M.W=200-250 | Page 10 of 25 | Heterocyclic Building Blocks-Benzoxazole

Chac, Le D.’s team published research in Chemistry of Natural Compounds in 2022-07-31 | CAS: 483-76-1

Chemical Composition and Antifungal Activity of Essential Oil from the Roots of Tinomiscium petiolare. 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.

Tinomiscium petiolare Hook. f. & Thomson is a medicinal species of the genus Tinomiscium (Menispermaceae). This species grows naturally in mixed forests at an altitude of 200 to 600 m in tropical Asian countries, including Vietnam. The literature search has not revealed any reports of the chem. composition and antifungal activity of the root oils of T. petiolare. The average yield of the essential oil was 0.05% ¡À 0.01 (v/w) calculated on a dry weight basis. In addition, significant quantities of ¦Ã-terpinene (5.50%), ¦Â-bisabolene (5.07%), geraniol (4.82%), geranyl acetate (4.70%), and (Z)-ligustilide (4.45%) were also present in the oil. This is to our knowledge the first report on the chem. composition of T. petiolare root oil. Results show that the root oil of T. petiolare inhibited the growth of Aspergillus niger with an MIC value of 200 ¦Ì g/mL. The antifungal activity of essential oil can be explained by the presence of geranial and neral.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Garcia-Carceles, Javier’s team published research in Journal of Medicinal Chemistry in 2022-09-22 | CAS: 145026-07-9

2-(Fluoromethoxy)-4′-(S-methanesulfonimidoyl)-1,1′-biphenyl (UCM-1306), an Orally Bioavailable Positive Allosteric Modulator of the Human Dopamine D1 Receptor for Parkinson’s Disease. 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.

Tolerance development caused by dopamine replacement with L-DOPA and therapeutic drawbacks upon activation of dopaminergic receptors with orthosteric agonists reveal a significant unmet need for safe and effective treatment of Parkinson’s disease. In search for selective modulators of the D1 receptor, the screening of a chem. library and subsequent medicinal chem. program around an identified hit resulted in new synthetic compound 26 [UCM-1306, 2-(fluoromethoxy)-4′-(S-methanesulfonimidoyl)-1,1′-biphenyl] (I) that increases the dopamine maximal effect in a dose-dependent manner in human and mouse D1 receptors, is inactive in the absence of dopamine, modulates dopamine affinity for the receptor, exhibits subtype selectivity, and displays low binding competition with orthosteric ligands. The new allosteric modulator potentiates cocaine-induced locomotion and enhances L-DOPA recovery of decreased locomotor activity in reserpinized mice after oral administration. The behavior of compound 26 supports the interest of a pos. allosteric modulator of the D1 receptor as a promising therapeutic approach for Parkinson’s disease.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yoshioka, Hiromasa’s team published research in ACS Chemical Biology in 2022-02-18 | CAS: 83730-53-4

Identification of a Small Molecule That Enhances Ferroptosis via Inhibition of Ferroptosis Suppressor Protein 1 (FSP1). 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.

Glutathione peroxidase 4 (GPX4) is an intracellular enzyme that oxidizes glutathione while reducing lipid peroxides, and is a promising target for cancer therapy. Till date, several GPX4 inhibitors have been reported to exhibit cytotoxicity against cancer cells. However, some cancer cells are less sensitive to the known GPX4 inhibitors. This study aimed to explore compounds showing synergistic effects with GPX4 inhibitors. We screened a chem. library and identified a compound named NPD4928 (I), whose cytotoxicity was enhanced in the presence of a GPX4 inhibitor. Furthermore, we identified ferroptosis suppressor protein 1 (FSP1) as its target protein. The results indicate that NPD4928 enhanced the sensitivity of various cancer cells to GPX4 inhibitors, suggesting the combination to possibly have therapeutic potential via the induction of ferroptosis.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yang, Lu’s team published research in Organic Chemistry Frontiers in 2018 | CAS: 145026-07-9

Synthesis of N-sulfenyl-sulfoximines and -sulfenamides through a metal-free N-H/S-H dehydrocoupling reaction. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A metal-free, iodine-catalyzed N-H/S-H dehydrocoupling reaction of sulfoximines R1S(O)(R2)=NH (R1 = Ph, 4-CH3OC6H4, 4-ClC6H4, etc.; R2 = Ph, Me, cyclopropyl, etc.) and anilines R4C6H4NHR5 (R4 = H, 4-Me, 4-Br, 4-C(O)OCH3, etc.; R5 = H, Me) with various thiols R3SH (R3 = 3-CH3C6H4, pyridin-2-yl, 1,3-benzothiazol-2-yl, etc.) to construct sulfur-nitrogen bonds is herein presented. A variety of structurally diverse N-sulfenylsulfoximines R1S(O)(R2)=NSR3 and sulfenamides R4C6H4N(R5)SC6H5 was prepared with up to 97% yield. The reaction was carried out in the presence of hydrogen peroxide in PEG400 under mild conditions.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yang, Yanqin’s team published research in Food Chemistry in 2022-09-01 | CAS: 483-76-1

Insight into aroma dynamic changes during the whole manufacturing process of chestnut-like aroma green tea by combining GC-E-Nose, GC-IMS, and GC x GC-TOFMS. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Processing is the crucial factor for green tea aroma quality. In this study, the aroma dynamic changes throughout the manufacturing process of chestnut-like aroma green tea were investigated with gas chromatog. electronic nose (GC-E-Nose), gas chromatog.-ion mobility spectrometry (GC-IMS), and comprehensive two-dimensional gas chromatog. coupled to time-of-flight mass spectrometry (GC x GC-TOFMS). GC-IMS identified 33 volatile compounds while GC x GC-TOFMS identified 211 volatile components. Drying exerted the greatest influence on the volatile components of chestnut-like aroma green tea, and promoted the generation of heterocyclic compounds and sulfur compounds which were commonly generated via the Maillard reaction during the roasting stage. A large number of heterocyclic compounds such as 1-methyl-1H-pyrrole, pyrrole, methylpyrazine, furfural, 2-ethyl-5-methylpyrazine, 1-ethyl-1H-pyrrole-2-carboxaldehyde, and 3-acetylpyrrole were newly formed during the drying process. This study also validated the suitability of GC-E-Nose combined with GC-IMS and GC x GC-TOFMS for tracking the changes in volatile components of green tea throughout the manufacturing process.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Schumacher, Christian’s team published research in Organic Chemistry Frontiers in 2020 | CAS: 145026-07-9

N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines: synthesis, X-ray crystallography, and halogen bonding. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

In the presence of KOH, NH-sulfoximines react with pentafluoropyridine to give N-(tetrafluoropyridyl)sulfoximines (NTFP-sulfoximines) I (R1 = Me, Ph, 4-MeC6H4, 4-ClC6H4, etc.; R = Me, i-Pr, 2-Py, 2-thiophenyl, etc.; ) in moderate to excellent yields. Either a solution-based or a superior solvent-free mechanochem. protocol can be followed. X-Ray diffraction analyses of 26 products provided insight into the bond parameters and conformational rigidity of the mol. scaffold. In solid-state structures, sulfoximines with halo substituents on the S-bound arene are intermolecularly linked by C-X¡¤¡¤¡¤O=S (X = Cl, Br) halogen bonds. Hirshfeld surface anal. is used to assess the type of non-covalent contacts present in mols. For mixtures of three different S-pyridyl-substituted NTFP-sulfoximines and N-iodosuccinimide (NIS) in CDCl3, association constants were determined by 1H NMR spectroscopy. The data revealed a dependence of the halogen bond strength on the position of the pyridyl nitrogen indicating the presence of N-I¡¤¡¤¡¤N(S-pyridyl) interactions. Neither the S=O oxygen nor the tetrafluoropyridyl-substituted nitrogen of the sulfoximine appeared to be involved in halogen bonding.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Moessner, Christian’s team published research in Organic Letters in 2005-06-23 | CAS: 145026-07-9

Cu(OAc)2-catalyzed N-arylations of sulfoximines with aryl boronic acids. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A simple and mild copper salt-catalyzed N-arylation of sulfoximines in high yields is reported. Cu(OAc)2 activated arylboronic acids for the reaction with NH-sulfoximines without addnl. base or heating. Furthermore, this method allowed the preparation of N-arylated sulfoximines, which have previously been more difficult to access.

Cu(OAc)2-catalyzed N-arylations of sulfoximines with aryl boronic acids. 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

Wang, Xu’s team published research in Chemical Research in Toxicology in 2022-02-21 | CAS: 83730-53-4

Cysteine-Based Protein Covalent Binding and Hepatotoxicity Induced by Emodin. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Emodin (EMD) is a major ingredient of Polygonum multiflorum Thunb. (PMT), which has shown adverse liver reactions. Despite multiple pharmacol. activities, EMD is reported to show various toxicities. Our early study demonstrated the reactivity of EMD to glutathione. This study aimed to determine the covalent interaction of hepatic protein with EMD and the correlation of the protein modification with hepatotoxicity induced by EMD. EMD-derived protein adduction was detected in an incubation mixture containing mouse liver homogenates and EMD. Such protein adduction was also observed in hepatic protein obtained from mice exposed to EMD. The protein covalent binding occurred in time- and dose-dependent manners. Pre-treatment of L-buthionine-sulfoximine significantly potentiated EMD-induced adduction and hepatotoxicity caused by EMD and lipopolysaccharide co-treatment. As expected, EMD-derived protein modification was observed in mouse primary hepatocytes treated with EMD. The increase in EMD exposure concentration intensified EMD-derived protein adduction and increased EMD-induced cell death. The susceptibility of hepatocytes to EMD cytotoxicity and the intensity of EMD-induced protein adduction were attenuated by the co-treatment of hepatocytes with N-acetyl cysteine. A good association of protein modification with hepatotoxicity induced by EMD was illustrated, which facilitates the understanding of the mechanism of hepatotoxicity induced by EMD.

Cysteine-Based Protein Covalent Binding and Hepatotoxicity Induced by Emodin. 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

Agwunobi, Desmond O.’s team published research in Proteomics in 2022-07-31 | CAS: 483-76-1

Proteomic analysis suggests that monoterpenes in lemongrass disrupt Ca2+ homeostasis in Haemaphysalis longicornis leading to mitochondrial depolarization and cytotoxicity. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Complex mixtures of bioactive ingredients in plant essential oils present complex chemistries which involve different modes of action. An increasing body of scientific reports has recently focused on the acaricidal activities of plant essential oils attributed to their monoterpene components, but information about their underlying mol. mechanism of action is scarce. Here, after the chem. anal. of lemongrass oil, a proteomic anal. of the ovary, salivary gland, and midgut of Haemaphysalis longicornis exposed to Cymbopogon citratus (lemongrass) essential oil was performed via data-independent acquisition mass spectrometry (DIA-MS) technol. to further elucidate the mol. mechanisms involved. Pathway anal. reveals the activation of metabolic pathways mediated by oxidoreductases and transferases. Furthermore, the upregulation of various calcium-associated proteins and the upregulation of cytochrome c1, cytochrome c oxidase polypeptide IV, and programmed cell death protein 6-like isoform X1 suggest a cytotoxic mode of action via the formation of reactive oxygen species (ROS), mitochondrial Ca2+ overload, mitochondrial uncoupling, and depolarization, and ATP depletion leading to either apoptotic or necrotic death. Morphol. alterations observed after the RNAi of a major detoxification enzyme (glutathione S-transferase) merit further investigation. Hence, the cytotoxic mode of action exhibited by C. citratus oil could be vital for the development of eco-friendly acaricide.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Li, Huan’s team published research in International Journal of Biological Macromolecules in 2022-09-01 | CAS: 483-76-1

Emulsifying properties and bioavailability of clove essential oil Pickering emulsions stabilized by octadecylaminated carboxymethyl curdlan. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

In the present study, clove essential oil (CEO) Pickering emulsions were stabilized by octadecylamine-modified carboxymethyl curdlan (CMCD-ODA) at different pH values. The droplet size and neg. charged zeta potential of the CMCD-ODA emulsions decreased as the pH increased from 3.0 to 11.0. Rheol. results indicated that the CMCD-ODA polymer/emulsion prepared at pH 5.0 showed higher apparent viscosity and viscoelasticity than other pH conditions, which might prevent droplets from flocculating. The Pickering emulsions obtained at pH 5.0 were spherical droplets with a uniform size distribution and a mean diameter of 9.54¦Ìm, and they exhibited excellent stability during 28 days of storage. The morphol. structures of the emulsions investigated by confocal laser scanning microscopy and SEM indicated that the CMCD-ODA Pickering emulsion obtained at pH 5.0 was stabilized by loading amphiphilic CMCD-ODA polymer around the spherical oil droplets and forming a weak gel network structure. The CEO-loaded CMCD-ODA emulsions had higher antioxidant capacity than free CEO after 28 days of storage at pH 5.0. Given the good emulsion stability, antioxidant activity, and great antibacterial effect, the CEO-loaded carboxymethyl curdlan Pickering emulsion has promising applications in food, cosmetic, and biomedicine industries.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem