December 2022 | Page 20 of 28 | Heterocyclic Building Blocks-Benzoxazole

Zlatanovic, Ivana’s team published research in Natural Product Communications in 2022-06-30 | CAS: 483-76-1

Comprehensive Analysis of the Herbal Mixture Made of Juniperus oxycedrus L. Berries, Inner Bark of Betula pendula Roth., and Grains of Avena 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.

This is the first report of the high-performance liquid chromatog. and gas chromatog.-mass spectrometry profile of a herbal mixture (HM) made of Juniperus oxycedrus L. (redberry juniper) berries, inner bark of Betula pendula Roth. (silver birch), and grains of Avena sativa L. (oat), and its effect on the Number of micronuclei (MN) in human lymphocytes and toxicity toward Artemia salina. Constituents represented by over 1000¦Ìg per g of methanol dry extract were gallic acid, protocatechuic acid, and amentoflavone. The methanol extract of the HM at a concentration of 2.0¦Ìg/mL decreased MN frequency by 38.3%, which was more than 3 times greater than that of the radioprotectant amifostine. The essential oil isolated from the HM was composed mainly of ¦Â-myrcene (32%) and showed weaker toxicity toward Artemia salina than the pos. control after both incubation periods (24 h and 48 h). These findings suggest that the examined HM, beside its ethnopharmacol. relevance on the elimination of renal calculi, also significantly reduces the Number of MN in human lymphocytes.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Chenyang’s team published research in Organic Chemistry Frontiers in 2021 | CAS: 145026-07-9

Visible light-promoted NH-halogenation of sulfoximines with dichloromethane or dibromomethane. 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.

In visible light, dichloro- and dibromomethane are the halogen sources for converting NH-sulfoximines to their corresponding N-halo derivatives via an in-situ formed sulfoximidoyl-containing hypervalent iodine reagent. The reactions proceeded in air and were catalyst- and additive-free. The products were obtained in good to excellent yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yu, Xie-an’s team published research in Theranostics in 2020 | CAS: 83730-53-4

A cancer-specific activatable theranostic nanodrug for enhanced therapeutic efficacy via amplification of oxidative stress. 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.

Rationale: Despite considerable advances, the reactive oxygen species (ROS)-mediated cancer treatment suffers from the problems of up-regulation of adaptive antioxidants in cancer cells as well as side effects to normal cells. Therefore, development of a new generation of cancer-specific nanomedicine capable of amplifying oxidative stress would be of great interest for accurate and effective cancer treatment. Methods: Herein, transferrin (Tf)-decorated, dihydroartemisinin (DHA), L-buthionine-sulfoximine (BSO), and CellROX-loaded liposomal nanoparticles (Tf-DBC NPs) were developed for precise cancer theranositcs. Tf-DBC NPs could specifically recognize cancer cells via Tf-Tf receptor binding and be uptaken into the lysosomes of cancer cells, where Tf-DBC NPs were activated to release Fe(II), DHA, and BSO. ROS was generated by DHA in the presence of Fe(II), and GSH was depleted by BSO to disrupt the redox balance in cancer cells. Furthermore, CellROX, as a fluorescent probe for imaging of intracellular oxidative stress, was used to monitor the therapeutic efficacy. Results: The integration of Tf, DHA, and BSO into the acidic pH-responsive liposomes selectively and effectively killed cancer cells and prevented the oxidative injury to normal cells. The high oxidative state was visualized at the tumor site and the amplification of oxidative stress enabled tumor eradication by Tf-DBC NPs, demonstrating the successful implementation of this novel strategy in vivo. Conclusion: Our study provides a new paradigm for the design of ROS-mediated therapeutics and offers a promising perspective for precise cancer treatment.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Muneeswara, Madithedu’s team published research in Synthesis in 2016-05-31 | CAS: 145026-07-9

Iron-Catalyzed One-Pot N-Aroylation of NH-Sulfoximines with Methylarenes through Benzylic C-H Bond Oxidation. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

An efficient catalytic method has been developed for the synthesis of N-aroylated sulfoximines ArC(O)N=S(O)R1R2 (Ar = C6H5, 3-H3COC6H4, naphthalen-1-yl, etc.; R1 = C6H5, 4-BrC6H4, 3-O2NC6H4, etc.; R2 = CH3, CH2CH3) from readily available toluenes (methylarenes) ArCH3 as source of the aroyl coupling partner and NH-sulfoximines NHS(O)R1R2, employing an environmentally benign iron catalyst. This protocol involves oxidation of benzylic C-H bonds of toluenes to generate aroyl radical intermediates followed by oxidative coupling with NH-sulfoximines to form N-aroylated sulfoximines in good to excellent yields. The intermediate aroyl radical is successfully trapped with TEMPO to prove the radical pathway of the reaction.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yu, Hao’s team published research in Angewandte Chemie, International Edition in 2018-01-01 | CAS: 145026-07-9

Iron(II)-Catalyzed Direct Synthesis of NH Sulfoximines from Sulfoxides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

Free NH-sulfoximines were directly prepared from sulfoxides through iron catalysis by applying a readily available, shelf-stable hydroxylamine triflic acid salt. No addnl. oxidant is needed, and the substrate scope is broad, including a range of heterocyclic compounds Thus, e.g., imidation of PhS(:O)Me with O-(4-nitrobenzoyl)hydroxylamine.HOTF in presence of FeSO4 and 1,10-phenanthroline afforded PhS(:O)(:NH)Me (98%, 93% isolated).

Iron(II)-Catalyzed Direct Synthesis of NH Sulfoximines from Sulfoxides. 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, Chenyang’s team published research in Organic Letters in 2020-11-20 | CAS: 1621962-30-8

Use of Hypervalent Iodine Reagents in Visible Light-Promoted ¦Á-Ketoacylations of Sulfoximines with Aryl Alkynes. 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.

In visible light, sulfoximidoyl-containing hypervalent iodine reagents react with aryl alkynes to give N-¦Á-ketoacylated sulfoximines in good to high yields. The process is metal- and base-free, providing the diketonic products without the use of highly oxygenated reagents such as peroxides. Results from mechanistic investigations suggest the intermediacy of radicals and reveal the importance of mol. oxygen.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Schumacher, Ricardo F.’s team published research in European Journal of Organic Chemistry in 2012 | CAS: 145026-07-9

Synthesis of N-Methyl-2-indolyl- and N-Methyl-2-benzo[b]furyl-Substituted Sulfoximines by Pd/Cu Co-Catalyzed Domino Cross-Coupling/Cyclization Reactions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

Domino cross-coupling/cyclization reactions of N-propargyl sulfoximines and 2-iodophenols or 2-iodoanilides are catalyzed by a cooperative palladium/copper system to provide benzo[b]furan and indole derivatives in good to excellent yields. The reactions occur under mild conditions and tolerate a wide variety of functional groups. E.g., in presence of PdCl2(PPh3)2 and CuI, cross-coupling/cyclization of N-propargyl sulfoximine derivative (I) with 2-IC6H4OH gave 90% benzofuran derivative (II).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Long’s team published research in Advanced Synthesis & Catalysis in 2013 | CAS: 50578-18-2

The Copper-Catalyzed Oxidative N-Acylation of Sulfoximines. 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.

An oxidative cross-coupling reaction between aldehydes and sulfoximines involving dual C-H/N-H functionalization was developed. This reaction process is facilitated by a simple copper catalyst (1 mol% loading) and tert-Bu hydroperoxide (TBHP) as the oxidant and proceeds under mild reaction conditions to afford a series of valuable N-acylated sulfoximine derivatives in excellent yields.

The Copper-Catalyzed Oxidative N-Acylation of Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Schweikl, Helmut’s team published research in Dental Materials in 2021-01-31 | CAS: 83730-53-4

HEMA-induced oxidative stress inhibits NF-¦ÊB nuclear translocation and TNF release from LTA- and LPS-stimulated immunocompetent cells. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

The release of inflammatory cytokines from antigen-stimulated cells of the immune system is inhibited by resin monomers such as 2-hydroxyethyl methacrylate. Although the formation of oxidative stress in cells exposed to HEMA is firmly established, the mechanism behind the inhibited cytokine secretion is only partly known. The present investigation presents evidence regarding the role of HEMA-induced oxidative stress in the secretion of the pro-inflammatory cytokine TNF¦Á from cells exposed to the antigens LTA or LPS of cariogenic microorganisms using BSO or NAC to inhibit or stabilize the amounts of the antioxidant glutathione. RAW264.7 mouse macrophages were treated with LTA, LPS or HEMA in the presence of BSO or NAC for 1h or 24h. Secretion of TNF¦Á from cell cultures was analyzed by ELISA, and the formation of reactive oxygen or nitrogen species was determined by flow cytometry. Protein expression was detected by Western blotting. The release of TNF¦Á in both LTA- and LPS-exposed cells was decreased by HEMA, and this concentration-dependent inhibitory effect was amplified by BSO or NAC. LTA- and LPS-stimulated expression of the redox-sensitive transcription factor NF-¦ÁB (p65) in cell nuclei decreased in the presence of HEMA because the translocation of p65 from the cytosol was prevented by oxidative stress specifically increased by the monomer. A disturbance of the cellular redox balance, particularly induced by HEMA, is a crucial factor in the inhibition of LTA- and LPS-stimulated signalling pathways leading to TNF¦Á secretion.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yigitkan, Serkan’s team published research in South African Journal of Botany in 2022-09-30 | CAS: 483-76-1

Comprehensive study of chemical composition and biological activity of Thymus pubescens Boiss. et Kotschy ex Celak. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

The use of Thymus species amongst the public and their importance in the scientific world is increasing day by day. In addition to being consumed as tea and spice, Thymus species are used as folk medicine for respiratory, digestive, skin, circulatory, genital, nervous, visual and urinary diseases. In this study, it was aimed to examine the essential oil and ethanol extract of the root and aerial parts of Thymus pubescens Boiss. et Kotschy ex Celak in the terms of their biol. activity and chem. content. The phenolic content of the species was determined by LC-MS/MS, while triterpenoid content, the chem. composition of the essential oil as well as flavor was determined by GC-MS. In addition, their antioxidant and cytotoxic activities, as well as acetyl- (AChE) and butyrylcholinesterase (BChE), urease, tyrosinase, elastase, collagenase, HMG-CoA reductase and angiotensin-converting enzyme (ACE) inhibitory activities were studied. Thymol (53.33%) was determined as the major component in the essential oil, while ¦Â-fenchyl alc. (43.87%) was determined as the major component of the flavor. According to the LC-MS/MS and GC-MS results, it was found that especially the aerial parts of the species have a high amount of rosmarinic acid (3875.76 ¦Ìg analyte/g extract), quinic acid (2392.55), naringenin (970.39), oleanolic (92785.96) and ursolic (63373.32) acids. The essential oil of T. pubescens species was observed to show high activity in four antioxidant assays, e.g. inhibition of lipid peroxidation, DPPH and ABTS radical scavenging activity as well as CUPRAC, while the ethanol extracts showed moderate antioxidant activity. In enzyme inhibition assays, the aerial parts exerted marked BChE, elastase, and collagenase inhibitory activities (92.43¡À1.28%, 42.59¡À0.56, and 48.61¡À0.39 at 100 ¦Ìg/mL, resp.). On the other hand, AChE, urease, tyrosinase, HMG-CoA reductase and ACE inhibitory activities of all extracts were from low to moderate levels. In particular, the aerial parts of the species displayed a high cytotoxic effect (vitality%: 6.82¡À0.01 at 200 ¦Ìg/mL) in breast cancer (MCF-7) cell line. Due to its remarkable antioxidant capacity, high content of rosmarinic, oleanolic, and ursolic acids and especially BChE, elastase, and collagenase inhibitory activity, T. pubescens has the potential for using in food supplements, food preservatives, cosmetics, and pharmaceutical industries.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem