4-nitrocinnamic acid 
• 619-14-7 3-hydroxy-4-nitro-benzoic acid 
• 861081-87-0 2,6-dibromo-3-hydroxy-4-nitro-benzaldehyde 
• 112367-63-2 3-hydroxy-4-nitro-benzaldehyde-thiosemicarbazone 
• 80410-57-7 3-methoxy-4-nitrobenzaldehyde 
• 138744-14-6 9-(3-Hydroxy-4-nitro-phenyl)-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione 
• 852233-77-3 ethyl 2-(5-formyl-2-nitrophenoxy)acetate 

Relevant academic research and scientific papers

Microwave-enhanced Friedl?nder synthesis for the rapid assembly of halogenated quinolines with antibacterial and biofilm eradication activities against drug resistant and tolerant bacteria

Herein, we disclose the development of a catalyst- and protecting-group-free microwave-enhanced Friedl?nder synthesis which permits the single-step, convergent assembly of diverse 8-hydroxyquinolines with greatly improved reaction yields over traditional oil bath heating (increased from 34% to 72%). This rapid synthesis permitted the discovery of novel biofilm-eradicating halogenated quinolines (MBECs = 1.0-23.5 μM) active against MRSA, MRSE, and VRE. These small molecules exhibit activity through mechanisms independent of membrane lysis, further demonstrating their potential as a clinically useful treatment option against persistent biofilm-associated infections.

COMBINATION THERAPY FOR TREATING INFECTIONS DISEASES

The present invention provides compositions comprising a quinoline, a potentiating agent, and optionally a pharmaceutically acceptable carrier, for treating and/or preventing infectious diseases. The provided compositions may also include another therapeutic agent (e.g., antibiotic). The provided compositions may be useful in treating and/or preventing bacterial infections as well as inhibiting and eradicating biofilm formation.

A Phytochemical-Halogenated Quinoline Combination Therapy Strategy for the Treatment of Pathogenic Bacteria

With the continued rise of drug-resistant bacterial infections coupled with the current discouraging state of the antibiotic pipeline, the need for new antibacterial agents that operate through unique mechanisms compared with conventional antibiotics and work in synergy with other agents is at an all-time high. We have discovered that gallic acid, a plant-derived phytochemical, dramatically potentiates the antibacterial activities of several halogenated quinolines (up to 11 800-fold potentiation against Staphylococcus aureus) against pathogenic bacteria, including drug-resistant clinical isolates. S. aureus demonstrated the highest sensitivity towards gallic acid-halogenated quinoline combinations, including one halogenated quinoline that demonstrated potentiation of biofilm eradication activity against a methicillin-resistant S. aureus (MRSA) clinical isolate. During our studies, we also demonstrated that these halogenated quionlines operate through an interesting metal(II) cation-dependent mechanism and display promising mammalian cytotoxicity.

Chemoselective reduction and self-immolation based FRET probes for detecting hydrogen sulfide in solution and in cells

Hydrogen sulfide (H2S) has been regarded as the third gaseous transmitter. Based on the mechanism of chemoselective azido reduction and self-immolation, five fluorescence resonance energy transfer (FRET) probes for the detection of H2S were designed and synthesized. The effect of functional substitution of the self-immolative moiety on azido reduction and quinone-methide rearrangement were investigated. Their fluorescence responses and chemoselectivity for H2S detection were evaluated in solutions and in cells. This strategy may provide a general route for designing H 2S probes with many commercially available FRET pairs. the Partner Organisations 2014.

A green chemistry method for the regeneration of carbonyl compounds from oximes by using cupric chloride dihydrate as a recoverable promoter for hydrolysis

A mild, efficient, general, and green method for the regeneration of carbonyl compounds from their corresponding oximes is described. Cupric salts promoted hydrolysis of oximes was studied, and the best reaction conditions for the hydrolysis have been found. Carbonyl compounds were obtained in 85-98% yields after the treatment of oximes with 2 molar equivalent of CuCl 22H2O at reflux (around 75 C) in a mixed solvent of acetonitrile and water (4:1). In addition, cupric salt was readily recovered in an almost quantitative yield via the complete precipitation of Cu(OH) 22H2O. Georg Thieme Verlag Stuttgart · New York.

A novel simple and efficient bromination protocol for activated arenes

An efficient, high yielding, and environmentally benign bromination using an alkali metal bromide as the bromine source is disclosed. Investigation of the protocol revealed that the method operates for activated arenes producing the corresponding monobrominated products in good to excellent yields.

2-(Amino or substituted amino)-5-(substituted oxymethyl)-phenol compounds, dyeing compositions containing them, and use thereof

Disclosed are 2-(amino or substituted amino)-5-(substituted oxymethyl)-phenol compounds according to the Formula (I), as defined herein. Also, compositions for the oxidative dyeing of keratin fibers, comprising a medium suitable for dyeing and a compound of the Formula (II), as defined herein. The substituents of both formulae may themselves be substituted or unsubstituted. Further, methods for oxidative dyeing of keratin fibers, comprising applying such compositions in the presence of an oxidizing agent, for a period which is sufficient to develop the desired coloration.

Isoquinoline compound melanocortin receptor ligands and methods of using same

The invention relates to melanocortin receptor ligands and methods of using the ligands to alter or regulate the activity of a melanocortin receptor. The invention further relates to tetrahydroisoquinoline aromatic amines that function as melanocortin receptor ligands and as agents for controlling cytokine-regulated physiologic processes and pathologies, and combinatorial libraries thereof.

Potential photoaffinity labels for tubulin. Synthesis and evaluation of diazocyclohexadienone and azide analogs of colchicine, combretastatin, and 3,4,5-trimethoxybiphenyl

Analogs of tubulin assembly inhibitors such as colchicine, combretastatin, and 3,4,5-trimethoxybiphenyl which incorporate a 6-diazo-2,4-cyclohexadienone (o-quinone diazide) ring have been synthesized and characterized. The compounds synthesized include 6-diazo-4-(2',3',4'-trimethoxyphenyl)cyclohexa-2,4-dien-1-one and its 3-methyl and 3-ethyl analogs (1a-c), 6-diazo-3-(2,3,4-trimethoxyphenyl)-2,4-cyclohexadien-1-one and its 4-methyl and 4-ethyl derivatives (2a-c), 4-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dienon e (3), 3-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dien-1 -one (4), the corresponding dihydro derivatives (5, 6) and two isomeric diazocyclohexadienones derived from N-acetylcolchinol (7, 8). Compounds in which the cyclohexadienone oxygen is approximately isostructural with carbonyl or hydroxy functions of the parent compounds exhibit good activity in the tubulin assembly inhibition assay. 2'-Alkyl-4'azido-3,4,5-trimethoxy-1,1'-biphenyls also show good activity as tubulin assembly inhibitors.