59394-93-3

Upstream product

• 613-94-5 benzoic acid hydrazide 
• 1122-91-4 4-bromo-benzaldehyde 
• 93-89-0 benzoic acid ethyl ester 

Downstream Products

• 1259388-05-0 N'-(1-(4-bromophenyl)-2,2-difluoro-3-oxo-3-phenylpropyl)benzohydrazide 
• 1242282-86-5 diethyl 2-[(E)-1-benzoyl-2-(4-bromobenzylidene)hydrazinyl]fumarate 
• 957045-51-1 2-phenyl-5-[4-(phenylethynyl)phenyl]-1,3,4-oxadiazole 
• 1448781-80-3 ((3R,3aS,6aS)-3-(4-bromophenyl)-2,3,3a,4-tetrahydrocyclopenta[c]pyrazol-1(6aH)-yl)(phenyl)methanone 
• 1366284-20-9 N-(1-(4-bromophenyl)-2,2-difluoro-3-oxo-3-phenylpropyl)benzohydrazide 
• 1333150-37-0 C₁₇H₁₇BrN₂O 
• 1236309-94-6 C₁₈H₁₅BrN₂O₂ 
• 1191940-79-0 C₁₈H₁₈BrClN₂O₃ 
• 1198616-56-6 C₁₇H₁₇BrN₂O 
• 77420-68-9 N-[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-N'-[1-phenyl-1-thiocyanato-meth-(Z)-ylidene]-hydrazine 
• 77420-74-7 [1-(4-Bromo-phenyl)-meth-(E)-ylidene]-(5-phenyl-[1,3,4]thiadiazol-2-yl)-amine 

Relevant academic research and scientific papers

Sodium hypochlorite-mediated synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from hydrazides and aldehydes

[Figure not available: see fulltext.] A simple and convenient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed. Structurally divergent symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles can be obtained in moderate to high yields via NaOCl-mediated oxidative cyclization of N-acylhydrazones, generated in situ from aliphatic and aromatic hydrazides and aldehydes.

Oxadiazole based Os(IV) compounds as potential DNA intercalator and cytotoxic agents

Os(IV) compounds and ligands have been synthesized and well characterized. DNA cleavage tendency of compounds has been evaluated using gel electrophoresis and binding behavior has been evaluated by viscosity measurements, absorption titration, fluorescenc

Experimental and Theoretical Studies on the Mechanism of DDQ-Mediated Oxidative Cyclization of N-Aroylhydrazones

The controversial single-electron-transfer process, frequently proposed in many 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated reactions, was investigated experimentally and theoretically using the oxidative cyclization of aroylhydrazone with DDQ. DDQ-mediated oxadiazole formation involves several processes, including cyclization to form an oxadiazole ring and N-H bond cleavage, either by proton, hydride, or hydrogen atom transfer. The detailed mechanistic study using the M06-2X density functional theory, and the 6-31+G(d,p) basis set, suggests that the pathways involving radical ion pair (RIP) intermediates, which resulted from single-electron transfer (SET), were found to be energetically nearly identical to the pathway without the SET. The substituent-dependent reactivity of oxadiazole formation was consistent with the free energy profiles of both pathways, with or without the SET. This result indicates that in addition to the electron-transfer pathway, the nucleophilic addition/elimination pathway for DDQ should be considered as a possible mechanism of the oxidative transformation reaction using DDQ.

An efficient one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles from aldehydes and hydrazides using Lawesson’s reagent

Five-membered heterocyclic-ring systems, such as thiadiazoles, remain an important and prevalent scaffold in the development of novel leads in medicinal chemistry for a variety of therapeutic targets. A two-step, one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from aryl hydrazides and aryl aldehydes using Lawesson’s reagent is described, yielding 2,5-disubstituted-1,3,4-thiadiazoles in moderate-to-high yields. Based on preliminary biological experiments, some of the newly synthesized thiadiazoles show antioxidant activity.

Synthesis of New Alkynyl-Bridged 2,5-Disubstituted 1,3,4-Oxadiazoles

A synthesis of new alkynyl-derived 2,5-disubstituted 1,3,4-oxadiazoles through palladium/copper-catalyzed Sonogashira cross-coupling between oxadiazole-substituted phenyl bromides and various arylacetylenes is described. Investigation of the absorption and emission spectra of the target compounds indicates emission profiles in the near-blue and blue region and high luminescence intensities. The presented approach is very convenient for the synthesis of luminescent small-molecules or precursors of other complex derivatives that are useful in the preparation of OLEDs as electron-transporting components.

N-(1'-naphthyl)-3,4,5-trimethoxybenzohydrazide as microtubule destabilizer: Synthesis, cytotoxicity, inhibition of cell migration and in vivo activity against acute lymphoblastic leukemia

Tubulin-interacting agents, like vinca alkaloid and taxanes, play a fundamental role in cancer chemotherapy, making cellular microtubules (MT), one of the few validated anticancer targets. Cancer resistance to classical MT inhibitors has motivated the development of novel molecules with increased efficacy and lower toxicity. Aiming at designing structurally-simple inhibitors of MT assembly, we synthesized a series of thirty-one 3,4,5-trimethoxy-hydrazones and twenty-five derivatives or analogs. Docking simulations suggested that a representative N-acylhydrazone could adopt an appropriate stereochemistry inside the colchicine-binding domain of tubulin. Several of these compounds showed anti-leukemia effects in the nanomolar concentration range. Interference with MT polymerization was validated by the compounds' ability to inhibit MT assembly at the biochemical and cellular level. Selective toxicity investigations done with the most potent compound, a 3,4,5-trimethoxy-hydrazone with a 1-naphthyl group, showed remarkably selective toxicity against leukemia cells in comparison with stimulated normal lymphocytes, and no acute toxicity in vivo. Finally, this molecule was as active as vincristine in a murine model of human acute lymphoblastic leukemia at a weekly dose of 1 mg/kg.

Efficient oxidative cyclization of N -acylhydrazones for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles using t-BuOI under neutral conditions

An efficient procedure for the oxidative cyclization of N -acylhydrazones was developed utilizing tert-butyl hypoiodite (t-BuOI), which is generated in situ from t -BuOCl and NaI. A variety of 2,5-disubstituted 1,3,4-oxadiazoles were synthesized in high yields within short reaction time. The method is also suitable for cyclization of N -acylhydrazones derived from heterocyclic aldehydes and aliphatic aldehydes. Mild reaction conditions and simple workup operations make the procedure a good alternative for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles.

One-pot, three component synthesis of 2,5-disubstituted 1,3,4-oxadiazoles catalyzed by heteropolyacid

H6[PMo9V3O40] was used as an efficient catalyst for the preparation of 1-aroyl-2-arylidene hydrazines. 2,5-Disubstituted 1,3,4-oxadiazoles have been synthesized by oxidation of 1-aroyl-2-arylidene hydrazines with CrO3 in excellent yields.

Synthesis, characterization and biological studies of mononuclear copper(II) complexes with ciprofloxacin and N, O donor ligands

The mixed ligand Cu(II) complexes of ciprofloxacin and N, O donor Schiff bases have been prepared and characterized by physicochemical techniques. In these complexes, ciprofloxacin acts as bidentate deprotonated ligand bound to the metal through the pyrid

Efficient oxidative cyclisation of acid hydrazides to 2,5-disubstituted 1,3,4-oxadiazoles catalysed by Bu4NI with t-BuOOH as oxidant

Acid hydrazides or araldehyde N-acylhydrazones can be converted in good yields to, respectively, symmetrical or unsymmetrical, 2,5-disubstituted 1,3,4-oxadiazoles at 60 °C by a Bu4NI-catalysed procedure which requires the presence of a base and 2.5 equiv. of t-butyl hydroperoxide.