November 2022 | Page 8 of 14 | Heterocyclic Building Blocks-Benzoxazole

Kong, Deshen’s team published research in ACS Sustainable Chemistry & Engineering in 2022-03-07 | CAS: 145026-07-9

Mechanochemical Solvent-Free N-Sulfenylations of Sulfoximines and Sulfonimidamides. 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.

Mechanochem. N-sulfenylations of sulfoximines and sulfonimidamides mediated by silver oxide under solvent-free conditions has been developed. The reactions are easy to perform and proceed well on a gram scale. A wide range of functional groups in the substrates were tolerated. Compared to its solvent-based counterpart, the mechanochem. approach showed significant ecol. advantages.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Toplan, Gizem Gulsoy’s team published research in South African Journal of Botany in 2022-07-31 | CAS: 483-76-1

Phytochemical screening and biological evaluation of Salvia hydrangea Dc. ex Benth. growing in eastern Anatolia. 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.

Salvia species have lately gained significant interest as a result of their suitable utilization in various industries. In the current study, S. hydrangea, one of the most consumed sages in the eastern region of Turkey, has been evaluated for phytochem. composition as well as in vitro pharmacol. potential comparatively for the first time. The phytochem. composition of S.hydrangea was investigated by LC-MS/MS, GC-FID, and GC/MS. To reveal its biol. activities, antioxidant, antimicrobial, and also acetylcholinesterase activities of different solvent extracts such as water, n-hexane, chloroform, and methanol were determined According to GC/MS anal., the primary components of the oil were identified as camphor (46.0%), 1,8-cineole (7.5%), camphene (6.8%), limonene (6.5%), a-pinene (5.6%) and b-pinene (6.1%). Addnl., in the infusion and methanol extract, rosmarinic acid and luteolin glycoside were detected as predominant phenolics by LC-MS/MS. In DPPH¡¤, CUPRAC, and FRAP test results of the samples indicated strong to moderate antioxidant ability in all samples studied, addnl., among them, the infusion exhibited significant acetylcholine inhibition properties comparable with galanthamine. With regard to antimicrobial activity, all of the tested microorganisms had MIC values ranging from 15 to 2000¦Ìg/mL. Based on these findings, S. hydrangea may have promising properties for a variety of industrial applications in the pharmaceutical, food, and cosmetic industries.

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

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

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

Chen, Lu’s team published research in Organic & Biomolecular Chemistry in 2022 | CAS: 4381-25-3

Rhodium(III)-catalyzed cascade C-H functionalization/annulation of sulfoximines with iodonium ylides for the synthesis of cyclohexanone-1,2-benzothiazines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

(S-Methylsulfonimidoyl)benzene (BD302898) 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: 83730-53-4 and 1621962-30-8.

A highly efficient Rh(III)-catalyzed cascade C-H activation/annulation of sulfoximines 2-R-3-R1-4-R2C6H2S(O)(=NH)R3 (R = H, Me, OMe, Cl, Br; R1 = H, Me, OMe, Br, NO2; R2 = H, F, CN, C(O)Me, etc.; R1R2 = -CH=CH-CH=CH-; R3 = Me, Et, Bn, etc.) with iodonium ylides I (n = 0, 1; R4 = H, Me, Ph; R5 = H, Me) under metal-oxidant-free conditions has been reported. The fused cyclohexanone-1,2-benzothiazine scaffolds II is readily achieved with a one-pot process in this reaction. This protocol exhibits good functional group tolerance and moderate to excellent yields. Addnl., the olefination of the target product II (n = 1; R = R1 = R2 = H; R3 = Me; R4 = R5 = H) illustrates the promising usefulness of this strategy.

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

(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.

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

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

Issekutz, Bela. Sr.’s team published research in Magyar Tudomanyos Akad. Biol. es Orvosi Tudomanyok Osztalyanak Kozlemenyei in 1961 | CAS: 5233-42-1

Diuretic effect of hydrochlorothiazide derivatives. Recommended basis is hydrochlorothiazide 20. Products is: https://www.ambeed.com/products/742-20-1.html, 432499-63-3

1. The impurity of diuretic hydrochlorothiazide 04, also be a medical intermediate.
2. It’s mainly used for the detection of drug impurities, the synthesis of hydrochlorothiazide and the screening of medical structural fragments.
3. Presents a weak alkaline,refrigeration.

. Recommended Products is: 5250-72-6 and 22503-72-6.

As compared with chlorothiazide, the effect of hydrochlorothiazide (I) was 10-fold stronger. Its effect could be increased further by introducing a dichloromethyl group at C-3, or by building a 3rd ring into the compound at this point. The resulting 3,3-pentamethylene-I and 3,3-(3-thiapenta-methylene)-I were 2-4-fold more effective than I. The I derivatives increased Na excretion. As long as a Na excess was present in the organism, the K excretion was not affected. Extirpation of the adrenals did not alter the effect of I if the rats were kept on a physiol. sufficient cortexone and hydrocortisone regimen. Excess cortexone doses >1.5 mg./kg. or >0.1 mg. aldosterone/kg. inhibited the I effect.

Diuretic effect of hydrochlorothiazide derivatives. Recommended basis is hydrochlorothiazide 20. Products is: https://www.ambeed.com/products/742-20-1.html, 432499-63-3

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