16578-92-0

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 100-63-0 phenylhydrazine 
• 371-14-2 4-fluorophenylhydrazine 

Downstream Products

• 46886-90-2 N-indol-3-ylmethyl-N'-phenyl-hydrazine 
• 87582-37-4 C₂₁H₁₆FN₅ 
• 87582-34-1 C₂₂H₁₉N₅O 
• 88246-25-7 [(1H-Indol-3-yl)-(4,5,6,7-tetrahydro-benzo[1,3]dithiol-2-ylidene)-methyl]-phenyl-diazene 
• 87582-53-4 1-phenyl-3-(3'-indole)-5-(p-chlorophenyl) formazan 
• 87582-35-2 C₂₂H₁₉N₅O 
• 91047-81-3 C₂₂H₁₇N₅O₂ 
• 93704-44-0 3-Chloro-4-(1H-indol-3-yl)-1-phenylamino-azetidin-2-one 
• 87582-33-0 1-phenyl-3-(3'-indole)-5-phenyl formazan 
• 87582-38-5 C₂₃H₂₁N₅O 
• 87582-36-3 C₂₂H₁₉N₅ 
• 87582-48-7 2-(4-Chloro-phenyl)-5-(1H-indol-3-yl)-3-phenyl-3H-tetrazol-2-ium; bromide 
• 87582-49-8 2-(4-Chloro-phenyl)-5-(1H-indol-3-yl)-3-phenyl-3H-tetrazol-2-ium; iodide 
• 87582-46-5 2-phenyl-5-(3'-indole)-3-phenyl tetrazolium bromide 

Relevant academic research and scientific papers

Biological activity of a small molecule indole analog, 1-[(1H-indol-3-yl)methylene]-2-phenylhydrazine (HMPH), in chronic inflammation

A synthetic small molecule, 1-[(1H-indol-3-yl)methylene]-2-phenylhydrazine (HMPH) was conveniently synthesised by a one-step reaction, purified and characterised by chromatographic and spectroscopic methods. HMPH scavenged free radicals and inhibited lipo

Fluorescence Enhancement Based Quantification of Human Serum Albumin from Biological Sample Using Indole Based Nanosuspension: Molecular Interactions and Molecular Docking Studies

Fluorescent 3-[(E)-(2-phenylhydrazinylidene) methyl]-1H-indole (PHI) was synthesized by condensation of indole-3-carboxaldehyde and phenyl hydrazine in presence of acetic acid and ethanol and after spectral characterization used further to prepare its aqu

Pharmacophore modeling and 3D-QSAR study of indole and isatin derivatives as antiamyloidogenic agents targeting Alzheimer’s disease

Thirty-six novel indole-containing compounds, mainly 3-(2-phenylhydrazono) isatins and structurally related 1H-indole-3-carbaldehyde derivatives, were synthesized and assayed as inhibitors of beta amyloid (Aβ) aggregation, a hallmark of pathophysiology of Alzheimer’s disease. The newly synthesized molecules spanned their IC50 values from sub- to two-digit micromolar range, bearing further information into structure-activity relationships. Some of the new compounds showed interesting multitarget activity, by inhibiting monoamine oxidases A and B. A cell-based assay in tau overexpressing bacterial cells disclosed a promising additional activity of some derivatives against tau aggregation. The accumulated data of either about ninety published and thirty-six newly synthesized molecules were used to generate a pharmacophore hypothesis of antiamyloidogenic activity exerted in a wide range of potencies, satisfactorily discriminating the ‘active’ compounds from the ‘inactive’ (poorly active) ones. An atom-based 3D-QSAR model was also derived for about 80% of ‘active’ compounds, i.e., those achieving finite IC50 values lower than 100 μM. The 3D-QSAR model (encompassing 4 PLS factors), featuring acceptable predictive statistics either in the training set (n = 45, q2 = 0.596) and in the external test set (n = 14, r2ext = 0.695), usefully complemented the pharmacophore model by identifying the physicochemical features mainly correlated with the Aβ anti-aggregating potency of the indole and isatin derivatives studied herein.

Indole-3-carbaldehydes Arylhydrazones as Multisite C-Nucleophiles in the Reactions with Quinazoline

Abstract: C,C-Coupling of indole-3-carbaldehyde arylhydrazones with quinazoline in trifluoroacetic acid has occurred at position 5 or 7′ of the hydrazone molecule and has afforded the σ-adducts. The C,C-coupling has been accompanied by a change in the E-configuration of the C=N bond of the starting hydrazones to the Z-configuration in the formed quinazoline trifluoroacetyl hydrazides.

The use of enaminones and enamines as effective synthons for MSA-catalyzed regioselective synthesis of 1,3,4-tri- And 1,3,4,5-tetrasubstituted pyrazoles

In the present work, an efficient regioselective synthesis of 1,3,4-tri- and 1,3,4,5-tetrasubstituted pyrazoles via a methanesulfonic acid (MSA)-catalyzed reaction of hydrazones with enaminones or enamines is reported. Mechanistically, the formation of the title compounds involves the [2+3] cycloaddition of hydrazones with enaminones or enamines followed by aromatization with acid and oxygen. This convenient method under mild conditions with various hydrazones, enaminones, and enamines was well-tolerated to afford products in good to excellent yields. Compared with the literature methods, this strategy has advantages such as materials that are available economically, metal-free catalysis, excellent regioselectivity, and high efficiency.

Room temperature ionic liquid choline chloride-oxalic acid: A versatile catalyst for acid-catalyzed transformation in organic reactions

An efficient and facile synthesis of hydrazones, bis(indolyl)methanes and bis(4-hydroxycoumarin)methanes is facilitated by room temperature ionic liquid choline chloride-oxalic acid (ChCl:Ox). ChCl:Ox (10 mol%) efficiently catalyzes condensation of aldehydes with phenylhydrazine giving corresponding hydrazones in high yield (92-96%) within short reaction time of 3-5 min. Electrophilic cyclization reaction of indole and 4-hydroxy coumarin with aromatic aldehyde was effectively promoted by 30 mol% of ChCl:Ox giving corresponding bis(indolyl)arylmethanes and bis (4-hydroxycoumarin)methanes in good yield at room temperature. Procedure is very simple, solvent free and completely eliminates use of toxic acid catalyst. ChCl:Ox is biodegradable, can be recycled and reused without the loss of efficiency with respect to yield.

Synthesis of novel indole hydrazone derivatives and evaluation of their antiplatelet aggregation activity

Based on the existing reports regarding the antiplatelet aggregation activity of hydrazone derivatives, a series of indole hydrazone derivatives were considered as potential antiplatelet agents and synthesized. The structures of the synthesized compounds

Novel indole based colorimetric and "turn on" fluorescent sensors for biologically important fluoride anion sensing

A novel indole Hydrazone receptor 1 has been synthesized by one step of condensation, which can act as an efficient colorimetric and "turn on" fluorescent sensor for fluoride anions; Benesi-Hildebrand equation indicates that 1 associates with F-/sup

Microwave assisted synthesis and antimicrobial evaluation of schiff bases of indole-3-aldehyde

In order to develop new antimicrobial agents, a series of Schiff bases of indole-3-aldehyde were synthesized by microwave assisted synthesis by taking DMF as solvent and evaluated for their antimicrobial activity. All the synthesized compounds were charac

Aminyl and iminyl radicals from arylhydrazones in the photo-induced DNA cleavage

Photolytic cleavage of the nitrogen-nitrogen single bond in benzaldehyde phenylhydrazones produced aminyl (R2N·) and iminyl (R2C=N·) radicals. This photochemical property was utilized in the development of hydrazones as photo-induced DNA-cleaving agents. Irradiation with 350nm UV light of arylhydrazones bearing substituents of various types in a phosphate buffer solution containing the supercoiled circular φX174 RFI DNA at pH6.0 resulted in single-strand cleavage of DNA. Attachment of the electron-donating OMe group to arylhydrazones increased their DNA-cleaving activity. Results from systematic studies indicate that both the aminyl and the iminyl radicals possessed DNA-cleaving ability.