64328-60-5

Usage

Uses

Used in Pharmaceutical Industry:
4-Propoxy-benzoic acid hydrazide is used as a pharmaceutical intermediate for the synthesis of various organic compounds. Its versatility in chemical reactions makes it a valuable component in the development of new drugs and pharmaceuticals.
Used in Corrosion Inhibition:
4-Propoxy-benzoic acid hydrazide is used as a corrosion inhibitor to protect materials from degradation and wear. Its potential use in this area is currently being studied to determine its effectiveness and applicability in various industries.
Used in Material Development:
4-Propoxy-benzoic acid hydrazide is used in the development of new materials, where its unique properties can contribute to the creation of innovative and improved products.
Used in Antitumor Applications:
4-Propoxy-benzoic acid hydrazide is used as a potential antitumor agent, with ongoing research investigating its effectiveness against various types of cancer.
Used in Antiviral Applications:
4-Propoxy-benzoic acid hydrazide is used as a potential antiviral agent, with studies exploring its ability to inhibit viral replication and reduce the severity of viral infections.
Used in Enzyme Inhibition:
4-Propoxy-benzoic acid hydrazide is used as a potential inhibitor of enzymes involved in inflammatory processes, with research being conducted to determine its efficacy in treating inflammatory conditions.

InChI:InChI=1/C10H14N2O2/c1-2-7-14-9-5-3-8(4-6-9)10(13)12-11/h3-6H,2,7,11H2,1H3,(H,12,13)

Upstream product

• 115478-59-6 methyl 4-propoxy benzoate 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 5438-19-7 4-propoxybenzoic acid 
• 99-76-3 methyl 4-hydroxylbenzoate 

Downstream Products

• 134313-85-2 [(4-Propoxy-benzoyl)-hydrazono]-acetic acid 
• 406934-66-5 4-amino-5-(4-propyloxyphenyl)-2,4-dihydro-3H[1,2,4]triazole-3-thione 
• 139397-49-2 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenyl-2-{2-[(4-propoxy-benzoyl)-hydrazono]-acetylamino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 1609020-86-1 3-acetyl-5-(4-propoxy-phenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro-1,3,4-oxadiazole 
• 500195-02-8 4-propoxy-N’-((5-nitrofuran-2-yl)methylene)benzohydrazide 
• 1630012-42-8 C₁₁H₁₂N₂O₃ 
• 1630012-90-6 4-butyl-5-(4-propoxyphenyl)-2H-1,2,4-triazole-3(4H)-one 
• 890298-05-2 C₁₅H₂₃N₃O₃ 

Relevant academic research and scientific papers

Synthesis, Antiproliferative and Antioxidant Activity of 3-Mercapto-1,2,4-Triazole Derivatives as Combretastatin A-4 Analogues

Two series of 3-mercapto-1,2,4-triazole derivatives containing alkoxy substituents different in size and position were synthesized and their structures were characterized by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. The synthesized compounds were assessed for their antiproliferative activity against colon cancer cell line (SW480). The results indicated that the size and position of the alkoxy group significantly influenced the antiproliferative activity. The highest cancer cell growth inhibition values were observed for the compounds containing 3,4,5-trimethoxyphenyl groups in their structures (57.74, 54.14 and 60.70% at 50 μM for compounds 5a, 12b and 14, respectively). The synthesized compounds were also subjected to DPPH protocol for evaluating the antioxidant activity. The results showed that all compounds had moderate to high levels of antioxidant capacity as compared to ascorbic acid as standard, the highest free radical scavenging capacity of 75% was observed for compound 4a at 50 μM.

Designing and exploring active N′-[(5-nitrofuran-2-yl) methylene] substituted hydrazides against three Trypanosoma cruzi strains more prevalent in Chagas disease patients

Chagas disease affects around 8 million people worldwide and its treatment depends on only two nitroheterocyclic drugs, benznidazole (BZD) and nifurtimox (NFX). Both drugs have limited curative power in chronic phase of disease. Nifuroxazide (NF), a nitroheterocyclic drug, was used as lead to design a set of twenty one compounds in order to improve the anti-Trypanosoma cruzi activity. Lipinski's rules were considered in order to support drug-likeness designing. The set of N′-[(5-nitrofuran-2-yl) methylene] substituted hydrazides was assayed against three T. cruzi strains, which represent the discrete typing units more prevalent in human patients: Y (TcII), Silvio X10 cl1 (TcI), and Bug 2149 cl10 (TcV). All the derivatives, except one, showed enhanced trypanocidal activity against the three strains as compared to BZD. In the Y strain 62% of the compounds were more active than NFX. The most active compound was Ng€2-((5-nitrofuran-2-yl) methylene)biphenyl-4-carbohydrazide (C20), which showed IC50 values of 1.17 ± 0.12 μM; 3.17 ± 0.32 μM; and 1.81 ± 0.18 μ4M for Y, Silvio X10 cl1, and Bug 2149 cl10 strains, respectively. Cytotoxicity assays with human fibroblast cells have demonstrated high selectivity indices for several compounds. Exploratory data analysis indicated that primarily topological, steric/geometric, and electronic properties have contributed to the discrimination of the set of investigated compounds. The findings can be helpful to drive the designing, and subsequently, the synthesis of additional promising drugs against Chagas disease.

Synthesis and anticonvulsant activity evaluation of 4-butyl-5-(4- alkoxyphenyl)-2H-1,2,4-triazole-3(4H)-ones

A series of 4-butyl-5-(4-alkoxyphenyl)-2H-1,2,4-triazole-3(4H)-ones (6a-6u) was designed and synthesized. The anticonvulsant effects and neurotoxicity of the compounds were evaluated with maximal electroshock test and rotarod test. Among the synthetic compounds, 4-butyl-5-(4-(2-fluorinebenzyl)phenyl)-2H-1,2,4- triazole-3 (4H)-one (6k) was the most potent with ED50 value of 27.4 mg/kg and protective index (PI = TD50/ED50) value of 12.0. Besides the anti-MES efficacy, the potency of compound 6k against seizures induced by pentylenetetrazole (PTZ), 3-mercaptopropionic acid (3-MP), and bicuculline (BIC) was also established, which suggested that the mechanisms of action including enhancing of GABAergic activity might be involved in its anticonvulsant activity.

Ligand-based design, synthesis, and experimental evaluation of novel benzofuroxan derivatives as anti-Trypanosoma cruzi agents

A set of substituted-[N′-(benzofuroxan-5-yl)methylene]benzohydrazides (4a-t), previously designed and synthesized, was experimentally assayed against Trypanosoma cruzi, the etiological agent of Chagas' disease, one of the most neglected tropical diseases. Exploratory data analysis, Hansch approach and VolSurf formalism were applied to aid the ligand-based design of novel anti-T. cruzi agents. The best 2D-QSAR model showed suitable statistical measures [n = 18; s = 0.11; F = 42.19; R2 = 0.90 and Q2 = 0.77 (SDEP = 0.15)], and according to the optimum 3D-QSAR model [R2 = 0.98, Q 2 = 0.93 (SDEP = 0.08)], three latent variables explained 62% of the total variance from original data. Steric and hydrophobic properties were pointed out as the key for biological activity. Based upon the findings, six novel benzofuroxan derivatives (4u-z) were designed, synthesized, and in vitro assayed to perform the QSAR external prediction. Then, the predictability for the both models, 2D-QSAR (Rpred2 = 0.91) and 3D-QSAR (Rpred2 = 0.77), was experimentally validated, and compound 4u was identified as the most active anti-T. cruzi hit (IC50 = 3.04 μM).

Synthesis, molecular modeling and preliminary biological evaluation of a set of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole as potential antibacterial, anti-Trypanosoma cruzi and antifungal agents

A series of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives was synthesized and their activity screened in vitro against Staphylococcus aureus, Trypanosoma cruzi, and Candida albicans. The bioactivity was expressed as minimum inhibitory concentration (MIC) for S. aureus strains, and as fifty-percent inhibitory concentration (IC50) of parasite population growth for T. cruzi. A molecular modeling approach was performed to establish qualitative relationships regarding the biological data and the compounds' physicochemical properties. The 5-(4-OC4H9Ph, 5μ), and 5-(4-CO2CH3Ph, 5o) derivatives were the most active compounds for S. aureus ATCC 25923 (MIC = 1.95 -1.25 μg/mL) and T. cruzi (IC50 = 7.91 μM), respectively. Also, a preliminary evaluation against C. albicans involving some compounds was performed and the 5-(4-CH 3Ph, 5e) derivative was the most active compound (MIC = 3.28-2.95 μg/mL). In this preliminary study, all synthesized 3-acetyl-2,5- disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives were active against all microorganisms tested.

A new class of nifuroxazide analogues: Synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus

Hospital-acquired methicillin-resistant Staphylococcus aureus (MRSA) has been an increasing problem worldwide since the initial reports over 40 years ago. To examine new drug leads with potential antibacterial activities, 14 p-substituted benzoic acid [(5-nitro-thiophen-2-yl)-methylene]-hydrazides were designed, synthesized, and tested against standard and multidrug-resistant S. aureus strains by serial dilution tests. All compounds exhibited significant bacteriostatic activity and some of them also showed bactericidal activity. The results confirmed the potential of this class of compounds as an alternative for the development of selective antimicrobial agents.

Smectic A liquid crystals from dihydrazide derivatives with lateral intermolecular hydrogen bonding

Six dissymmetrical dihydrazide derivatives, N-(4-alkoxybenzoyl)-N′- (4′-nitrobenzoyl) hydrazine (Cn-NO2) and N-(4-alkoxybenzoyl)- N′-(4′-biphenyl carbonyl) hydrazine (Cn-Ph), were synthesized and investigated by means of differential scanning c