Heterocyclic Building Blocks-Benzoxazole

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

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.

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

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

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.

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

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

Terhorst, Steven’s team published research in Organic Letters in 2022-06-17 | CAS: 4381-25-3

Sulfonimidamides by Sequential Mechanochemical Chlorinations and Aminations of Sulfinamides. 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.

Here, the first mechanochem. synthesis of sulfonimidamides, e.g., I was reported. The one-pot, two-step method requires neither a solvent nor inert conditions. In a mixer mill, sulfinamides ArS(O)NH(R) (Ar = Ph, 4-methylphenyl; R = pivaloyl, Boc) are rapidly converted to sulfonimidoyl chlorides ArS(O)NR(Cl) by oxidative chlorination with N-chlorosuccinimide (NCS). Subsequent substitutions with amines such as benzyl amine, 3-methyl-1H-pyrazole, piperazine, etc. provides a wide range of diversely substituted sulfonimidamides.

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

(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.

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

Rajbongshi, Kamal K.’s team published research in Synthesis in 2020-04-30 | CAS: 145026-07-9

Microwave-Accelerated N-Acylation of Sulfoximines with Aldehydes under Catalyst-Free Conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

An efficient catalyst-free radical cross-coupling reaction between sulfoximines R1S(O)(=NH)R2 [R1 = Me, Ph, 4-methoxyphenyl, 4-bromophenyl; R2 = Me, Ph; R1R2 = -(CH2)4-] and aromatic aldehydes R3CHO (R3 = 2-chlorophenyl, naphthalen-1-yl, furan-2-yl, etc.) was developed. The reaction took place in the presence of N-bromosuccinimide as the radical initiator under microwave irradiation to afford the corresponding acylated sulfoximines R1S(O)(R2)=NC(O)R3 in moderate to excellent yields (27 examples). This protocol is proved to be rapid, easy to handle, and applicable to a broad scope of substrates.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Baranauskiene, Renata’s team published research in Food Research International in 2022-10-31 | CAS: 483-76-1

Valorisation of Roman chamomile (Chamaemelum nobile L.) herb by comprehensive evaluation of hydrodistilled aroma and residual non-volatile fractions. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Valorization of botanicals for the development of natural food-grade ingredients is an important task in terms of sustainability and processing waste reduction In this study, Roman chamomile (Chamaemelum nobile L.) herb was collected at six different vegetation phases in the period 26 May – 23 August 2019 and subjected to biorefining into the several valuable fractions. The yield of hydro-distilled essential oil (EO) was in the range of 0.22% (intensive vegetative growth) to 0.80% (full flowering). Angelic, isobutyric, butyric and methacrylic acid esters and some monoterpene and sesquiterpene derivatives were the major EO constituents: 3-methylpentyl angelate (20.11-27.56%), methallyl angelate (7.28-10.33%), isoamyl angelate (5.57-9.02%), iso-Bu angelate (4.84-6.79%), 2-methylbutyl angelate (3.11-6.32%), 3-methylamyl methacrylate (5.04-6.17%), 3-methylpentyl isobutyrate (4.29-6.64%), 3-methylamyl isobutyrate (4.29-6.64%), ¦Á-pinene (1.61-6.37%) and pinocarvone (1.46-4.67%). In order to valorize water soluble and solid EO distillation residues their antioxidant potential was evaluated by several in vitro assays: water extracts were considerably stronger antioxidants than acetone extracts isolated from the solid residues. Water extracts of the plants collected at flowering phases were the strongest antioxidants; their TPC, FRAP and ORAC values were up to 143.2 mg gallic acid equivalent/g, 650, and 5601 ¦Ìmol TE/g dry extract, resp., while effective concentrations (EC50) of DPPH? and ABTS?+ scavenging, were down to 0.59 and 0.49 mg/mL, resp. Among 7 tentatively identified by UPLC/Q-TOF/MS phenolic constituents the intensity of mol. ion of 3,5-dicaffeoyl quinic acid was the largest. The results obtained may assist for developing flavorings, antioxidants and health beneficial preparations from C. nobile extracts

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Alimi, Dhouha’s team published research in Waste and Biomass Valorization in 2022-10-31 | CAS: 483-76-1

Valorization of Volatile Oils and Some Crude Extracts from the Tunisian Plants Juniperus communis and Origanum majorana for the Control of Hyalomma scupense (Acari: Ixodidae). Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

This investigation tested the in vitro acaricidal activity of essential oils and raw extracts of Juniperus communis and Origanum majorana compared with the synthetic acaricide amitraz against various stage of Hyalomma scupense cattle tick. The hydrodistilation technique was used to extract essential oils, while chem. components in the plants were obtained using solvents of increasing polarity (hexane, Et acetate and methanol). The evaluation on H. scupense was performed with the adult immersion test at concentrations ranging from 1.25 to 10 mg/mL and the larval packet test from 0.625 to 10 mg/mL. Qual. anal. of J. communis essential oil showed ¦Á-pinene (52.31%), ¦Ä 3-carene (12.77%), ¦Â-phellandrene (7.60%), 1,8 cineole (6.95%) and ¦Á-terpinenyl acetate (6.58%) as the major chem. components. O. majorana oil was mainly composed of 4-terpineol (23.05%), Cis-Thujan-4-ol (18.30%), ¦Ä-terpinene (13.61%), ¦Á-terpinene (9.16%) and sabinene (7.96%). In adult immersion test, J. communis essential oil, at 10 mg/mL concentration exhibited strong acaricidal efficacy and reproductive inhibitory effects on treated ticks (100%) than O. majorana oil (91.95%). In larval packet test, J. communis oil had 100% mortality at 10 mg/mL, 24 h of exposure, whereas O. majorana oil had 90.64% mortality of H. scupense larvae. J. communis essential oil showed greater efficacy than all tested extracts and amitraz on both female adults and larvae of H. scupense. Quant. anal. showed that J. communis methanolic extract had the greatest ability to extract such phenolic compounds, with a total phenol content of 188.17 (mg gallic acid equivalent/g dry weight) and also had the highest acaricidal activity against engorged females and larvae of H. scupense with LC50 values of 2.46 and 4.12 mg/mL, resp. The results showed that both plants, particularly J. communis considered as potential candidates for biocontrol of H. scupense in the field.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Cadavid Vargas, J. F.’s team published research in JBIC, Journal of Biological Inorganic Chemistry in 2022-04-30 | CAS: 83730-53-4

Enhanced antitumor effect of L-buthionine sulfoximine or ionizing radiation by copper complexes with 2,2-biquinoline and sulfonamides on A549 2D and 3D lung cancer cell models. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Two ternary copper(II) complexes with 2,2-biquinoline (BQ) and with sulfonamides: sulfamethazine (SMT) or sulfaquinoxaline (SDQ) whose formulas are Cu(SMT)(BQ)Cl and Cu(SDQ)(BQ)Cl¡¤CH3OH, in what follows SMTCu and SDQCu, resp., induced oxidative stress by increasing ROS level from 1.0 ¦ÌM and the reduction potential of the couple GSSG/GSH2. The co-treatment with L-buthionine sulfoximine (BSO), which inhibits the production of GSH, enhanced the effect of copper complexes on tumor cell viability and on oxidative damage. Both complexes generated DNA strand breaks given by-at least partially-the oxidation of pyrimidine bases, which caused the arrest of the cell cycle in the G2/M phase. These phenomena triggered processes of apoptosis proven by activation of caspase 3 and externalization of phosphatidylserine and loss of cell integrity from 1.0 ¦ÌM. The combination with BSO induced a marked increase in the apoptotic population. On the other hand, an improved cell proliferation effect was observed when combining SDQCu with a radiation dose of 2 Gy from 1.0 ¦ÌM or with 6 Gy from 1.5 ¦ÌM. Finally, studies in multicellular spheroids demonstrated that even though copper(II) complexes did not inhibit cell invasion in collagen gels up to 48 h of treatment at the higher concentrations, multicellular resistance outperformed several drugs currently used in cancer treatment. Overall, our results reveal an antitumor effect of both complexes in monolayer and multicellular spheroids and an improvement with the addition of BSO. However, only SDQCu was the best adjuvant of ionizing radiation treatment.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zhu, Yueyue’s team published research in Journal of Organic Chemistry in 2022-09-02 | CAS: 4381-25-3

Synthesis of Isoquinolone, 1,2-Benzothiazine, and Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine Derivatives via Rhodium(III)-Catalyzed (4 + 2) Annulation. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A novel and efficient synthetic method to construct isoquinolone e.g., I scaffold via the Rh(III)-catalyzed (4 + 2) annulation of benzamide RC(O)NHOMe (R = Ph, naphthalen-2-yl, 2-OMeC6H4) with an unreported coupling reagent Me 2-chloroacrylate was reported. Accordingly, other valuable 1,2-benzothiazine II (R1 = Me, Et, Ph; R2 = OMe, H, F, etc.; R3 = OMe, H, Cl; R4 = Cl, H, Br) and naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine e.g., III derivatives are also obtained through a similar synthetic protocol. Thus, the developed method is highlighted by high yield and reaction versatility.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem