M.W=200-250 | Page 11 of 25 | Heterocyclic Building Blocks-Benzoxazole

Li, Yan-Nan’s team published research in Food Control in 2022-07-31 | CAS: 483-76-1

Linalool, the main volatile constituent from Zanthoxylum schinifolium pericarp, prevents growth of Aspergillus flavus in post-harvest grains. 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.

Plant volatile organic compounds (PVOCs) have shown great potential as alternatives to synthetic insecticides or fungicides for stored grain management. Zanthoxylum schinifolium pericarp, a traditional Chinese spice, is conventionally buried in grain piles to prevent fungal spoilage of stored grains in China. However, the chem. basis and antifungal mechanism of PVOCs from Z. schinifolium pericarp by which they inhibit spoilage remain unclear. In this study, the effectiveness of PVOCs from Z. schinifolium pericarp against Aspergillus flavus growth in high-moisture wheat grains was studied under simulated storage conditions. The growth of A. flavus in the grains was inhibited in a dose-dependent manner. The chem. composition of PVOCs from Z. schinifolium pericarp was determined using gas chromatog.-mass spectrometry; linalool (50.31%) and D-limonene (20.92%) were the two main components. An antifungal experiment showed that 0.571 and 1.2 ¦ÌL/mL concentrations of linalool completely inhibited A. flavus growth upon vapor and liquid contact, resp. D-limonene showed much lower antifungal activity, indicating that linalool is responsible for the antifungal activity of PVOCs from Z. schinifolium pericarp. Linalool treatment disrupted the cell membrane of A. flavus, resulting in increased electrolyte leakage and A260nm in the culture supernatant. After 6 h of exposure to 1.2 ¦ÌL/mL linalool, metabolomic anal. revealed 90 differentially expressed metabolites in A. flavus mycelia, including 69 upregulated and 21 downregulated metabolites. It was speculated that linalool inhibited A. flavus by disrupting the permeability and integrity of cell membranes, tricarboxylic acid cycle, and ATP binding cassette transport and by inducing mitochondrial dysfunction and oxidative stress. This study shows the potential of PVOCs from Z. schinifolium pericarp as biofumigants for stored grain management and provides a new perspective on their antifungal mechanism against A. flavus growth.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Bohnen, Christian’s team published research in Organic Letters in 2015-06-19 | CAS: 145026-07-9

N-Trifluoromethylthiolated Sulfoximines. 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.

Air- and moisture-stable N-trifluoromethylthio sulfoximines, R1R2S(O):NSCF3 (R1 = Ph, cyclopropyl, Me, CF3, R2 = Ph, 4-BrC6H4, 2-ClC6H4, etc.), have been prepared from N-H-sulfoximines via the corresponding N-Br derivatives in excellent yields. The two-step process starts with an easy-to-perform bromination at the sulfoximine nitrogen, followed by a reaction with silver trifluoromethanethiolate. A one-pot reaction sequence allows difficult to prepare products to be obtained.

N-Trifluoromethylthiolated 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

Peng, Haibo’s team published research in Organic & Biomolecular Chemistry in 2015 | CAS: 145026-07-9

The N-silylation of sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

The copper-catalyzed N-silylation of sulfoximines was achieved in the presence of di-tert-Bu peroxide. Notably, alkyl, Ph and alkoxyl silanes were all suitable reaction partners. Mechanistic studies revealed that N-silyl acetamide serves as the intermediate.

The N-silylation 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

Jiang, Hui’s team published research in Frontiers in Pharmacology in 2022 | CAS: 83730-53-4

Bismuth reduces cisplatin-induced nephrotoxicity via enhancing glutathione conjugation and vesicular transport. 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.

Bismuth drugs have long been used against gastrointestinal diseases, especially the gastric infection of Helicobacter pylori. Cisplatin is a widely used anticancer drug that tends to accumulate at renal proximal tubules and causes severe nephrotoxicity. It was found that bismuth pretreatment reduces cisplatin-induced nephrotoxicity, but the mechanism of action remains unclear. To understand bismuth’s effect on renal tubules, we profiled the proteomic changes in human proximal tubular cells (HK-2) upon bismuth treatment. We found that bismuth induced massive glutathione biosynthesis, glutathione S-transferase activity, and vesicular transportation, which compartmentalizes bismuth to the vesicles and forms bismuth-sulfur nanoparticles. The timing of glutathione induction concurs that of bismuth-induced cisplatin toxicity mitigation in HK-2, and bismuth enhanced cisplatin sequestration to vesicles and incorporation into bismuth-sulfur nanoparticles. Finally, we found that bismuth mitigates the toxicity of general soft metal compounds but not hard metal compounds or oxidants. It suggests that instead of through oxidative stress reduction, bismuth reduces cisplatin-induced toxicity by direct sequestration.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Cheng, Ying’s team published research in Organic Letters in 2014-04-04 | CAS: 145026-07-9

Iron-Catalyzed Hetero-Cross-Dehydrogenative Coupling Reactions of Sulfoximines with Diarylmethanes: A New Route to N-Alkylated Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

An efficient iron-catalyzed C-N bond formation by hetero-cross-dehydrogenative coupling (CDC) between sulfoximines and diarylmethanes is described. The reaction shows good functional group tolerance and provides N-alkylated sulfoximines in moderate to good yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Karacelik, Ayca Aktas’s team published research in Chemistry & Biodiversity in 2022-10-31 | CAS: 483-76-1

Phytochemical Composition and Biological Activities of Angelica sylvestris L. var. stenoptera Ave-Lall ex Boiss.: An Endangered Medicinal Plant of Northeast Turkey. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Angelica sylvestris L. var. stenoptera Ave-Lall ex Boiss. (ASS) is an endangered endemic plant to Turkey. The objective of the study was to determine antioxidant activities, total phenolics, and phytochem. properties of methanolic extracts (MEs) and essential oil (EO) from ASS for the first time with the methods of 2,2-diphenyl-1-picrylhydrazyl (DPPH¡¤) radical scavenging activities, 2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS¡¤+), ferric reducing/antioxidant power (FRAP), the Folin-Ciocalteu, liquid chromatog.-tandem mass spectrometry (LC-MS/MS), and gas chromatog.-mass spectrometry (GC-MS), resp. The leaf extract of ASS was found to be the richest in phenolic content (543.91¡À6.33 GAE, ¦Ìg/mL) and showed the highest DPPH¡¤ and FRAP activities (IC50: 0.1140¡À0.0011 mg/mL, 675.62¡À15.01 ¦ÌM TEAC). EO of ASS root showed DPPH¡¤ and FRAP activities (IC50: 1.3248¡À0.0572 mg/mL, 346.67¡À12.75 ¦ÌM TEAC). 19 phenolics were detected in MEs of different parts of ASS by LC/MS/MS. In the chem. composition of ASS root EO by GC/MS, globulol (70.70 %) was found to be the major compound Our results indicate that ASS can be used a source of phytochems. and antioxidants for conservation and sustainability of endangered plants.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zimmermann, Rubens Candido’s team published research in Industrial Crops and Products in 2022-08-31 | CAS: 483-76-1

Insecticidal and antifungal activities of Melaleuca rhaphiophylla essential oil against insects and seed-borne pathogens in stored products. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Essential oils (EOs) are substances with biol. properties that can be used to inhibit insects and fungi in storage systems. The EOs from plants of the genus Melaleuca (Myrtaceae) show insecticidal and antifungal activities. However, so far, there are no reports regarding Melaleuca rhaphiophylla (Myrtaceae) EO. Therefore, we sought to investigate the insecticidal and antifungal activities of M. rhaphiophylla EO against storage pests and fungi. The plant’s EO was extracted in a vat using the steam drag method and analyzed by gas chromatog.-mass spectrometry. The insecticidal effect against Sitophilus zeamais and Sitophilus oryzae (Coleoptera: Curculionidae) was evaluated through contact and fumigation methods in order to select the optimized exposure route. Then, the lethal concentration (LC), lethal time (LT), and mean survival time (MST) were estimated Antifungal activity against Aspergillus flavus, Aspergillus niger, Aspergillus nomius and Fusarium graminearum was tested through volatilization and direct contact. Twenty-two compounds were identified in the chem. composition of M. rhaphiophylla EO and the major compounds were ¦Á-terpinene (6.46%), 1,8-cineole (11.54%), ¦Ã-terpinene (13.2%), terpinolene (28.72%) and terpinen-4-ol (19.82%). The fumigation method of application caused the highest mortality in both insects. The values for LC50 (90.55 and 72.88 of substance L-1 of air), LT50 (0.92 and 1.23 h) and MST (92.17 and 92.67 h) were similar between species (S. zeamais and S. oryzae, resp.). The volatilization method showed low fungicidal activity (< 30% of inhibition) against all isolates. The contact method showed an inhibition greater than 90%with higher toxicity for Aspergillus. Our results showed that M. rhaphiophylla EO has potential as an alternative product to control storage pests and fungi. Insecticidal and antifungal activities of Melaleuca rhaphiophylla essential oil against insects and seed-borne pathogens in stored products. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Alsabte, Ahmed’s team published research in Phytoparasitica in 2022-07-31 | CAS: 483-76-1

Effects of Volatile Organic Compounds (VOCs) emitted by citrus infested with Aonidiella aurantii on the predator Rhyzobius lophanthae attraction. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

This study identifies the volatile organic compounds (VOCs) emitted by citrus when infested with California red scale (Aonidiella aurantii) and determines which of these elicit behavior responses in the predator Rhyzobius lophanthae. Headspace solid-phase micro extractions (HS-SPME) technique combined with gas chromatog.-mass spectrometry (GC-MS) was used to identify compounds and Y-tube olfactometer to determine R. lophanthae behavior responses. According to the results, 22 VOCs were detected in infested citrus plants and some of them were increased in lemon, orange and tangerine by A. aurantii infestation. R. lophanthae individuals were attracted to infested citrus saplings. According to bioassays with the olfactometer, they were attracted to Me salicylate and D-limonene at dosages of 1 and 10¦ÌL/mL by using a Y-tube olfactometer. These results explain how citrus volatiles can affect the response of the predator R. lophanthae.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Lin, Zhuoying’s team published research in Journal of Experimental & Clinical Cancer Research in 2021-12-31 | CAS: 83730-53-4

FOXC1 promotes HCC proliferation and metastasis by Upregulating DNMT3B to induce DNA Hypermethylation of CTH promoter. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Forkhead box C1 (FOXC1), as a member of the FOX family, is important for promote HCC invasion and metastasis. FOX family protein lays a pivotal role in metabolism ROS is involved in tumor progression and is associated with the expression of lots of transcription factors. We next explored the mechanism underlying FOXC1 modulating the metabolism and ROS hemostasis in HCC. We used amino acids arrays to verify which metabolism is involved in FOXC1-induced HCC. The kits were used to detect the ROS levels in HCC cells with over-expression or down-expression of FOXC1. After identified the downstream target genes and candidate pathway which regulated by FOXC1 during HCC progression in vitro and in vivo, we used western blot, immunohistochem., bisulfite genomic sequencing, methylation-specific PCR, chromatin immunoprecipitation anal. and luciferase reporter assays to explore the relationship of FOXC1 and downstream genes. Moreover, the correlation between FOXC1 and target genes and the correlation between target genes and the recurrence and overall survival were analyzed in two independent human HCC cohorts. Here, we reported that FOXC1 could inhibit the cysteine metabolism and increase reactive oxygen species (ROS) levels by regulating cysteine metabolism-related genes, cystathionine ¦Ã-lyase (CTH). Overexpression of CTH significantly suppressed FOXC1-induced HCC proliferation, invasion and metastasis, while the reduction in cell proliferation, invasion and metastasis caused by the inhibition of FOXC1 could be reversed by knockdown of CTH. Meanwhile, FOXC1 upregulated de novo DNA methylase 3B (DNMT3B) expression to induce DNA hypermethylation of CTH promoter, which resulted in low expression of CTH in HCC cells. Moreover, low levels of ROS induced by N-acetylcysteine (NAC) which is an antioxidant inhibited the cell proliferation, migration, and invasion abilities mediated by FOXC1 overexpression, whereas high levels of ROS induced by L-Buthionine-sulfoximine (BSO) rescued the suppression results mediated by FOXC1 knockdown. Our study demonstrated that the overexpression of FOXC1 that was induced by the ROS dependent on the extracellular regulated protein kinases 1 and 2 (ERK1/2)- phospho-ETS Transcription Factor 1 (p-ELK1) pathway. In human HCC tissues, FOXC1 expression was pos. correlated with oxidative damage marker 8-hydroxy-2′-deoxyguanosine (8-OHdG), p-ELK1 and DNMT3B expression, but neg. correlated with CTH expression. HCC patients with pos. co-expression of 8-OHdG/FOXC1 or p-ELK1/FOXC1 or FOXC1/DNMT3B had the worst prognosis, whereas HCC patients who had pos. FOXC1 and neg. CTH expression exhibited the worst prognosis. In a word, we clarify that the pos. feedback loop of ROS-FOXC1-cysteine metabolism-ROS is important for promoting liver cancer proliferation and metastasis, and this pathway may provide a prospective clin. treatment approach for HCC.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Cho, Gae Young’s team published research in Journal of Organic Chemistry in 2005-03-18 | CAS: 145026-07-9

Synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

The asym. synthesis and chem. modification of p-bromophenyl Me sulfoximine is described. Starting from p-bromophenyl menthyl sulfinate, enantiopure 4-bromophenyl Me sulfoximine can be obtained in a short reaction sequence involving a well-established substitution reaction followed by stereospecific imination with O-mesitylenesulfonylhydroxylamine (MSH). Palladium-catalyzed Buchwald/Hartwig, Suzuki, and Stille coupling reactions allow a broad variation of the sulfoximine aryl group, which is otherwise difficult to achieve. The incorporation of a p-morpholino-substituted derivative into a pseudo-tripeptide, e.g., I. demonstrated the applicability of the sulfoximine derivatives

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem