14850-91-0

Upstream product

• 65-85-0 benzoic acid 
• 93-58-3 benzoic acid methyl ester 
• 104-88-1 4-chlorobenzaldehyde 
• 613-94-5 benzoic acid hydrazide 

Downstream Products

• 1874-43-7 2-(4-chlorophenyl)-5-phenyl-1,3,4-oxadiazole 
• 872419-36-8 1-(2-(4-chlorophenyl)-5-phenyl-1,3,4-oxadiazol-3(2H)-yl)ethan-1-one 
• 113367-86-5 N-[2-(4-chlorophenyl)-4-oxo-1,3-thiazolidin-3-yl]benzamide 
• 1065518-98-0 C₁₆H₁₁ClN₂OS 
• 1242282-85-4 diethyl 2-[(E)-1-benzoyl-2-(4-chlorobenzylidene)hydrazinyl]fumarate 

Relevant academic research and scientific papers

Modulation of estrogen-related receptors subtype selectivity: Conversion of an ERRβ/γ selective agonist to ERRα/β/γ pan agonists

Estrogen Related Receptors (ERRs) are key regulators of energy homeostasis and play important role in the etiology of metabolic disorders, skeletal muscle related disorders, and neurodegenerative diseases. Among the three ERR isoforms, ERRα emerged as a potential drug target for metabolic and neurodegenerative diseases. Although ERRβ/γ selective agonist chemical tools have been identified, there are no chemical tools that effectively target ERRα agonism. We successfully engineered high affinity ERRα agonism into a chemical scaffold that displays selective ERRβ/γ agonist activity (GSK4716), providing novel ERRα/β/γ pan agonists that can be used as tools to probe the physiological roles of these nuclear receptors. We identified the structural requirements to enhance selectivity toward ERRα. Molecular modeling shows that our novel modulators have favorable binding modes in the LBP of ERRα and can induce conformational changes where Phe328 that originally occupies the pocket is dislocated to accommodate the ligands in a rather small cavity. The best agonists up-regulated the expression of target genes PGC-1α and PGC-1β, which are necessary to achieve maximal mitochondrial biogenesis. Moreover, they increased the mRNA levels of PDK4, which play an important role in energy homeostasis.

Synthesis, biological evaluation, drug-likeness, and in silico screening of novel benzylidene-hydrazone analogues as small molecule anticancer agents

A series of fifteen benzylidene-hydrazone analogues (3a-o), including eight new compounds, were synthesized and evaluated for their cytotoxic activities in four human cancer cell lines and for their antioxidant activities using DPPH. Of the tested compounds 3e, which possesses two methoxy substituents in its benzylidene phenyl ring, was found to be potently cytotoxic to all cancer cell lines tested with IC50 values of 0.12 (lung), 0.024 (ovarian), 0.097 (melanoma), and 0.05 μM (colon), and these IC50 values were comparable to those of the doxorubicin standard (IC50 = 0.021, 0.074, 0.001, and 0.872 μM, respectively). DPPH assay showed compounds 3f, 3i, and 3g had IC50 values of 0.60, 0.99, and 1.30 μM, respectively, which were comparable to that of ascorbic acid (IC50 = 0.87 μM). Computational parameters such as, drug-likeness, ADME properties, toxicity effects, and drug scores were evaluated, and none of the fifteen compounds violated Lipinski's rule of five or Veber's rule, and thus they demonstrated good drug-likeness properties. In addition, all fifteen compounds had a higher drug score than the doxorubicin and BIBR1532. In silico screening was also conducted by docking of the active compounds on the active site of telomerase reverse transcriptase catalytic subunit, an important therapeutic target of anticancer agents, to determine the probable binding properties. The total binding energies of docked compounds are correlated well with cytotoxic potencies (pIC50) against lung, ovarian, melanoma, and colon cancer cell lines indicating that the benzylidene-hydrazones could use for the development of new anticancer agents as a telomerase inhibitor.

Biological and quantitative-SAR evaluations, and docking studies of (E)-N′-benzylidenebenzohydrazide analogues as potential antibacterial agents

A series of 15 (E)-N′-benzylidenebenzohydrazide analogues were evaluated for their antimicrobial activities against eleven pathogenic and food-borne microbes, namely, S. aureus (G+), L. monocytogenes (G+), B. subtilis (G+), K. pneumonia (G-), C. sakazakii (G-), C. freundii (G-), S. enterica (G-), S. enteritidis (G-), E. coli (G-), Y. pestis (G-), and P. aeruginosa (G-). Most of the compounds exhibited selective activity against some Gramnegative bacterial strains. Of the compounds tested (3a-o), 3b and 3g were most active against C. freundii (MIC = ~19 μg mL-1). Whereas, compounds 3d, 3i, 3k and 3n exhibited MIC values ranging from 37.5 to 75 μg mL-1 against C. freundii, and compounds 3e, 3l and 3n had MIC values of ~75 μg mL-1 against K. pneumonia. Quantitative structure-antibacterial activity relationships were studied using physicochemical parameters and a good correlation was found between calculated octanol-water partition coefficients (clogP; a lipophilic parameter) and antibacterial activities. In silico screening was also performed by docking high (3b and 3g) and low (3n) activity compounds on the active site of E. coli FabH receptor, which is an important therapeutic target. The findings of these in silico screening studies provide a theoretical basis for the design and synthesis of novel benzylidenebenzohydrazide analogues that inhibit bacterial FabH.

Sustainable Synthesis of Oximes, Hydrazones, and Thiosemicarbazones under Mild Organocatalyzed Reaction Conditions

Pyrrolidine catalyzes very efficiently, presumably via iminium activation, the formation of acyloximes, acylhydrazones, and thiosemicarbazones derived from aromatic and aliphatic aldehydes using equimolar amounts of reagents and green solvents. Experimental simplicity and excellent yields after a simple filtration are the main advantages of the method, being an alternative to those currently available especially for the acyl derivatives, which do not work under uncatalyzed conditions. Its application to the synthesis of acyloximes by direct condensation between aldehydes and acylhydroxylamines is unprecedented.

Quantum-Chemical Studies to Approach the Antioxidant Mechanism of Nonphenolic Hydrazone Schiff Base Analogs: Synthesis, Molecular Structure, Hirshfeld and Density Functional Theory Analyses

In the present study, five nonphenolic (E)-N′-benzylidenebenzohydrazides including three new compounds were synthesized and evaluated for their free radical scavenging activities using 2,2-diphenyl-1-picrylhydrazyl (DPPH). X-Ray analysis of a single cryst

Synthesis, oxidation and dehydrogenation of cyclic N,O- and N,S-acetals. Part III. [1,2] Transformation of N,O-acetals: 3-Acyl-1,3,4-oxadiazolines

(Chemical Equation Presented) Various aldehyde and ketone acylhydrazones are synthesized and, under acylating conditions, cyclized into 3-acyl-1,3,4-oxadiazolines. The scope and limitations of these cyclizations and the possible side reactions (e.g. formation of the open-chain N,O-acylhydrazinocarbinols) are dissected. For the first time, simple, convenient and efficient dehydrogenations of 3-acyl-1,3,4-oxadiazolines to oxadiazoles by treatment with potassium permanganate, or more conveniently, with ammonium cerium(IV) nitrate (CAN) are presented. CAN oxidation of 2,2-disubstituted 3-acyl-1,3,4-oxadiazolines, as well as that of aldehyde diacylhydrazones (open-chain isomers of 2,5-disubstituted 3-acyl-1,3,4- oxadiazolines) regenerates the parent carbonyl compounds.

Indium-mediated asymmetric allylation of acylhydrazones using a chiral urea catalyst

(Chemical Equation Presented) Urea-ka! A new role for urea-based chiral catalysts has been uncovered in the asymmetric allylation of acylhydrazones with allylindium reagents (see scheme; Bz: benzoyl). The best results were obtained using the bifunctional

Microwave assisted syntheses of 2,5-disubstituted 1,3,4-oxadiazoles

2,5-Di-substituted 1,3,4-oxadiazoles have been synthesized from the oxidation of 1-aroyl-2-arylidene hydrazines with potassium permanganate on the surface of solid mineral support as well as in the mixture of acetone and water under microwave irradiation. 2,5-Disubstituted 1,3,4-oxadiazoles have been synthesized by oxidation of 1-aroyl-2-arylidene hydrazines with potassium permanganate on the surface of a solid mineral support as well as in mixtures of acetone and water under microwave irradiation.