Heterocyclic Building Blocks-Benzoxazole

Chavan, Omprakash S.’s team published research in World Journal of Pharmaceutical Research in 2022 | CAS: 4381-25-3

Comparative study of various synthetic methods of 1,2,3-triazoles via click reaction: a mini review. 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.

Different derivatives of azides were condensed with different derivatives of terminal alkynes via click condensation reaction to form resp. derivatives of 1,2,3-triazoles in various reaction conditions. Present paper deals with the comparative study of synthesis of derivatives of 1,2,3-triazoles with respect to yield, reaction time and reaction conditions. All products were characterized by spectral data and elemental anal.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Xianliang’s team published research in Organic Letters in 2022-10-14 | CAS: 1621962-30-8

Superbase-Mediated gem-Difluoroalkenylations of Sulfoximines. 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.

At ambient temperature, deprotonated sulfoximines R1S(O)(R2)=NH (R1 = Ph, 2-naphthyl, 2-pyridyl, 2-thienyl, etc.; R2 = Me, phenyl) react with 1-trifluoromethylalkenes ArC=CH2(CF3) (Ar = Ph, 1-naphthyl, 2-benzofuryl, 3-pyridyl, etc.) to provide either N- or C-gem-difluoroalkenylated products R1S(O)(R2)=NCH2C(Ar)=CF2. The reaction site depends upon the N substituent of the starting material. The optimal conditions involve the use of a superbasic system NaOH in DMSO. The reactions are characterized by a broad substrate scope and medium to high yields. Scale-up experiments of both the N- and C-gem-difluoroalkenylations proceeded well. Treatment of N-difluoroallyl sulfoximine with 4-methoxybenzene-1-thiol under dioxygen afforded the corresponding oxygenated addition product {3,3-difluoro-2-hydroxy-3-[(4-methoxyphenyl)thio]-2-phenylpropyl}imino(methyl)(phenyl)l6-sulfanone.

Superbase-Mediated gem-Difluoroalkenylations of 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

Mendonca Matos, Priscilla’s team published research in Organic Letters in 2020-04-03 | CAS: 4381-25-3

General Method for the Asymmetric Synthesis of N-H Sulfoximines via C-S Bond Formation. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A versatile method for the synthesis of enantioenriched N-H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent stereofidelity with alkyl, aryl, and heteroaryl Grignard reagents. The chiral auxiliary is readily removed from the resultant sulfoximines via an unusual oxidative debenzylation protocol that utilizes mol. oxygen as the terminal oxidant. This provides a general strategy for the synthesis of highly enantioenriched N-H sulfoximines.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Emami, Shabnam’s team published research in Biologia (Cham, Switzerland) in 2022-10-31 | CAS: 483-76-1

Cinnamon extract and its essential oil nanoliposomes – preparation, characterization and bactericidal activity assessment. 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.

The cinnamon essential oil and extract nanoliposomes were prepared through thin layer hydration-ultrasonication technique, using lecithin and three different co-surfactants namely, glycerol, triacetin and propylene glycol, and Tween 80 as surfactant. Results showed that the propylene glycol led to production of the nanoliposomes with the smallest mean particle size (92.03 nm) with spherical-shaped and the greatest net-zeta potential value (-24.1 mV) and was selected as more suitable co-surfactant. While, all prepared nanoliposomes had DPPH radical scavenging activities, the antioxidant activity of cinnamon extract nanoliposome was the greatest (78 ¡À 5%). Different amounts of cinnamon essential oil (0.25, 0.5 and 1.25 mL) were selected to prepared cinnamon essential oil nanoliposomes using propylene glycol and their antioxidant and antibacterial activities were evaluated. A good correlation was observed between amounts of cinnamon essential oil of nanoliposomes and their antioxidant activities (R2 = 0.9945). Although antibacterial activity of cinnamon essential oil and extract were greater than those were encapsulated into nanoliposomes, both cinnamon essential oil and extract nanoliposomes exhibited high antibacterial activities against Escherichia coli and Listeria monocytogenes bacteria strains. Results indicated that based on the min. inhibitory and bactericidal concentrations of the prepared samples, L. monocytogenes had higher resistance to the prepared cinnamon nanoliposomes.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Garcia Mancheno, Olga’s team published research in Organic Letters in 2007-09-13 | CAS: 50578-18-2

Iodinane- and Metal-Free Synthesis of N-Cyano Sulfilimines: Novel and Easy Access of NH-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.

The synthesis of N-cyanosulfilimines can readily be achieved by reaction of the corresponding sulfides with cyanogen amine in the presence of a base and NBS or I2 as halogenating agents. E.g., imination of PhSMe by H2NCN/NBS/t-BuOK gave 91% PhSMe:NCN. Oxidation followed by C-N bond cleavage affords synthetically useful NH-free sulfoximines, e.g., I.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yu, Hao’s team published research in Chemistry – An Asian Journal in 2016 | CAS: 145026-07-9

Copper-Catalyzed Direct Sulfoximination of Heteroaromatic N-Oxides by Dual C-H/N-H Dehydrogenative Cross-Coupling. 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 dual C-H/N-H dehydrogenative coupling of quinoline-type N-oxides with sulfoximines that leads to N-(hetero)arylsulfoximines in high yields was realized by using a catalytic amount of CuBr in air. The method does not require any addnl. ligand, base, reactivity modifier or oxidant and provides a practical route towards a series of sulfoximidoyl-functionalized quinolines and derivatives

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Hou, Anguo’s team published research in Synthetic Communications in 2017 | CAS: 145026-07-9

Copper-catalyzed preparation of N-aroylated sulfoximines from methylarenes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A copper-catalyzed methodol. for the preparations of N-aroylated sulfoximines from methylarenes was herein demonstrated. The transformation proceeded with the assistance of external oxidant tert-Bu hydroperoxide, requiring for no addnl. solvents or ligands. The good compatibility and high efficiency of the newly developed protocol were well described by 21 examples and up to 91% yields. Moreover, the protocol was proved by the control reactions to proceed through a radical pathway.

Copper-catalyzed preparation of N-aroylated sulfoximines from methylarenes. 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

Qian, Pu-Fan’s team published research in ACS Catalysis in 2022-11-18 | CAS: 4381-25-3

Ru(II)/Chiral Carboxylic Acid-Catalyzed Asymmetric [4 + 3] Annulation of Sulfoximines with ¦Á,¦Â-Unsaturated Ketones. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

The synthesis of chiral benzothiazepine-1-oxides with a seven-membered ring via achiral Ru(II)-catalyzed asym. [4 + 3] annulation of sulfoximines with ¦Á,¦Â-unsaturated ketones assisted by chiral carboxylic acid (CCA) was reported. A broad range of chiral benzothiazepine-1-oxides bearing various functional groups was prepared in up to 90% yield with up to >99% ee, expanding the chem. space of chiral sulfoximines. Notably, the oxidative cleavage of the double bonds in the products gave chiral N-benzoyl sulfoximines with a C-S chiral axis.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Jiang, Wenlong’s team published research in Science China: Chemistry in 2019-09-30 | CAS: 145026-07-9

Visible light promoted synthesis of N-aroylsulfoximines by oxidative C-H acylation of NH-sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

The visible light-promoted synthesis of N-aroylsulfoximines was accomplished via an oxidative dehydrogenative coupling at room temperature under air without the addition of a photosensitizer, metal catalyst or base. This process exhibited good functional group tolerance, allowed facile isolation and purification and afforded N-aroylsulfoximines with high efficiency. The efficiency of the newly developed protocol was described in detail with 27 examples with yields ranging from 80% to 96%. Furthermore, the chirality of the NH-sulfoximine was completely maintained in the desired N-aroylsulfoximine product (< 99% ee). Visible light promoted synthesis of N-aroylsulfoximines by oxidative C-H acylation of NH-sulfoximines. 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

Xiao, Shuting’s team published research in Chemical Engineering Journal (Amsterdam, Netherlands) in 2020-09-15 | CAS: 83730-53-4

Multifunctional FeS2 theranostic nanoparticles for photothermal-enhanced chemodynamic/photodynamic cancer therapy and photoacoustic imaging. 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.

Chemodynamic therapy (CDT) and photodynamic therapy (PDT) mediated by reactive oxygen species (ROS) hold great potential for cancer therapy. However, they are still limited by rigorous reaction conditions of efficacious Fenton reaction, reliance on oxygen, and inherent defects of traditional common photosensitizers (PSs). Herein, we reported an L-Buthionine-sulfoximine (BSO) modified FeS2 nanoparticles (BSO-FeS2 NPs) with enhanced ROS generation under single wavelength (808 nm) laser irradiation First, FeS2 NPs showed high photothermal conversion efficiency (49.5%) and enhanced ¡¤O-2 and ¡¤OH generation capability via direct electron transfer presenting photothermal-improved Fenton reaction and photocatalytic ability. With the BSO modification, BSO-FeS2 NPs could inhibit the synthesis of glutathione (GSH) and accelerate the accumulation of ROS, which further enhanced the PDT/CDT treatment efficacy and resulted in high in vivo tumor inhibition rate (95%). Second, BSO-FeS2 NPs could activate the repolarization of macrophages from M2 to M1 for potential tumor immunotherapy. Last, BSO-FeS2 NPs showed good performance on photoacoustic imaging (PAI). All these results establish the capability of BSO-FeS2 NPs as nano-theranostic agents in PAI guided PTT/CDT/PDT combination therapy for cancer treatment.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem