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Synthesis, anti-inflammatory, and anticancer activity evaluation of some heterocyclic amidine and bis-amidine derivatives

Figure represented. Heterocyclic amidine derivatives of benzothiazole (6a-c), benzimidazole (6d-f), benzoxazole (6g-i), and bis-amidine derivatives of pyrimidine, (7a, 7b) & triazole (7c-e) ring system have been synthesized by nucleophilic addition reaction. All these compounds were screened for anti-inflammatory and anticancer activities. At a dose of 50 mg/kg p.o., compounds 6c (39%), 6e (39%), and 6f (39%) exhibited anti-inflammatory activity comparable to standard drug ibuprofen, which showed 39% activity and compounds 6b, 6e, 7a, and 7c exhibited moderate anticancer activity against cervix (HELA); neuroblastoma (IMR-32); breast (MCF-7), leukemia (THP-1); and cervix (HELA) human cancer cell lines, respectively.

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Copper promoted desulfurization and C-N cross coupling reactions: Simple approach to the synthesis of substituted 2-aminobenzoxazoles and 2,5-disubstituted tetrazole amines

Copper-supported novel, facile and efficient methods for the synthesis of various 2-amino-benzoxazoles and 2,5-diphenyltetrazoleamines have been demonstrated. The reaction procedures are simple, with excellent substrate tolerance in good to high yields thus paving an excellent and useful way to establish a library of potentially active drug molecules. This methodology represents the first concept of copper-catalyst promoted domino C-N cross-coupling reaction towards the construction of 2-aminobenzoxazoles. In addition, we described report for the synthesis of 2,5-diaryltetrazoleamines using copper via inter molecular C-N cross-coupling reaction with aryl iodides. The proposed reaction mechanism involves copper based desulphurization/nucleophilic substitution and subsequent C-N cross-coupling reactions. We established numerous applications of this methodology for synthesizing diverse heterocyclic derivatives i.e. both electron rich and electron deficient systems.

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Benzoxazole – Wikipedia,
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Facile ring opening reaction of oxazolone enables efficient amidation for aminoisobutyric acid

Abstract: 4,4-Dimethyloxazolones derived from N-protected aminoisobutyric acid (AIB) are particularly known as poor electrophiles due to the steric hindrance around the carbonyl and not employed as useful intermediates for amidation whereas numerous examples have been reported to support the utility of other oxazolones in amidation. AIB is an important and strategical synthon in medicinal chemistry but the peptide bond formation of the N-protected urethane derivatives of AIB is known to be often unproductive due to the rapid formation of the stable 4,4-dimethyloxazolone via an intramolecular cyclization. We discovered that the 4,4-dimethyloxazolone of an AIB urethane is in fact an excellent electrophile that enables efficient amidation even with weakly reactive nucleophiles. The 4,4-dimethyloxazolone can be stored in a pure form and used as a reagent offering an efficient and convenient synthetic tool for generating AIB-peptide analogs.

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OXIDATION OF 2-MERCAPTOBENZOHETERAZOLES BY DIMETHYLDIOXIRANE. A NEW METHOD FOR A SYNTHESIS OF C-2 SUBSTITUTED BENZIMIDAZOLE, BENZOXAZOLE, AND BENZOTHIAZOLE DERIVATIVES

New and efficient reactions in which 2-mercaptobenzoheterazoles are selectively converted by dimethyldioxirane, under mild experimental conditions, to several C-2 substituted benzoimidazole, benzoxazole, and benzothiazole derivatives are reported.

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Green Approach for the Synthesis of a New Class of Diamidomethane-linked Benzazolyl Pyrazoles and Evaluation as Antifungals

A new class of diamidomethane-linked benzoxazolyl pyrazoles, benzothiazolyl pyrazoles, and benzimidazolyl pyrazoles were synthesized from the synthetic intermediates N-benzazolylcarbamoylmethylcinnamides adopting environmentally benign methods. In fact, nitrile imine was generated from araldehyde phenylhydrazone in the presence of iodosobenzene and cetyltrimethylammonium bromide followed by oxidation with iodine in dimethylsulfoxide. The structures of compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectra. The title compounds were also evaluated for their antifungal activity. Amongst all the tested compounds benzimidazolyl pyrazolyl carboxamides (13a and 13b) were found to be potential antifungal agents.

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Benzoxazole – Wikipedia,
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Metal-Free Synthesis of Thiosulfonates via Insertion of Sulfur Dioxide

A simple and catalyst-free strategy was developed for the synthesis of unsymmetrical thiosulfonates using readily available DABCO?(SO2)2 as a solid and bench-stable sulfur dioxide surrogate. The corresponding thiosulfonates were obtained through a radical pathway with good functional group tolerance. This strategy offers a promising synthesis method for the construction of diverse and useful thiosulfonates in the field of synthetic and pharmaceutical chemistry and extends the number of still limited sulfur dioxide fixation strategies. (Figure presented.).

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Benzoxazole – Wikipedia,
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Ring Contraction of 1,2,4-Benzoxadiazines to Benzoxazoles

1,2,4-Benzoxadiazines (1) undergo a ring contraction to benzoxazoles (2) on heating.Other products of the reaction have been identified as nitrogen and ammonia.A mechanism is suggested for this reaction which involves (i) electrocyclic ring opening to an o-benzoquinone imine, (ii) recyclisation to a diaziridine, and (iii) extrusion of a nitrene fragment.Evidence is presented which is consistent with this proposal: thus, the benzoxazole (7) is produced on heating 3,5-di-t-butyl-o-benzoquinone with benzamidine and 4-nitrobenzoylnitrene is intercepted as the ylide (11) from the thermolysis of the substituted benzoxadiazine (10).

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Development of electroorganic reactions utilizing stabilized reactive species and its application to organic energy storage materials

Reactive species generated by the oxidation and reduction of organic compounds are generally unstable. To utilize the reactive species as intermediates for organic synthesis and functional materials, it is crucial how to treat them. In this headline, electrochemical reactions utilizing stabilized reactive cations, which enabled benzylic C-H/aromatic C-H cross-coupling, aromatic C-H/C-H cross-coupling, and aromatic C-H amination are demonstrated. Furthermore, energy storage materials utilizing stabilized anions, which enabled to develop organic materials for lithium-ion batteries with high voltage of ca. 3V and solvent-free redox flow batteries with high energy density, are demonstrated. These studies show the usefulness of stabilized reactive species.

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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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4570-41-6, Catalysts are substances that increase the reaction rate of a chemical reaction without being consumed in the process. 4570-41-6, Name is Benzo[d]oxazol-2-amine, molecular formula is C7H6N2O. In a Article, authors is Mukku, Narasimharao£¬once mentioned of 4570-41-6

On water catalyst-free synthesis of benzo[: D] imidazo[2,1- b] thiazoles and novel N -alkylated 2-aminobenzo [d] oxazoles under microwave irradiation

A highly efficient unprecedented catalyst-free microwave-assisted procedure for synthesizing benzo[d]imidazo[2,1-b]thiazoles and N-alkylated 2-aminobenzo[d]oxazol in green media was developed. The transformation provided rapid access to functionalized benzo[d]imidazo[2,1-b]thiazoles from 2-aminobenzothiazole and N-alkylated 2-aminobenzo[d]oxazole from 2-aminobenzoxazole scaffolds under mild transition-metal-free conditions. This synthetic manipulation is expected to greatly expand the repertoire of reaction types in heterocyclic chemistry and pave the way for new syntheses of bioactive compounds.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem