November 30, 2022 | Heterocyclic Building Blocks-Benzoxazole

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

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.

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

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.

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

Porcher, Alexis’s team published research in Annals of Botany (Oxford, United Kingdom) in 2020 | CAS: 83730-53-4

Ascorbate glutathione-dependent H2O2 scavenging is an important process in axillary bud outgrowth in rosebush. 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.

Branching is an important mechanism of plant shape establishment and the direct consequence of axillary bud outgrowth. Recently, hydrogen peroxide (H2O2) metabolism, known to be involved in plant growth and development, has been proposed to contribute to axillary bud outgrowth. However, the involvement of H2O2 in this process remains unclear. ? Methods We analyzed the content of H2O2 during bud outgrowth and characterized its catabolism, both at the transcriptional level and in terms of its enzymic activities, using RT-qPCR and spectrophotometric methods, resp. In addition, we used in vitro culture to characterize the effects of H2O2 application and the reduced glutathione (GSH) synthesis inhibitor L-buthionine sulfoximine (BSO) on bud outgrowth in relation to known mol. markers involved in this process. ? Key Results Quiescent buds displayed a high content of H2O2 that declined when bud outgrowth was initiated, as the consequence of an increase in the scavenging activity that is associated with glutathione pathways (ascorbate-glutathione cycle and glutathione biosynthesis); catalase did not appear to be implicated. Modification of bud redox state after the application of H2O2 or BSO prevented axillary bud outgrowth by repressing organogenesis and newly formed axis elongation. Hydrogen peroxide also repressed bud outgrowth-associated marker gene expression. ? Conclusions These results show that high levels of H2O2 in buds that are in a quiescent state prevents bud outgrowth. Induction of ascorbate-glutathione pathway scavenging activities results in a strong decrease in H2O2 content in buds, which finally allows bud outgrowth.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Bouymajane, Aziz’s team published research in International Journal of Food Microbiology in 2022-12-16 | CAS: 483-76-1

Chemical profile, antibacterial, antioxidant, and anisakicidal activities of Thymus zygis subsp. gracilis essential oil and its effect against Listeria monocytogenes. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

In this work, the chem. composition of Thymus zygis subsp. gracilis collected from Ifrane, Morocco, along with the evaluation of the antibacterial, anti-biofilm of Listeria monocytogenes activities, larvicidal effect against L3 larvae of Anisakis, and antioxidant properties of its essential oil (TZG-EO), are reported. GC-MS and GC-FID analyses highlighted the presence of 84 volatile components and strong bactericidal and anti-biofilm activities against L. monocytogenes at a concentration of 0.02 % were demonstrated. Also, larvicidal effect against Anisakis larvae at concentrations of 0.01 and 0.005 % was attained leading to the death of all tested larvae within 4 h. The in situ antibacterial activity of TZG-EO (0.01 and 0.005 %) in smoked fish showed high efficiency against L. monocytogenes growth. TZG-EO could be used as potential antibacterial and larvicidal agents for fighting against foodborne pathogens and extending shelf life of food products.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Sriramavaratharajan, Venkatraman’s team published research in Process Biochemistry (Oxford, United Kingdom) in 2022-07-31 | CAS: 483-76-1

Multi target interactions of essential oil nanoemulsion of Cinnamomum travancoricum against diabetes mellitus via in vitro, in vivo and in silico approaches. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

This study reports antidiabetic activity of leaf essential oil (EO) of Cinnamomum travancoricum from the Western Ghats, India via in vitro , in vivo and in silico methods. EO was characterized by GC-MS and GC-FID. Essential oil nanoemulsions (EN) were prepared and characterized. Antidiabetic potential was evaluated through in vitro assays namely, ¦Á-amylase and ¦Á-glucosidase inhibition, glucose uptake and insulin secretion assays. In vivo study was conducted on STZ-induced diabetic Wistar rats. Mol. docking was conducted to find the lead antidiabetic compounds Of the 42 compounds identified in the EO, ¦Á-phellandrene (5.9%), ¦Â-phellandrene (12.6%), linalool (23.6%), safrole (6.8%) and shyobunol (5.1%) were major constituents. Of the two ENs formulated, 1:2 ratio (EO to surfactants) was better in zeta size (51.4 nm) and potential (-30.9). In vitro results were impressive. EN lowered elevated blood glucose level to normal (p < 0.01) and improved the insulin secretion (p < 0.01) in diabetic rats. Further, serum AST, ALT, ALP, triglyceride and pancreatic ¦Â-cell damage were seen reduced (p < 0.05). Mol. docking studies showed minor constituents of EO, namely, ¦Ä-cadinene, elemol, spathulenol and ¦Á-copaen-11-ol playing active role in antidiabetic activity through ¦Á-amylase, ¦Á-glucosidase, insulin receptor, and insulin secretion proteins. Multi target interactions of essential oil nanoemulsion of Cinnamomum travancoricum against diabetes mellitus via in vitro, in vivo and in silico approaches. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Furukawa, Naomichi’s team published research in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1981-03-31 | CAS: 50578-18-2

Enhanced reactivities in substitution and elimination reactions in dimethyl sulfoximide. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

The preparation and dielec. constants of di-Me sulfoximide (I), tetramethylene sulfoximide, and di-Me N-methylsulfoximide are reported, and the kinetics examined for typical nucleophilic substitution and base-catalyzed elimination reactions in I as solvent. The rate enhancements indicate that the sulfoximides belong to a new type of solvent which is protic but behaves like a characteristic polar aprotic solvent. Also reported is the solvolysis of alkyl toluenesulfonates and halides in I to give the corresponding N-alkyl sulfoximides. Thus, octyl toluenesulfonate was heated in I at 95¡ã for 20 h to give 83% di-Me N-octylsulfoximide.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Cho, Gae Young’s team published research in Journal of Organic Chemistry in 2010-01-15 | CAS: 145026-07-9

Synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine. [Erratum to document cited in CA142:355003]. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

On page 2347, Scheme 1 is incorrect due to the wrong stereochem. assignment of compound 5 thereby making the configuration of Compound 6 incorrect as well; the correct version of Scheme 1 is given. Sulfoximine 2 as well as all subsequent mols. derived thereof should have the R-configuration at sulfur.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem