M.W=200-250 | Page 2 of 25 | Heterocyclic Building Blocks-Benzoxazole

Knany, Alaa’s team published research in Free Radical Biology & Medicine in 2020-11-20 | CAS: 83730-53-4

S-nitrosocysteine and glutathione depletion synergize to induce cell death in human tumor cells: Insights into the redox and cytotoxic mechanisms. 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.

Nitric oxide (NO)-dependent signaling and cytotoxic effects are mediated in part via protein S-nitrosylation. The magnitude and duration of S-nitrosylation are governed by the two main thiol reducing systems, the glutathione (GSH) and thioredoxin (Trx) antioxidant systems. In recent years, approaches have been developed to harness the cytotoxic potential of NO/nitrosylation to inhibit tumor cell growth. However, progress in this area has been hindered by insufficient understanding of the balance and interplay between cellular nitrosylation, other oxidative processes and the GSH/Trx systems. In addition, the mechanistic relationship between thiol redox imbalance and cancer cell death is not fully understood. Herein, we explored the redox and cellular effects induced by the S-nitrosylating agent, S-nitrosocysteine (CysNO), in GSH-sufficient and -deficient human tumor cells. We used L-buthionine-sulfoximine (BSO) to induce GSH deficiency, and employed redox, biochem. and cellular assays to interrogate mol. mechanisms. We found that, under GSH-sufficient conditions, a CysNO challenge (100-500¦ÌM) results in a marked yet reversible increase in protein S-nitrosylation in the absence of appreciable S-oxidation In contrast, under GSH-deficient conditions, CysNO induces elevated and sustained levels of both S-nitrosylation and S-oxidation Experiments in various cancer cell lines showed that administration of CysNO or BSO alone commonly induce minimal cytotoxicity whereas BSO/CysNO combination therapy leads to extensive cell death. Studies in HeLa cancer cells revealed that treatment with BSO/CysNO results in dual inhibition of the GSH and Trx systems, thereby amplifying redox stress and causing cellular dysfunction. In particular, BSO/CysNO induced rapid oxidation and collapse of the actin cytoskeletal network, followed by loss of mitochondrial function, leading to profound and irreversible decrease in ATP levels. Further observations indicated that BSO/CysNO-induced cell death occurs via a caspase-independent mechanism that involves multiple stress-induced pathways. The present findings provide new insights into the relationship between cellular nitrosylation/oxidation, thiol antioxidant defenses and cell death. These results may aid future efforts to develop NO/redox-based anticancer approaches.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Sumunnee, Ladawan’s team published research in Organic & Biomolecular Chemistry in 2018 | CAS: 145026-07-9

Persulfate-promoted oxidative C-N bond coupling of quinoxalinones and NH-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.

The persulfate-meditated oxidative C-N bond coupling of the C-H bond of quinoxalinones and the N-H bond of NH-sulfoximines is reported. The reaction proceeds smoothly under transition metal-free conditions and provides good to excellent yields of sulfoximidoyl-functionalized quinoxalinone products under mild conditions. The optimized conditions were found to be suitable for a range of sulfoximine and quinoxalinone substrates. This reaction offers a new and convenient strategy to directly install the sulfoximine moiety into the C3 position of quinoxalinone.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Luz, Tassio Romulo Silva Araujo’s team published research in Experimental Parasitology in 2022-12-31 | CAS: 483-76-1

Seasonal variation in the chemical composition and larvicidal activity against Aedes aegypti L. of essential oils from Brazilian Amazon. 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.

Arthropod-borne viral diseases are important public health threats in tropical countries. In the Americas, diseases such as Dengue, Zika, Chikungunya, Mayaro, and Yellow fever, which are mainly transmitted by Aedes aegypti L. are responsible for high rates of morbidity and mortality in the populations. The incidence of those viruses has increased in the last few years, due to the decrease of vector control programs, as well as, the resistance of this vector in front of many products that have been used in this proposal. Plant-based products such as essential oils are a promising alternative for Ae. aegypti control. In this context, the present work aims to investigate the seasonality effect on the larvicidal potential and safety of essential oils from 4 endemic plants of the Brazilian Amazon, as well as to verify their larvicidal activity and safety. The species were collected in the rainy and dry periods (Eugenia uniflora L., Lantana camara L., Ocimum basilicum L., Plectranthus neochilus Schlrt.). The essential oils were extracted by hydrodistillation and chem. composition was determined by gas chromatog. coupled to mass spectrometry. The larvicidal activity was performed according to the methodol. recommended by the World Health Organization. The safety of the oil use was evaluated against two non-target organisms: Artemia salina Leach and Danio rerio Hamilton Buchanan. Essential oils of E. uniflora, L. camara, O. basilicum, P. neochilus, presented as major compounds, in both collection periods, the substances Curzerene, Germacrene D, Me chavicol and, Caryophyllene, resp. However, showed a qual. and quant. variation of this composition All oils showed promising results against Ae. aegypti larvae with LC50 between 41.7 and 275.8 ¦Ìg/mL. They were efficient against Ae. aegypti but showed high toxicity to non-target organisms, requiring addnl. safety studies. Despite these results showing that those essential oils are not ideal larvicides because they presented toxicity to non-target organisms, bioprospection is a promising tool to help reduce the dissemination of arboviruses, and they can use in artificial breeders of Ae. aegypti larvae, where water will not be reused for human consumption or have other cohabiting organisms.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

He, Li-Li’s team published research in Scientia Horticulturae (Amsterdam, Netherlands) in 2023-01-27 | CAS: 483-76-1

In vitro and in vivo antifungal activity of Cymbopogon citrates essential oils from different climate conditions against Botrytis cinerea. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Essential oils (EOs) are natural, volatile and aromatic substances extracted from some specific plants. EOs are the secondary metabolite of plants and usually varies with different plants and climate conditions, even in the same plant species but different climate conditions. The antifungal properties of EOs from medicinal as well as other edible plants have been recognized for very long time. Cymbopogon citratus oil, which is used as a food flavoring agent, possesses a broad spectrum of in vitro antifungal activities attributed to the high content of monoterpenoids such as ¦Á-Citral and ¦Â-Citral. In this study we focused on the changes of components of EOs in C. citratus growing in different climate conditions and their antifungal activities as well. The samples of C. citrates, fresh and dried, obtained from five different climate conditions in Southern and Southwestern China (Kunming, Jinghong, Fangchenggang, Zengcheng, Yuxi). The C. citrates EOs were extracted by the steam distillation method and analyzed by gas chromatog. coupled with mass spectrometry (GC-MS) and gas chromatog.-flame ionization detection (GC-FID). The results showed that the content of ¦Á-Citral was the highest in ten EOs. Fresh and dried C. citratus EOs accounted for 38.7% and 43.3% in Zengcheng, resp. However, fresh and dried C. citratus EOs accounted for 24.2% and 23.1% in Kunming. The effects of C. citratus EOs from different climate conditions against Botrytis cinerea were studied. All EOs had good inhibition against mycelial growth and spore germination of B. cinerea in vitro. At 15.63 mg/L, the inhibition of mycelial growth with the dried C. citrates EO from Zengcheng was significantly greater than that with the other EOs, with an inhibitory effect of 96.3%. It completely inhibited the mycelial growth of B. cinerea at 31.25 mg/L. Ten EOs also had good inhibitory effects on the rotten area of cherry tomatoes infected by B. cinerea in vivo. At 125 mg/L, the decay area of cherry tomatoes was reduced by more than 90%. The results indicated that the constituents in EOs of C. citrates are different from one growing place to another. The EOs of C. citrates may be considered as potential candidates to protect postharvest fruit from B. cinerea damage.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Tsao, Nai-Wen’s team published research in Journal of Wood Science in 2022-12-31 | CAS: 483-76-1

Composition analysis of exudates produced by conifers grown in Taiwan and their antifungal activity. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Exudates are involved in the defense mechanism of trees; they could work against insects or microorganisms through a phys. or chem. system. The main components of exudates are terpenoids. This study identified the main compounds of exudates from 13 conifers of Taiwan using gas chromatogram-mass spectrometry (GC-MS) and spectroscopic anal. The results revealed that the main volatiles were ¦Á-pinene, ¦Â-ocimene, ¦Â-pinene, sabinene, and caryophyllene. On the other hand, the main nonvolatile compounds were diterpenoids, which were classified into three skeletons (abietane-, labdane-, and pimarane-types). Among these, abietane-type presented in Pinaceae and in most of Cupressaceae; labdane-type presented in Pinaceae and in all of Cupressaceae and Araucariaceae; pimarane-type existed in both Pinaceae and Cupressaceae. Furthermore, the epigenetics of conifers anal. results by GC-MS and heteronuclear single quantum coherence (HSQC) of NMR (NMR) fingerprints were similar to traditional taxonomy classification; it indicated that exudates chemotaxonomy by using GC-MS and HSQC profiling is a useful technol. to classify the conifers. Besides, the exudates of Pinus elliottii, Pinus taiwanensis, Calocedrus macrolepis and Chamaecyparis formosensis possessed the strong antifungal activity. For white-rot fungus, Trametes versicolor, Pinus morrisonicola, Chamaecyparis obtusa, and Araucaria heterophylla exhibited the higher antifungal index. For brown-rot fungus, Laetiporus sulfureus, Pinus elliottii, Pinus morrisonicola, and Chamaecyparis formosensis revealed a good antifungal activity.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Shi, Yali’s team published research in Food Chemistry in 2022-11-15 | CAS: 483-76-1

Comprehensive investigation on non-volatile and volatile metabolites in four types of green teas obtained from the same tea cultivar of Longjing 43 (Camellia sinensis var. sinensis) using the widely targeted metabolomics. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

In this study, we produced roasted, baked, steamed, and sun-dried green tea products using the same batch of fresh tea leaves (FTL) of Longjing 43 (Camellia sinensis var. sinensis), and explored processing effects on the metabolic profiles of four types of green teas (FGTs) using the widely targeted metabolomics. Results showed that 146 differential metabolites including flavonoids, amino acids, lipids, and phenolic acids were screened among 1034 non-volatiles. In addition, nineteen differential metabolites were screened among 79 volatiles. Most of non-volatiles and volatiles metabolites changed notably in different manufacturing processes, whereas there were no significant differences (p>0.05) in the levels of total catechins between FGTs and FTL. The transformation of metabolites was the dominant trend during green tea processing. The results contribute to a better understanding of how the manufacturing process influences green tea quality, and provide useful information for the enrichment of tea biochem. theory.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zhang, Shiyu’s team published research in Toxicology and Applied Pharmacology in 2022-05-15 | CAS: 83730-53-4

DNA damage by reactive oxygen species resulting from metabolic activation of 8-epidiosbulbin E acetate in vitro and in vivo. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

8-Epidiosbulbin E acetate (EEA), a furan-containing diterpenoid lactone, is one of main component of Dioscorea bulbifera L.(DBL). It has been reported that EEA induces severe hepatotoxicity in mice and that its hepatotoxicity is associated with metabolic activation. The present study demonstrated that exposure to EEA (50, 100 or 200 ¦ÌM) induced DNA damage, including significant DNA fragmentation, increases of tail DNA and olive tail moment, H2AX phosphorylation and PARP-1 activation, in cultured mouse primary hepatocytes. Similar observation was obtained in mice administered EEA at 50, 100 or 200 mg/kg. Pre-treatment with 10 ¦ÌM ketoconazole (KTC), 200 ¦ÌM vitamin C (VC), or 200 ¦ÌM glutathione Et ester (GSH-OEt) reversed the over-production of reactive oxygen species (ROS) induced by EEA and attenuated susceptibility of hepatocytes to EEA-induced cytotoxicity and DNA damage in mouse primary hepatocytes. In contrast, pre-treatment with 1.0 mM L-buthionine sulfoximine (BSO) potentiated over-production of ROS, cytotoxicity and DNA damage induced by EEA. In summary, EEA induced DNA damage in cultured primary hepatocytes and the liver of mice. ROS, possibly along with DNA alkylation, participated in the observed DNA damage.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Pham, Ty Viet’s team published research in Natural Product Communications in 2022-09-30 | CAS: 483-76-1

Volatile Constituents and Anti-Osteoporotic Activity of the n-Hexane Extract From Homalomena gigantea Rhizome. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

This study analyzed the chem. composition and anti-osteoporosis activity of the n-hexane extract of Homalomena gigantea rhizome. Sixty compounds, representing 92.0% of the extract, were identified by gas chromatog.-mass spectrometry. Linalool (15.3%), oplopanone (9.8%), (¦¥)-¦Á-atlantone (5.6%), khusinol acetate (5.4%), bullatantriol (4.3%), and ¦Â-sitosterol (3.8%) were the main constituents. The anti-osteoporotic activity of the n-hexane extract was determined by measuring alk. phosphatase (ALP) activity, collagen content, and the mineralization of MC3T3-E1 cells. At concentrations of 4.0 and 20.0 ¦Ìg/mL, the n-hexane extract increased ALP activity by 8.2% and 23.7%, and increased collagen secretion by MC3T3-E1 cells by 114.9% and 112.4%, resp. At 4 ¦Ìg/mL, the extract significantly promoted the mineralization of MC3T3-E1 cells by as much as 133.2% compared to the neg. control. These results suggested that H. gigantea rhizome contains a natural anti-osteoporotic compound

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Baranwal, Siddharth’s team published research in Asian Journal of Organic Chemistry in 2021-07-31 | CAS: 145026-07-9

Selenium Dioxide Promoted ¦Á-Keto N-Acylation of Sulfoximines Under Mild Reaction Conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A practical method for the synthesis of ¦Á-ketoamides of sulfoximines I [R1 = Ph, 4-MeC6H4, Bn, etc.; R2 = Me, Et, Ph, etc.; R3 = H, 4-F, 2-Cl, etc.] was developed from NH-sulfoximines and acetophenones using selenium dioxide as an oxidant. The reactions proceeded under mild conditions in the absence of any additives and provided good to excellent yields of ¦Á-keto-N-acylsulfoximines. Moreover, the optimized condition was well-suited to the task of ¦Á-ketoacylation of sulfoximines with phenylacetaldehyde and arylacetylenes. ¦Á-Hydroxy N-acylsulfoximines were obtained in good yields from ¦Á-keto N-acylsulfoximines via reduction or Grignard reactions.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Chen, Lu’s team published research in Organic & Biomolecular Chemistry in 2022 | CAS: 145026-07-9

Rhodium(III)-catalyzed cascade C-H functionalization/annulation of sulfoximines with iodonium ylides for the synthesis of cyclohexanone-1,2-benzothiazines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A highly efficient Rh(III)-catalyzed cascade C-H activation/annulation of sulfoximines 2-R-3-R1-4-R2C6H2S(O)(=NH)R3 (R = H, Me, OMe, Cl, Br; R1 = H, Me, OMe, Br, NO2; R2 = H, F, CN, C(O)Me, etc.; R1R2 = -CH=CH-CH=CH-; R3 = Me, Et, Bn, etc.) with iodonium ylides I (n = 0, 1; R4 = H, Me, Ph; R5 = H, Me) under metal-oxidant-free conditions has been reported. The fused cyclohexanone-1,2-benzothiazine scaffolds II is readily achieved with a one-pot process in this reaction. This protocol exhibits good functional group tolerance and moderate to excellent yields. Addnl., the olefination of the target product II (n = 1; R = R1 = R2 = H; R3 = Me; R4 = R5 = H) illustrates the promising usefulness of this strategy.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem