Properties and Exciting Facts About Benzo[d]oxazol-2-amine

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Synthesis, antimicrobial and cytotoxic activities of pyrimidinyl benzoxazole, benzothiazole and benzimidazole

A variety of pyrimidinyl benzoxazoles, benzothiazoles and benzimidazoles linked by thio, methylthio and amino moieties were prepared and studied their antimicrobial and cytotoxic activities. The compound pyrimidinyl bis methylthio benzimidazole 22 was a potent antimicrobial agent particularly against Staphylococcus aureus (29 mm, MIC 12.5 mug/mL) and Penicillium chrysogenum (38 mm, MIC 12.5 mug/mL). The amino linked pyrimidinyl bis benzothiazole 24 exhibited cytotoxic activity on A549 cells with IC50 value of 10.5 muM.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Carbon?Nitrogen Bond Formation Through Cross-Dehydrogenative Coupling Reactions

There are many methods available in the synthetic toolbox to construct carbon?nitrogen bonds, but these standardly require preactivation of the substrate. These involve classical, nonmetal catalyzed methods (e.g., nucleophilic substitutions) and catalytic methods (e.g., the Ullmann condensation reaction) as well as modern metal-catalyzed approaches with wide scope (Buchwald?Hartwig reaction, hydrogen-borrowing reactions). Cross-dehydrogenative couplings (CDCs) couple a C?H with an N?H bond and do not require any preactivation and are therefore considered the ?nec plus ultra? in amination chemistry. Based on the ubiquitous nature of C?H bonds in substrates and the wide availability of amines as reactants they inherently show great application potential. Especially from a sustainable chemistry point of view it holds great promise, provided green oxidants can be used in a safe manner. However, though major advances have been made in the field, this last addition to the carbon?nitrogen bond forming toolbox is still in its infancy. The major investigations and advances dealing with CDCs for C?N bond formation since 2014 are summarized in this review. Intra- and intermolecular direct oxidative amination reactions on C(sp2)?H as well as C(sp3)?H bonds are included. Both metal-catalyzed and metal-free approaches are covered, as well as the corresponding mechanistic proposals.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Preventive and/or therapeutic agent of immune disease

Provided is a preventive and/or therapeutic agent for immune diseases containing a compound having a BTK inhibitory activity or a salt thereof, as an active ingredient. A preventive and/or therapeutic agent of immune diseases, comprising a compound represented by Formula (I), where R1 to R3, W, X, Y, Z, and n represent those as defined in the specification, or a salt thereof, as an active ingredient.

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SYNTHESIS OF 2-AMINOBENZOXAZOLE COMPOUNDS

A method for forming an optionally substituted 2-aminobenzoxazole compound includes: contacting an optionally substituted 2-aminophenol compound with (1) an amine of the formula NHR2R3, wherein R2 and R3 are each independently selected from H, an optionally substituted alkyl group or an optionally substituted aryl group, or R2 and R3, taken together with the nitrogen atom to which they are attached, form an optionally substituted heterocyclic ring; and (2) a reactant selected from the group consisting of: (a) C(OR)4, wherein R represents an alkyl group; (b) C(OAr)4, wherein Ar represents an aryl group; and (c) CCl2(OAr)2, wherein Ar represents an aryl group, in combination with a base; thereby forming the optionally substituted 2-aminobenzoxazole compound.

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Synthesis of benzohetero[3, 2-a]pyrimidines using cyclic beta-keto lactone as a building block

A novel method for the synthesis of 3-(2-substituted ethyl)-2- methylbenzohetero[3,2-a]pyrimidines in high yield (80-85%) was achieved, which involves a dihydrofuranone intermediate, readily obtained from beta-ketolactone to 2-aminobenzoheterocycles. The major advantage of the methodology is the high yield and product purity. Graphical Abstract: [Figure not available: see fulltext.]

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Benzoxazole – Wikipedia,
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Stability of 2-aminobenzoxazole and 2-aminobenzimidazole heterocycles in reactions with propylene oxide

In reaction of 2-aminobenzoxazole with propylene oxide in protic solvents, opening of the heterocycle ring occurs along with alkylation. In the case of 2-aminobenzimidazole, only alkylation occurs under similar conditions. We have studied the compositions of the reaction mixtures and the dynamics of formation of the reaction products by mass spectrometry.

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Benzoxazole – Wikipedia,
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A microwave radiation in the aqueous phase benzamide compound synthesis benzoxazole method (by machine translation)

The invention discloses a microwave radiation in the aqueous phase benzamide compound synthesis benzoxazole method, in the aqueous phase under microwave conditions to join the benzamide compound under alkaline condition […] benzene and oxazole reaction, invention an environment-friendly, the operation is simple, cheap and safe, efficient preparation BENZOXAZOL method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection; . (by machine translation)

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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An efficient solid-phase parallel synthesis of 2-amino and 2-amidobenzo[d]oxazole derivatives via cyclization reactions of 2-hydroxyphenylthiourea resin

An efficient solid-phase methodology has been developed for the synthesis of 2-amino and 2-amidobenzo[d]- oxazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo- [d]oxazole resins 4 by cyclization reaction of 2-hydroxyphenylthiourea resin 3. The resin-bound 2-hydroxyphenylthiourea 3 is produced by the addition of 2-aminophenol to the isothiocyanate-terminated resin 2 and serve as a key intermediate for the linker resin. This core skeleton 2-aminobenzo[d]oxazole resin 4 undergoes functionalization reaction with various electrophiles, such as alkylhalides and acid chlorides to generate 2- amino and 2-amidobenzo[d]oxazole resins 5 and 6 respectively. Finally, 2-amino and 2-amidobenzo[d]oxazole derivatives 7 and 8 are then generated in good yields and purities by cleavage of the respective resins 5 and 6 under trifluoroacetic acid (TFA) in dichloromethane (CH2Cl2).

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Benzoxazole – Wikipedia,
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Benzothiazole-Based LRRK2 Inhibitors as Wnt Enhancers and Promoters of Oligodendrocytic Fate

Leucine rich repeat kinase 2 (LRRK2) is an enigmatic enzyme and a relevant target for Parkinson’s disease (PD). However, despite the significant amount of research done in the past decade, the precise function of LRRK2 remains largely unknown. Moreover, the therapeutic potential of its inhibitors is in its infancy with the first clinical trial having just started. In the present work, the molecular mechanism of LRRK2 in the control of neurogenesis or gliogenesis was investigated. We designed and synthesized novel benzothiazole-based LRRK2 inhibitors and showed that they can modulate the Wnt/beta-catenin signaling pathway. Furthermore, compounds 5 and 14 were able to promote neural progenitors proliferation and drive their differentiation toward neuronal and oligodendrocytic cell fates. These results suggest potential new avenues for the application of LRRK2 inhibitors in demyelinating diseases in which oligodendrocyte cell-death is one of the pathological features.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

More research is needed about Benzo[d]oxazol-2-amine

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Synthesis and evaluation of arylpiperazine-reverse amides as biased dopamine D3 receptor ligands

The dopamine D3 receptor (D3R) preferential ligands have been universally adopted as a strategy for the treatment of drug addiction and other neuropsychiatric disorders due to fewer side effects. However, the high sequence homology between D3R and the D2 receptor (D2R) challenges the development of D3R-biased compounds. Herein, we design and synthesize a novel series of reverse amide-piperazine hybrid ligands and evaluate their biological affinities in vitro. Compound 4d was found to be the most potent D3R-selective ligand among these hybrid derivatives. Molecular modeling revealed that extracellular loop 1 (EL1) and loop 2 (EL2) of D3R together likely contribute to D3R selectivity over D2R. In particular, Gly94 in EL1 of D3R may act as a molecular determinant for D3R specificity.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem