December 7, 2022 | Page 2 of 4 | Heterocyclic Building Blocks-Benzoxazole

Kobayashi, Fumiyuki’s team published research in Journal of Food Processing and Preservation in 2022-08-31 | CAS: 483-76-1

Effect of various seasonings on the quality retention of dried mackerel (Scomber scombrus Linnaeus). 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.

The effect of seasonings on the quality retention of dried mackerel (Scomber scombrus Linnaeus) was investigated by analyzing the components of the seasonings and prepared dried mackerel. The pH, water content, salt concentration, and inosinic acid content of dried mackerel were influenced by the water content of seasoning liquid The free amino acid content of dried mackerel depended on the seasoning liquid The DPPH radical-scavenging activity of mirin seasoning liquid was significantly higher than that of salt and chorizo, and that of black seven spices (shichimi) and chorizo seasoning powders was extremely high. The content of some aldehydes, alkenes, and alkane of dried mackerel flavored with mirin, shichimi, and chorizo was significantly lower than that flavored with salt. Hexanal concentration further decreased in dried mackerel flavored with shichimi and chorizo. Therefore, the use of shichimi and chorizo as seasoning powders was effective for maintaining the quality of dried mackerel. The production and consumption of dried fish have decreased yearly in Japan. Recently, two types of seasonings flavored with shichimi and chorizo have been, therefore, developed for preparing dried mackerel. These seasonings consisted of liquid and powder. This is the first attempt to use seasoning powders in the production of dried mackerel. This study demonstrated that the generation of fishy volatile components from dried mackerel was inhibited by the shichimi and chorizo seasoning powders.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Chenyang’s team published research in Organic Letters in 2020-11-20 | CAS: 50578-18-2

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, 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.

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

Choi, Wonseok’s team published research in Organic Letters in 2015-09-18 | CAS: 145026-07-9

Synthesis of N-Imidoyl and N-Oxoimidoyl Sulfoximines from 1-Alkynes, N-Sulfonyl Azides, and Sulfoximines [Erratum to document cited in CA163:145350]. 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.

Addtional text regarding the HRMS should be added to the Section 1 of the Exptl. on page S2; the corrected text is given.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Huong, Le Thi’s team published research in Chemistry of Natural Compounds in 2022-09-30 | CAS: 483-76-1

Chemical Composition and Antimicrobial Activity of the Leaf Essential Oil of Vernonia solanifolia. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

This article discusses about chem. composition and antimicrobial activity of the leaf essential oil of Vernonia solanifolia. The leaves of Vernonia solanifolia were collected from Hanh Dich Commune and essential oil was obtained by hydrodistillation The instrumental anal. of the essential oil was achieved using gas chromatog. The antimicrobial activity was measured by the determination of MIC and median inhibitory concentration . The major constituents of the essential oil of Vernonia solanifolia have shown antimicrobial activity against E. faecalis, S. aureus, B. cereus, and C. albicans

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wei, Cheng’s team published research in Arabian Journal of Chemistry in 2022-11-30 | CAS: 483-76-1

Efficient separation of Cinnamomum camphora leaf essential oil and in vitro evaluation of its antifungal activity. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Cinnamomum camphora leaf essential oil was extracted using enzymic-ultrasound pretreatment followed by microwave assisted extraction method and simultaneously studied as a mycelial growth inhibitor against five important pathogens which cause potato dry rot. The optimum EUP-MAE conditions with a real CEO yield of 19.23 ¡À 0.12 mg/g were obtained through Plackett-Burman design and Box-Behnken design as follows: 3% of enzyme dosage, 2 h of pretreatment time, 5 of pH, 210 W of ultrasound power, 50¡ãC pretreatment temperature, 16 mL/g of water to solid ratio, 30 min of microwave time and 500 W of microwave power. Compared to the reference methods, EUP-MAE possessed a highest CEO yield than these of ultrasound-microwave assisted extraction (U-MAE) and traditional hydrodistillation (HD). Gas chromatog.-mass spectrometry (GC-MS) anal. demonstrated that eucalyptol, camphor, and ¦Á-terpineol were the three main constituents of CEO. Results from in vitro antifungal activity assay revealed that the mycelial growths of all the five tested Fusarium solani, Fusarium culmorum, Fusarium trichothecioides, Fusarium sporotrioides, and Fusarium avenaceum were apparently affected by CEO. These findings not only provide a potential paradigm for the separation of plant essential oil, but also guarantee a promising utilization of the CEO for potato protection to control the Fusarium spp.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Frings, Marcus’s team published research in European Journal of Medicinal Chemistry in 2017-01-27 | CAS: 50578-18-2

Sulfoximines from a Medicinal Chemist’s Perspective: Physicochemical and in vitro Parameters Relevant for Drug Discovery. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Sulfoximines, sulfondiimides and sulfonimidamides are fascinating but not yet fully explored variants of the common sulfone or sulfonamide motif. In this study, we report the physicochem. and in vitro properties of sulfoximines and compare them with related analogs and isosteres. Furthermore, we present a matched mol. pair anal. of compounds from drug discovery projects within Boehringer Ingelheim. We demonstrate that the sulfoximine moiety is a chem. stable, comparatively polar and weakly basic functional group, often leading to favorable aqueous solubility, permeability and metabolic stability. Moreover, their addnl. vectors at nitrogen enable simple chem. modifications and thus facilitate exploration and fine-tuning of the mol. properties. We conclude that sulfoximines and their congeners do not exhibit any intrinsic flaw but significantly enrich the toolbox of medicinal chemists.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Xu, Qianhe’s team published research in Biochimica et Biophysica Acta, Molecular Cell Research in 2022-10-31 | CAS: 83730-53-4

Revealing PACMA 31 as a new chemical type TrxR inhibitor to promote cancer cell apoptosis. 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.

Thioredoxin reductase (TrxR) is a pivotal regulator of redox homeostasis, while dysregulation of redox homeostasis is a hallmark for cancer cells. Thus, there is considerable potential to inhibit the aberrantly upregulated TrxR in cancer cells to discover selective cancer therapeutic agents. Nevertheless, the structural types of TrxR inhibitors presented currently are still relatively limited. We herein report that PACMA 31, previously reported to inhibit protein disulfide isomerase (PDI), is a potent TrxR inhibitor. PACMA 31 possesses a pharmacophore scaffold that is structurally different from the announced TrxR inhibitors and exhibits effective cytotoxicity against cervical cancer cells. Our results reveal that PACMA 31 selectively inhibits TrxR over the related glutathione reductase (GR) and in the presence of reduced glutathione (GSH). Further studies with mutant enzyme and mol. docking suggest that the propynamide fragment of PACMA 31 interacts covalently with the selenocysteine residue of TrxR. Moreover, PACMA 31 effectively and selectively curbs TrxR activity in cells and further stimulates the production of reactive oxygen species (ROS) at low micromolar concentrations, which in turn triggers the accumulation of oxidized thioredoxin (Trx) and GSSG in cells. Follow-up studies demonstrate that PACMA 31 targets TrxR in cells to induce oxidative stress-mediated cancer cell apoptosis. Our results provide a new structural type of TrxR inhibitor that may serve as a useful probe for investigating the biol. of TrxR-implicated pathways, and uncover a new target of PACMA 31 that contributes to it becoming a candidate for cancer treatment.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Romero, Rodrigo’s team published research in Nature Cancer in 2020-06-02 | CAS: 83730-53-4

Keap1 mutation renders lung adenocarcinomas dependent on Slc33a1. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Approx. 20-30% of human lung adenocarcinomas (LUADs) harbor mutations in Kelch-like ECH-associated protein 1 (KEAP1) that hyperactivate the nuclear factor, erythroid 2-like 2 (NFE2L2) antioxidant program. We previously showed that Kras-driven Keap1-mutant LUAD is highly aggressive and dependent on glutaminolysis. Here we performed a druggable genome CRISPR screen and uncovered a Keap1-mutant-specific dependency on solute carrier family 33 member 1 (Slc33a1), as well as several functionally related genes associated with the unfolded protein response. Genetic and biochem. experiments using mouse and human Keap1-mutant tumor lines, as well as preclin. genetically engineered mouse models, validate Slc33a1 as a robust Keap1-mutant-specific dependency. Furthermore, unbiased genome-wide CRISPR screening identified addnl. genes related to Slc33a1 dependency. Overall, our study provides a rationale for stratification of patients harboring KEAP1-mutant or NRF2-hyperactivated tumors as likely responders to targeted SLC33A1 inhibition and underscores the value of integrating functional genetic approaches with genetically engineered mouse models to identify and validate genotype-specific therapeutic targets.

Keap1 mutation renders lung adenocarcinomas dependent on Slc33a1. 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

Lohier, Jean-Francois’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2017 | CAS: 50578-18-2

Mechanistic investigation of the NH-sulfoximination of sulfide. Evidence for ¦Ë6-sulfanenitrile intermediates. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

We report a new procedure for the preparation of NH-sulfoximines from sulfides using PIDA as an oxidant and ammonium carbamate as the ammonia source. Excellent yields were obtained with a wide range of sulfides. The formation of acetoxy- and methoxy-¦Ë6-sulfanenitrile as intermediates was proposed, both of which were converted to the NH-sulfoximine by the action of the solvent. The structure of these intermediates was confirmed by 1H, 13C and 15N NMR and HRMS anal.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Hendriks, Christine M. M.’s team published research in Advanced Synthesis & Catalysis in 2014 | CAS: 145026-07-9

N-Alkylations of NH-sulfoximines and NH-sulfondiimines with alkyl halides mediated by potassium hydroxide in dimethyl sulfoxide. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A general method for the N-alkylation of NH-sulfoximines and NH-sulfondiimines has been developed, employing alkyl bromides with KOH in DMSO at room temperature A variety of previously inaccessible N-alkylated sulfoximines and sulfondiimines was prepared in good to excellent yields (up to 97%). As an application, the conditions were used to access the biol. active Suloxifen.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem