December 7, 2022 | Heterocyclic Building Blocks-Benzoxazole

Wang, Jian’s team published research in Chemistry Letters in 2022 | CAS: 145026-07-9

TEMPO/PhI(OAc)2-mediated Direct Sulfoximination of Benzoxazoles under Metal-free 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.

A metal-free reaction system consisting of TEMPO and PhI(OAc)2 for the oxidative C-N coupling of benzoxazoles with NH-sulfoximines had been developed to obtain arylsulfoximines I [R1 = H, 5-Cl, 7-Br, etc.; R2 = Me, Et, n-Bu, Bn; R3 = Ph, 4-FC6H4, 2-BrC6H4, etc.]. The reaction could proceed under ambient atm. without any metal catalyst at room temperature to afford the corresponding 2-iminoazoles in moderate to high yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Feng, Tao’s team published research in Synthetic Communications in 2021 | CAS: 4381-25-3

Photocatalytic N-benzylation of NH-sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

(S-Methylsulfonimidoyl)benzene (BD302898) 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: 83730-53-4 and 1621962-30-8.

N-Benzylation of NH-sulfoximines via visible light photocatalysis is realized. Under mild reaction conditions, photocatalyst promotes the direct cross-coupling of NH-sulfoximines with benzyl bromides to form N-benzyl sulfoximines. Superbases which are usually used in reported coupling of NH-sulfoximines with alkyl halides were not needed. This method is also suitable for the synthesis of N-allyl sulfoximines.

Photocatalytic N-benzylation of NH-sulfoximines. 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

Wang, Jianping’s team published research in Tetrahedron Letters in 2017-01-25 | CAS: 50578-18-2

Eaton’s reagent-mediated metal-free and efficient synthesis of NH-sulfoximines. 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.

NH-sulfoximines were prepared efficiently from corresponding sulfoxides in the presence of sodium azide and Eaton’s reagent. This metal-free and efficient methodol. was applicable to a wide variety of functionalized sulfoxides to afford NH-sulfoximines in good to excellent yields with shorter reaction time than previously reported methods.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Huang, Zeqian’s team published research in Chemical Engineering Journal (Amsterdam, Netherlands) in 2020-11-01 | CAS: 83730-53-4

Bone-targeted oxidative stress nanoamplifier for synergetic chemo/chemodynamic therapy of bone metastases through increasing generation and reducing elimination of ROS. 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.

The treatment of bone metastases remains an enormous challenge in clin. application. Strategies utilizing reactive oxygen species (ROS) to induce cell death show great potential for enhanced cancer therapy. Thus, for the first time, a versatile alendronate (ALN)-functionalized and cinnamaldehyde (CA)-loaded nanoscale coordination polymer (denoted as CA/ALN@FcB) based on 1,1¡ä-ferrocenedicarboxylicacid (Fc) and L-buthionine-sulfoximine (BSO) was properly fabricated as an oxidative stress nanoamplifier for synergetic chemo/chemodynamic therapy of bone metastases. With appropriate size and strong bone affinity of ALN, CA/ALN@FcB can preferentially accumulate in the bone metastatic site. In this nanoamplifier, CA can act as the ROS generator to produce ROS to damage cancer cells and boost intracellular hydrogen peroxide (H2O2) level, which can be converted into hydroxyl radical (?OH) with the catalysis of Fc via Fenton reaction. Simultaneously, glutathione (GSH) depletion mediated by BSO can inhibit ROS elimination to maintain H2O2 level and ?OH amount, ultimately leading to superior antitumor effect. Both in vitro and in vivo results demonstrated the self-enhanced synergetic chemo/chemodynamic therapy of CA/ALN@FcB. Such a nanoamplifier can generate and maintain sufficient ROS without the introduced external light triggering, exactly addressing the dilemma posed by fewer light penetration as well as the uncertain location of bone metastases. This study not only provides a novel strategy to achieve excellent cancer therapy by boosting ROS generation and simultaneously inhibiting ROS elimination, but also creates the precedent for the application of chemodynamic therapy for bone metastases treatment.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Skoric, Marijana’s team published research in Industrial Crops and Products in 2022-09-15 | CAS: 483-76-1

Bioactivity-guided identification and isolation of a major antimicrobial compound in Cistus creticus subsp. creticus leaves and resin “”ladano””. 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.

Cistus creticus subsp. creticus is a shrubby Mediterranean plant used since ancient times in folk medicine for the treatment of different diseases. C. creticus extracts and resin contain different types of secondary metabolites, such as terpenoids (predominantly labdane type diterpenoids), and phenylpropanoids. Growth conditions seem to influence the content of labdane-type diterpenes and flavan-3-ols in leaves of C. creticus subsp. creticus. Histochem. staining of leaves ¡ä trichomes and comprehensive phytochem. characterization of resin, leaves and their exudates, indicated that long-stalked capitate trichomes of C. creticus subsp. creticus, grown both in vitro (IV) and in greenhouse (GH), are capable of producing bioactive oleoresin-related terpenoids and phenylpropanoids compounds Bioactivity-guided approach was implemented in search for the major antibacterial compound in C. creticus resin against two Gram-neg. (Escherichia coli and Pseudomonas aeruginosa) and two Gram-pos. bacteria (Bacillus cereus and Micrococcus flavus). Bioautog. assay on TLC plates with separated components of Cistus resin extract, revealed a pronounced zone of microbial growth inhibition, corresponded to a highly active compound with Rf values of 0.45, structurally characterized and identified as ent-3¦Â-acetoxy-13-epi-manoyl oxide. This finding opens the route for focusing on isolation and functional characterization of genes involved in the biosynthesis of ent-3¦Â-acetoxy-13-epi-manoyl oxide and its precursor ent-3¦Â-hydroxy-13-epi-manoyl oxide, with the aim to establish sustainable in vitro biotechnol. protocols for its large-scale production in homologous and heterologous plant and microbial hosts.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zhao, Mu’s team published research in Food Chemistry in 2022-08-15 | CAS: 483-76-1

Characterization of key aroma-active compounds in Hanyuan Zanthoxylum bungeanum by GC-O-MS and switchable GC x GC-O-MS. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

The present study sought to characterize the composition of volatile aroma compounds and key aroma-active compounds of dried Hanyuan Zanthoxylum bungeanum. The volatile aroma compounds were analyzed by the solid-phase microextraction (SPME) combined with gas chromatog.-olfactometry-mass spectrometry (GC-O-MS) and two-dimensional comprehensive gas chromatog.-olfactometry-mass spectrometry (GC x GC-O-MS). The key aroma-active compounds were analyzed by the aroma extract dilution anal. and odor activity value. A total of 72 volatile compounds were identified by GC-O-MS, of which 28 were aroma-active. Meanwhile, 116 volatile compounds were identified by GC x GC-O-MS, of which 43 were aroma-active. These results revealed that myrcene, (+)-limonene, (E)-¦Â-ocimene, ¦Â-cubebene, Germacrene D, cineole, linalool, and linalyl acetate were the key aroma-active compounds of dried Hanyuan Zanthoxylum bungeanum.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Chen, Xiao Yun’s team published research in Organic Letters in 2014-07-18 | CAS: 145026-07-9

Copper-Catalyzed N-Alkynylations of Sulfoximines with Bromoacetylenes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

N-Alkynylated sulfoximines have been obtained by copper-catalyzed cross-coupling reactions starting from NH-sulfoximines and bromoacetylenes in moderate to good yields. The reaction conditions are mild, and the substrate scope is wide.

Copper-Catalyzed N-Alkynylations of Sulfoximines with Bromoacetylenes. 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

Coskun, Yasemin’s team published research in Flavour and Fragrance Journal in 2022-09-30 | CAS: 483-76-1

Influence of biotic and abiotic elicitors on artemisinin, quercetin, caffeic acid and essential oil production in Artemisia dracunculus L.. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Artemisia dracunculus L. (tarragon) is valuable for its medicinal uses such as antimalarial, antibacterial and anticancer. Biotechnol. methods need to be developed for the production of phytochem. compounds in plants with high and stable quality. Elicitation is one of the best tools for increasing secondary metabolites in various in vitro cultures. The current study determines the application of different concentrations of chitosan (25, 50, 100 and 150 mg/L) and UV-C (5/10, 5/15, 10/10 and 10/15 min/cm) as biotic and abiotic elicitors in tarragon leaf callus cultures. The main aim was to increase the accumulation of artemisinin, quercetin, caffeic acid and essential oil content. For this purpose, callus formation rates and morphol. features were also investigated. The results show that highest callus formation, weight and diameter were observed in UV-C treated cultures. HPLC analyses revealed significant high accumulation of artemisinin (1.9¦Ìg/g), quercetin (4.2¦Ìg/g) and caffeic acid (2.9¦Ìg/g) contents in 5/10 min/cm UV-C treated samples. GC-MS analyses of callus cultures indicate high production of total amount of monoterpenes in all chitosan applications, best in 25 mg/L (90.75%). The major compound was ¦Â-phellandrene in chem. composition of tarragon (19.61%) and increased the most in 10/15 min/cm UV-C application (43.39%). The results show that the phys. elicitor UV-C can be effectively used in tarragon callus culture for enhancing pharmacol. active compounds in industrial production

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

Essential Oil Compositions and Antimicrobial Activity of the Leaves and Rhizomes of Alpinia calcicola from Vietnam. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Essential oil compositions and antimicrobial activity of leaves and rhizomes of Alpinia calcicola rom vietnam. The min. inhibitory concentration (MIC) and median inhibitory concentration (IC50) values were measured by the microdilution broth susceptibility assay. The essential oils from the leaves and rhizomes of A. calcicola displayed antimicrobial activity against five of the seven tested microorganisms

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Lin, Chun-Ya’s team published research in Biochemical Systematics and Ecology in 2022-12-31 | CAS: 483-76-1

Chemotaxonomic identification of Chamaecyparis formosensis Matsumura and Chamaecyparis obtusa var. formosana (Hayata) Rehder using characteristic compounds of wood essential oils. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Chamaecyparis formosensis Matsumura and C. obtusa var. formosana (Hayata) Rehder are important, precious, and well-known species grown in Asia. Renowned for excellent natural durability, their wood logs are regularly used as quality building materials or furniture. However, these two species have similar appearances, e.g., leaf, twig, wood, hardly distinguishable by the naked eye. The purpose of the present study is to phytochem. differentiate these two species using volatile compounds from the woods. Wood essential oils were obtained by 6-h hydrodistillation The chem. composition was identified by GC-MS, and semi-quantification was carried out to determine the content of each compound Furthermore, compounds with a significantly higher content than those of the other species were screened by t-test and principal component anal. (PCA). Results from semi-quantification and t-test showed that C. formosensis contained higher content of cis-myrtanol (ratio 37.1 ¡À 19.8), chamaecynone (11.0 ¡À 6.7), and ¦Á-eudesmol (8.5 ¡À 7.9), while C. obtusa var. formosana comprised mainly of ¦Á-terpineol (30.2 ¡À 10.1) and borneol (24.0 ¡À 16.1). Moreover, PCA results showed that the representative compounds of C. formosensis were cis-myrtanol and chamaecynone, while those of C. obtusa var. formosana were ¦Á-terpineol, borneol, and ¦Á-cadinol. Taken together, the above-mentioned results suggested significant compositional differences between these two species. For distinguishing the two kinds of wood, C. formosensis should be easily identified by its two characteristic compounds: cis-myrtanol and chamaecynone; while C. obtusa var. formosana could also be distinguished by its characteristic compounds: ¦Á-terpineol and borneol.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem