Heterocyclic Building Blocks-Benzoxazole

Ma, Ding’s team published research in Organic Letters in 2022-03-25 | CAS: 1621962-30-8

Introduction of Lipophilic Side-Chains to NH-Sulfoximines by Palladium Catalysis Under Blue Light Irradiation. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

4-(S-Methylsulfonimidoyl)benzonitrile (BD00975057) 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.

Palladium catalysis under blue (LED) light irradiation allows to convert NH-sulfoximines into products with long lipophilic side-chains attached to the S=N moiety. The three-component reactions involve both radicals and organometallic intermediates stemming from alkyl bromides and butadienes. The substrate scope is broad, and the products are formed in moderate to good yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Li, Jun-Yi’s team published research in ACS Catalysis in 2022-08-05 | CAS: 4381-25-3

Ir(III)-Catalyzed Asymmetric C-H Activation/Annulation of Sulfoximines Assisted by the Hydrogen-Bonding Interaction. 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.

Herein, an Ir(III)-catalyzed asym. C-H activation enabled by noncovalent interactions was described. A broad range of sulfur-stereogenic sulfoximines, e.g., I was prepared in high yields with excellent enantioselectivities via the asym. C-H activation/annulation of sulfoximines with diazo compounds Desymmetrization, kinetic resolution, and parallel kinetic resolution were compatible with this protocol. Detailed DFT calculations suggested that the N-H¡¤¡¤¡¤O hydrogen bonding interaction between sulfoximine and the chiral carboxylic acid ligand was crucial for the high enantiocontrol. Moreover, chiral iridacycle intermediates were isolated, characterized, and subjected to stoichiometric reactions. Computational and exptl. studies suggested that the C-H cleavage step was the rate- and enantio-determining step.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Jianping’s team published research in Tetrahedron Letters in 2017-01-25 | CAS: 145026-07-9

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, 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.

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

Campos Alencar Oldoni, Fernanda’s team published research in Food Chemistry in 2022-09-15 | CAS: 483-76-1

Fruit quality parameters and volatile compounds from ¡äPalmer¡ä mangoes with internal breakdown. 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.

The internal breakdown (IB) is a premature and uneven mango pulp ripening physiol. disorder that is noticed only when the fruit is sliced for consumption. Thus, there is a demand for anal. methods to detect IB in mangoes to avoid consumer dissatisfaction and reduce postharvest waste. In this work, physicochem. and volatile compounds were determined to evaluate the ability to predict pulp IB. Principal components anal. (PCA) and partial least squares discriminant anal. (PLS-DA) of the data show that color, firmness, and volatiles compounds are important to give some information about the physiol. changes caused by IB. The volatile compounds methacrylic acid, Et ester, isopentyl ethanoate, limonene oxide, (E)-2-pentenal, tetradecane, and ¦Ã-elemene were identified as chem. markers of IB. Therefore, mango phys. and chem. characteristics combined with PCA and PLS-DA were successfully employed for the identification of IB in mangoes, showing significant differences between healthy and IB fruits.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zhang, Guocai’s team published research in ChemSusChem in 2020-03-01 | CAS: 1621962-30-8

Synthesis of NH-Sulfoximines by Using Recyclable Hypervalent Iodine(III) Reagents under Aqueous Micellar Conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

FwThe synthesis of NH-sulfoximines I [R = Ph, Bn, 3-ClC6H4, etc.; R1 = Me, Et, Ph, etc.] from sulfides was developed under mild conditions in an aqueous solution with surfactant TPGS-750-M as catalyst and recyclable hypervalent iodine(III) reagent at room temperature A newly developed hypervalent iodine(III) reagent could readily oxidize sulfides and afforded the corresponding trifluoroiodobenzene, which could be efficiently recovered from the reaction mixture by a simple liquid-liquid biphasic extraction procedure. This protocol was compatible with a broad range of functional groups and could be easily performed on a gram scale, providing a green protocol for the synthesis of compounds I.

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

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

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

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.

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

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