51707-38-1

Usage

Uses

Used in Organic Synthesis:
3,5-Dimethoxybenzhydrazide is used as a reagent in the synthesis of various complex chemical compounds. Its functional groups, including the methoxy groups and the carbohydrazide moiety, contribute to its reactivity and versatility in forming new molecules.
Used in Pharmaceutical Industry:
3,5-Dimethoxybenzhydrazide is used as an intermediate in the development of pharmaceutical compounds. Its unique structure allows for the creation of new drug candidates with potential therapeutic applications.
Used in Research and Development:
3,5-Dimethoxybenzhydrazide is used as a research compound in academic and industrial laboratories. Its properties and reactivity are studied to understand its potential applications and to develop new synthetic methods for its preparation and use.
Note: The specific details about the compound, such as its melting point, boiling point, and density, would need to be determined experimentally or through reliable resources.

InChI:InChI=1/C9H12N2O3/c1-13-7-3-6(9(12)11-10)4-8(5-7)14-2/h3-5H,10H2,1-2H3,(H,11,12)

Upstream product

• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 99-10-5 3,5-Dihydroxybenzoic acid 

Downstream Products

• 19949-29-2 5-(3,5-dimethoxy-phenyl)-[1,3,4]oxadiazol-2-ylamine 
• 14631-79-9 N-[5-(3,5-dimethoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-methanesulfonamide 
• 14631-78-8 N-[5-(3,5-dimethoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-toluene-4-sulfonamide 
• 51707-07-4 3-[(3,5-dimethoxy-benzoylhydrazono)-methyl]-rifamycin 
• 75996-26-8 azido(3,5-dimethoxyphenyl)methanone 
• 54132-76-2 3,5-dimethoxyphenyl isocyanate 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 1284312-40-8 3-(3',5'-dimethoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 749902-08-7 5-(3,5-dmethoxyphenyl)-1,3,4-oxadiazole-2-thiol 
• 717895-03-9 2-(benzylthio)-5-(3,5-dimethoxyphenyl)-1,3,4-oxadiazole 
• 1429183-46-9 2-(3,5-Dimethoxyphenyl)-5-((2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)thio)-1,3,4-oxadiazole 
• 106728-68-1 5-(3,5-Dimethoxyphenyl)-1,3,4-oxadiazolin-2-one 
• 500-66-3 Olivetol 
• 151-10-0 1,3-Dimethoxybenzene 

Relevant academic research and scientific papers

Synthesis, crystal structures and insulin-like activity of three new oxidovanadium(V) complexes with aroylhydrazone ligand

Three new oxidovanadium(V) complexes were designed, synthesized and characterized by C, H, N elemental analysis, single crystal X-ray diffraction，UV/Vis and IR spectra. Complex 1: [VOL1X] (H2L1 = (E)-N′-(2-hydroxybenzylidene)-3-methbenzohydrazide, HX = ethylmaltol = 2-ethyl-3-hydroxy-4-pyrone), Complex 2: [VOL2(CH3O)(CH3OH)], (H2L2 = C16H16N2O4 = (E)-N′-(2-hydroxybenzylidene)-3,5-dimethoxybenzohydrazide, CH3OH = methanol), Complex 3: [VOL3X] (H2L3 = (E)-N′-(3-ethoxy-2-hydroxybenzylidene)-3,5-dimethoxybenzohydrazide). The insulin-like activity of the three complexes was tested. Both normal and streptozotocin (STZ)-diabetic mice were administered intragastrically for two weeks. It was found that the complexes at doses of 10.0 and 5.0 mg V·kg?1 can significantly decrease the blood glucose level in STZ-diabetic mice, and the blood glucose level in the treated normal mice was not altered. The lesions of kidney and liver caused by diabetes have varying degrees of improvement.

Hydrazide compounds

The invention discloses hydrazide compounds. The compounds are characterized by having a structure represented by a formula I shown in the description, wherein Ar1 and Ar2 are each independently selected from the group consisting of aryl, azinyl, piperazinyl, pyrazolyl, imidazolyl, pyrrolyl, phenyl, naphthyl, thiazolyl, thienyl, furyl, aryl, phenyl, piperazinyl, piperidinyl, piperazinyl, and-C13H9represented by a formula 9 shown in the description, only one of the Ar1 and the Ar2 is phenyl, the Ar1 has m substituents R1, Ar2 has n substituents R2, m=0 to 3, and n=0 to 3; and if the formula Ihas a plurality of substituents R1 and R2, the plurality of substituents R1 and R2 are independent with one another, can select the same substituents or different substituents, and the R1 and the R2 are each independently selected from the group consisting of halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 alkoxy, amino, C1-C3 alkyl substituted amino, C1-C3 alkyl disubstituted amino, perfluoro C1-C3alkyl and fluoro substituted C1-C3 alkoxy.

Synthesis, pharmacological evaluation and docking study of a new modulator of microtubule polymerization

Objectives: The main goal of this paper was to conduct the synthesis to determine cytotoxic activity and to carry out docking studies on new LASSBio-1586 isosteres. LASSBio-1586 is a new combretastatin A4 (CA4) analogue previously identified as a simple antitumor drug candidate, able to inhibit microtubule polymerization with broad in vitro and in vivo cytotoxic activity. Methods: The new isosteres (7b-7h, 8a and 9a) were evaluated against HL-60, OVCAR-8, HCT8 and LUCENA tumor cell lines, using cytotoxic test of MTT. The tubulin polymerization assay was performed using a tubulin polymerization assay kit from cytoskeletonR and by CEREP employing a single concentration of 10 μM. Binding mode at β-tubulin colchicine binding site was stablished by blind molecular docking studies. Results: LASSBio-1920 (7h) was identified as the most potent cytotoxic compound with IC50 values ranging from 0.75 nM to 11.5 nM, although it was inactive against MDR tumor cell line LUCENA (IC50 = 80 μM). This compound presented remarkable cytotoxic selective index in comparison with CA4 and LASSBio-1586. Its ability to modulate microtubule polymerization was confirmed and its mode of interaction with colchicine binding site in β-tubulin was demonstrated. Conclusion: Compound 7h is a new isostere of LASSBio-1586 that displayed potent cytotoxic activity and better cytotoxic selectivity index and has been shown to interact with DAMA-colchicine in its co-crystal with β-tubulin.

Method for synthesizing aryl formaldehyde compound from aryl formate compound

The invention discloses a method for synthesizing an aryl formaldehyde compound from an aryl formate compound. The method comprises the following steps: taking the aryl formate compound as a raw material, and reacting under the action of excessive hydrazine hydrate; after the end of the reaction, standing, cooling, filtering and washing, thus respectively obtaining filtrate and filter cake, wherein the filtrate is the hydrazine hydrate, and the filter cake is an aryl formylhydrazine compound; recycling and reusing the filtrate; then dissolving the aryl formylhydrazine compound in a solvent, reacting under the existence of 2-iodoxybenzoic acid and alkali, and carrying out aftertreatment, thus obtaining the aryl formaldehyde compound and a byproduct-2-iodosobenzoic acid; regenerating the 2-iodoxybenzoic acid after oxidizing the 2-iodosobenzoic acid, and repeatedly using the 2-iodoxybenzoic acid. According to the method disclosed by the invention, recycling and cyclic utilization of materials are fully realized, emissions are less, environment friendliness is realized, and the yield is higher.

Design, synthesis, biological evaluation, and 3D-QSAR analysis of podophyllotoxin–dioxazole combination as tubulin targeting anticancer agents

The advancement of cancer-fighting drugs has never been a simple linear process. Those drug design professionals begin to find inspiration from the nature after failing to find the ideal products by creative drug design and high-throughput screening. To obtain new molecules for inhibiting tubulin, podophyllotoxin was adopted as the leading compound and 1,3,4-oxadiazole was brought in to the C-4 site of podophyllotoxin in this research. A series of seventeen podophyllotoxin-derived esters have been achieved and then evaluated their antitumor activities against four different cancer cell lines: A549, MCF-7, HepG2, and HeLa. Among all the compounds, compound 7c showed the best antiproliferating properties with IC50?=?2.54?±?0.82?μm against MCF-7 cancer cell line. It was obvious that the content of ROS grew significantly in MCF-7 in a way depending on the dosage. The time- and dose-dependent cell cycle assays revealed that compound 7c could apparently block cell cycle in the phase of G2/M along with the upregulation of cyclin A2 and CDK2 protein. According to further studies, confocal microscopy experiment has certified that compound 7c could restrain cancer from growing by blocking the polymerization of microtubule. Meanwhile, compound 7c could be ideally integrated with the colchicine site of tubulin. In future, it would be feasible to selectively design tubulin inhibitors with the help of 3D-QSAR. This means that it is hopeful to develop compound 7c as a potential agent against cancer due to its biological characteristics.

Development of 3,5-Dinitrobenzylsulfanyl-1,3,4-oxadiazoles and Thiadiazoles as Selective Antitubercular Agents Active Against Replicating and Nonreplicating Mycobacterium tuberculosis

Herein, we report the discovery and structure-activity relationships of 5-substituted-2-[(3,5-dinitrobenzyl)sulfanyl]-1,3,4-oxadiazoles and 1,3,4-thiadiazoles as a new class of antituberculosis agents. The majority of these compounds exhibited outstanding in vitro activity against Mycobacterium tuberculosis CNCTC My 331/88 and six multidrug-resistant clinically isolated strains of M. tuberculosis, with minimum inhibitory concentration values as low as 0.03 μM (0.011-0.026 μg/mL). The investigated compounds had a highly selective antimycobacterial effect because they showed no activity against the other bacteria or fungi tested in this study. Furthermore, the investigated compounds exhibited low in vitro toxicities in four proliferating mammalian cell lines and in isolated primary human hepatocytes. Several in vitro genotoxicity assays indicated that the selected compounds have no mutagenic activity. The oxadiazole and thiadiazole derivatives with the most favorable activity/toxicity profiles also showed potency comparable to that of rifampicin against the nonreplicating streptomycin-starved M. tuberculosis 18b-Lux strain, and therefore, these derivatives, are of particular interest.

Radiosynthesis and characterisation of a potent and selective GPR139 agonist radioligand

Compound 1 is a selective and potent agonist of the G protein-coupled receptor GPR139 (EC50 = 39 nM). In this study, we describe the synthesis, radiolabelling and in vitro evaluation of [3H]-1 for the characterisation of GPR139 and its spatial expression in the brain using autoradiography. Two different synthesis routes for the radiolabelling of 1 based on a reductive debromination strategy were investigated using deuterium (D2, g). The route based on reductive debromination of the bromonaphthyl precursor 5 proved superior over arylbromide 4 and was employed for the radiolabelling experiments. Reductive debromination of precursor 5 was accomplished using 3H2, Pd/C and triethylamine in DMF at ambient temperature to give target molecule [3H]-1 with a specific activity of 19.3 Ci mmol-1 and a radiochemical purity of ≥95%. By application of autoradiography and binding studies, it was not possible to discriminate [3H]-1 binding to wildtype mice brains from GPR139 knockout mice brains and total binding from non-specific binding in CHO-k1 cells stably expressing human GPR139 receptor. Based on these experiments we conclude that [3H]-1 is not a suitable radioligand for the characterisation of GPR139.

Structure activity relationship of brevenal hydrazide derivatives

Brevenal is a ladder frame polyether produced by the dinoflagellate Karenia brevis. This organism is also responsible for the production of the neurotoxic compounds known as brevetoxins. Ingestion or inhalation of the brevetoxins leads to adverse effects such as gastrointestinal maladies and bronchoconstriction. Brevenal shows antagonistic behavior to the brevetoxins and shows beneficial attributes when administered alone. For example, in an asthmatic sheep model, brevenal has been shown to increase tracheal mucosal velocity, an attribute which has led to its development as a potential treatment for Cystic Fibrosis. The mechanism of action of brevenal is poorly understood and the exact binding site has not been elucidated. In an attempt to further understand the mechanism of action of brevenal and potentially develop a second generation drug candidate, a series of brevenal derivatives were prepared through modification of the aldehyde moiety. These derivatives include aliphatic, aromatic and heteroaromatic hydrazide derivatives. The brevenal derivatives were tested using in vitro synaptosome binding assays to determine the ability of the compounds to displace brevetoxin and brevenal from their native receptors. A sheep inhalation model was used to determine if instillation of the brevenal derivatives resulted in bronchoconstriction. Only small modifications were tolerated, with larger moieties leading to loss of affinity for the brevenal receptor and bronchoconstriction in the sheep model.

Synthesis, characterization and antimicrobial activities of mercaptoxadiazoles, mercaptotriazoles and their derivatives

Five member heterocycles are famous for their universal activities. Starting with suitably substituted hydrazides 1,3,4-oxadiazole-2-thiones (1-5) and 1,2,4-triazolethionamines (6-11) were synthesized which were later on converted into Mannich products (13-22) and traizolothiadiazines (23-28) respectively. Structures were established by FTIR, hydrogen, carbon NMR, and mass spectrometric analysis. Compounds were evaluated for their antimicrobial studies. Compounds 13, 19 and 23 showed maximum inhibitions in opposition to the bacterial strains while compounds 7, 11, 13 and 27 showed utmost percentage inhibition aligned with the yeast cells.

Synthesis, antibacterial and anticancer evaluation of 5-substituted (1,3,4-oxadiazol-2-yl)quinoline

2-Chloroquinoline-3-carbaldehyde (2) was synthesized via Vilsmeier-Haack method using acetanilide. Phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1H-benzimidazol-1-yl)acetohydrazide (7a-c) were synthesized using 2-[2-(phenoxy/naphthalen-1-yl/naphthalen-2-yloxy methyl)-1H-benzimidazol-1-yl]acetohydrazide (6a-c). The title compounds 2-chloro-3-{5-[(2-phenoxy/naphthalene-1-yl/naphthalen-2-yloxy methyl-1-H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-yl}quinolone (8a-c) were prepared using chloramine-T. In the second series, (2-chloroquinolin-3-yl)methylidene]-substituted benzohydrazide (11a-i) were prepared by the reaction of 2-chloroquinoline-3-carbaldehyde (2) and an acid hydrazide (10a-i). The synthesized compounds were characterized by IR, NMR, Mass spectrometry, elemental analysis and screened for their antibacterial (serial dilution technique and disc diffusion method) and anticancer activity by NCI 60 cell screen at a single high dose (10-5 M) on various panel/cell lines. The synthesized compounds (8a, 8c, 12a, 12b, 12c and 12h) were acting as a magic bullet against gram-positive strains of Bacillus cereus MTCC1305, and the compounds (12a, 12c and 12h) were also found to be extremely active against Klebsiella pneumonia NCTC7447. In the in vitro screen on tested cancer cell line, the compound (12d) showed 95.70 growth percent (GP) and highly active on SNB-75 (CNS cancer) and UO-31 (renal cancer) (GP = 53.35 and 64.35, respectively), and the compound (8a) showed 96.86 GP and highly active on SNB-75 (CNS cancer GP 51.27).