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Usage

Uses

Used in Pharmaceutical Research:
N'-HYDROXY-2-METHOXYBENZENECARBOXIMIDAMIDE is used as a substrate for inhibiting aldose reductase, an enzyme involved in the development of diabetic complications. Its role in this process is crucial for managing and potentially preventing the progression of diabetes-related issues.
Used in Cancer Treatment Research:
In the field of oncology, N'-HYDROXY-2-METHOXYBENZENECARBOXIMIDAMIDE is studied for its potential as an anticancer agent, exhibiting inhibitory effects on the growth of cancer cells. This property makes it a valuable compound in the search for novel therapeutic approaches to combat cancer.
Used in Organic Synthesis:
N'-HYDROXY-2-METHOXYBENZENECARBOXIMIDAMIDE is utilized in the synthesis of various organic compounds, contributing to the development of new chemical entities that may have applications in different industries, including pharmaceuticals, materials science, and agrochemicals.
Used in Antioxidant Research:
N'-HYDROXY-2-METHOXYBENZENECARBOXIMIDAMIDE has been investigated for its antioxidant properties, which could be beneficial in various health and industrial applications where oxidative stress is a concern, such as in the prevention of cellular damage and the development of new preservative technologies.

Upstream product

• 64-17-5 ethanol 
• 6609-56-9 2-methoxy-benzonitrile 
• 71590-96-0 2-hydroxy-6-methoxybenzonitrile 

Downstream Products

• 75907-92-5 O-(4,4-Dinitropentanoyl)-2-methoxybenzamidoxime 
• 844498-72-2 C₁₀H₁₁ClN₂O₃ 
• 138129-01-8 {3-[3-(2-Methoxy-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid ethyl ester 
• 110722-46-8 {3-[3-(2-Methoxy-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid 
• 110704-43-3 5-Chloromethyl-3-(2-methoxy-phenyl)-[1,2,4]oxadiazole 
• 1597516-82-9 {(S)-2-[3-(2-methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]pyrrolidin-1-yl}-(5-methyl-2-[1,2,3]triazol-2-yl-phenyl)methanone 

Relevant academic research and scientific papers

Synthesis and evaluation of new 1,2,4-oxadiazole based trans- acrylic acid derivatives as potential PPAR-alpha/gamma dual agonist

Diabetes is a ubiquitously a metabolic disorder and life-threatening disease. Peroxisome proliferator-activated receptors (PPARs) belong to the class of nuclear receptors which acts as transcription factors to regulate lipid and glucose metabolism. PPAR alpha/gamma dual agonists tend to corroborate the functions of both thiazolidinediones and fibrates and they hold substantial promise for ameliorating the type 2 diabetic treatments and providing potential therapeutic diabetic interventions. New 1,2,4-oxadiazole based trans- acrylic acid derivatives compounds possessing aryl/methylene linker in between pharmacophore head and lipophilic tail for dual PPAR-alpha/gamma agonists are studied. AutoDock Vina used for potential PPAR alpha/gamma dual agonists and 6 compounds 9a, 9g, 9 m, 9n, 9o, and 9r were identified comparable to PPAR gamma agonist Pioglitazone on the basis of their affinity scores and further their in-silico toxicity and in-silico ADME properties. The selected compounds showed better-calculated lipophilicity (iLogP) was found to be 0.92 to 3.19. Compound 9n and 9a were found to be most potent on both PPAR alpha and gamma receptors with EC50 of 0.07 ± 0.0006 μM, 0.06 ± 0.0005 μM and 0.781 ± 0.008 μM, 3.29 μM ± 0.03 respectively as better to pioglitazone having EC50 of 32.38 ± 0.2 and 38.03 ± 0.13 for both receptors. The in-vivo evaluation found to reduce the plasma glucose level and total cholesterol level significantly in diabetic rats compared to pioglitazone at 5 mg/kg/day dose for 7 days of treatment. Thus, trans- acrylic acid derivatives can be further developed as oral therapeutic agents for diabetic interventions as PPAR alpha/gamma dual agonists.

Continued exploration of 1,2,4-oxadiazole periphery for carbonic anhydrase-targeting primary arene sulfonamides: Discovery of subnanomolar inhibitors of membrane-bound hCA IX isoform that selectively kill cancer cells in hypoxic environment

An expanded set of diversely substituted 1,2,4-oxadiazole-containing primary aromatic sulfonamides was synthesized and tested for inhibition of human carbonic anhydrase I, II, IX and XII isoforms. The initial biochemical profiling revealed a significantly

Oxadiazole Derivatives as Dual Orexin Receptor Antagonists: Synthesis, Structure–Activity Relationships, and Sleep-Promoting Properties in Rats

The orexin system plays an important role in the regulation of wakefulness. Suvorexant, a dual orexin receptor antagonist (DORA) is approved for the treatment of primary insomnia. Herein, we outline our optimization efforts toward a novel DORA. We started our investigation with rac-[3-(5-chloro-benzooxazol-2-ylamino)piperidin-1-yl]-(5-methyl-2-[1,2,3]triazol-2-ylphenyl)methanone (3), a structural hybrid of suvorexant and a piperidine-containing DORA. During the optimization, we resolved liabilities such as chemical instability, CYP3A4 inhibition, and low brain penetration potential. Furthermore, structural modification of the piperidine scaffold was essential to improve potency at the orexin 2 receptor. This work led to the identification of (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-{(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl}methanone (51), a potent, brain-penetrating DORA with in vivo efficacy similar to that of suvorexant in rats.

COMPOUNDS AND USES THEREOF

The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

AZETIDINE AMIDE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS

The present invention relates to azetidine amide derivatives derivatives of formula (I) wherein rings A1 A2 and A3 are as described in the description, to pharmaceutically acceptable salts thereof, to their preparation, to

An experimental and theoretical study of reaction mechanisms between nitriles and hydroxylamine

The industrially relevant reaction between nitriles and hydroxylamine yielding amidoximes was studied in different molecular solvents and in ionic liquids. In industry, this procedure is carried out on the ton scale in alcohol solutions and the above transformation produces a significant amount of unexpected amide by-product, depending on the nature of the nitrile, which can cause further analytical and purification issues. Although there were earlier attempts to propose mechanisms for this transformation, the real reaction pathway is still under discussion. A new detailed reaction mechanistic explanation, based on theoretical and experimental proof, is given to augment the former mechanisms, which allowed us to find a more efficient, side-product free procedure. Interpreting the theoretical results obtained, it was shown that the application of specific imidazolium, phosphonium and quaternary ammonium based ionic liquids could decrease simultaneously the reaction time while eliminating the amide side-product, leading to the targeted product selectively. This robust and economic procedure now affords a fast, selective amide free synthesis of amidoximes.

Benzohydroxamic acids as potent and selective anti-HCV agents

A diverse collection of 40 derivatives of benzohydroxamic acid (BHAs) of various structural groups were synthesized and tested against hepatitis C virus (HCV) in full-genome replicon assay. Some of these compounds demonstrated an exceptional activity, suppressing viral replication at sub-micromolar concentrations. The compounds were inactive against key viral enzymes NS3, and NS5B in vitro assays, suggesting host cell inhibition target(s). The testing results were consistent with metal coordination by the BHAs hydroxamic group in complex with a target(s). Remarkably, this class of compounds did not suppress poliomyelitis virus (PV) propagation in RD cells indicating a specific antiviral activity of BHAs against HCV.

COMPOUNDS HAVING AN ETHR INHIBITING ACTIVITY - USE OF SAID COMPOUNDS AS DRUGS - PHARMACEUTICAL COMPOSITION AND PRODUCT CONTAINING SAID COMPOUNDS

The present invention relates to compounds of Formula (I), wherein R1 is chosen among the following radicals : (II); (III); (IV), (V), (VI) (VII) and n= 1 or 2 and m=1 or 2 with the proviso that m=2 when R1 is (VIII). The present invention also relates to the use thereof as drugs, more particularly in the treatment of mycobacterial infections and more particularly in the treatment of tuberculosis.

Ethionamide boosters. 2. Combining bioisosteric replacement and structure-based drug design to solve pharmacokinetic issues in a series of potent 1,2,4-oxadiazole EthR inhibitors

Mycobacterial transcriptional repressor EthR controls the expression of EthA, the bacterial monooxygenase activating ethionamide, and is thus largely responsible for the low sensitivity of the human pathogen Mycobacterium tuberculosis to this antibiotic.

Formation of aromatic amidoximes with hydroxylamine using microreactor technology

In this contribution, the application of microreactor technology for amidoxime formation is demonstrated, with different aromatic nitriles reacted with a 50% solution of hydroxylamine (HA) under homogeneous conditions to reach full conversion. All reactio