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Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with beta-ketoesters and beta-ketoamides

Two regiodivergent approaches to intermolecular cyclization of 2-aminobenzothiazoles with beta-ketoesters and amides have been developed, controlled by the reagents employed. With the Br¡ãnsted base KOt-Bu and CBrCl3 as radical initiator, benzo[d]imidazo[2,1-b]thiazoles are synthesized via attack at the alpha-carbon and keto carbon of the beta-ketoester moiety. In contrast, switching to the Lewis acid catalyst, In(OTf)3, results in the regioselective nucleophilic attack at both carbonyl groups forming benzo[4,5]thiazolo[3,2-a]pyrimidin-4-ones instead.

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Benzoxazole – Wikipedia,
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N-Methylation of Amines with Methanol Catalyzed by a Cp?Ir Complex Bearing a Functional 2,2?-Bibenzimidazole Ligand

A new type of Cp?Ir complex bearing a functional 2,2?-bibenzimidazole ligand was designed, synthesized, and found to be a highly effective and general catalyst for the N-methylation of a variety of amines with methanol in the presence of a weak base (0.3 equiv of Cs2CO3).

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Synthesis and antimicrobial activity of pyrimidinyl bis(benzazoles)

A new class of pyrimidinyl bis(benzoxazoles/benzothiazoles/benzimidazoles) linked by amino sulfamido moieties were prepared and tested for antimicrobial activity. The bis(benzazolyl)pyrimidines (9, 10) displayed higher activity than the corresponding azolyl pyrimidines (4?7). In fact, bis(benzimidazolylamino)pyrimidinylsulfamide (9c), bis(benzothiazolylmethylamino)pyrimidinylsulfamide (10b), bis(benzimidazolylmethylamino)-pyrimidinylsulfamide (10c) were found to be potential antimicrobial agents against S. aureus and P. chrysogenum.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 4570-41-6, name is Benzo[d]oxazol-2-amine, introducing its new discovery. Formula: C7H6N2O

Synthesis and structure-activity relationship studies of 4-((2-hydroxy-3-methoxybenzyl)amino)benzenesulfonamide derivatives as potent and selective inhibitors of 12-lipoxygenase

Human lipoxygenases (LOXs) are a family of iron-containing enzymes which catalyze the oxidation of polyunsaturated fatty acids to provide the corresponding bioactive hydroxyeicosatetraenoic acid (HETE) metabolites. These eicosanoid signaling molecules are involved in a number of physiologic responses such as platelet aggregation, inflammation, and cell proliferation. Our group has taken a particular interest in platelet-type 12-(S)-LOX (12-LOX) because of its demonstrated role in skin diseases, diabetes, platelet hemostasis, thrombosis, and cancer. Herein, we report the identification and medicinal chemistry optimization of a 4-((2-hydroxy-3-methoxybenzyl)amino) benzenesulfonamide-based scaffold. Top compounds, exemplified by 35 and 36, display nM potency against 12-LOX, excellent selectivity over related lipoxygenases and cyclooxygenases, and possess favorable ADME properties. In addition, both compounds inhibit PAR-4 induced aggregation and calcium mobilization in human platelets and reduce 12-HETE in beta-cells.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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A one-pot parallel reductive amination of aldehydes with heteroaromatic amines

A parallel reductive amination of heteroaromatic amines has been performed using a combination of ZnCl2-TMSOAc (activating agents) and NaBH(OAc)3 (reducing agent). A library of diverse secondary amines was easily prepared on a 50-300 mg scale.

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Benzoxazole – Wikipedia,
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Synthesis and antimicrobial activity of benzazolyl azolyl urea derivatives

A new class of benzazolyl azolyl urea derivatives were prepared by the reaction of methyl benzazoyl carbamates with azolyl amines in the presence of mild base potassium tert-butoxide. The presence of electron withdrawing substituents on the aromatic ring enhanced the activity. Nitro substituted benzothiazolyl thiazolyl urea, benzothiazolyl imidazolyl urea and benzimidazolyl thiazolyl urea exhibited potential antibacterial activity against Bacillus subtilis. The compound benzothiazolyl imidazolyl urea and nitro substituted benzimidazolyl imidazolyl urea showed potential antifungal activity against Aspergillus niger.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Quantitative gas-solid reactions with ClCN and BrCN: Synthesis of cyanamides, cyanates, thiocyanates, and their derivatives

Gas-solid reaction techniques allow quantitative cyanations with ClCN and BrCN. Three primary and four secondary cyanamides, a cyanimide, four cyanates, and four thiocyanates were all prepared as solids in 100% yield from solid anilines, benzimidazoles, imides, phenolates, and thiolates, respectively. Intramolecular solid-state reactions of cyanated o-aminophenol and of cyanated hydrazides gave heterocyclic compounds. When comparable reactions were performed in solution the reported product yields were considerably less than 100% in all cases. The reasons for the success of the environmentally benign solid-state syntheses are discussed in terms of phase rebuilding, phase transformation, and crystal disintegration. Atomic force microscopy (AFM) of selected systems indicates the occurrence of long-range molecular movements which are governed by the crystal packing. This is evident from the obvious correlations between the molecular movements and the known crystal packing data. A new type of geometric surface feature, a rectangular and a rhombic depression which resembles a swimming-pool basin, was found in the cyanation of o-aminophenol and benzohydrazide.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Benzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17Beta-HSD10 with implications to Alzheimer?s disease treatment

Human 17beta-hydroxysteroid dehydrogenase type 10 is a multifunctional protein involved in many enzymatic and structural processes within mitochondria. This enzyme was suggested to be involved in several neurological diseases, e.g., mental retardation, Parkinson?s disease, or Alzheimer?s disease, in which it was shown to interact with the amyloid-beta peptide. We prepared approximately 60 new compounds based on a benzothiazolyl scaffold and evaluated their inhibitory ability and mechanism of action. The most potent inhibitors contained 3-chloro and 4-hydroxy substitution on the phenyl ring moiety, a small substituent at position 6 on the benzothiazole moiety, and the two moieties were connected via a urea linker (4at, 4bb, and 4bg). These compounds exhibited IC50 values of 1?2 muM and showed an uncompetitive mechanism of action with respect to the substrate, acetoacetyl-CoA. These uncompetitive benzothiazolyl inhibitors of 17beta-hydroxysteroid dehydrogenase type 10 are promising compounds for potential drugs for neurodegenerative diseases that warrant further research and development.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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An efficient synthetic protocol for amide derivatives of Boc-2-aminoisobutyrate

Abstract: Aminoisobutyric acid (AIB) is an important building block widely incorporated by medicinal chemists in molecular design. Owing to the steric challenge, elaborating AIB?s carboxylic acid using conventional amidation protocols is often problematic. We discovered that an amidation protocol utilizing methyl Boc-aminoisobutyrate and magnesium amidates of various reactivities produces the corresponding amide derivatives in good to excellent yields.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Synthesis of Monofluoromethyl Selenoethers of Aryl and Alkyl from Organoselenocyanate via One-Pot Reaction

The first practical and feasible approach for the monofluoromethylselenolation of aryl and alkyl halides via one-pot multistep synthesis using KSeCN and ICFH2 is described. Good yields and broad functional group compatibility were obtained. The successful preparation of monofluoromethylselenolated drug-like compounds good practicability of this method. This protocol offered a number of new monofluoromethyl selenoethers, which would accelerate the use of such compounds in the areas of life science. (Figure presented.).

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem