M.W=200-250 | Page 6 of 25 | Heterocyclic Building Blocks-Benzoxazole

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

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.

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

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

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.

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

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

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

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

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

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

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

Chen, Feng’s team published research in Dalton Transactions in 2022 | CAS: 83730-53-4

Effect of cysteine thiols on the catalytic and anticancer activity of Ru(II) sulfonyl-ethylenediamine complexes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Authors have synthesized a series of novel substituted sulfonyl ethylenediamine (en) RuII arene complexes 1-8 of [(¦Ç6-arene)Ru(R1-SO2-EnBz)X], where the arene is benzene, HO(CH2)2O-Ph or biphenyl (biph), X = Cl or I, and R1 is Ph, 4-Me-Ph, 4-NO2-Ph or dansyl. The ‘piano-stool’ structure of complex 3, [(¦Ç6-biph)Ru(4-Me-phenyl-SO2-EnBz)I], was confirmed by x-ray crystallog. The values of their aqua adducts were determined to be high (9.1 to 9.7). Complexes 1-8 have antiproliferative activity against human A2780 ovarian, and A549 lung cancer cells with IC50 values ranging from 4.1 to >50¦ÌM, although, remarkably, complex 7 [(¦Ç6-biph)Ru(phenyl-SO2-EnBz)Cl] was inactive towards A2780 cells, but as potent as the clin. drug cisplatin towards A549 cells. All these complexes also showed catalytic activity in transfer hydrogenation (TH) of NAD+ to NADH with sodium formate as hydride donor, with TOFs in the range of 2.5-9.7 h-1. The complexes reacted rapidly with the thiols glutathione (GSH) and N-acetyl-L-cysteine (NAC), forming dinuclear bridged complexes [(¦Ç6-biph)2Ru2(GS)3]2- or [(¦Ç6-biph)2Ru2(NAC-H)3]2-, with the liberation of the diamine ligand which was detected by LC-MS. In addition, the switching on of fluorescence for complex 8 in aqueous solution confirmed release of the chelated DsEnBz ligand in reactions with these thiols. Reactions with GSH hampered the catalytic TH of NAD+ to NADH due to the decomposition of the complexes. Co-administration to cells of complex 2 [(¦Ç6-biph)Ru(4-Me-phenyl-SO2-EnBz)Cl] with L-buthionine sulfoximine (L-BSO), an inhibitor of GSH synthesis, partially restored the anticancer activity towards A2780 ovarian cancer cells. Complex 2 caused a concentration-dependent G1 phase cell cycle arrest, and induced a significant level of reactive oxygen species (ROS) in A2780 human ovarian cancer cells. The amount of induced ROS decreased with increase in GSH concentration, perhaps due to the formation of the dinuclear Ru-SG complex.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Xavier, Julia Karla A. M.’s team published research in Chemistry & Biodiversity in 2022-10-31 | CAS: 483-76-1

The volatile profiles and DNA barcodes of Lauraceae species from the Ocotea complex with occurrence in the Brazilian Amazon. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

The Ocotea complex accommodates most of the taxonomic diversity of Neotropical Lauraceae with economic importance and biol. potential attributed to their essential oils (EOs) and extracts However, the botanical taxonomy has had limitations due to the difficulty of identifying and delimiting species and genera. The chem. and mol. markers of Ocotea complex species in Para state, Brazil, were assessed according to their EO compositions and DNA sequences of matK, trnL-trnF, and ITS regions. The multivariate anal. of EOs constituents has classified them into two main clusters characterized by oils rich in (I) terpenoids and phenylpropanoids and (II) sesquiterpenes. We conducted a phylogenetic anal. of species based on DNA barcode sequences on the Bayesian Inference (PP: 0.70-1,0) and Maximum Likelihood (BS: 72-100 %). The comparison between the volatile profiles and phylogenetic data indicates two main groups for these species collected from the Ocotea complex.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Di Sotto, Antonella’s team published research in Industrial Crops and Products in 2022-09-01 | CAS: 483-76-1

Phytochemical and pharmacological profiles of the essential oil from the inflorescences of the Cannabis sativa L.. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Industrial hemp (Cannabis sativa L.) female inflorescences have long been considered as waste material in the hemp production chain. However, past studies focused on the valorization of female inflorescences as high-quality byproducts with promising health-promoting applications. In line with this evidence, the present research investigated the phytochem. and pharmacol. properties with a comparative approach on two essential oils (EOs) obtained from the inflorescences of the industrial hemp varieties Kompolti and Tisza. The EOs composition in terpenes and terpenophenols was determined The effects of the EOs in modulating the viability of different cancer cell lines was investigated. Whereas, in hypothalamic HypoE22 cells, the release of dopamine, norepinephrine, and serotonin was measured, as an index of neuromodulatory activity. Moreover, the EO mycostatic properties were explored towards different dermatophyte species. The prominent terpenes were iso-caryophyllene, ¦Á-humulene, and ¦Â-caryophyllene oxide in both Kompolti and Tisza EOs, whereas cannabidiol and cannabigerolic acid were the main terpenophenols, resp. Both essential oils inhibited the viability of different cancer cells; particularly, the essential oil of Tisza variety displayed a marked cytotoxicity in cholangiocarcinoma cells. A possible role of both terpenophenols and caryophyllane sesquiterpenes as bioactive anticancer compounds has been hypothesized. While cannabidiol could contribute to the stimulation of hypothalamic serotonin release by Kompolti EO. The essential oils also produced antimycotic effects, for which ¦Â-caryophyllene oxide could be partly responsible. Overall, the present findings highlight pharmacol. properties of Kompolti and Tisza EOs, which deserve further investigations and strengthen the interest in industrial hemp inflorescences as valuable source of bioactive extracts and compounds

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Porey, Arka’s team published research in Asian Journal of Organic Chemistry in 2016 | CAS: 145026-07-9

Direct N-acylation of sulfoximines with aldehydes by N-heterocyclic carbene catalysis under oxidative conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

An active acyl donor intermediate generated in-situ from an aldehyde by oxidative N-heterocyclic carbene (NHC)-catalysis enabled direct acylation of NH-sulfoximine, affording various N-acylsulfoximines in excellent yields. The reaction was performed with an inexpensive carbene catalyst and easily accessible bisquinone oxidant. This straightforward transformation demonstrated a broad substrate scope with respect to sulfoximines and aldehydes. Importantly, the method allowed amidation of several unactivated aliphatic aldehydes in good-to-moderate yields. Preparative synthesis of N-acylsulfoximine (up to >2 g) was achieved with this simple method.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem