M.W=200-250 | Page 22 of 25 | Heterocyclic Building Blocks-Benzoxazole

Yu, Hao’s team published research in Chemistry – An Asian Journal in 2016 | CAS: 145026-07-9

Copper-Catalyzed Direct Sulfoximination of Heteroaromatic N-Oxides by Dual C-H/N-H Dehydrogenative Cross-Coupling. 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.

A dual C-H/N-H dehydrogenative coupling of quinoline-type N-oxides with sulfoximines that leads to N-(hetero)arylsulfoximines in high yields was realized by using a catalytic amount of CuBr in air. The method does not require any addnl. ligand, base, reactivity modifier or oxidant and provides a practical route towards a series of sulfoximidoyl-functionalized quinolines and derivatives

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Emami, Shabnam’s team published research in Biologia (Cham, Switzerland) in 2022-10-31 | CAS: 483-76-1

Cinnamon extract and its essential oil nanoliposomes – preparation, characterization and bactericidal activity assessment. 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.

The cinnamon essential oil and extract nanoliposomes were prepared through thin layer hydration-ultrasonication technique, using lecithin and three different co-surfactants namely, glycerol, triacetin and propylene glycol, and Tween 80 as surfactant. Results showed that the propylene glycol led to production of the nanoliposomes with the smallest mean particle size (92.03 nm) with spherical-shaped and the greatest net-zeta potential value (-24.1 mV) and was selected as more suitable co-surfactant. While, all prepared nanoliposomes had DPPH radical scavenging activities, the antioxidant activity of cinnamon extract nanoliposome was the greatest (78 ¡À 5%). Different amounts of cinnamon essential oil (0.25, 0.5 and 1.25 mL) were selected to prepared cinnamon essential oil nanoliposomes using propylene glycol and their antioxidant and antibacterial activities were evaluated. A good correlation was observed between amounts of cinnamon essential oil of nanoliposomes and their antioxidant activities (R2 = 0.9945). Although antibacterial activity of cinnamon essential oil and extract were greater than those were encapsulated into nanoliposomes, both cinnamon essential oil and extract nanoliposomes exhibited high antibacterial activities against Escherichia coli and Listeria monocytogenes bacteria strains. Results indicated that based on the min. inhibitory and bactericidal concentrations of the prepared samples, L. monocytogenes had higher resistance to the prepared cinnamon nanoliposomes.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Teng, Fan’s team published research in Organic Letters in 2015-06-19 | CAS: 145026-07-9

Silver-Mediated N-Trifluoromethylation of Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

An unprecedented approach to N-trifluoromethylations of electron-rich nucleophilic sites following a radical pathway is reported. Accordingly, various sulfoximines (19 examples) have been N-trifluoromethylated, providing previously unreported products with satisfying functionality tolerance in moderate to good yields. With a C-N bond length at the N-CF3 moiety of 1.341 ? the resp. linkage is shorter than a traditional C-N single bond and comparable with that of a C-N double bond.

Silver-Mediated N-Trifluoromethylation of Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Ta, Na’s team published research in Proceedings of the National Academy of Sciences of the United States of America in 2022-09-06 | CAS: 83730-53-4

Mitochondrial outer membrane protein FUNDC2 promotes ferroptosis and contributes to doxorubicin-induced cardiomyopathy. 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.

Ferroptosis is an iron-dependent programmed necrosis characterized by glutathione (GSH) depletion and lipid peroxidation (LPO). Armed with both the pro- and antiferroptosis machineries, mitochondria play a central role in ferroptosis. However, how mitochondria sense the stress to activate ferroptosis under (patho-)physiol. settings remains incompletely understood. Here, we show that FUN14 domain-containing 2, also known as HCBP6 (FUNDC2), a highly conserved and ubiquitously expressed mitochondrial outer membrane protein, regulates ferroptosis and contributes to doxorubicin (DOX)-induced cardiomyopathy. We showed that knockout of FUNDC2 protected mice from DOX-induced cardiac injury by preventing ferroptosis. Mechanistic studies reveal that FUNDC2 interacts with SLC25A11, the mitochondrial glutathione transporter, to regulate mitoGSH levels. Specifically, knockdown of SLC25A11 in FUNDC2-knockout (KO) cells reduced mitoGSH and augmented erasin-induced ferroptosis. FUNDC2 also affected the stability of both SLC25A11 and glutathione peroxidase 4 (GPX4), key regulators for ferroptosis. Our results demonstrate that FUNDC2 modulates ferroptotic stress via regulating mitoGSH and further support a therapeutic strategy of cardioprotection by preventing mitoGSH depletion and ferroptosis.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

de Souza, Diego Pereira’s team published research in Industrial Crops and Products in 2022-10-15 | CAS: 483-76-1

Untargeted metabolomics used to describe the chemical composition and antimicrobial effects of the essential oil from the leaves of Guatteria citriodora Ducke. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Plant oils are sources of metabolites that have enormous potential for industrial applications. Herein, the chem. profile and in vitro antimicrobial activity of the essential oil (EO) from the leaves of Guatteria citriodora Ducke (Annonaceae) have been investigated for the first time. The composition of the hydrodistd. EO was analyzed using gas chromatog.-mass spectrometry (GC-MS), which permitted the identification of oxygenated monoterpenes as the most highly representative class, and included citronellal (40.99%) and citronellol (14.6%) as the main compounds The antimicrobial activity of G. citriodora EO (GcEO) was evaluated against pathogenic bacteria and phytopathogenic fungi. The exptl. design was completely randomized (CRD), and used doses for each microorganism. Gram-pos. strains were the most sensitive with a min. inhibitory concentration (MIC) of 5.0¦ÌL mL-1, while Gram-neg. strains were 10.0¦ÌL mL-1. The most potent antifungal activity was against Alternaria alternata (MIC of 1.25¦ÌL mL-1). In addition, it fully inhibited A. alternata conidia germination at the min. inhibitory concentration The nucleic acid and soluble protein contents were significantly released from the conidia of A. alternata after treatment with GcEO. Using SEM (SEM), morphol. alterations were observed in the conidia, which indicates that a lesion in the cytoplasmic membrane is one of its mechanisms of action. Overall, these results indicate that GcEO is an antimicrobial agent with potential applications in the agriculture, food, and pharmaceutical industries.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Mingshi’s team published research in iScience in 2022-09-16 | CAS: 83730-53-4

Selenium nanoparticle rapidly synthesized by a novel highly selenite-tolerant strain Proteus penneri LAB-1. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Microorganisms with high selenite-tolerant and efficient reduction ability of selenite have seldom been reported. In this study, a highly selenite-resistant strain (up to 500 mM), isolated from lateritic red soil, was identified as Proteus penneri LAB-1. Remarkably, isolate LAB-1 reduced nearly 2 mM of selenite within 18 h with the production of selenium nanoparticles (SeNPs) at the beginning of the exponential phase. Moreover, in vitro selenite reduction activities of strain LAB-1 were detected in the membrane protein fraction with or without NADPH/NADH as electron donors. Strain LAB-1 transported selenite to the membrane via nitrate transport protein. The selenite was reduced to SeNPs through the glutathione pathway and the catalysis of nitrate reductase, and the glutathione pathway played the decisive role. P. penneri LAB-1 could be a potential candidate for the selenite bioremediation and SeNPs synthesis.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yildizhan, Kenan’s team published research in Molecular Neurobiology in 2020-08-31 | CAS: 83730-53-4

Glutathione Depletion and Parkinsonian Neurotoxin MPP+-Induced TRPM2 Channel Activation Play Central Roles in Oxidative Cytotoxicity and Inflammation in Microglia. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

PD is one of most common neurodegenerative diseases. Environmental stressors such as oxidative stress (OS), calcium ion influx, apoptosis, and inflammation mechanisms are linked to activated microglia in patients with PD. The OS-dependent activated transient receptor potential melastatin 2 (TRPM2) channel is modulated in several neurons by glutathione (GSH). However, the cellular and mol. effects of GSH alteration on TRPM2 activation, OS, apoptosis, and inflammation in the microglia remain elusive. The microglia of TRPM2 wild-type (TRPM2-WT) and knockout (TRPM2-KO) mice were divided into control, PD model (MPP), L-buthionine sulfoximine (BSO), MPP + BSO and MPP + BSO + GSH groups. MPP-induced increases in apoptosis, death, OS, lipid peroxidation, PARP1, caspase-3 and caspase-9, inflammatory cytokines (IL-1beta, TNF-a, IL-6), and intracellular free Zn2+ and Ca2+ levels in the microglia of TRPM2-WT mice were further increased by the BSO treatment, although they were diminished by the GSH treatment. Their levels were further reduced by PARP1 inhibitors (PJ34 and DPQ) and TRPM2 blockers (ACA and 2-APB). However, the effects of MPP and BSO were not observed in the microglia of TRPM2-KO mice. Taken together, our data demonstrate that maintaining GSH homeostasis is not only important for quenching OS in the microglia of patients with PD but also equally critical to modulating TRPM2, thus suppressing inflammatory responses elicited by environmental stressors.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Kong, Xianqiang’s team published research in Journal of Organic Chemistry in 2021-10-01 | CAS: 145026-07-9

Electrochemical Oxidative C(sp3)-H/N-H Coupling of Diarylmethanes with Sulfoximines or Benzophenone Imine. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

An efficient electrochem. method for the synthesis of N-alkylated sulfoximines I [R = Ph, 2-BrC6H4, 4-MeOC6H4, etc.; R1 = Me, Et, n-Bu, Ph, 4-MeC6H4; Ar1 = Ph, 4-FC6H4, 4-ClC6H4; Ar2 = Ph, 4-FC6H4] by electrochem. oxidative C(sp3)-H/N-H coupling of sulfoximines and diarylmethanes was developed. In addition, used the same conditions for electrochem. dehydrogenative amination of diarylmethanes with benzophenone imine as an aminating agent to obtain II [Ar3 = Ph, 4-MeC6H4, 4-FC6H4; Ar4 = Ph, 4-MeC6H4, 4-FC6H4, 4-ClC6H4]. The reactions showed good functional group tolerance and afforded the corresponding products in moderate to good yields without the use of a stoichiometric oxidant, a metal catalyst, or an activating agent.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Hsu, Kuang-Ping’s team published research in Natural Product Communications in 2022-07-31 | CAS: 483-76-1

Chemical Compositions and Anti-Mildew Effects of Cinnamomum micranthum Leaf and Twig Essential Oils on Paper. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

In this study, we evaluated the anti-mildew effects of paper treated with essential oils of leaves, twigs, and their main constituents from Cinnamomum micranthum. The main ingredients with the greater anti-mildew effects on paper capability were also purified and identified. Fresh leaves and twigs of C. micranthum were hydrodistillated in a Clevenger-type apparatus, and the resulting oil characterized using GC-FID and GC-MS instruments. The leaf essential oil consisted principally of n-decanal (50.1%), (E)-beta-ocimene (7.9%), (E)-nerolidol (6.5%), and (E)-beta-caryophyllene (3.8%), and the twig oil¡äs main components were tau-cadinol (18.3%), (E)-beta-ocimene (16.4%), alpha-cadinol (13.6%), n-decanal (10.6%), and beta-selinene (5.8%). Comparing the mildew resistance of the oils on paper exhibited that twig oil was the best anti-mildew activity; at 200 ¦Ìg/cm2, the twig oil completely inhibited the growth of Aspergillus clavatus, Cladosporium cladosporioides, Chaetonium globosum, Myrothecium verrucaria, and Penicillium citrinum. The twig oil was further divided into 8 fractions (TO1-TO8). TO4 fraction had moderate anti-mildew effects; at the concentration of 200 ¦Ìg/cm2, all fungi strains were totally inhibited, except A niger, and Trichoderma viride, which were 83.5%, and 93.2% inhibited, resp. The main ingredients of TO4 fraction were tau-cadinol, and alpha-cadinol, so we isolated and used the for anti-mildew effect tests; tau-cadinol, and alpha-cadinol showed moderate anti-mildew activities. Since C. micranthum twig essential oil, tau-cadinol, and alpha-cadinol were exhibited a great anti-mildew effects on paper, they are worth further investigations and utilization.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Soares, Krissie D.’s team published research in Journal of Ethnopharmacology in 2022-10-28 | CAS: 483-76-1

Chemical composition and anti-inflammatory activity of the essential oils of Piper gaudichaudianum and Piper mikanianum. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Inflammation is the bodys normal protective response to injury and is stimulated by pathogens, toxic compounds, damaged cells or radiation, promoting healing and restoring homeostasis to the injured tissue. Leaves of Piper gaudichaudianum Kunth, known as “”pariparoba”” are widely used in folk medicine for the relief of toothache, while the fresh roots are used as anti-inflammatory and to treat liver disorders. For P. mikanianum (Kunth) Steud is known as “”aguaxima””, is widely used in the treatment of inflammation, rheumatism and ulcer, with its roots being used for stomach disorders and as a diaphoretic in intermittent fevers. Therefore, this work aims to chem. characterize the essential oil of Piper gaudichaudianum and Piper mikanianum, as well as the evaluation of neutrophil antichemotactic activity of both essential oils in order to complement the information of its traditional use, taking the leaves as plant material and, with that, corroborating its use in folk medicine for the treatment of inflammatory diseases. The essential oil from leaves of both Piper species were obtained from crushed fresh samples, by hydrodistillation using a Clevenger type-apparatus for 4 h. The yield determination was performed as vol/wt (v/w) and in triplicate. The amount of essential oil obtained was quantified in mL. The identification and quantification of the compounds was performed using gas chromatog.-mass spectrometry (GC-MS) and gas chromatog.-flame ionization detection (GC-FID). The in vitro anti-inflammatory activity was evaluated using the model of modified Boyden chamber. In this test the essential oils were tested for their ability to inhibit leukocyte chemotaxis stimulated by Escherichia coli lipopolysaccharide. The chem. composition of the essential oils revealed the identification of 26 constituents for P. gaudichaudianum being the sesquiterpenes ¦Â-selinene (14.0%) and viridiflorene (10.5%) the main compounds, followed by caryophyllene oxide (9.3%) and (E)-nerolidol (9.0%). For P. mikanianum essential oil, ¦Â-myrcene (17.2%) and bicyclogermacrene (26.3%) were the major components in the monoterpenes and sesquiterpene fractions, resp. The essential oils were also tested for their ability to inhibit neutrophil chemotaxis in vitro when stimulated by Escherichia coli lipopolysaccharide. Both essential oils showed antichemotactic effect with reduction in migration of 0-72.2% for P. gaudichaudianum and 8.6-100% for P. mikanianum to same concentrations, suggesting a response to acute inflammatory processes. Since up to date there is no report of this biol. activities by this mechanism (antichemotactic assay) for essential oils this species. These results showed that the essential oils of P. gaudichaudianum and P. mikanianum have a great capacity to inhibit neutrophil chemotaxis in an inflammatory process, in a dose-dependent way, suggesting anti-inflammatory potential, by preventing its accumulation at the injury site with the possibility of tissue damage. Findings of these studies support the traditional use of these species in the treatment of inflammatory processes.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem