42466-50-2

Usage

Uses

Used in Organic Synthesis:
Thiophene-3-carboxaldoxime is utilized as a building block in the production of a wide array of compounds across various fields, including pharmaceuticals, agrochemicals, and materials. Its structural properties allow it to participate in diverse chemical reactions such as rearrangement, substitution, and addition reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Medicinal Chemistry and Drug Discovery:
Due to its potential biological activities, Thiophene-3-carboxaldoxime is studied for its antimicrobial and anticancer properties. In the realm of medicinal chemistry, it serves as a promising candidate for the development of new drugs, particularly those targeting infectious diseases and cancer.
Used in Pharmaceutical Industry:
Within the pharmaceutical sector, Thiophene-3-carboxaldoxime is employed as a key intermediate in the synthesis of therapeutic agents. Its ability to engage in multiple types of chemical reactions facilitates the creation of novel pharmaceutical compounds with potential applications in treating a range of health conditions.
Used in Agrochemical Industry:
In agrochemical applications, Thiophene-3-carboxaldoxime is leveraged as a precursor for the development of pesticides and other agricultural chemicals. Its chemical versatility aids in the design of effective compounds aimed at enhancing crop protection and productivity.
Used in Materials Science:
Thiophene-3-carboxaldoxime contributes to the advancement of materials science by serving as a component in the synthesis of new materials with unique properties. Its incorporation into material formulations can lead to the development of innovative products with applications in various industries.

InChI:InChI=1/C5H5NOS/c7-6-3-5-1-2-8-4-5/h1-4,7H/b6-3+

Upstream product

• 498-62-4 3-thiophene carboxaldehyde 
• 3199-44-8 3-formylthiophene diethyl acetal 

Downstream Products

• 51460-47-0 3-carbamoylthiophene 
• 51305-57-8 4-methyl-N-(thiophen-3-ylmethyl)aniline 
• 27757-86-4 (3-thienylmethyl)amine 

Relevant academic research and scientific papers

Discovery of a novel isoxazoline derivative of prednisolone endowed with a robust anti-inflammatory profile and suitable for topical pulmonary administration

A novel glucocorticoids series of (GCs), 6α,9α-di-Fluoro 3-substituted C-16,17-isoxazolines was designed, synthesised and their structure-activity relationship was evaluated with glucocorticoid receptor (GR) binding studies together with GR nuclear translocation cell-based assays. This strategy, coupled with in silico modelling analysis, allowed for the identification of Cpd #15, an isoxazoline showing a sub-nanomolar inhibitory potency (IC50 = 0.84 nM) against TNFα-evoked IL-8 release in primary human airways smooth muscle cells. In Raw264.7 mouse macrophages, Cpd #15 inhibited LPS-induced NO release with a potency (IC50 = 6 nM) > 10-fold higher with respect to Dexamethasone. Upon intratracheal (i.t.) administration, Cpd #15, at 0.1 μmol/kg significantly inhibited and at 1 μmol/kg fully counteracted eosinophilic infiltration in a model of allergen-induced pulmonary inflammation in rats. Moreover, Cpd #15 proved to be suitable for pulmonary topical administration given its sustained lung retention (t1/2 = 6.5 h) and high pulmonary levels (>100-fold higher than plasma levels) upon intratracheal administration in rats. In summary, Cpd #15 displays a pharmacokinetic and pharmacodynamic profile suitable for topical treatment of conditions associated with pulmonary inflammation such as asthma and COPD.

Synthesis, crystal structure, and characterization of thiophene-3- carboxaldoxime complexes with cobalt(II), nickel(II) and copper(II) halides

The reaction of cobalt(II), nickel(II), copper(II) chlorides and bromides with thiophene-3-carboxaldoxime (3TCOH) leads to a series of new complexes: [CoCl2(3TCOH)4], [CoBr2(3TCOH)4], [NiCl2(3TCOH)4], [NiBr2(3TCOH)4], [CuCl2(3TCOH)4], [CuBr2(3TCOH)2] respectively. The crystal structures of [CoBr2(3TCOH)4], [NiBr2(3TCOH)4] have been determined by X-ray diffraction methods showing octahedral complex species. In all complexes, the oxime functional group remains protonated and the coordination occurs through the nitrogen atom of the oxime moiety.

Novel selective ido1 inhibitors with isoxazolo[5,4-d]pyrimidin-4(5h)-one scaffold

Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising target in immunomodulation of several pathological conditions, especially cancers. Here we present the synthesis of a series of IDO1 inhibitors with the novel isoxazolo[5,4-d]pyrimidin-4(5H)-one scaffold. A focused library was prepared using a 6-or 7-step synthetic procedure to allow a systematic investigation of the structure-activity relationships of the described scaffold. Chemistry-driven modifications lead us to the discovery of our best-in-class inhibitors possessing p-trifluoromethyl (23), p-cyclohexyl (32), or p-methoxycarbonyl (20, 39) substituted aniline moieties with IC50 values in the low micromolar range. In addition to hIDO1, compounds were tested for their inhibition of indoleamine 2,3-dioxygenase 2 and tryptophan dioxygenase, and found to be selective for hIDO1. Our results thus demon-strate a successful study on IDO1-selective isoxazolo[5,4-d]pyrimidin-4(5H)-one inhibitors, defining promising chemical probes with a novel scaffold for further development of potent small-molecule immunomodulators.

Synthesis, Identification, and Structure-Activity Relationship Analysis of GATA4 and NKX2-5 Protein-Protein Interaction Modulators

Transcription factors GATA4 and NKX2-5 directly interact and synergistically activate several cardiac genes and stretch-induced cardiomyocyte hypertrophy. Previously, we identified phenylisoxazole carboxamide 1 as a hit compound, which inhibited the GATA4-NKX2-5 transcriptional synergy. Here, the chemical space around the molecular structure of 1 was explored by synthesizing and characterizing 220 derivatives and structurally related compounds. In addition to the synergistic transcriptional activation, selected compounds were evaluated for their effects on transcriptional activities of GATA4 and NKX2-5 individually as well as potential cytotoxicity. The structure-activity relationship (SAR) analysis revealed that the aromatic isoxazole substituent in the southern part regulates the inhibition of GATA4-NKX2-5 transcriptional synergy. Moreover, inhibition of GATA4 transcriptional activity correlated with the reduced cell viability. In summary, comprehensive SAR analysis accompanied by data analysis successfully identified potent and selective inhibitors of GATA4-NKX2-5 transcriptional synergy and revealed structural features important for it.

ISOXAZOLE-AMIDES FOR TREATING CARDIAC DISEASES

The present invention concerns compounds of Formula 1a and its uses as a drug, particularly in treatment of cardiac diseases, and in methods and products relating to cell differentiation.

Metal- and Base-Free Room-Temperature Amination of Organoboronic Acids with N-Alkyl Hydroxylamines

We have found that readily available N-alkyl hydroxylamines are effective reagents for the amination of organoboronic acids in the presence of trichloroacetonitrile. This amination reaction proceeds rapidly at room temperature and in the absence of added metal or base, it tolerates a remarkable range of functional groups, and it can be used in the late-stage assembly of two complex units.

Systematic structure-activity relationship (SAR) exploration of diarylmethane backbone and discovery of a highly potent novel uric acid transporter 1 (URAT1) inhibitor

In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a-1x and 1ha-1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly potent novel URAT1 inhibitor, 1h, which was 200-and 8-fold more potent than parent lesinurad and benzbromarone, respectively (IC50 = 0.035 μM against human URAT1 for 1h vs. 7.18 μM and 0.28 μM for lesinurad and benzbromarone, respectively). Compound 1h is the most potent URAT1 inhibitor discovered in our laboratories so far and also comparable to the most potent ones currently under development in clinical trials. The present study demonstrates that the diarylmethane backbone represents a very promising molecular scaffold for the design of potent URAT1 inhibitors.

Alkyl Nitrites: Novel Reagents for One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Aldoximes and Alkynes

An efficient, one-pot approach has been described for the synthesis of 3,5-disubstituted isoxazoles from substituted aldoximes (mixture of E and Z) and alkynes, using alkyl nitrites under conventional heating conditions. The key nitrile oxide intermediates that are required for the synthesis of isoxazoles are formed by treatment of substituted aldoxime with either tert-butyl nitrite or isoamyl nitrite. The generated nitrile oxides underwent in situ [3+2] dipolar cycloaddition to the substituted alkynes to give 3,5-disubstituted isoxazoles regioselectively in high to excellent yields. The developed synthetic methodology was applied for the synthesis of a previously reported potent hDGAT1 inhibitor.

Five-membered azole heterocyclic compound and its preparation method, pharmaceutical composition and use thereof

The present invention relates to a five-membered azole heterocycle compound represented by the following general formula (I), a preparation method of the five-membered azole heterocycle compound, a drug composition of the five-membered azole heterocycle compound, and a use of the five-membered azole heterocycle compound in preparation of drugs for prevention or treatment of TGR5-mediated diseases. The formula (I) is represented by the instruction.

APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT

PROBLEM TO BE SOLVED: To prepare analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. SOLUTION: The present invention relates to an N6-substituted adenosine derivative and an N6-substituted adenine derivative selected from the group consisting of specific compounds. The present invention also relates to a pharmaceutical composition at least comprising a therapeutically effective amount of the compounds and a pharmaceutically acceptable carrier. The invention further relates to the compounds used in preparation of analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. COPYRIGHT: (C)2016,JPO&INPIT