29683-84-9

Usage

Uses

Used in Organic Synthesis:
Thiophene-2-carboxaldoxime is used as a building block for the synthesis of complex organic molecules, leveraging its ability to participate in various chemical reactions and form a wide range of molecular structures.
Used in Pharmaceutical Development:
As a precursor in the development of new drugs, Thiophene-2-carboxaldoxime contributes to the creation of novel pharmaceutical compounds, capitalizing on its chemical properties and reactivity.
Used in Coordination Chemistry and Material Development:
Thiophene-2-carboxaldoxime is utilized in the development of new materials and catalysts due to its capacity to chelate metal ions, showcasing its importance in coordination chemistry.
Used in Catalyst Development:
THIOPHENE-2-CARBOXALDOXIME's ability to form chelates with metal ions makes it a candidate for use in the development of catalysts, which are essential in various chemical processes and reactions.

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

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 27757-85-3 2-Aminomethylthiophene 
• 554-14-3 2-Methylthiophene 

Downstream Products

• 98-03-3 thiophene-2-carbaldehyde 
• 1003-31-2 thiophene-2-carbonitrile 
• 5813-89-8 2-thiophenylcarboxamide 
• 67-68-5 dimethyl sulfoxide 
• 10354-43-5 thiophene-2-carboxylic acid benzylamide 
• 527-72-0 2-thiophenylcarboxylic acid 
• 21985-10-4 5-phenyl-3-(thiophen-2-yl)isoxazole 
• 34243-33-9 2-thiophen-2-yl-quinoline 
• 204910-49-6 3-(thiophen-2-yl)-1,2-oxazole-5-carboxylic acid 
• 695224-56-7 5-phenyl-3-(2-thienyl)-1,2,4-oxadiazole 

Relevant academic research and scientific papers

Isoxazole derivatives as new nitric oxide elicitors in plants

Several 3,5-disubstituted isoxazoles were obtained in good yields by regiospecific 1,3-dipolar cycloaddition reactions between aromatic nitrile oxides, generated in situ from the corresponding hydroxyimidoyl chlorides, with non-symmetrical activated alkyn

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.

AN IMPROVED PROCESS FOR PREPARATION OF PURE ALDOXIME

The present invention relates to an improved process for preparing aldoximes of formula (I) with high purity and high yield. The improved process for preparing aldoxime is fast, simple, highly efficient, and reproducible. The improved process for the preparation of aldoxime, which is synthesized in the higher yield under oximation reaction of aldehyde with hydroxylamine hydrochloride merely in aqueous medium using of in situ heat generation.

Synthesis and SAR study of simple aryl oximes and nitrofuranyl derivatives with potent activity against Mycobacterium tuberculosis

Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight nitrofuranyl compounds, 2-nitrofuranyl-X, II. Results: Among the oximes, I: Ar = 2-OH-4-OH, 42, and I: Ar = 5-nitrofuranyl, 46, possessed the best activity at 3.74 and 32.0 μM, respectively. Also, 46, the nitrofuran compounds, II; X = MeO, 55, and II: X = NHCH2Ph, 58, (14.6 and 12.6 μM, respectively), exhibited excellent biological activities and were non-cytotoxic. Conclusion: The compound 55 showed a selectivity index of 9.85. Further antibacterial tests were performed with compound 55 which was inactive against Enterococcus faecalis, Klebisiella pneumonae, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhymurium and Shigel-la flexneri. This study adds important information to the rational design of new lead anti-TB drugs. Structure-activity Relationship (SAR) is reported.

1,3-Dipolar Cycloaddition, HPLC Enantioseparation, and Docking Studies of Saccharin/Isoxazole and Saccharin/Isoxazoline Derivatives as Selective Carbonic Anhydrase IX and XII Inhibitors

Two series of saccharin/isoxazole and saccharin/isoxazoline hybrids were synthesized by 1,3-dipolar cycloaddition. The new compounds showed to be endowed with potent and selective inhibitory activity against the cancer-related human carbonic anhydrase (hCA) IX and XII isoforms in the nanomolar range, while no affinity was encountered for off-targets, such as hCA I and II. Successive enantioseparation on a milligram scale of the most representative compounds led to the discovery that (S)-isomers were more potent than their corresponding (R)-enantiomers. Lastly, molecular modeling studies were conducted to define those structural requirements that were responsible for the discrimination among selected human isoforms of carbonic anhydrases. Two nanomolar hCA IX and XII inhibitors were also screened for their selective toxicity against non tumoral primary cells (fibroblasts) and against a breast adenocarcinoma cell line (MCF7) in hypoxic environment. The efficacious combination of these compounds with doxorubicin on MCF7 cells was demonstrated after 72 h of treatment.

Potassium Poly(Heptazine Imide): Transition Metal-Free Solid-State Triplet Sensitizer in Cascade Energy Transfer and [3+2]-cycloadditions

Polymeric carbon nitride materials have been used in numerous light-to-energy conversion applications ranging from photocatalysis to optoelectronics. For a new application and modelling, we first refined the crystal structure of potassium poly(heptazine imide) (K-PHI)—a benchmark carbon nitride material in photocatalysis—by means of X-ray powder diffraction and transmission electron microscopy. Using the crystal structure of K-PHI, periodic DFT calculations were performed to calculate the density-of-states (DOS) and localize intra band states (IBS). IBS were found to be responsible for the enhanced K-PHI absorption in the near IR region, to serve as electron traps, and to be useful in energy transfer reactions. Once excited with visible light, carbon nitrides, in addition to the direct recombination, can also undergo singlet–triplet intersystem crossing. We utilized the K-PHI centered triplet excited states to trigger a cascade of energy transfer reactions and, in turn, to sensitize, for example, singlet oxygen (1O2) as a starting point to synthesis up to 25 different N-rich heterocycles.

Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles

Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

SO 2 F 2 -Promoted Dehydration of Aldoximes: A Rapid and Simple Access to Nitriles

A rapid, simple and mild process for the dehydration of aldoximes to give the corresponding nitriles, which utilizes SO 2 F 2 as an efficient reagent, has been developed. A variety of (hetero)arene, alkene, alkyne and aliphatic aldoximes proceeded with high efficiency to afford nitriles in excellent to quantitative yields with great functional group compatibilities in acetonitrile under ambient conditions. Furthermore, an eco-friendly synthetic protocol to access nitriles from aldehydes with ortho -, meta - and para -nitrile groups was also described in aqueous methanol by using inorganic base Na 2 CO 3, and a one-pot synthetic strategy to generate nitriles from aldehydes was proved to be feasible.

7-Oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-Dioxides: Mechanochemical Synthesis by Tandem Michael Addition–1,3-Dipolar Cycloaddition of Aldoximes and Evaluation of Antibacterial Activities

A solvent-free, green, and efficient mechanochemical method for the synthesis of a series of bridged bicyclo aza-sulfone derivatives, namely 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxides through tandem Michael addition–1,3-dipolar cycloaddition of aldoximes was developed. Mechanochemical grinding/milling facilitates quick formation of aldoximes from corresponding aldehydes and hydroxylamine, which upon reaction with divinyl sulfone in a mixer mill affords 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxide derivatives in good overall yields. The newly synthesized bicyclo aza-sulfone derivatives 4 were screened for antibacterial activities. Mostly bicyclo aza-sulfones derived from electron-rich aromatic aldehydes inhibit the growth of Mycobacterium smegmatis (mc2155) and those from aliphatic aldehydes the growth of Escherichia coli (DH5α) in moderate to good effect. However, butyraldehyde-derived compound 4r was very effective against both M. smegmatis and E. coli. The key advantages of this mechanochemical method are catalyst- and solvent-free conditions, shorter reaction time, and formation of a new series of 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxide derivatives, which are good antibacterial agents against M. smegmatis and E. coli.