December 6, 2022 | Heterocyclic Building Blocks-Benzoxazole

Rajbongshi, Kamal K.’s team published research in Synthesis in 2020-04-30 | CAS: 145026-07-9

Microwave-Accelerated N-Acylation of Sulfoximines with Aldehydes under Catalyst-Free Conditions. 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.

An efficient catalyst-free radical cross-coupling reaction between sulfoximines R1S(O)(=NH)R2 [R1 = Me, Ph, 4-methoxyphenyl, 4-bromophenyl; R2 = Me, Ph; R1R2 = -(CH2)4-] and aromatic aldehydes R3CHO (R3 = 2-chlorophenyl, naphthalen-1-yl, furan-2-yl, etc.) was developed. The reaction took place in the presence of N-bromosuccinimide as the radical initiator under microwave irradiation to afford the corresponding acylated sulfoximines R1S(O)(R2)=NC(O)R3 in moderate to excellent yields (27 examples). This protocol is proved to be rapid, easy to handle, and applicable to a broad scope of substrates.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Baranauskiene, Renata’s team published research in Food Research International in 2022-10-31 | CAS: 483-76-1

Valorisation of Roman chamomile (Chamaemelum nobile L.) herb by comprehensive evaluation of hydrodistilled aroma and residual non-volatile fractions. 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.

Valorization of botanicals for the development of natural food-grade ingredients is an important task in terms of sustainability and processing waste reduction In this study, Roman chamomile (Chamaemelum nobile L.) herb was collected at six different vegetation phases in the period 26 May – 23 August 2019 and subjected to biorefining into the several valuable fractions. The yield of hydro-distilled essential oil (EO) was in the range of 0.22% (intensive vegetative growth) to 0.80% (full flowering). Angelic, isobutyric, butyric and methacrylic acid esters and some monoterpene and sesquiterpene derivatives were the major EO constituents: 3-methylpentyl angelate (20.11-27.56%), methallyl angelate (7.28-10.33%), isoamyl angelate (5.57-9.02%), iso-Bu angelate (4.84-6.79%), 2-methylbutyl angelate (3.11-6.32%), 3-methylamyl methacrylate (5.04-6.17%), 3-methylpentyl isobutyrate (4.29-6.64%), 3-methylamyl isobutyrate (4.29-6.64%), ¦Á-pinene (1.61-6.37%) and pinocarvone (1.46-4.67%). In order to valorize water soluble and solid EO distillation residues their antioxidant potential was evaluated by several in vitro assays: water extracts were considerably stronger antioxidants than acetone extracts isolated from the solid residues. Water extracts of the plants collected at flowering phases were the strongest antioxidants; their TPC, FRAP and ORAC values were up to 143.2 mg gallic acid equivalent/g, 650, and 5601 ¦Ìmol TE/g dry extract, resp., while effective concentrations (EC50) of DPPH? and ABTS?+ scavenging, were down to 0.59 and 0.49 mg/mL, resp. Among 7 tentatively identified by UPLC/Q-TOF/MS phenolic constituents the intensity of mol. ion of 3,5-dicaffeoyl quinic acid was the largest. The results obtained may assist for developing flavorings, antioxidants and health beneficial preparations from C. nobile extracts

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Alimi, Dhouha’s team published research in Waste and Biomass Valorization in 2022-10-31 | CAS: 483-76-1

Valorization of Volatile Oils and Some Crude Extracts from the Tunisian Plants Juniperus communis and Origanum majorana for the Control of Hyalomma scupense (Acari: Ixodidae). Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

This investigation tested the in vitro acaricidal activity of essential oils and raw extracts of Juniperus communis and Origanum majorana compared with the synthetic acaricide amitraz against various stage of Hyalomma scupense cattle tick. The hydrodistilation technique was used to extract essential oils, while chem. components in the plants were obtained using solvents of increasing polarity (hexane, Et acetate and methanol). The evaluation on H. scupense was performed with the adult immersion test at concentrations ranging from 1.25 to 10 mg/mL and the larval packet test from 0.625 to 10 mg/mL. Qual. anal. of J. communis essential oil showed ¦Á-pinene (52.31%), ¦Ä 3-carene (12.77%), ¦Â-phellandrene (7.60%), 1,8 cineole (6.95%) and ¦Á-terpinenyl acetate (6.58%) as the major chem. components. O. majorana oil was mainly composed of 4-terpineol (23.05%), Cis-Thujan-4-ol (18.30%), ¦Ä-terpinene (13.61%), ¦Á-terpinene (9.16%) and sabinene (7.96%). In adult immersion test, J. communis essential oil, at 10 mg/mL concentration exhibited strong acaricidal efficacy and reproductive inhibitory effects on treated ticks (100%) than O. majorana oil (91.95%). In larval packet test, J. communis oil had 100% mortality at 10 mg/mL, 24 h of exposure, whereas O. majorana oil had 90.64% mortality of H. scupense larvae. J. communis essential oil showed greater efficacy than all tested extracts and amitraz on both female adults and larvae of H. scupense. Quant. anal. showed that J. communis methanolic extract had the greatest ability to extract such phenolic compounds, with a total phenol content of 188.17 (mg gallic acid equivalent/g dry weight) and also had the highest acaricidal activity against engorged females and larvae of H. scupense with LC50 values of 2.46 and 4.12 mg/mL, resp. The results showed that both plants, particularly J. communis considered as potential candidates for biocontrol of H. scupense in the field.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Cadavid Vargas, J. F.’s team published research in JBIC, Journal of Biological Inorganic Chemistry in 2022-04-30 | CAS: 83730-53-4

Enhanced antitumor effect of L-buthionine sulfoximine or ionizing radiation by copper complexes with 2,2-biquinoline and sulfonamides on A549 2D and 3D lung cancer cell models. 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.

Two ternary copper(II) complexes with 2,2-biquinoline (BQ) and with sulfonamides: sulfamethazine (SMT) or sulfaquinoxaline (SDQ) whose formulas are Cu(SMT)(BQ)Cl and Cu(SDQ)(BQ)Cl¡¤CH3OH, in what follows SMTCu and SDQCu, resp., induced oxidative stress by increasing ROS level from 1.0 ¦ÌM and the reduction potential of the couple GSSG/GSH2. The co-treatment with L-buthionine sulfoximine (BSO), which inhibits the production of GSH, enhanced the effect of copper complexes on tumor cell viability and on oxidative damage. Both complexes generated DNA strand breaks given by-at least partially-the oxidation of pyrimidine bases, which caused the arrest of the cell cycle in the G2/M phase. These phenomena triggered processes of apoptosis proven by activation of caspase 3 and externalization of phosphatidylserine and loss of cell integrity from 1.0 ¦ÌM. The combination with BSO induced a marked increase in the apoptotic population. On the other hand, an improved cell proliferation effect was observed when combining SDQCu with a radiation dose of 2 Gy from 1.0 ¦ÌM or with 6 Gy from 1.5 ¦ÌM. Finally, studies in multicellular spheroids demonstrated that even though copper(II) complexes did not inhibit cell invasion in collagen gels up to 48 h of treatment at the higher concentrations, multicellular resistance outperformed several drugs currently used in cancer treatment. Overall, our results reveal an antitumor effect of both complexes in monolayer and multicellular spheroids and an improvement with the addition of BSO. However, only SDQCu was the best adjuvant of ionizing radiation treatment.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zhu, Yueyue’s team published research in Journal of Organic Chemistry in 2022-09-02 | CAS: 4381-25-3

Synthesis of Isoquinolone, 1,2-Benzothiazine, and Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine Derivatives via Rhodium(III)-Catalyzed (4 + 2) Annulation. 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 novel and efficient synthetic method to construct isoquinolone e.g., I scaffold via the Rh(III)-catalyzed (4 + 2) annulation of benzamide RC(O)NHOMe (R = Ph, naphthalen-2-yl, 2-OMeC6H4) with an unreported coupling reagent Me 2-chloroacrylate was reported. Accordingly, other valuable 1,2-benzothiazine II (R1 = Me, Et, Ph; R2 = OMe, H, F, etc.; R3 = OMe, H, Cl; R4 = Cl, H, Br) and naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine e.g., III derivatives are also obtained through a similar synthetic protocol. Thus, the developed method is highlighted by high yield and reaction versatility.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Liang, Lu’s team published research in LWT–Food Science and Technology in 2022-09-15 | CAS: 483-76-1

Untargeted metabolomics analysis based on HS-SPME-GC-MS and UPLC-Q-TOF/MS reveals the contribution of stem to the flavor of Cyclocarya paliurus herbal extract. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

The herbal tea made from the leaves and stems of Cyclocarya paliurus is thought to be more flavorful than those made from the leaves only. However, evidence supporting this view is not available yet. 53 VOCs and 54 non-VOCs were identified via HS-SPME-GC-MS and UPLC-Q-TOF/MS, resp., which were found to vary dramatically in three groups of samples (combination of stems and leaves, separated leaves, and separated stems). 11 VOCs and 18 non-VOCs potential markers are responsible for the change of metabolic effects through the biosynthesis of flavonoids, the synthesis of terpenoids, and the oxidation of fatty acids and carotenoids. In response, the stems were effective to enhance fatty odors, the initial astringency and bitterness and the aftertaste of sweetness of the leaves. Stems are conducive to increasing total phenolic content, total flavonoid content and antioxidant capacity of Cyclocarya paliurus herbal extract because of the increase in polyphenols. In addition, the stems have the potential to be used as raw materials for nerolidol and polyphenols extraction This study has been the first to determine the contribution of stem to the flavor of Cyclocarya paliurus herbal tea and these results provide the theor. basis for making Cyclocarya paliurus herbal tea with stems.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Johnson, Carl R.’s team published research in Journal of Organic Chemistry in 1989-02-17 | CAS: 50578-18-2

Preparation of free sulfoximines by treatment of N-tosylsulfoximines with sodium anthracenide. 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.

A solution of sodium anthracenide in DME was added dropwise to a stirred solution or suspension of N-tosylsulfoximes RR1S(O):NTs [I; Ts = tosyl, R = R1 = Me, Bu; R = Me, R1 = morpholino, Bu2N; RR1 = (CH2)4] in DMF under argon at 0¡ã to afford 68-98% sulfoximines RR1S(O):NH. I (R = Et, R1 = MeCCl2) gave S,S-diethylsulfoximine; I (R = Me, R1 = Ph, PhCH2) were unreactive.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Han, Min’s team published research in Tetrahedron Letters in 2022-07-20 | CAS: 145026-07-9

Electrochemical oxidation chemoselective sulfimidation of thioether with sulfonamide via catalytic iodobenzene. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

Sulfilimines, the aza-analogs of sulfoxides, are valuable building blocks in organic synthesis and serve as important functional groups in medicinal chem. Herein authors reported an efficient and environmentally friendly method of preparing sulfilimines from readily available thioether and sulfonamide as substrate. The reaction proceeds via the in-situ produced hypervalent iodine from catalytic simple iodobenzene under electrooxidation conditions. A series of sulfilimines were obtained in moderate to good yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zou, Ya’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2015 | CAS: 145026-07-9

Transition metal-free aroylation of NH-sulfoximines with methyl arenes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A novel protocol towards N-aroylated sulfoximines from NH-sulfoximines and Me arenes is demonstrated. The reaction took place in the presence of elemental iodine, requiring no external organic solvents, transition metal-catalysts or ligands. The aroylated products were obtained from the oxidative transformation in moderate to excellent yields (up to 94% yield) with a broad substrate scope through a radical pathway.

Transition metal-free aroylation of NH-sulfoximines with methyl arenes. 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

Razmjoo, Fatemeh’s team published research in Journal of Food Processing and Preservation in 2022-10-31 | CAS: 483-76-1

Fabrication and application of functional active packaging material based on carbohydrate biopolymers formulated with Lemon verbena/Ferulago angulata extracts for the preservation of raw chicken meat. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

In this research using Zedo gum (ZG) and CM-cellulose (CMC) as well as Lemon and Ferulago extracts (LVE/FAE) new active packaging was designed. Biodegradable films with five various proportions of ZG to CMC were made by applying the casting process. The incorporation of LVE or FAE into CMC/ZG composite films significantly reduced moisture content (MC) and water vapor permeability (WVP). The tensile strength increased from 6.92 (MPa) for CMC/ZG film to 11.51 MPa for CMC/ZG/2.5¦Ìl LVE and FAE film; as well as elongation at break decreased from 24.21% for CMC/ZG film to 6.10% for CMC/ZG/2.5¦Ìl LVE and FAE film. In conclusion, the 20:80 proportion of ZG/CMC along with 2.5¦Ìl LVE and FAE can be used as the best ratio for mech. properties, moisture content, and permeability compared to the CMC/ZG film with individual FAE or LVE and can be a good source for making edible films. Novelty impact statement : The most important novelty is related to using of Lemon verbena and Ferulago angulata extracts in the combination of Zedo gum and CM-cellulose. Producing active packaging with Lemon verbena and Ferulago angulata extracts in polymer matric. Increasing the shelf life of compounds such as raw chicken meat with active packaging.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem