December 2022 | Page 3 of 28 | Heterocyclic Building Blocks-Benzoxazole

Sumunnee, Ladawan’s team published research in Organic & Biomolecular Chemistry in 2018 | CAS: 145026-07-9

Persulfate-promoted oxidative C-N bond coupling of quinoxalinones and 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.

The persulfate-meditated oxidative C-N bond coupling of the C-H bond of quinoxalinones and the N-H bond of NH-sulfoximines is reported. The reaction proceeds smoothly under transition metal-free conditions and provides good to excellent yields of sulfoximidoyl-functionalized quinoxalinone products under mild conditions. The optimized conditions were found to be suitable for a range of sulfoximine and quinoxalinone substrates. This reaction offers a new and convenient strategy to directly install the sulfoximine moiety into the C3 position of quinoxalinone.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Knany, Alaa’s team published research in Free Radical Biology & Medicine in 2020-11-20 | CAS: 83730-53-4

S-nitrosocysteine and glutathione depletion synergize to induce cell death in human tumor cells: Insights into the redox and cytotoxic mechanisms. 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.

Nitric oxide (NO)-dependent signaling and cytotoxic effects are mediated in part via protein S-nitrosylation. The magnitude and duration of S-nitrosylation are governed by the two main thiol reducing systems, the glutathione (GSH) and thioredoxin (Trx) antioxidant systems. In recent years, approaches have been developed to harness the cytotoxic potential of NO/nitrosylation to inhibit tumor cell growth. However, progress in this area has been hindered by insufficient understanding of the balance and interplay between cellular nitrosylation, other oxidative processes and the GSH/Trx systems. In addition, the mechanistic relationship between thiol redox imbalance and cancer cell death is not fully understood. Herein, we explored the redox and cellular effects induced by the S-nitrosylating agent, S-nitrosocysteine (CysNO), in GSH-sufficient and -deficient human tumor cells. We used L-buthionine-sulfoximine (BSO) to induce GSH deficiency, and employed redox, biochem. and cellular assays to interrogate mol. mechanisms. We found that, under GSH-sufficient conditions, a CysNO challenge (100-500¦ÌM) results in a marked yet reversible increase in protein S-nitrosylation in the absence of appreciable S-oxidation In contrast, under GSH-deficient conditions, CysNO induces elevated and sustained levels of both S-nitrosylation and S-oxidation Experiments in various cancer cell lines showed that administration of CysNO or BSO alone commonly induce minimal cytotoxicity whereas BSO/CysNO combination therapy leads to extensive cell death. Studies in HeLa cancer cells revealed that treatment with BSO/CysNO results in dual inhibition of the GSH and Trx systems, thereby amplifying redox stress and causing cellular dysfunction. In particular, BSO/CysNO induced rapid oxidation and collapse of the actin cytoskeletal network, followed by loss of mitochondrial function, leading to profound and irreversible decrease in ATP levels. Further observations indicated that BSO/CysNO-induced cell death occurs via a caspase-independent mechanism that involves multiple stress-induced pathways. The present findings provide new insights into the relationship between cellular nitrosylation/oxidation, thiol antioxidant defenses and cell death. These results may aid future efforts to develop NO/redox-based anticancer approaches.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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

Chemical composition and antioxidant activity of essential oil from fruit of Schisandra perulata. 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.

Schisandra (Schisandraceae) grow in East Asia and number 30 species. They are rich sources of lignans and triterpenoids that are known to activate various useful biol. process. S. perulata Gagnep. is an endemic species of the genus Schisandra found in Vietnam. We analyzed the composition and antioxidant activity of essential oil obtained from fruit of S. perulata. Essential oils were collected,dried over anhydrous Na2SO4, and stored at 4¡ãC for further anal. Each extraction was performed in triplicate. The chem. compositions of essential oils from fruit of S. perulata were determined by gas chromatog. (GC)and GC-mass-spectrometry (GC-MS) using the published method . Anal. of GC-MS spectra of the essential oil detected 46 compounds making up 90.25% of the oil (Table 1). The essential oil was dominated by sesquiterpenes (76.90%). Oxygen-saturated sesquiterpenes, monoterpenes, and oxygen-saturated monoterpenes made up 4.94, 4.86, and 3.55%,resp. The main oil constituents were ¦Ä-cadinene (24.74%), ¦Á-ylangene (16.38), trans-¦Á-bergamotene (7.84), ¦Â-elemene(6.91), and ¦Â-himachalene (6.27). This is the first report on the chem. composition of essential oil from fruit of S. perulata.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Goldberg, Frederick W.’s team published research in Tetrahedron in 2014-09-16 | CAS: 1621962-30-8

General synthetic strategies towards N-alkyl sulfoximine building blocks for medicinal chemistry and the use of dimethylsulfoximine as a versatile precursor. 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.

The sulfoximine group has great potential as a substituent in drug discovery, as evidenced by two new clin. candidates, and can be viewed as an isosteric alternative to the commonly used sulfone. Our aim was to improve the accessibility of this group by synthesizing a diverse range of S-alkyl and N-alkyl sulfoximine building blocks with procedures that are applicable on a practical scale (>10 g). In particular, synthesis of the less well exploited N-alkyl sulfoximines and the use of dimethylsulfoximine as a versatile, com. available precursor is discussed.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Jianping’s team published research in Tetrahedron Letters in 2017-01-25 | CAS: 1621962-30-8

Eaton’s reagent-mediated metal-free and efficient synthesis of NH-sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

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

Wimmer, Alexander’s team published research in Advanced Synthesis & Catalysis in 2018 | CAS: 1621962-30-8

Visible-Light-Mediated Photoredox-Catalyzed N-Arylation of NH-Sulfoximines with Electron-Rich Arenes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

The direct C-H/N-H dehydrogenative cross-coupling of NH-sulfoximines with electron-rich arenes was realized by oxidative visible-light photoredox catalysis, applying 9-mesityl-10-methylacridinium perchlorate as an organic photocatalyst. Sulfoximines display diverse desirable properties for medicinal chem. and the pharmaceutical industry. However, their preparation is still challenging. Our reaction proceeds without sacrificial oxidant, at room temperature and is highly selective for the C-N bond forming reaction. The scope of the reaction includes mono- and multi-alkylated and halogenated arenes, which are reacted with aromatic and aliphatic electron-rich and electron-poor NH-sulfoximines, giving moderate to excellent yields of the N-arylated sulfoximines. In addition, we successfully conducted the developed reaction on a gram scale (1.5 g). Mechanistic investigations show that both arene and NH-sulfoximine interact with the excited-state of the photocatalyst. We propose a radical-based mechanism, where both the arene and the NH-sulfoximine are photo-oxidized to their resp. radical intermediates. Radical-radical cross-coupling subsequently leads to the N-arylated sulfoximine. Two electrons and two protons are released during the reaction and are subsequently converted into H2 by a proton-reducing cobalt-catalyst.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Tan, Mingchao’s team published research in Asian Journal of Organic Chemistry in 2019 | CAS: 145026-07-9

I2-Catalyzed Oxidative N-P Cross-Coupling of Diarylphosphine Oxides and Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A new synthetic method for the synthesis of N-phosphinyl sulfoximines that proceeds by an I2-catalyzed oxidative N-P cross-coupling reaction has been developed. N-phosphinylated sulfoximines are synthesized from sulfoximines and diarylphosphine oxides using 10 mol% I2 as a catalyst, one equiv H2O2 as a green oxidant and PEG400 as a greener solvent. Chirality of S-methyl-S-phenylsulfoximine is retained in the coupling products (100% ee).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Ganthi, Hari Kishan Reddy’s team published research in American Journal of Analytical Chemistry in 2016 | CAS: 5233-42-1

Stability indicating RP-HPLC method for quantification of impurities in valsartan and hydrochlorothiazide FDC tablet dosage form. Recommended basis is hydrochlorothiazide 20. Products is: https://www.ambeed.com/products/742-20-1.html, 432499-63-3

1. The impurity of diuretic hydrochlorothiazide 04, also be a medical intermediate.
2. It’s mainly used for the detection of drug impurities, the synthesis of hydrochlorothiazide and the screening of medical structural fragments.
3. Presents a weak alkaline,refrigeration.

. Recommended Products is: 5250-72-6 and 22503-72-6.

A stability-indicating RP-HPLC method has been developed and validated for simultaneous determination of Valsartan & Hydrochlorothiazide and their impurities in FDC (Fixed Dose Combination) tablet dosage form. The method was developed using L1 column (250 ¡Á 4.6 mm; 5 ¦Ìm) with gradient elution using the mobile phase consisting of solvent-A (0.1% Ortho phosphoric acid) and solvent-B (100% Acetonitrile); the gradient program (Tmin/%B) was set as 0/10, 5/10, 20/60, 40/60, 41/10 and 50/10. The eluted compounds were monitored at 265 nm. The developed method was validated as per ICH guidelines with respect to specificity, linearity, limit of detection, limit of quantitation, accuracy, precision and robustness. The influence of Acid, Alk., Oxidative, Photolytic, Thermal and Humidity stress conditions, on drug product was studied. The limit of quantification results of Valsartan, Hydrochlorothiazide and their impurities are, VAL: 0.303 ¦Ìg/mL, HCTZ: 0.019 ¦Ìg/mL, VAL RC-B: 0.085 ¦Ìg/mL, VAL RC-C: 0.327 ¦Ìg/mL, HCT RC-A: 0.017 ¦Ìg/mL, CTZ: 0.080 ¦Ìg/mL and 5-Chloro HCT: 0.047 ¦Ìg/mL. The proposed method is suitable for the estimation of Valsartan & Hydrochlorothiazide impurities in tablets dosage form.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Chenyang’s team published research in Organic Letters in 2021-09-03 | CAS: 1621962-30-8

Photocatalytic Synthesis of Difluoroacetoxy-containing Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

[Bis(difluoroacetoxy)iodo]benzene and NH-sulfoximines reacted to give new hypervalent iodine(III) reagents, which under photocatalysis transferred difluoroacetoxy and sulfoximidoyl groups to styrenes with high regioselectivity. The results of mechanistic investigations suggested the intermediacy of radicals and revealed the importance of the difluoroacetoxy group on the iodine reagent.

Photocatalytic Synthesis of Difluoroacetoxy-containing 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

Cheng, Ying’s team published research in Chemistry – A European Journal in 2016 | CAS: 145026-07-9

Rhodium-Catalyzed ortho-Amidations in the Preparation of Thiadiazine 1-Oxides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

Rhodium-catalyzed ortho-amidations of sulfoximines R1C6H4S(O)(=N)R2 (R1 = H, 4-Br, 5-CH3, etc.; R2 = CH3CH2, octyl, C6H5, etc.) lead to key intermediates for the preparation of thiadiazine 1-oxides I (R = H, 4-CH3, 4-Br, 4-C6H5, 3-NO2). Following a straightforward protocol, a variety of synthetically valuable compounds can be obtained, thus circumventing common multistep approaches towards potentially bioactive products.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem