43038-36-4

Usage

Uses

Used in Pharmaceutical Synthesis:
Benzoic acid, 4-cyano-, hydrazide (9CI) is utilized as an intermediate in the production of various pharmaceuticals. Its role in this application is attributed to its ability to react with other compounds to form new molecules that possess therapeutic properties.
Used in Organic Chemistry as a Reagent:
In the realm of organic chemistry, Benzoic acid, 4-cyano-, hydrazide (9CI) functions as a reagent, particularly in the formation of hydrazones and other chemical derivatives. This use capitalizes on its reactivity to facilitate the synthesis of complex organic structures.
Used in Medicinal Chemistry and Drug Development:
Benzoic acid, 4-cyano-, hydrazide (9CI)'s potential applications in medicinal chemistry and drug development stem from its capacity to form diverse chemical structures. This makes it a promising candidate for the design and synthesis of new drugs with specific therapeutic targets.
Used in Research and Development:
Benzoic acid, 4-cyano-, hydrazide (9CI) is also employed in research settings to explore its chemical properties and potential interactions with other molecules. This can lead to the discovery of new applications and uses in various chemical and pharmaceutical processes.

InChI:InChI=1/C8H7N3O/c9-5-6-1-3-7(4-2-6)8(12)11-10/h1-4H,10H2,(H,11,12)

Upstream product

• 7153-22-2 ethyl 4-cyanobenzoate 
• 623-00-7 4-bromobenzenecarbonitrile 
• 1644630-63-6 C₁₄H₇ClN₂O₄ 
• 302-01-2 hydrazine 
• 6068-72-0 4-cyanobenzoyl chlorIde 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 7803-57-8 hydrazine hydrate 
• 32792-60-2 4-nitrophenyl 4-cyanobenzoate 
• 619-65-8 4-cyanobenzoic Acid 

Downstream Products

• 128772-82-7 5-(4-cyanophenyl)-1,3,4-oxadiazol-2(3H)-one 
• 143667-33-8 [(4-Cyano-benzoyl)-hydrazono]-acetic acid 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 149899-18-3 3-(4-Cyano-phenyl)-5-[4-(2-methoxycarbonyl-ethyl)-phenyl]-1,2,4-triazole 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 1118428-69-5 (Z)-2-[5-(4-cyanophenyl)-3-methyl-1,2,4-triazol-4-yl]-3-(1-naphthyl)-2-propeonic acid 
• 1354340-13-8 (R)-N'-(2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxy-3-methylbutanoyl)-4-cyanobenzohydrazide 
• 1373516-17-6 4-cyano-benzoic acid N'-[2-(3-iodo-phenyl)-acetyl]-hydrazide 
• 1373516-18-7 4-[5-(3-iodo-benzyl)-[1,3,4]oxadiazol-2-yl]-benzonitrile 
• 1373516-21-2 4-[5-(3-iodo-benzyl)-[1,3,4]thiadiazol-2-yl]-benzonitrile 
• 13041-79-7 (E)-1-cyano-4-styryl-benzene 
• 1628297-59-5 N-4-[octyloxy(phenoxy)]salicylidene-N'-cyanobenzoylhydrazine 
• 160890-96-0 4-(5-methyl-1,3,4-oxadiazol-2-yl)benzonitrile 
• 1874-33-5 4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzonitrile 

Relevant academic research and scientific papers

Synthesis, molecular docking study and in vitro thymidine phosphorylase inhibitory potential of oxadiazole derivatives

We have synthesized oxadiazole derivatives (1–16), characterized by 1H NMR, 13C NMR and HREI-MS and screened for thymidine phosphorylase inhibitory potential. All derivatives display varied degree of thymidine phosphorylase inhibitio

Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties

A series of new symmetrical s-tetrazine derivatives, coupled via a 1,4-phenylene linkage with a 4H-1,2,4-triazole ring, were obtained. The combination of these two rings in an extensively coupled system has significant potential applications, mainly in op

Design, synthesis, and biological evaluation of phenyloxadiazole derivatives as potential antifungal agents against phytopathogenic fungi

Abstract: A novel series of picarbutrazox-inspired oxadiazole hybrids was synthesized and the derivatives’ biological activity against phytopathogenic fungi was investigated. The molecules were designed by retaining the active fragment of tetrazolyl phenyloxime ether of lead compound picarbutrazox, while introducing the potentially active oxadiazole-derived fragment. Bioassay results revealed that some of the title compounds showed potent in vivo antifungal activities to control cucumber downy mildew. Therefore, this novel oxadiazole phenyloxadiazole derivative can be used as a potential antifungal agent to control cucumber downy mildew and other phytopathogenic fungi for crop protection. Graphic abstract: [Figure not available: see fulltext.].

[1,2,4]TRIAZOLO[1,5-C]QUINAZOLIN-5-AMINES

The present invention covers [1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds of general formula (I) in which R1, R2, R3, R4, R5, R6, R7 and R8 are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of cancer or conditions with dysregulated immune responses or other disorders associated with aberrant AHR signaling, as a sole agent or in combination with other active ingredients.

Highly fluorescent 1,2,4,5-tetrazine derivatives containing 1,3,4-oxadiazole ring conjugated via a 1,4-phenylene linker

Symmetrical and unsymmetrical 1,2,4,5-tetrazine derivatives containing 1,3,4-oxadiazole ring were obtained in high yields using commercially-available 4-cyanobenzoic acid, hydrazine hydrate and carboxylic acid chlorides. The few-step transformation involved the Pinner reaction and the subsequent mild oxidation of 1,4-dihydro-1,2,4,5-tetrazines using hydrogen peroxide at room temperature. The obtained compounds exhibited luminescent properties and large quantum yields.

Synthesis of isoquinolones by visible-light-induced deaminative [4+2] annulation reactions

Herein a metal-free approach for the synthesis of isoquinolone derivatives by means of photoinitiated deaminative [4+2] annulation of alkynes and N-amidepyridinium salts is described. This protocol exhibits a broad scope and good functional group tolerance and regioselectivity under benign reaction conditions. Preliminary studies suggest that the critical amide radical is derived from the photocatalytic cleavage of the N-N bond of the N-amidepyridinium salt, which adds to the triple bond of the alkyne and undergoes the annulation process to afford the desired isoquinolones.

Design and synthesis of new norfloxacin-1,3,4-oxadiazole hybrids as antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA)

Toward the search of new antibacterial agents to control methicillin-resistant Staphylococcus aureus (MRSA), a class of new norfloxacin-1,3,4-oxadiazole hybrids were designed and synthesized. Antibacterial activities against drug-sensitive bacteria S. aureus and clinical drug resistant isolates of MRSA were evaluated. Compound 5k exhibited excellent antibacterial activities against S. aureus (MIC: 2 μg/mL) and MRSA1–3 (MIC: 0.25–1 μg/mL). The time-kill kinetics demonstrated that compound 5k had an advantage over commonly used antibiotics vancomycin in killing S. aureus and MRSA. Moreover, compound 5k could inhibit the bacteria and destroy their membranes in a short time, and showed very low cytotoxicity to NRK-52E cells. Some interesting structure-activity relationships (SARs) were also discussed. These results indicated that these norfloxacin-1,3,4-oxadiazole hybrids could be further developed into new antibacterial agents against MRSA.

Novel Molecular Hybrids of N-Benzylpiperidine and 1,3,4-Oxadiazole as Multitargeted Therapeutics to Treat Alzheimer's Disease

Multitargeted hybrids of N-benzylpiperidine and substituted 5-phenyl-1,3,4-oxadiazoles were designed, synthesized, and evaluated against Alzheimer's disease (AD). Tested compounds exhibited moderate to excellent inhibition against human acetylcholinesterase (hAChE), butyrylcholinesterase (hBChE), and beta-secretase-1 (hBACE-1). The potential leads 6g and 10f exhibited balanced inhibitory profiles against all the targets, with a substantial displacement of propidium iodide from the peripheral anionic site of hAChE. Hybrids 6g and 10f also elicited favorable permeation across the blood-brain barrier and were devoid of neurotoxic liability toward SH-SY5Y neuroblastoma cells. Both leads remarkably disassembled Aβ aggregation in thioflavin T-based self- and AChE-induced experiments. Compounds 6g and 10f ameliorated scopolamine-induced cognitive dysfunctions in the Y-maze test. The ex vivo studies of rat brain homogenates established the reduced AChE levels and antioxidant activity of both compounds. Compound 6g also elicited noteworthy improvement in Aβ-induced cognitive dysfunctions in the Morris water maze test with downregulation in the expression of Aβ and BACE-1 proteins corroborated by Western blot and immunohistochemical analysis. The pharmacokinetic study showed excellent oral absorption characteristics of compound 6g. The in silico molecular docking and dynamics simulation studies of lead compounds affirmed their consensual binding interactions with PAS-AChE and aspartate dyad of BACE-1.

SAR Studies on Aromatic Acylhydrazone-Based Inhibitors of Fungal Sphingolipid Synthesis as Next-Generation Antifungal Agents

Recently, the fungal sphingolipid glucosylceramide (GlcCer) synthesis has emerged as a highly promising new target for drug discovery of next-generation antifungal agents, and we found two aromatic acylhydrazones as effective inhibitors of GlcCer synthesis based on HTP screening. In the present work, we have designed libraries of new aromatic acylhydrazones, evaluated their antifungal activities (MIC80 and time-kill profile) against C. neoformans, and performed an extensive SAR study, which led to the identification of five promising lead compounds, exhibiting excellent fungicidal activities with very large selectivity index. Moreover, two compounds demonstrated broad spectrum antifungal activity against six other clinically relevant fungal strains. These five lead compounds were examined for their synergism/cooperativity with five clinical drugs against seven fungal strains, and very encouraging results were obtained; e.g., the combination of all five lead compounds with voriconazole exhibited either synergistic or additive effect to all seven fungal strains.

TBSOTf-promoted versatile N-formylation using DMF at room temperature

Hydrazides and amines were N-formylated by DMF in the presence of tert-butyldimethylsilyl triflate (TBSOTf) at room temperature, in good to excellent yields.