Heterocyclic Building Blocks-Benzoxazole

Wang, Chenyang’s team published research in Organic Letters in 2020-11-20 | CAS: 145026-07-9

Use of Hypervalent Iodine Reagents in Visible Light-Promoted ¦Á-Ketoacylations of Sulfoximines with Aryl Alkynes. 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.

In visible light, sulfoximidoyl-containing hypervalent iodine reagents react with aryl alkynes to give N-¦Á-ketoacylated sulfoximines in good to high yields. The process is metal- and base-free, providing the diketonic products without the use of highly oxygenated reagents such as peroxides. Results from mechanistic investigations suggest the intermediacy of radicals and reveal the importance of mol. oxygen.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Luca, Simon Vlad’s team published research in Industrial Crops and Products in 2022-11-01 | CAS: 483-76-1

Supercritical CO2 extraction of hemp flowers: A systematic study to produce terpene-rich and terpene-depleted cannabidiol 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.

Despite their high-added value, terpenes currently have limited exploitation in the hemp industry, often ending up in the sidestream of cannabidiol extraction and/or purification In this work, the influence of different combinations of pressures (80-300 bar) and temperatures (40-50¡ãC) on the recovery of three representative terpenes (caryophyllene, humulene, caryophyllene oxide) and, secondarily, cannabidiol, from hemp flowers by supercritical fluid extraction with carbon dioxide (SC-CO2) was investigated systematically. In the preliminary experiments, the influence of the particle size and storage time on the SC-CO2 process was evaluated, being noticed that a good recovery of the target compounds was obtained with freshly grounded hemp flowers. By comparing the extraction curves obtained for the studied pressure and temperature conditions, it was observed that pressures from 90 to 110 bar and temperatures from 40¡ã to 50¡ãC could allow a fast and efficient extraction of the three hemp terpenes. In contrast, higher pressures (200-300 bar) are needed for a superior recovery of cannabidiol. Based on the isocratic experiments, the gradient temperature (from 40¡ã to 50¡ãC) and pressure (from 100 to 300 bar) conditions were selected for the online fractionation of hemp flowers; thus, the proof-of-concept step-gradient SC-CO2 experiment generated terpene-rich and terpene-depleted cannabidiol fractions. In conclusion, our study brings essential knowledge on selecting the SC-CO2 process parameters for efficiently extracting hemp terpenes or performing the simultaneous removal of terpenes and extraction of cannabidiol from hemp flowers using step-gradient SC-CO2.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Effah, Evans’s team published research in Scientific Reports in 2022-12-31 | CAS: 483-76-1

Exploring plant volatile-mediated interactions between native and introduced plants and insects. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

In invasion scenarios, native and introduced species co-occur creating new interactions and modifying existing ones. Many plant-plant and plant-insect interactions are mediated by volatile organic compounds (VOCs), however, these have seldom been studied in an invasion context. To fill this knowledge gap, we explored some interactions mediated by VOCs between native and introduced plants and insects in a New Zealand system. We investigated whether a native plant, Leptospermum scoparium (manuka), changes its volatile profile when grown adjacent to two European introduced plants, Calluna vulgaris (heather) and Cytisus scoparius (Scotch broom), in a semi-field trial using potted plants without above- or below-ground phys. contact. We also investigated the influence of plant cues on the host-searching behavior of two beetles, the native Pyronota festiva (manuka beetle), and the introduced biocontrol agent Lochmaea suturalis (heather beetle), by offering them their host-plant and non-host volatiles vs. clean air, and their combination in a Y-tube olfactometer. As a follow-up, we performed preference/feeding tests in Petri dishes with fresh plant material. Results of the semi-field experiment show a significant reduction in green leaf volatiles, sesquiterpenes and total volatile emissions by manuka plants neighboring heather. In the Y-tube assays, the native beetle P. festiva performed poorly in discriminating between host and non-host plants based on plant volatile cues only. However, it performed relatively well in the Petri dish tests, where other cues (i.e., visual, gustatory or tactile) were present. In contrast, the introduced beetle L. suturalis showed high host-specificity in both Y-tube and Petri dish assays. This study illustrates the importance of VOCs in mediating interactions between introduced and native species, suggesting that invasive plants can disrupt native plants’ communication and affect the host-searching behavior of native insects. It also reinforces the relevance of regular host testing on introduced weed biocontrol agents to avoid unwanted host shifts or host-range expansion.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Guo, Jianshuang’s team published research in Biochemical Pharmacology (Amsterdam, Netherlands) in 2022-06-30 | CAS: 83730-53-4

A rational foundation for micheliolide-based combination strategy by targeting redox and metabolic circuit in cancer 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.

Accumulating evidence has supported that targeting oxidative stress and metabolic alterations of cancer is an effective strategy to combat cancer. We previously reported that Dimethylaminomicheliolide (DMAMCL) and its active metabolite micheliolide (MCL) can cause oxidative stress and cell death in leukemia and glioblastoma. However, the detailed mechanism underlying MCL or DMAMCL triggered oxidative stress remains elusive. Herein, using leukemia HL60 cells and glioblastoma U118MG cells as models, we found that MCL-induced oxidative stress is mainly mediated by reduced glutathione (GSH). Overproduced reactive oxygen species (ROS) can lead to oxidative damage to mitochondrial, impairing the ability of the tricarboxylic acid (TCA) cycle and causing dysfunction of mitochondrial respiratory chain. On the other hand, the depletion of GSH activates GSH biosynthesis pathway and has possibility to give rise to more GSH to scavenge ROS in cancer cells. Targeting this redox and metabolic circuit, we identified L-buthionine sulfoximine (BSO), an inhibitor in GSH biosynthesis, as an agent that can enhance MCL regimen to inhibit GSH compensatory event and thereby further facilitate cancer cell oxidative stress. Together, these results illustrate that targeting redox and metabolic pathway by MCL/DMAMCL combination with BSO is a potent therapeutic intervention for the treatments of glioblastoma and acute-myelocytic leukemia.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Tavallali, Vahid’s team published research in Plant Physiology and Biochemistry (Issy-les-Moulineaux, France) in 2022-07-15 | CAS: 483-76-1

Developmental and phytochemical changes in pot marigold (Calendula officinalis L.) using exogenous application of polyamines. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Polyamines (PAs) are natural active compounds having more than two amino groups that play important roles in many physiol. and developmental processes in plants. The purpose of this research was to see how foliar polyamine spray affected growth and photosynthetic indexes, as well as secondary metabolites and antioxidant activity of the aqueous and methanolic extracts of pot marigold (Calendula officinalis L.). The experiment lasted for three months and was arranged in a randomized complete design with four replications. Three sep. concentrations (0.5, 1 and 2.5 mM) of spermine (SPM), spermidine (SPD), and putrescine (PUT) were sprayed at four/five fully expanded leaf stage and some physiochem. attributes were evaluated. The treatments caused a significant increase in morphol. and photosynthetic parameters and total oil. There were also significant variations in total phenolic and flavonoid content. Compared to other polyamines, 1 mM SPD foliar spraying showed the greatest effect. Furthermore, the highest antioxidant capacity (DPPH* scavenging assay, ferric reducing antioxidant power (FRAP), Trolox equivalent antioxidant capacity (TEAC) and ¦Â-carotene bleaching activity) was observed in the 1 mM SPD treatment. The results showed that the calendula essential oils (EOs) were rich in sesquiterpenes hydrocarbons (55.92-95.94%), with c-Cadinene and d-Cadinene as the major sesquiterpenes in the EOs. Also, the flowers were rich sources of carotenoids (lutein, flavoxanthin and luteoxanthin) following polyamines application. Hence, it can be inferred that polyamines specially spermidine would find a wide range of application in pharmaceutical industries due to its impact on antioxidant properties of phenolic and flavonoid compounds

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Miyasaka, Mitsuru’s team published research in Organic Letters in 2011-02-04 | CAS: 145026-07-9

Copper-Catalyzed Direct Sulfoximination of Azoles and Polyfluoroarenes under Ambient Conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

The direct dehydrogenative C-N coupling of azoles or polyfluoroarenes with N-H sulfoximines proceeds effectively in the presence of a copper catalyst at room temperature under air to afford the corresponding N-arylsulfoximines, e.g. I and II, in good to high yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yoshida, Suguru’s team published research in Chemistry Letters in 2017-01-31 | CAS: 50578-18-2

Reactions of arynes with sulfoximines: formal sulfinylamination vs. N-arylation. 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.

Reactions of arynes with sulfoximines were reported. The fate of these reactions depended on the substituents of the sulfoximines. S,S-Diarylsulfoximines reacted with arynes to selectively afford o-sulfinylanilines, whereas a simple N-arylation reaction was observed when S-alkyl-S-aryl- or S,S-dialkylsulfoximine was used to selectively afford the corresponding N-arylated sulfoximines.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yohana, Revocatus’s team published research in Malaria Journal in 2022-12-31 | CAS: 483-76-1

Anti-mosquito properties of Pelargonium roseum (Geraniaceae) and Juniperus virginiana (Cupressaceae) essential oils against dominant malaria vectors in Africa. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

More than 90% of malaria cases occur in Africa where the disease is transmitted by Anopheles gambiae and Anopheles arabiensis. This study evaluated the anti-mosquito properties of Juniperus virginiana (JVO) and Pelargonium roseum (PRO) essential oils (EOs) against larvae and adults of An. gambiae sensu lato (s.l.) from East Africa in laboratory and semi-field conditions. EOs was extracted from the aerial green parts of Asian herbs by hydrodistillation Their constituents were characterized by gas chromatog.-mass spectrometry (GC-MS). Larvicidal activities of JVO, PRO, and PRO components [citronellol (CO), linalool (LO), and geraniol (GO)] were investigated against An. gambiae sensu stricto (s.s.). The percentage of knockdown effects and mortality rates of all oils were also evaluated in the adults of susceptible An. gambiae s.s. and permethrin-resistant An. arabiensis. GC-MS analyses identified major constituents of JVO (sabinene, dl-limonene, ¦Â-myrcene, bornyl acetate, and terpinen-4-ol) and PRO (citronellol, citronellyl formate, L-menthone, linalool, and geraniol). Oils showed higher larvicidal activity in the laboratory than semi-field trials. The LC50 values for JVO/PRO were computed as 10.82-2.89/7.13-0.9 ppm and 10.75-9.06/13.63-8.98 ppm in laboratory and semi-field environments, resp. at exposure time of 24-72 h. The percentage of knockdown effects of the oils were also greater in An. gambiae s.s. than in An. arabiensis. Filter papers impregnated with JVO (100 ppm) and PRO (25 ppm) displayed 100% mortality rates for An. gambiae s.s. and 3.75% and 90% mortality rates, for An. arabiensis populations, resp. Each component of CO, LO, and GO exhibited 98.13%, 97.81%, and 87.5%, resp., and a mixture of the PRO components indicated 94.69% adult mortality to permethrin-resistant An. arabiensis. The findings of this study show that PRO and its main constituents, compared to JVO, have higher anti-mosquito properties in terms of larvicidal, knockdown, and mortality when applied against susceptible laboratory and resistant wild populations of An. gambiae s.l. Consequently, these oils have the potential for the development of new, efficient, safe, and affordable agents for mosquito control.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Aithagani, Sravan Kumar’s team published research in Journal of Organic Chemistry in 2016-07-15 | CAS: 50578-18-2

Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine N-Oxides: Approach for the Synthesis of N-Azine Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Herein, we report a simple and metal-free method for the synthesis of N-azine sulfoximines by the nucleophilic substitution of azine N-oxides with NH-sulfoximines. The present method works at room temperature with wide functional group compatibility and gives several unprecedented N-azine sulfoximines. The reaction conditions were also found suitable with enantiopure substrates and furnished products without any racemization. It also finds an application in the sulfoximination of azine-based functional mols. such as 2,2′-bipyridine, 1,10-phenanthroline, and quinine.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Sripahco, Teerapong’s team published research in Scientific Reports in 2022-12-31 | CAS: 483-76-1

Chemical composition, antioxidant, and antimicrobial activity of Elsholtzia beddomei C. B. Clarke ex Hook. f. essential oil. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

The essential oil of Elsholtzia beddomei C. B. Clarke ex Hook. f. was investigated for its chem. composition and tested for antioxidant and antimicrobial activities. The E. beddomei essential oil was extracted using hydrodistillation for 4 h (yield of 1.38% weight/weight). Forty-three volatile compounds were identified in the E. beddomei essential oil, including linalool (83.67%), perillaldehyde (4.68%), neral (3.68%), perillene (1.65%), E-caryophyllene (1.55%), and ¦Á-zingiberene (1.06%) as the major compounds The antioxidant activity of the E. beddomei essential oil was determined using 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical and 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation scavenging activity. The IC50 values calculated using the DPPH and ABTS methods were 148.31 and 172.22¦Ìg/mL, resp. In addition, using disk diffusion and broth microdilution methods, the antimicrobial activities of the E. beddomei essential oil against Escherichia coli, Pseudomonas aeruginosa, Enterobacter aerogenes, Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, and Candida albicans were evaluated. The E. beddomei essential oil possessed an inhibitory effect with the min. inhibitory concentration in the range of 31.25-250.00¦Ìg/mL among these pathogens. The results indicated that E. beddomei essential oil is an alternative raw material of food, and medicinal products for use in pharmaceutical applications.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem