M.W=200-250 | Page 9 of 25 | Heterocyclic Building Blocks-Benzoxazole

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

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.

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

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

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

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

Dong, Shunxi’s team published research in Journal of the American Chemical Society in 2016-02-24 | CAS: 145026-07-9

Organocatalytic Kinetic Resolution of Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

An efficient kinetic resolution of sulfoximines with enals was realized using chiral N-heterocyclic carbene (NHC) catalysts. The stereoselective amidation proceeds without addnl. acyl transfer agent. Both enantiomers of the sulfoximines can be obtained with excellent ee values (up to 99% ee and -97% ee, resp.). Performing the catalysis on a gram scale allowed using the recovered sulfoximine (+)-MeO2CC6H4SMe(O)(:NH) in an asym. synthesis of FXa inhibitor (+)-F.

Organocatalytic Kinetic Resolution 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

Nasri, Chaimae’s team published research in Biocatalysis and Agricultural Biotechnology in 2022-09-30 | CAS: 483-76-1

Seven Persea americana varieties essential oils comparison: Chemical composition, toxicity, antibacterial, and antioxidant activities. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

The present study aims at comparing the chem. composition of seven varieties of Persea americana leaves essential oils and at evaluating some of its activities such as antibacterial activity, antioxidant activity and acute toxicity. The results showed strong variations in the volatile compounds present in some of the studied oils from these varieties. Estragol was the major component of Ettinger (30.04%) and Fuerte (36.74%) leaf essential oils and is absent from four varieties. Regarding the EO of Hass, Bacon and Maluma Hass, the 2-(8Z,11Z)-8,11-heptadecadienyl-furan was the main volatile compound (67,37%, 43.61% and 59.9% resp.) while Caryophyllene was the main substance in the leaf EO of Reed (36.61%) and Zutano (17.68%) varieties. Concerning the acute toxicity test of these essential oils, the results obtained showed that the LD (LD50) is higher than 2000 mg/kg for EO of Maluma Hass, Reed and Ettinger varieties, whereas it is greater than 300 mg/kg for those of Zutano, Bacon, Hass and Fuerte. The study of antioxidant and antibacterial activities revealed promising values against gram-pos. bacteria (Staphylococcus epidermidis, Staphylococcus aureus) and an encouraging antioxidant power. Based on these results, it appears that avocado leaf essential oils are in fact a potential source of bioactive phytochems. for medical and cosmetic use, and could also be considered as the first report on Persea americana grown in Morocco.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wan, Lihui’s team published research in Journal of Colloid and Interface Science in 2020-08-01 | CAS: 83730-53-4

A novel intratumoral pH/redox-dual-responsive nanoplatform for cancer MR imaging and therapy. 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 integration of diagnostic and therapeutic functions in a nanoplatform has been a rapidly emerging method in the management of cancer. The application of imaging technol. paves the way to track the pharmacokinetics of the nanoplatforms, to guide the treatment, and to monitor the therapeutic processes and outcomes. Herein, we reported a novel type of monodisperses mesoporous silica-coated superparamagnetic iron oxide-based multifunctional nanoplatform (DOX@MMSN-SS-PEI-cit) for the diagnosis and treatment of cancer. The fabrication process included the surface modification of monodisperses mesoporous silica nanoparticle (MMSN) with branched polyethyleneimine (PEI) via disulfide bonds and the further coupling of citraconic anhydride to PEI. Typically, the hydrolysis of amide bonds in the tumor microenvironment (TME) could lead to a neg.-to-pos. charge reversion, which can enhance the endosomal escape of the resulting nanoplatform. The rapid release of doxorubicin hydrochloride (DOX) directly killed the cancer cells. Due to the superparamagnetic iron oxide-based high-resolution T2-weighted MR imaging contrast agents, this novel multifunctional nanoplatform successfully realized MR imaging, targeted drug delivery and controlled release in one system, and achieved significant improvement in tumor diagnosis and therapy. In summary, the therapeutic nanoplatform is a promising option in precise cancer treatment.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Gran, Evan Rizzel’s team published research in Nanomedicine (New York, NY, United States) in 2021-10-31 | CAS: 83730-53-4

Human astrocytes and astrocytoma respond differently to resveratrol. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A fundamental problem in oncol. is that anticancer chemotherapeutics kill both cancer and healthy cells in the surrounding tissues. Resveratrol is a natural antioxidant with intriguing and opposing biol. properties: it reduces viability of some cancer cells but not of non-transformed ones (in equimolar concentrations). Therefore, we examined resveratrol in human non-transformed primary astrocytes and astrocytoma. Resveratrol reduced reactive oxygen species in astrocytes, but not in astrocytoma. Such cell-type dependent response is particularly evident with analyses at the single cell level showing clear population difference in high and low glutathione levels. Due to resveratrol¡äs poor aqueous solubility that limits its use in clinics, we incorporated it into stimulus-responsive micelles assembled from miktoarm polymers. This could be an attractive chemotherapeutic delivery strategy in nano-oncol. As a proof of principle, we show that these formulations containing resveratrol markedly decrease astrocytoma viability, particularly in combination with temozolomide, a first line chemotherapeutic for astrocytoma.

Human astrocytes and astrocytoma respond differently to resveratrol. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Ko, Gi Hoon’s team published research in Advanced Synthesis & Catalysis in 2017 | CAS: 145026-07-9

Synthesis of Indolo-1,2-Benzothiazines from Sulfoximines and 3-Diazoindolin-2-imines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A rhodium-catalyzed cyclization reaction of sulfoximines with 3-diazoindolin-2-imines was described. This protocol provided a wide range of indolo[2,3-c][1,2]-benzothiazines in moderate to excellent yields together with the release of mol. nitrogen and p-toluenesulfonamide. This method involved the N-H/C-H activation of S-aryl sulfoximines and had the advantages of a broad substrate scope.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Ma, Ding’s team published research in Organic Letters in 2021-11-05 | CAS: 145026-07-9

Three-Dimensional Heterocycles by 5-exo-dig Cyclizations of S-Methyl-N-ynonylsulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

Upon treatment with Cs2CO3, S-methyl-N-ynonylsulfoximines R1S(O)(CH3)=NC(O)CCR2 (R1 = Ph, pyridin-2-yl, 3-fluorophenyl, etc.; R2 = Ph, 4-cyanophenyl, 2-fluorophenyl, etc.) undergo 5-exo-dig cyclizations to give three-dimensional heterocycles (Z)-I. The reactions proceed at ambient temperature with a wide range of substrates affording the corresponding products (Z)-I in good to excellent yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Choi, Yeon Su’s team published research in Biomaterials in 2022-01-31 | CAS: 83730-53-4

Beyond hydrophilic polymers in amphiphilic polymer-based self-assembled NanoCarriers: Small hydrophilic carboxylate-capped disulfide drug delivery system and its multifunctionality and multispatial targetability. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Due to increasing safety and intracellular delivery concerns about hydrophilic polymers in amphiphilic polymer-based nanoparticles (NPs), this study investigates small hydrophilic mol.-stabilized NPs for effective intracellular delivery with multiorganelle targetability and dual responsiveness to acidic pH/glutathione (GSH). In the construction of small hydrophilic mol.-stabilized NP (MSPCL-NP), the A-B-A-type amphiphilic polymer (MSPCL-P) is composed of two short hydrophilic carboxylate-capped disulfide derivatives (A) that replace hydrophilic polymers and assist in providing colloidal stability and preventing antibody (e.g., at least anti-PEG antibody)-mediated specific interactions and complement activation in the plasma and a hydrophobic multiple disulfide-containing poly(¦Å-caprolactone) block (B) that carries hydrophobic drugs. The carboxylates on the surface of MSPCL-NP target the acidic extratumoral/endolysosomal milieu by sensing and buffering acidic pH values, and the hydrophobic carboxylic acids improve adsorptive endocytosis and effective endosomal escape. Multiple disulfide linkages selectively target cytosolic GSH, resulting in rapid drug release from the destroyed MSPCL-NP via the cleavage of disulfide bonds in MSPCL-P. Doxorubicin (DOX)-loaded NP (DOX@MSPCL-NP) exerts strong effects on killing cells in vitro and inhibits tumor growth in HCT116 xenograft tumor-bearing mice. In conclusion, the multifunctionality and multispatial targetability of MSPCL-NP might effectively overcome various sequential drug delivery hurdles, ranging from blood circulation to drug release. Furthermore, the introduction of small hydrophilic mols. represents a potential strategy to make self-assembled NPs without the use of hydrophilic polymers.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem