M.W=200-250 | Page 20 of 25 | Heterocyclic Building Blocks-Benzoxazole

Choi, Wonseok’s team published research in Organic Letters in 2015-07-02 | CAS: 145026-07-9

Synthesis of N-Imidoyl and N-Oxoimidoyl Sulfoximines from 1-Alkynes, N-Sulfonyl Azides, and 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.

N-Imidoylation of sulfoximines is developed from a Cu-catalyzed three-component reaction from 1-alkynes, N-sulfonyl azides, and sulfoximines in THF at room temperature under air. In addition, N-oxoimidoylation of sulfoximines is accessed from a Cu-catalyzed three-component reaction from 1-alkynes, N-sulfonyl azides, and sulfoximines in THF at room temperature followed by a Cu-catalyzed oxidative reaction at 50 ¡ãC under air, producing N-oxoimidoyl sulfoximines.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Priebbenow, Daniel L.’s team published research in Organic Letters in 2013-12-20 | CAS: 145026-07-9

Copper-Catalyzed Oxidative Decarboxylative Couplings of Sulfoximines and Aryl Propiolic Acids. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A method has been developed for the preparation of N-alkynylated sulfoximines e. g., I involving the copper-catalyzed decarboxylative coupling of sulfoximines with aryl propiolic acids. A range of substituents on both the sulfoximidoyl moiety and the aryl group of the propiolic acid were compatible with this reaction process to afford a series of sulfoximidoyl-functionalized alkynes.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Davari, Mahdi’s team published research in Archives of Microbiology in 2022-08-31 | CAS: 483-76-1

Mycelial inhibitory effects of antagonistic fungi, plant essential oils and propolis against five phytopathogenic Fusarium species. 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.

Fusarium spp. are considered as one of the most devastating plant pathogenic fungi worldwide. In this study, the effect of essential oil (EO) of Mentha longifolia, M. spicata, Achillea sp. and Foeniculum vulgare, ethanolic extract of Propolis (EEP), and Trichoderma harzianum T447 and T. hamatum T622 was investigated against five phytopathogenic Fusarium species. The results showed that the fungal species, the type of EO, and concentrations play a substantial role in inhibiting the mycelial growth of Fusarium spp. GC-MS anal. of the EOs showed that the piperitone oxide and cis-piperitone oxide were found as the main components of M. longifolia. Our results also revealed that EEP possessed the growth inhibitory effect against Fusarium spp. It was observed that the extracellular secretions of T. harzianum T447 showed very high inhibition against the fungi. Our results highlighted the need for further research to apply them as a safe alternative to the chem. pesticides.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Ramazani, Yasaman’s team published research in PLoS One in 2021 | CAS: 83730-53-4

Therapeutic concentrations of calcineurin inhibitors do not deregulate glutathione redox balance in human renal proximal tubule cells. 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.

The calcineurin inhibitors (CNI) cyclosporine A and tacrolimus comprise the basis of immunosuppressive regimes in all solid organ transplantation. However, long-term or high exposure to CNI leads to histol. and functional renal damage (CNI-associated nephrotoxicity). In the kidney, proximal tubule cells are the only cells that metabolize CNI and these cells are believed to play a central role in the origin of the toxicity for this class of drugs, although the underlying mechanisms are not clear. Several studies have reported oxidative stress as an important mediator of CNI-associated nephrotoxicity in response to CNI exposure in different available proximal tubule cell models. However, former models often made use of supra-therapeutic levels of tissue drug exposure. In addition, they were not shown to express the relevant enzymes (e.g., CYP3A5) and transporters (e.g., P-glycoprotein) for the metabolism of CNI in human proximal tubule cells. Moreover, the used methods for detecting ROS were potentially prone to false pos. results. In this study, we used a novel proximal tubule cell model established from human allograft biopsies that demonstrated functional expression of relevant enzymes and transporters for the disposition of CNI. We exposed these cells to CNI concentrations as found in tissue of stable solid organ transplant recipients with therapeutic blood concentrations We measured the glutathione redox balance in this cell model by using organelle-targeted variants of roGFP2, a highly sensitive green fluorescent reporter protein that dynamically equilibrates with the glutathione redox couple through the action of endogenous glutaredoxins. Our findings provide evidence that CNI, at concentrations commonly found in allograft biopsies, do not alter the glutathione redox balance in mitochondria, peroxisomes, and the cytosol. However, at supra-therapeutic concentrations, cyclosporine A but not tacrolimus increases the ratio of oxidized/reduced glutathione in the mitochondria, suggestive of imbalances in the redox environment.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Li, Jun-Yi’s team published research in ACS Catalysis in 2022-08-05 | CAS: 145026-07-9

Ir(III)-Catalyzed Asymmetric C-H Activation/Annulation of Sulfoximines Assisted by the Hydrogen-Bonding Interaction. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

Herein, an Ir(III)-catalyzed asym. C-H activation enabled by noncovalent interactions was described. A broad range of sulfur-stereogenic sulfoximines, e.g., I was prepared in high yields with excellent enantioselectivities via the asym. C-H activation/annulation of sulfoximines with diazo compounds Desymmetrization, kinetic resolution, and parallel kinetic resolution were compatible with this protocol. Detailed DFT calculations suggested that the N-H¡¤¡¤¡¤O hydrogen bonding interaction between sulfoximine and the chiral carboxylic acid ligand was crucial for the high enantiocontrol. Moreover, chiral iridacycle intermediates were isolated, characterized, and subjected to stoichiometric reactions. Computational and exptl. studies suggested that the C-H cleavage step was the rate- and enantio-determining step.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Mouhoub, Anouar’s team published research in World Journal of Microbiology & Biotechnology in 2022-10-31 | CAS: 483-76-1

Assessment of the antioxidant, antimicrobial and antibiofilm activities of essential oils for potential application of active chitosan films in food preservation. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

In the food industry, the development of microbial biofilms is a serious problem that leads to the contamination and deterioration of food products. To overcome that, our aim consists of searching for natural antimicrobial and non-toxic compounds (essential oils EOs), which might be used alone or adsorbed on natural biopolymer films (chitosan). In this work, the antioxidant activity of eight EOs was evaluated by DPPH radical-scavenging method while their antibacterial activity was determined by diffusion on agar and microdilution methods. Among all tested EOs, Eugenia caryophyllus, Cinnamomum zeylanicum Blume and Thymus satureioides Cosson showed high antioxidant activities at the concentration of 25.6 mg/mL, with resp. values of (86.26%, 81.75%, and 76%), and strong antibacterial activity against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, and Enterococcus hirae, with (MIC) values ¡Ü 4¦ÌL/mL. At the concentration of 1¦ÌL/mL, these EOs tested alone, showed values of antibiofilm-forming activity ranging from 79.43 to 99.33% and from 44.18 to 94.17%, when they are adsorbed onto chitosan film. These promising results confirm that these three EOs have a good potential for an eventual application in the food industry, as antimicrobial and antioxidant agents, or as active biodegradable food packaging, if combined with chitosan.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Shi, Peng’s team published research in Organic Letters in 2020-11-20 | CAS: 145026-07-9

Synthesis of Benzothiadiazine-1-oxides by Rhodium-Catalyzed C-H Amidation/Cyclization. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A rhodium-catalyzed C-H amidation/cyclization sequence provides benzothiadiazine-1-oxides from sulfoximines and 1,4,2-dioxazol-5-ones in good yields. The reaction is characterized by a high functional group tolerance and, in contrast to most previous transformations of this type, is well-suited for S-alkyl-S-aryl-substituted sulfoximines.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Sharma, Alpa’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2022 | CAS: 145026-07-9

Visible-light-promoted iron-catalyzed C-H functionalization of 1,4-naphthoquinones via oxidative coupling with sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A catalytic oxidative addition of sulfoximines to naphthoquinones via C-H functionalization was achieved using an iron catalytic system, which exhibited good reactivity and high regioselectivity in the presence of visible light. This was the first report offering an efficient protocol for obtaining (naphtho)quinone-sulfoximine hybrid analogs in moderate to good yields with wide scope for both the substrates. This protocol was also applied on natural products for their modification, including vitamin K3, Juglone and some other modified natural scaffolds as well.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Ibdah, Mwafaq’s team published research in Phytochemistry (Elsevier) in 2022-10-31 | CAS: 483-76-1

Identification and characterization of three nearly identical linalool/nerolidol synthase from Acorus calamus. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Acorus calamus is a perennial aromatic medicinal plant from the Acorusaceae family, known for its pharmaceutical and medicinal value. A combined chem., biochem., and mol. study was conducted to evaluate the differential accumulation of volatile organic compounds (VOCs) in rhizomes and leaves of A. calamus essential oil. Here, we performed VOC profiling and transcriptome-based identification and functional characterization of terpene synthase (TPS) genes. A total of 110 VOCs were detected from the rhizomes and leaves of A. calamus, and some VOCs showed significant differences between them. The further transcriptome-based anal. led to the identification of six putative TPSs genes. In phylogenetic anal., three TPSs belonged to the TPS-g clade, one to each of the TPS-a, TPS-c, and TPS-e clades. The heterologous E. coli-based expression of recombinant TPSs identified three genes (AcTPS3, AcTPS4, and AcTPS5) as bifunctional linalool/nerolidol synthase. The correlation of TPS gene expression and VOC metabolite profiles supported the function of these genes in A. calamus. Our findings provide a roadmap for future efforts to enhance the mol. mechanisms of terpene biosynthesis and our understanding of Acorus-insect interactions.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Luo, Gang’s team published research in Yeast in 2021-11-30 | CAS: 83730-53-4

The mechanism of N-acetyl-L-cysteine in improving the secretion of porcine follicle-stimulating hormone in Pichia pastoris. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Our previous study revealed that N-acetyl-L-cysteine (NAC) could enhance the secretion of recombinant proteins by Pichia pastoris, but the corresponding mol. mechanisms are still unclear. In the present study, we explored whether other thiols have a similar action on the secretion of recombinant human serum albumin and porcine FSH fusion protein (HSA-pFSH¦Â), to reveal the mechanism of NAC on HSA-pFSH¦Â secretion. Transcriptome anal. showed that genes involved in oxidoreductase activity and oxidation-reduction process were upregulated in cells supplemented with NAC. The other three thiol-reducing regents including dimercaptopropanol (DT), thioglycolic acid, and mercaptolactic acid could improve HSA-pFSH¦Â production in the culture supernatant. Among them, only DT had similar effect as NAC on HSA-pFSH¦Â secretion and the increase of GSH content. Moreover, 1-20 mM GSH, 1-10 mM cysteine, or 1-20 mM N-acetyl-D-cysteine supplementation could improve the secretion of HSA-pFSH¦Â. Furthermore, 0.4-3.2 mM ethacrynic acid, rather than 1-16 mM BSO could inhibit the effect of NAC on the production of HSA-pFSH¦Â. These results indicated that NAC improved the secretion of HSA-pFSH¦Â by increasing the intracellular GSH content through its thiol activity rather than as a precursor for GSH synthesis. In conclusion, our results demonstrate, for the first time, that the secretion of recombinant HSA-pFSH¦Â in Pichia pastoris could be improved through thiol-reducing agent supplementation, and the mechanism of the effect NAC has on HSA-pFSH¦Â secretion is associated with improving the intracellular GSH content.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem