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

Mahanta, Bhaskar Protim’s team published research in Industrial Crops and Products in 2022-06-30 | CAS: 483-76-1

Phytotoxic essential oil from black turmeric (Curcuma caesia Roxb.) rhizome: Screening, efficacy, chemical basis, uptake and mode of transport. 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.

Plant-based phytotoxins play an important role in plant-plant interaction and are of great promise for the development of bioherbicide. In this study, screening of essential oils from six different Curcuma rhizomes identified black turmeric (Curcuma caesia Roxb.) oil as an efficient growth inhibitor in wheatgrass coleoptile bioassay (IC50 57.1¦Ìg/mL). The phytotoxic efficacy of this oil was further confirmed through the dose dependent (10.0-300.0¦Ìg/mL) inhibition of germination, coleoptile and radicle growth of wheatgrass seeds in water medium (IC50 176.7, 90.6 and 93.0¦Ìg/mL resp.) and the pre-germinated seeds in agar medium. Activity-guided fractionation and purification of the crude oil identified curzerenone, a major furanosesquiterpene in this oil as the most active phytotoxin (IC50 13.0¦Ìg/mL in coleoptile bioassay; 188.3, 34.7 and 36.7¦Ìg/mL resp. in water medium). Structure-activity relationship study indicated the importance of all the functional groups for its phytotoxicity. A significant contribution by the oxygenated monoterpenes towards oil phytotoxicity was also evidenced. Though inhibitory efficacy of the oil was comparatively weak in soil, a profound activity through aerial diffusion was observed against germination and/or growth of fresh and pre-germinated wheatgrass seeds (IC50 1.4-6.2 mg/L air). The study also confirmed the uptake of active phytotoxins with no detectable transformation by the seeds in water and their persistence in the soil for at least one and half months. Further, its applicability was demonstrated through an efficient post-emergence growth inhibition (IC50 37.0-81.4¦Ìg/mL) of bermudagrass weed in water and agar medium.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Miao, Jinmin’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2014 | CAS: 145026-07-9

Rhodium-catalyzed direct synthesis of unprotected NH-sulfoximines from sulfoxides. 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.

A novel rhodium-catalyzed imination of sulfoxides using O-(2,4-dinitrophenyl)hydroxylamine is developed under mild conditions with good functional group tolerance. This method provides an efficient access to free NH-sulfoximines, an important structural unit in a variety of biol. active compounds E.g., in presence of Rh2(esp)2 and O-(2,4-dinitrophenyl)hydroxylamine in trifluoroethanol, imination of sulfoxide derivative (I) gave 84% sulfoximine derivative (II).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Deba-Rementeria, Shuyana’s team published research in International Journal of Food Science and Technology in 2022-08-31 | CAS: 483-76-1

Orange peel fermentation using Lactiplantibacillus plantarum: microbiological analysis and physico-chemical characterisation. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Summary : To find an innovative use for orange peels discarded in the orange juice-making process, a fermentative process was assessed using a Lactiplantibacillus plantarum strain. Blanched or rinsed peels were submerged in a 5% NaCl-3% inoculated sucrose brine for 10 days. Total soluble solids, pH, sugars and total aerobic and anaerobic counts were determined in the brines to characterize the process. The final products were characterised by instrumental texture, color and volatile composition The blanching pretreatment had a significant effect on the whole process and the final product characteristics. Anaerobic bacteria total counts were significantly higher in the blanched samples during the whole fermentation, and pH decreased significantly slower in these samples than in the rinsed ones. Rinsed samples were characterised by higher aerobic total counts, higher sucrose consumption and higher glucose, fructose and polyalcs. production The texture was softer in the pretreated samples, probably due to the blanching process rather than the fermentation The volatile composition was quite similar between samples, although it was different from one of the raw orange peels due to a significant decrease in various volatile compounds

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Fusani, Pietro’s team published research in Industrial Crops and Products in 2022-11-01 | CAS: 483-76-1

Composition and biological activity of essential oils from Artemisia roxburghiana Besser and Elsholtzia fruticosa Rehder cultivated in Italy. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

The plants Artemisia roxburghiana Besser and Elsholtzia fruticosa Rehder were evaluated as innovative crops for the production of essential oils with valuable biol. activity. For both species, Clevenger distillation resulted in high essential oil contents of 1.08 and 1.79 mL¡¤100 g-1 dry weight for A. roxburghiana and E. fruticosa, resp. According to the results of GC/FID and GC/MS analyzes, the composition of essential oil of A. roxburghiana was characterized by cis-thujone (23.05%), 1,8-cineole (21.56%), and camphor (13.82%), while E. fruticosa oil was rich in 1,8-cineole (50.06%) and ¦Ã-terpinene (14.11%). The bioactivity of the oils of the two species was evaluated in vitro against both pathogenic Gram-pos. and Gram-neg. bacterial strains by disk diffusion assay and determination of the minimal inhibitory concentration They were also tested as natural insecticides by carrying out mortality and fecundity analyzes against the aphid Mizus persicae. E. fruticosa oil showed higher antibacterial activity compared to A. roxburghiana, particularly against Staphylococcus aureus (MIC 2.0 and 62.5 mg¡¤mL-1) and Escherichia coli (MIC 7.8 and 62.5 mg¡¤mL-1). Both plant species revealed high aphicidal activity against the polyphagous pest M. Persicae according to the nymph mortality and fecundity reduction, and their efficacy was comparable to that of azadyrachtin. This study shows the prospects of the two investigated species as possible innovative crops for the production of essential oils to be employed in agro-industry.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wimmer, Alexander’s team published research in Organic Letters in 2019-04-19 | CAS: 50578-18-2

N-Arylation of NH-Sulfoximines via Dual Nickel Photocatalysis. 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.

The pharmaceutically underexplored sulfoximine moiety has emerged as a potentially active pharmaceutical ingredient. We developed a scalable synthetic route to N-arylated sulfoximines from the resp. “”free”” NH-sulfoximines and bromoarenes. Our strategy is based on a dual nickel photocatalytic approach, is applicable for a broad scope of substrates, and exhibits a highly functional group tolerance. In addition, we could demonstrate that other sulfoximidoyl derivatives like sulfonimidamides and sulfinamides proceed smoothly under the developed reaction conditions.

N-Arylation of NH-Sulfoximines via Dual Nickel Photocatalysis. 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

Porey, Arka’s team published research in Asian Journal of Organic Chemistry in 2016 | CAS: 145026-07-9

Direct N-acylation of sulfoximines with aldehydes by N-heterocyclic carbene catalysis under oxidative conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

An active acyl donor intermediate generated in-situ from an aldehyde by oxidative N-heterocyclic carbene (NHC)-catalysis enabled direct acylation of NH-sulfoximine, affording various N-acylsulfoximines in excellent yields. The reaction was performed with an inexpensive carbene catalyst and easily accessible bisquinone oxidant. This straightforward transformation demonstrated a broad substrate scope with respect to sulfoximines and aldehydes. Importantly, the method allowed amidation of several unactivated aliphatic aldehydes in good-to-moderate yields. Preparative synthesis of N-acylsulfoximine (up to >2 g) was achieved with this simple method.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Di Sotto, Antonella’s team published research in Industrial Crops and Products in 2022-09-01 | CAS: 483-76-1

Phytochemical and pharmacological profiles of the essential oil from the inflorescences of the Cannabis sativa L.. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

Industrial hemp (Cannabis sativa L.) female inflorescences have long been considered as waste material in the hemp production chain. However, past studies focused on the valorization of female inflorescences as high-quality byproducts with promising health-promoting applications. In line with this evidence, the present research investigated the phytochem. and pharmacol. properties with a comparative approach on two essential oils (EOs) obtained from the inflorescences of the industrial hemp varieties Kompolti and Tisza. The EOs composition in terpenes and terpenophenols was determined The effects of the EOs in modulating the viability of different cancer cell lines was investigated. Whereas, in hypothalamic HypoE22 cells, the release of dopamine, norepinephrine, and serotonin was measured, as an index of neuromodulatory activity. Moreover, the EO mycostatic properties were explored towards different dermatophyte species. The prominent terpenes were iso-caryophyllene, ¦Á-humulene, and ¦Â-caryophyllene oxide in both Kompolti and Tisza EOs, whereas cannabidiol and cannabigerolic acid were the main terpenophenols, resp. Both essential oils inhibited the viability of different cancer cells; particularly, the essential oil of Tisza variety displayed a marked cytotoxicity in cholangiocarcinoma cells. A possible role of both terpenophenols and caryophyllane sesquiterpenes as bioactive anticancer compounds has been hypothesized. While cannabidiol could contribute to the stimulation of hypothalamic serotonin release by Kompolti EO. The essential oils also produced antimycotic effects, for which ¦Â-caryophyllene oxide could be partly responsible. Overall, the present findings highlight pharmacol. properties of Kompolti and Tisza EOs, which deserve further investigations and strengthen the interest in industrial hemp inflorescences as valuable source of bioactive extracts and compounds

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Xavier, Julia Karla A. M.’s team published research in Chemistry & Biodiversity in 2022-10-31 | CAS: 483-76-1

The volatile profiles and DNA barcodes of Lauraceae species from the Ocotea complex with occurrence in the Brazilian Amazon. Recommended basis is Cadinene. Products is: https://www.ambeed.com/products/189165-77-3.html, 51905-84-1

The Ocotea complex accommodates most of the taxonomic diversity of Neotropical Lauraceae with economic importance and biol. potential attributed to their essential oils (EOs) and extracts However, the botanical taxonomy has had limitations due to the difficulty of identifying and delimiting species and genera. The chem. and mol. markers of Ocotea complex species in Para state, Brazil, were assessed according to their EO compositions and DNA sequences of matK, trnL-trnF, and ITS regions. The multivariate anal. of EOs constituents has classified them into two main clusters characterized by oils rich in (I) terpenoids and phenylpropanoids and (II) sesquiterpenes. We conducted a phylogenetic anal. of species based on DNA barcode sequences on the Bayesian Inference (PP: 0.70-1,0) and Maximum Likelihood (BS: 72-100 %). The comparison between the volatile profiles and phylogenetic data indicates two main groups for these species collected from the Ocotea complex.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Terhorst, Steven’s team published research in Organic Letters in 2022-06-17 | CAS: 4381-25-3

Sulfonimidamides by Sequential Mechanochemical Chlorinations and Aminations of Sulfinamides. 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.

Here, the first mechanochem. synthesis of sulfonimidamides, e.g., I was reported. The one-pot, two-step method requires neither a solvent nor inert conditions. In a mixer mill, sulfinamides ArS(O)NH(R) (Ar = Ph, 4-methylphenyl; R = pivaloyl, Boc) are rapidly converted to sulfonimidoyl chlorides ArS(O)NR(Cl) by oxidative chlorination with N-chlorosuccinimide (NCS). Subsequent substitutions with amines such as benzyl amine, 3-methyl-1H-pyrazole, piperazine, etc. provides a wide range of diversely substituted sulfonimidamides.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Chen, Feng’s team published research in Dalton Transactions in 2022 | CAS: 83730-53-4

Effect of cysteine thiols on the catalytic and anticancer activity of Ru(II) sulfonyl-ethylenediamine complexes. 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.

Authors have synthesized a series of novel substituted sulfonyl ethylenediamine (en) RuII arene complexes 1-8 of [(¦Ç6-arene)Ru(R1-SO2-EnBz)X], where the arene is benzene, HO(CH2)2O-Ph or biphenyl (biph), X = Cl or I, and R1 is Ph, 4-Me-Ph, 4-NO2-Ph or dansyl. The ‘piano-stool’ structure of complex 3, [(¦Ç6-biph)Ru(4-Me-phenyl-SO2-EnBz)I], was confirmed by x-ray crystallog. The values of their aqua adducts were determined to be high (9.1 to 9.7). Complexes 1-8 have antiproliferative activity against human A2780 ovarian, and A549 lung cancer cells with IC50 values ranging from 4.1 to >50¦ÌM, although, remarkably, complex 7 [(¦Ç6-biph)Ru(phenyl-SO2-EnBz)Cl] was inactive towards A2780 cells, but as potent as the clin. drug cisplatin towards A549 cells. All these complexes also showed catalytic activity in transfer hydrogenation (TH) of NAD+ to NADH with sodium formate as hydride donor, with TOFs in the range of 2.5-9.7 h-1. The complexes reacted rapidly with the thiols glutathione (GSH) and N-acetyl-L-cysteine (NAC), forming dinuclear bridged complexes [(¦Ç6-biph)2Ru2(GS)3]2- or [(¦Ç6-biph)2Ru2(NAC-H)3]2-, with the liberation of the diamine ligand which was detected by LC-MS. In addition, the switching on of fluorescence for complex 8 in aqueous solution confirmed release of the chelated DsEnBz ligand in reactions with these thiols. Reactions with GSH hampered the catalytic TH of NAD+ to NADH due to the decomposition of the complexes. Co-administration to cells of complex 2 [(¦Ç6-biph)Ru(4-Me-phenyl-SO2-EnBz)Cl] with L-buthionine sulfoximine (L-BSO), an inhibitor of GSH synthesis, partially restored the anticancer activity towards A2780 ovarian cancer cells. Complex 2 caused a concentration-dependent G1 phase cell cycle arrest, and induced a significant level of reactive oxygen species (ROS) in A2780 human ovarian cancer cells. The amount of induced ROS decreased with increase in GSH concentration, perhaps due to the formation of the dinuclear Ru-SG complex.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem