November 2022 | Page 3 of 14 | Heterocyclic Building Blocks-Benzoxazole

Li, Jun-Yi’s team published research in ACS Catalysis in 2022-08-05 | CAS: 145026-07-9

Ir(III)-Catalyzed Asymmetric C-H Activation/Annulation of Sulfoximines Assisted by the Hydrogen-Bonding Interaction. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

1-Bromo-4-(S-methylsulfonimidoyl)benzene (BD336512) is a building block containing a sulfoximine group. Several CDK and ATR inhibitors have exemplified the utilization of the NH sulfoximine group as abioisostere for a sulfonamide group to overcome the main project hurdles of aqueous solubility, sulfonamide-mediated off-target activity and IP. Moreover, its NH group could be expediently further functionalized through Buchwald-Hartwig coupling reaction and multifarious nucleophilic reactions.. Recommended Products is: 4381-25-3 and 83730-53-4.

Herein, an Ir(III)-catalyzed asym. C-H activation enabled by noncovalent interactions was described. A broad range of sulfur-stereogenic sulfoximines, e.g., I was prepared in high yields with excellent enantioselectivities via the asym. C-H activation/annulation of sulfoximines with diazo compounds Desymmetrization, kinetic resolution, and parallel kinetic resolution were compatible with this protocol. Detailed DFT calculations suggested that the N-H¡¤¡¤¡¤O hydrogen bonding interaction between sulfoximine and the chiral carboxylic acid ligand was crucial for the high enantiocontrol. Moreover, chiral iridacycle intermediates were isolated, characterized, and subjected to stoichiometric reactions. Computational and exptl. studies suggested that the C-H cleavage step was the rate- and enantio-determining step.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yu, Hao’s team published research in Angewandte Chemie, International Edition in 2018-01-01 | CAS: 50578-18-2

Iron(II)-Catalyzed Direct Synthesis of NH Sulfoximines from Sulfoxides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

1-Iminotetrahydrothiophene 1-oxide (BD00963737) is a building block containing a sulfoximine group. Several CDK and ATR inhibitors have exemplified the utilization of the NH sulfoximine group as abioisostere for a sulfonamide group to overcome the main project hurdles of aqueous solubility, sulfonamide-mediated off-target activity and IP. Moreover, its NH group could be expediently further functionalized through Buchwald-Hartwig coupling reaction and multifarious nucleophilic reactions.. Recommended Products is: 4381-25-3 and 83730-53-4.

Free NH-sulfoximines were directly prepared from sulfoxides through iron catalysis by applying a readily available, shelf-stable hydroxylamine triflic acid salt. No addnl. oxidant is needed, and the substrate scope is broad, including a range of heterocyclic compounds Thus, e.g., imidation of PhS(:O)Me with O-(4-nitrobenzoyl)hydroxylamine.HOTF in presence of FeSO4 and 1,10-phenanthroline afforded PhS(:O)(:NH)Me (98%, 93% isolated).

Iron(II)-Catalyzed Direct Synthesis of NH Sulfoximines from Sulfoxides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Ramazani, Yasaman’s team published research in PLoS One in 2021 | CAS: 83730-53-4

Therapeutic concentrations of calcineurin inhibitors do not deregulate glutathione redox balance in human renal proximal tubule cells. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

(2S)-2-Amino-4-(butylsulfonimidoyl)butanoic acid (BD136012) is a building block containing a sulfoximine group. Several CDK and ATR inhibitors have exemplified the utilization of the NH sulfoximine group as abioisostere for a sulfonamide group to overcome the main project hurdles of aqueous solubility, sulfonamide-mediated off-target activity and IP. Moreover, its NH group could be expediently further functionalized through Buchwald-Hartwig coupling reaction and multifarious nucleophilic reactions.. Recommended Products is: 4381-25-3 and 1621962-30-8.

The calcineurin inhibitors (CNI) cyclosporine A and tacrolimus comprise the basis of immunosuppressive regimes in all solid organ transplantation. However, long-term or high exposure to CNI leads to histol. and functional renal damage (CNI-associated nephrotoxicity). In the kidney, proximal tubule cells are the only cells that metabolize CNI and these cells are believed to play a central role in the origin of the toxicity for this class of drugs, although the underlying mechanisms are not clear. Several studies have reported oxidative stress as an important mediator of CNI-associated nephrotoxicity in response to CNI exposure in different available proximal tubule cell models. However, former models often made use of supra-therapeutic levels of tissue drug exposure. In addition, they were not shown to express the relevant enzymes (e.g., CYP3A5) and transporters (e.g., P-glycoprotein) for the metabolism of CNI in human proximal tubule cells. Moreover, the used methods for detecting ROS were potentially prone to false pos. results. In this study, we used a novel proximal tubule cell model established from human allograft biopsies that demonstrated functional expression of relevant enzymes and transporters for the disposition of CNI. We exposed these cells to CNI concentrations as found in tissue of stable solid organ transplant recipients with therapeutic blood concentrations We measured the glutathione redox balance in this cell model by using organelle-targeted variants of roGFP2, a highly sensitive green fluorescent reporter protein that dynamically equilibrates with the glutathione redox couple through the action of endogenous glutaredoxins. Our findings provide evidence that CNI, at concentrations commonly found in allograft biopsies, do not alter the glutathione redox balance in mitochondria, peroxisomes, and the cytosol. However, at supra-therapeutic concentrations, cyclosporine A but not tacrolimus increases the ratio of oxidized/reduced glutathione in the mitochondria, suggestive of imbalances in the redox environment.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Davari, Mahdi’s team published research in Archives of Microbiology in 2022-08-31 | CAS: 483-76-1

Mycelial inhibitory effects of antagonistic fungi, plant essential oils and propolis against five phytopathogenic Fusarium species. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

1. Trivial name: delta-Cadinene.
2. It’s mainly derived from flue-cured tobacco, burley tobacco and flavoured tobacco, it has a strong aroma and a good fixing effect, suitable for perfume, cosmetics, can also be used in wine, cigarettes, and toothpaste.
. Recommended Products is: 29350-73-0 and 51905-84-1.

Fusarium spp. are considered as one of the most devastating plant pathogenic fungi worldwide. In this study, the effect of essential oil (EO) of Mentha longifolia, M. spicata, Achillea sp. and Foeniculum vulgare, ethanolic extract of Propolis (EEP), and Trichoderma harzianum T447 and T. hamatum T622 was investigated against five phytopathogenic Fusarium species. The results showed that the fungal species, the type of EO, and concentrations play a substantial role in inhibiting the mycelial growth of Fusarium spp. GC-MS anal. of the EOs showed that the piperitone oxide and cis-piperitone oxide were found as the main components of M. longifolia. Our results also revealed that EEP possessed the growth inhibitory effect against Fusarium spp. It was observed that the extracellular secretions of T. harzianum T447 showed very high inhibition against the fungi. Our results highlighted the need for further research to apply them as a safe alternative to the chem. pesticides.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Priebbenow, Daniel L.’s team published research in Organic Letters in 2013-12-20 | CAS: 145026-07-9

Copper-Catalyzed Oxidative Decarboxylative Couplings of Sulfoximines and Aryl Propiolic Acids. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A method has been developed for the preparation of N-alkynylated sulfoximines e. g., I involving the copper-catalyzed decarboxylative coupling of sulfoximines with aryl propiolic acids. A range of substituents on both the sulfoximidoyl moiety and the aryl group of the propiolic acid were compatible with this reaction process to afford a series of sulfoximidoyl-functionalized alkynes.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Choi, Wonseok’s team published research in Organic Letters in 2015-07-02 | CAS: 145026-07-9

Synthesis of N-Imidoyl and N-Oxoimidoyl Sulfoximines from 1-Alkynes, N-Sulfonyl Azides, and Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

N-Imidoylation of sulfoximines is developed from a Cu-catalyzed three-component reaction from 1-alkynes, N-sulfonyl azides, and sulfoximines in THF at room temperature under air. In addition, N-oxoimidoylation of sulfoximines is accessed from a Cu-catalyzed three-component reaction from 1-alkynes, N-sulfonyl azides, and sulfoximines in THF at room temperature followed by a Cu-catalyzed oxidative reaction at 50 ¡ãC under air, producing N-oxoimidoyl sulfoximines.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Bao’s team published research in Molecules in 2020 | CAS: 145026-07-9

Sulfoximines-assisted Rh(III)-catalyzed C-H activation and intramolecular annulation for the synthesis of fused isochromeno-1,2-benzothiazines scaffolds under room temperature. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A mild and facile Cp*Rh(III)-catalyzed C-H activation and intramol. cascade annulation protocol has been proposed for the furnishing of highly fused isochromeno-1,2-benzothiazines I (R1 = H, 2-Me, 2-F, 4-Br, 3-OMe, (CH2)4, etc.; R2 = Me, Et, Ph, Bn, etc.; R3 = H, 10-Me,10-OMe, 11-Cl, 11-F, etc.) scaffolds using S-phenylsulfoximides R4C6H4S(O)(=NH)(R2) and 4-diazoisochroman-3-imine II (R5 = H, 7-Me, 6-OMe, 7-OMe, 6-Cl, etc.) as substrates under room temperature This method features diverse substituents and functional groups tolerance and relatively mild reaction conditions with moderate to excellent yields. Addnl., retentive configuration of sulfoximides in the conversion has been verified.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Luan, Nannan’s team published research in Tetrahedron Letters in 2020-01-02 | CAS: 50578-18-2

PhI(OAc)2-mediated oxidative C-H sulfoximination of imidazopyridines under mild conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

A facile protocol for direct oxidative C-N bond coupling of unactivated imidazo[1,2-a]pyridines with NH-sulfoximines was disclosed using sulfoximines as the nitrogen sources in the presence of (diacetoxy)iodobenzene (PhI(OAc)2). The reaction proceeded smoothly under air without any metal catalyst to give a series of C-3 sulfoximidoyl-functionalized imidazo[1,2-a]pyridines products regioselectively.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Tavallali, Vahid’s team published research in Scientia Horticulturae (Amsterdam, Netherlands) in 2022-09-20 | CAS: 483-76-1

Modifications in Lemongrass (Cymbopogon spp.) in response to green synthesized nano-selenium complex. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Selenium nanoparticles (Se-NPs) have different applications in various technologies due to their individual properties. In order to investigate the impacts of different concentrations of a green-synthesized selenium nano-complex (0, 20, 40, 60, and 80 mg L-1) on the chem. composition, antioxidant capacity and antimicrobial activity of lemongrass essential oil (EO), an experiment was designed as a completely randomized design (CRD) with four replications. The application of 40 mg L-1 selenium nano-complex caused the highest EO yield (3.96 ¡À 0.09%). The dominant compounds in EO, geranial (44.12 ¡À 1.22%) and neral (32.53 ¡À 1.08%), were achieved by the application of 60 mg L-1 selenium nano-complex. HPLC anal. indicated that the extracts were rich in 5-o-cafeoylquinic acid, luteolin 6-c-pentosyl-8-c-pentoside, and luteolin 2-o-deoxyhexosyl-6-c-glucoside. The extracts of lemongrass plants treated with 40 and 60 mg L-1 selenium nano-complex achieved the highest amount of 5-o-cafeoylquinic acid (25.29¡À1.31 and 24.16¡À1.26 ¦Ìg mL-1, resp.). The highest antioxidant capacity was observed in the 40 mg L-1 selenium nano-complex treated plants. The min. inhibitory concentration (MIC) of EO derived from the 60 mg L-1 selenium nano-complex treated lemongrass for Salmonella typhimurium, Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Aspergillus niger and Candida albicans was 0.63¡À0.03, 1.84¡À0.1, 1.05¡À0.05, 0.008¡À0.01, 0.6¡À0.01 and 0.1¡À0.01 mg mL-1, resp. It is expected that the selenium nano-complex would find a wide range of applications in medicine for its antioxidant and antimicrobial properties. It may also be applied to medicinal plants to enhance the quality and quantity of EOs.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Qin, Yu-Liang’s team published research in Food Control in 2023-03-31 | CAS: 483-76-1

The effect of volatile compounds of Syzygium aromaticum flower buds against Aspergillus flavus growth on wheat grain at postharvest stage. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Reducing the postharvest loss of cereal grains caused by deleterious fungi is critically important for the grain supply chain. Exploring antifungal constituents of plant volatile organic compounds (PVOCs) could promote the development of natural gaseous fungicides in controlling the decay of postharvest grains. In this study, PVOCs were extracted from clove (Syzygium aromaticum L.) buds and the primary constituents thereof were investigated for their effect on Aspergillus flavus growth in media postharvest grains. Fumigation with clove buds volatiles effectively inhibited A. flavus proliferation in 20% moisture wheat grains under simulated storage conditions. Gas chromatog.-mass spectrometry anal. revealed that eugenol and caryophyllene were the two main constituents of clove bud volatiles (49.80% and 36.68%, resp.). An antifungal assay demonstrated that eugenol was responsible for the antifungal activity of clove bud volatiles against A. flavus. Eugenol can completely inhibit A. flavus growth at 0.12 and 0.40 ¦ÌL/mL in vapor phase fumigation and liquid contact, resp. The proliferation of A. flavus in 20% moisture wheat grains was completely controlled after fumigation with 600 ¦ÌL/L eugenol vapor. Eugenol treatment can damage the membrane integrity of A. flavus mycelia, resulting in increased intracellular electrolyte leakage. The 38 metabolites in A. flavus hyphae exposed to 0.40 ¦ÌL/mL eugenol were markedly differentially expressed and principally involved in the biosynthesis of glycerophospholipids, linoleic acid metabolism, fatty acid metabolism, sugar metabolism, and ATP-binding cassette transporters. Eugenol also causes phosphatidylserine eversion of the plasma membrane, increased reactive oxygen species, decreased ATP production, and damaged DNA in A. flavus. We propose that eugenol treatment can disrupt cell membrane integrity, fatty acid ¦Â-oxidation, and induce apoptosis in A. flavus. This study demonstrated the potential application of clove bud volatile organic compounds as biofumigants for postharvest grain management and provided new insights into the antifungal mechanism of the main constituents against A. flavus growth.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem