December 2022 | Page 27 of 28 | Heterocyclic Building Blocks-Benzoxazole

Kong, Deshen’s team published research in ACS Sustainable Chemistry & Engineering in 2022-03-07 | CAS: 1621962-30-8

Mechanochemical Solvent-Free N-Sulfenylations of Sulfoximines and Sulfonimidamides. 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.

Mechanochem. N-sulfenylations of sulfoximines and sulfonimidamides mediated by silver oxide under solvent-free conditions has been developed. The reactions are easy to perform and proceed well on a gram scale. A wide range of functional groups in the substrates were tolerated. Compared to its solvent-based counterpart, the mechanochem. approach showed significant ecol. advantages.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Hui’s team published research in Small in 2022-03-03 | CAS: 83730-53-4

Oxygen-Deficient BiOCl Combined with L-Buthionine-Sulfoximine Synergistically Suppresses Tumor Growth through Enhanced Singlet Oxygen Generation under Ultrasound Irradiation. 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.

Excess generation of reactive oxygen species (ROS) based on sensitizers under ultrasound (US) excitation can cause the death of tumor cells via oxidative damage, but sonosensitizers are largely unexplored. Herein, oxygen-deficient black BiOCl (B-BiOCl) nanoplates (NPs) are reported, with post-treatment on conventional BiOCl by simple UV excitation, showing stronger singlet oxygen (1O2) generation than com. TiO2 nanoparticles and their derivatives under US irradiation. Moreover, L-buthionine-sulfoximine (BSO), a GSH biosynthesis inhibitor, is incorporated into B-BiOCl NPs. The authors find that BSO can be released owing to the degradation of B-BiOCl NPs in the presence of acid and GSH, which are overexpressed in tumors. The results show that BSO/B-BiOCl-PEG NPs have a multifunctional synergistic effect on improving ROS production. In particular, BiOCl has remarkable near-IR light absorption after UV treatment and is good for photoacoustic imaging that can guide subsequent sonodynamic therapy. This work shows that just with a simple oxygen deficiency treatment, strong 1O2 generation can be provided to a conventional material under US irradiation and, interestingly, this effect can be amplified by using a small inhibitor BSO, and this is clearly demonstrated in cell and mice experiments

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Isidorov, Valery A.’s team published research in Journal of Atmospheric Chemistry in 2022-09-30 | CAS: 483-76-1

Emission of volatile organic compounds by plants on the floor of boreal and mid-latitude forests. 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 forests of the boreal and mid-latitude zones of the Northern Hemisphere are the largest source of reactive volatile organic compounds (VOCs), which have an important impact on the processes occurring in the atm. boundary layer. However, the composition of biogenic emissions from them remains incompletely characterized, as evidenced by the significant excess OH radical concentrations predicted by models in comparison with those observed under the forest canopy. The missing OH sink in the models may be related to the fact that they do not take into account the emission of highly reactive VOCs by vegetation on the forest floor. In this work, we report the results of laboratory determinations of the composition of VOCs emitted by representatives of different groups of plants that form the living soil cover (LSC) in the forests of the boreal and mid-latitude zones: bryophytes, small shrubs, herbaceous plants, and ferns. In the chromatograms of volatile emissions of all 11 studied plant species, 254 compounds with carbon atoms ranging in number from two to 20 were registered. All plants were characterized by the emission of terpenes, accounting for 112 compounds, and the second largest group (35 substances) was formed by carbonyl compounds Both groups of compounds are characterized by high reactivity and are easily included in the processes of gas-phase oxidation with the participation of radicals HO, NO3 and ozone. These data indicate the importance of a thorough study of the so far disregarded source of VOCs, i.e., the LSC in forests.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Vieira, Luiza V.’s team published research in Food Chemistry in 2022-10-01 | CAS: 483-76-1

The effects of drying methods and harvest season on piperine, essential oil composition, and multi-elemental composition of black pepper. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

This study aimed to evaluate the piperine content, essential oil composition, and multi-elemental composition of black pepper samples according to different drying methods and harvest season. Differences in essential oil composition and B, Ca, K, Mg, and S were noted according to sampling campaign, indicating secondary metabolism plant alterations. Mech. drying resulted in essential oil composition changes due to high temperature exposure during processing. Increases in Fe and Cr contents when employing mech. dryers with direct heating were also observed, due to direct contact with metallic structures and particulate material from the burning process. The As and Pb contents of several samples were higher than the maximum permissible limits, reaching 0.46 and 0.56 mg kg-1, resp., thus surpassing legislation safety limitations for human consumption.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Lin, Yan’s team published research in Catalysis Communications in 2018-07-05 | CAS: 50578-18-2

h-BN@Copper(II) nanomaterial catalyzed cross-coupling reactions between sulfoximines and N-(phenylthio)-succinimide under mild condition. 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.

A novel and efficient method was developed for the synthesis of N-sulfenyl sulfoximines I [R = Ph, Bn, 2-pyridyl, etc.; R1 = Me, Ph, 3-pyridyl, etc.; R2 = Me, 4-ClC6H4, 2-naphthyl, etc.; R1R2 = (CH2)4] via cross-coupling reaction of sulfoximines and N-thiosuccinimides using hexagonal boron nitride-supported copper-¦Ã-cyclodextrin nanocatalyst. This heterogeneous catalyst afforded the desired products with wide scope of substrates, good to excellent yields and low-toxicity solvent. Moreover, after being reused ten times, there was almost no significant loss of its catalytic activity.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Kemel, Meriem’s team published research in Chemistry Africa in 2022-08-31 | CAS: 483-76-1

Chemical Composition, Antioxidant and Anticorrosive Activities of Hammada articulata Essential Oil. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

The objective of this research was to investigate the chem. composition of the essential oil of Hammada articulata obtained by steam distillation and to investigate its antioxidant and anticorrosive activities. Gas chromatog.-mass spectrometry anal. of this oil resulted in the identification of 46 compounds, which accounted for 97.0% of the total oil. The major components found in this oil were hexahydrofarnesyl acetone (11.9%), ¦Â-bisabolene (10.7%), eugenol (7.7%) and 2-methyldecalin (5.3%). The DPPH radical scavenging technique was used to assess antioxidant activity. The sample of essential oil presented good antioxidant activity. This oil was tested as a corrosion inhibitor of stainless steel in 0.5 M HCl using weight loss measurements and electrochem. polarization methods. The corrosion rate of stainless steel was decreased in the presence of essential oil. The inhibition efficiency was found to increase with oil concentration to attain 96.68% at 1000 ppm. The adsorption of inhibitor on the stainless steel surface was found to be a spontaneous process and obeys Langmuir¡äs adsorption isotherm.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Kim, Ji-Eun’s team published research in Antioxidants in 2022 | CAS: 83730-53-4

Glutathione Regulates GPx1 Expression during CA1 Neuronal Death and Clasmatodendrosis in the Rat Hippocampus following Status Epilepticus. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Glutathione peroxidase-1 (GPx1) catalyze the reduction of H2O2 by using glutathione (GSH) as a cofactor. However, the profiles of altered GPx1 expression in response to status epilepticus (SE) have not been fully explored. In the present study, GPx1 expression was transiently decreased in dentate granule cells, while it was temporarily enhanced and subsequently reduced in CA1 neurons following SE. GPx1 expression was also transiently declined in CA1 astrocytes (within the stratum radiatum) following SE. However, it was elevated in reactive CA1 astrocytes, but not in clasmatodendritic CA1 astrocytes, in chronic epilepsy rats. Under physiol. condition, L-buthionine sulfoximine (BSO, an inducer of GSH depletion) increased GPx1 expression in CA1 neurons but decreased it in CA1 astrocytes. However, N-acetylcysteine (NAC, an inducer of GSH synthesis) did not influence GPx1 expression in these cell populations. Following SE, BSO aggravated CA1 neuronal death, concomitant with reduced GPx1 expression. Further. BSO also lowered GPx1 expression in CA1 astrocytes. NAC effectively prevented neuronal death and GPx1 downregulation in CA1 neurons, and restored GPx1 expression to the control level in CA1 astrocytes. In chronic epilepsy rats, BSO reduced GPx1 intensity and exacerbated clasmatodendritic degeneration in CA1 astrocytes. In contrast, NAC restored GPx1 expression in clasmatodendritic astrocytes and ameliorated this autophagic astroglial death. To the best of our knowledge, our findings report, for the first time, the spatiotemporal profiles of altered GPx1 expression in the rat hippocampus following SE, and suggest GSH-mediated GPx1 regulation, which may affect SE-induced neuronal death and autophagic astroglial degeneration.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Aithagani, Sravan Kumar’s team published research in Organic Letters in 2015-11-20 | CAS: 145026-07-9

Metal-Free Approach for the Synthesis of N-Aryl Sulfoximines via Aryne Intermediate. 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 and operationally simple N-arylation of NH-sulfoximines with aryne precursors is reported. E.g., in presence of KF/18-crown-6 in THF, reaction of o-TMSC6H4OTf and PhSMe(:O):NH gave 72% PhSMe(:O):NPh. Transition metal-free reaction conditions and shorter reaction times are the highlights of the present method. The mild optimized condition was also suitable with enantiopure substrates.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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

Chemical composition of phenylpropanoid rich chemotypes of Ocimum basilicum L. and their antimicrobial activities. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Ocimum basilicum L., is most popular fragrant herb renowned for its immense application. However, a plethora of studies revealed terpenoids and phenylpropanoids as marker chems. with known identities. We herein report two unique chemotypes developed in CSIR-CIMAP for their compositional variability and biol. activities. Essential oils obtained from aerial parts of both the chemotypes were analyzed in capillary gas chromatog. and mass spectrometry systems on 5% diphenyl- and cyclodextrin coated fused silica columns. The statistical anal. was carried out to validate the phytochem. data of consecutive years and also to calculate the variability. The phenylpropanoids dominated the volatile fractions of chemotype II (72.5-77.5%) in comparison to chemotype I (29.8-40.0%) essential oil. In the contrary, sesquiterpenoids (16.4-17.4%) and monoterpenoids (33.5-43.9%) contributed oil composition of chemotype I in diverse proportions. The presence of single images of R-(+)-camphor and R-(-)-linalool were established in both the oils analyzed on a Et substituted cyclodextrin-based column. Essential oils were tested for biol. activities against C. albicans, S. aureus, and E. coli. meta-Eugenol, the marker compound isolated from chemotype I showed best inhibition against C. albicans. In conclusion, meta-eugenol-rich chemotype I with high essential oil yield (0.1-0.8%) was identified as an alternative source for meta-eugenol.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Liu, Dong’s team published research in Angewandte Chemie, International Edition in 2021-04-26 | CAS: 1621962-30-8

Nickel-Catalyzed N-Arylation of NH-Sulfoximines with Aryl Halides via Paired Electrolysis. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A novel strategy for the N-arylation of NH-sulfoximines has been developed by merging nickel catalysis and electrochem. (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and yield are achieved. A preliminary mechanistic study indicates that the anodic oxidation of a NiII species is crucial to promote the reductive elimination of a C-N bond from the resulting NiIII species at room temperature

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem