December 7, 2022 | Page 3 of 4 | Heterocyclic Building Blocks-Benzoxazole

Rajbongshi, Kamal K.’s team published research in Synthesis in 2020-04-30 | CAS: 50578-18-2

Microwave-Accelerated N-Acylation of Sulfoximines with Aldehydes under Catalyst-Free Conditions. 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 efficient catalyst-free radical cross-coupling reaction between sulfoximines R1S(O)(=NH)R2 [R1 = Me, Ph, 4-methoxyphenyl, 4-bromophenyl; R2 = Me, Ph; R1R2 = -(CH2)4-] and aromatic aldehydes R3CHO (R3 = 2-chlorophenyl, naphthalen-1-yl, furan-2-yl, etc.) was developed. The reaction took place in the presence of N-bromosuccinimide as the radical initiator under microwave irradiation to afford the corresponding acylated sulfoximines R1S(O)(R2)=NC(O)R3 in moderate to excellent yields (27 examples). This protocol is proved to be rapid, easy to handle, and applicable to a broad scope of substrates.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Schumacher, Christian’s team published research in Organic Chemistry Frontiers in 2020 | CAS: 4381-25-3

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/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.

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

Sharma, Nidhi’s team published research in RSC Advances in 2016 | CAS: 50578-18-2

Palladium nanoparticles catalyzed aroylation of NH-sulfoximines with aryl iodides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

A novel approach towards aroylation of NH-sulfoximines using Pd nanoparticles stabilized by a binaphthyl backbone (Pd-BNP) was developed. This synthetic protocol involved the Pd-BNP promoted carbon monoxide insertion of aryl iodides to form an aroyl intermediate which further reacted with NH-sulfoximines to form N-aroyl sulfoximine derivatives in good to excellent yields. The Pd-BNP catalyst was recovered and reused up to six times.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Altenburg, Bianca’s team published research in ACS Medicinal Chemistry Letters in 2020-10-08 | CAS: 4381-25-3

Chiral Analogues of PFI-1 as BET Inhibitors and Their Functional Role in Myeloid Malignancies. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Structural analogs of PFI-1 varying at the sulfur core were prepared, and their activities as BET inhibitors in myeloid cell lines and primary cells from patients with acute myeloid leukemia were studied. Docking calculations followed by mol. dynamics simulations revealed the binding mode of the newly prepared inhibitors, suggesting explanations for the observed high enantiospecificity of the inhibitory activity.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Guan, Xin’s team published research in Advanced Functional Materials in 2020-07-06 | CAS: 83730-53-4

Tumor Metabolism-Engineered Composite Nanoplatforms Potentiate Sonodynamic Therapy via Reshaping Tumor Microenvironment and Facilitating Electron-Hole Pairs’ Separation. 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.

Reactive oxygen species (ROS) depletion and low ROS production that result from the intratumoral redox metabolism equilibrium and low energy conversion efficiency from ultrasound mech. energy to ROS-represented chem. energy, resp., are two vital inhibitory factors of sonodynamic therapy (SDT). To address the two concerns, a tumor metabolism-engineered composite nanoplatform capable of intervening intratumoral ROS metabolism, breaking the redox equilibrium, and reshaping the tumor microenvironment is constructed to reinforce SDT against tumors. In this metabolism-engineered nanoplatform, Nb2C nanosheets serve as the scaffold to accommodate TiO2 sonosensitizers and L-buthionine-sulfoximine. Systematic experiments show that such nanoplatforms can reduce ROS depletion via suppressing glutathione synthesis and simultaneously improving ROS production via the Nb2C-enhanced production and separation of electron-hole pairs. Contributed by the combined effect, net ROS content can be significantly elevated, which results in the highly efficient anti-tumor outcomes in vivo and in vitro. Moreover, the combined design principles, i.e., tumor metabolism modulation for reducing ROS depletion and electron-hole pair separation for facilitating ROS production, can be extended to other ROS-dependent therapeutic systems.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Dong, Ziliang’s team published research in Chem in 2020-06-11 | CAS: 83730-53-4

Corrigendum: Synthesis of CaCO3-Based Nanomedicine for Enhanced Sonodynamic Therapy via Amplification of Tumor Oxidative Stress [Erratum to document cited in CA173:313754]. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

In the originally published version of this article, the confocal images of 4T1 cells from the PBS group in Figure 3C were unfortunately identical to those in the BSO group as a result of a copy-and-paste error during figure compilation. The corrections are provided.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Jeldi, Lamya’s team published research in South African Journal of Botany in 2022-07-31 | CAS: 483-76-1

Chemical composition, antifungal and antioxidant activities of wild and cultivated Origanum compactum essential oils from the municipality of Chaoun, Morocco. 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.

Origanum compactum is a medicinal species endemic to Morocco and highly exploited for its therapeutic properties. In the present study, we examined the chem. composition and biol. activities of the essential oils from wild and cultivated O. compactum. The chem. composition was analyzed by gas chromatog. coupled with mass spectrometry (GC/MS). The yield of essential oils was 3.5% for the wild plants and 3.4% for the cultivated plants. Twelve compounds have been identified in the essential oils of wild plants. Carvacrol was the predominant compound (59.0%), followed by p-cymene (18.4%) and then by ¦Ã-terpinene (8.4%). For the cultivated plants, 27 compounds were identified. Here again, carvacrol was the predominant compound (45.3%), followed by p-cymene (22.2%) and by ¦Ã-terpinene (10.1%). The antifungal activity of essential oils was evaluated against four Candida strains using the aromatogram method, the min. inhibitory concentration (MIC) and the min. fungicidal concentration (MFC). In semi-solid medium, essential oils were active against all the strains tested. In liquid medium, MIC values ranged from 216 to 234¦Ìg/mL, while the MFC was 288¦Ìg/mL. Antioxidant activity was investigated by 2,2-diphenyl-1,1,picrylhydrazil radical (DPPH) and the findings showed that the essential oils of both plants have a good antioxidant effect. In conclusion, domestication is a practical approach to preserve O. compactum from extinction without compromising its biol. activities. Besides, the essential oils of O. compactum could be a promising and sustainable alternative to replace the synthetic compounds used currently in pharmaceutical and food industries.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zheng, Guangfan’s team published research in Organic Chemistry Frontiers in 2018 | CAS: 1621962-30-8

Rhodium(III)-catalyzed annulative coupling between arenes and sulfoxonium ylides via C-H activation. 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.

An efficient strategy was developed for the synthesis of 1,2-benzothiazines and isoquinolines I [R = H, 6-Me, 8-F, etc.; R1 = Me, Ph, NHPh, etc.; R2 = Me, t-Bu, 2-FC6H4, etc.; X = C, S(O)] via Rh-catalyzed annulative coupling of aryl-imines/sulfoximines with sulfoxonium ylides. This protocol was also extended for the synthesis of isoquinoline-N-oxides such as II [R3 = Me, Et; R4 = H, 6-t-Bu, 7-Cl, etc.; Ar = Ph, 2-MeC6H4, 4-FC6H4, etc.] and naphthoimidazo[1,2-a]pyridines III [R5 = H, 2-Me, 3-Cl, etc.] from ketoximes and 2-arylimidazo[1,2-a]pyridines resp.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Aher, Yogesh N.’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2018 | CAS: 145026-07-9

Cp*Ir(III)-catalyzed C-H/N-H functionalization of sulfoximines for the synthesis of 1,2-benzothiazines at room temperature. 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 first Cp*Ir(III)-catalyzed C-H/N-H bond functionalization of sulfoximines with ¦Á-diazocarbonyl compounds has been developed for the synthesis of 1,2-benzothiazines under redox-neutral conditions. The reactions proceed at room temperature with excellent functional group tolerance and high yields without the requirement of any silver additive.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Pintatum, Aknarin’s team published research in Arabian Journal of Chemistry in 2022-10-31 | CAS: 483-76-1

Volatile constituents of Amomum argyrophyllum Ridl. and Amomum dealbatum Roxb. and their antioxidant, tyrosinase inhibitory and cytotoxic activities. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

The volatile components from fresh rhizomes and leaves of Amomum argyrophyllum Ridl. and Amomum dealbatum Roxb. were performed using HS-SPME and charac-terized by GC-MS. A total of 49, 47, 49, and 34 compounds were identified from the rhizomes and leaves of A. argyrophyllum and A. dealbatum, resp. The major components were ¦Â-pinene, ¦Á-pinene, and o-cymene. The rhizome extracts exhibited total phenolic content of 2.9 ¡À 0.5 and 2.1 ¡À 0.6 mg gallic acid equivalent The IC50 values of DPPH and ABTS were 179.8 ¡À 3.9 ¦Ìg/mL, 392.9 ¡À 2.6 ¦Ìg/mL, 120.3 ¡À 2.5 ¦Ìg/mL, and 328.6 ¡À 3.3 ¦Ìg/mL, resp. The FRAP values were 76.5 ¡À 7.8 and 84.9 ¡À 4.4 ¦ÌM ascorbic acid equivalent The extracts showed weak antibacterial activity and tyrosinase inhibitory activity of 69.0 ¡À 3.6 and 53.7 ¡À 7.4 mg kojic acid equivalent The cytotoxicity effect was assessed with the MTT assay at 200 ¦Ìg/mL. The extracts showed no toxicity. In addition, the anti-inflammatory properties of extracts were evaluated, and showed potential to inhibit nuclear factor-¦ÊB (NF-¦ÊB) activity.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem