This invention relates to novel compounds of Formula (I) to (VII), and compositions thereof, useful in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).

Il-8 receptor antagonists

Desulfurization Mediated by Hypervalent Iodine(III): A Novel Strategy for the Construction of Heterocycles

In a one-pot procedure, bromine less brominating reagent 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) has been utilized as an efficient desulfurizing agent for the construction of a library of heterocycles containing N, O, and S starting from aryl/alkyl isothiocyanates. In this approach, aryl/alkyl isothiocyanate reacts with o-phenylenediamine (o-PD), o-aminophenol, and o-aminothiophenol to form their monothiourea which on desulfurization with EDPBT led to the formation of corresponding 2-aminobenzimidazoles, 2-aminobenzoxazoles, and 2-aminobenzothiazoles, respectively. An interesting regioselectivity was observed for unsymmetrical thiourea having a naphthyl moiety on the one side and an ortho amino or an ortho hydroxy phenyl group on the other side giving a completely different product which is mainly dependent on the nature of the nucleophiles (-OH or -NH(2)). Further, the bis-thioureas resulted from the aliphatic 1,2-diamine with 2 equiv of aryl isothiocyanates on treatment with EDPBT gave imidazolidenecarbothioamides, whereas bis-thioureas resulted from aromatic 1,2-diamine yielded benzimidazoles with concurrent expulsion of an isothiocyanate unit. This method is simple and applied to various substrates which are amenable to bromination that reveals the desulfurizing ability of EDPBT predominating over its brominating ability. Finally, the spent reagent EDPDB can be recovered, regenerated, and reused without any loss of activity.

One-pot synthesis of five and six membered N, O, S-heterocycles using a ditribromide reagent.

A general synthesis of N-aryl- and N-alkyl-2-aminobenzoxazoles

Highly Efficient One-Pot Synthesis of 2-Aminobenzoxazoles Using Triflic Acid as a Cyclodesulfurizing Reagent

The cyclization of sulfonamide derivatives of alkylated 2-hydroxyphenylthioureas in the presence of an ammoniacal solution of silver oxide gives 2-alkylaminobenzoxazole-5-sulfonamides or the corresponding 3-alkyl-2-alkyliminobenzoxazolines. Alkyl-substituted 2-aminobenzoxazole-5-sulfonamides were also obtained by the reaction of benzoxazolylthione with secondary amines and aniline.

Synthesis of 2-aminobenzoxazoles and 2-iminobenzoxazolines

Charge-transfer complexes (CTC) of some phenothiazine derivatives with π-electron acceptors were obtained. They were used to determine the ionization potentials of the investigated donor compounds. The complexing constants of phenothiazine and some of its N-substituted derivatives were found. The experimental data obtained make it possible to draw conclusions relative to their configurations.

Charge-transfer complexes of phenothiazine derivatives with π-electron acceptors

The reaction of N-phenylsulfonylbenzoxazolone with amines was investigated in order to study the mechanism of the reaction between aryloxazolones and amines. The sulfonyl group accelerates the reaction considerably. The structure of 2-(phenylsulfamido)phenyl esters of the corresponding N-substituted carbamic acids was assigned to the products on the basis of the IR spectra and alternative synthesis. The reaction with secondary aliphatic amines (dimethyl- and diethylamine)proceeds considerably more slowly and results in the formation of 2-(phenylsulfamido)phenol.

Reaction of N-phenylsulfonylbenzoxazolone with some amines

A phenylsulfonyl group in the 3 position accelerates and changes the direction of aminolysis of benzothiazolone and leads to the formation of 2-phenylsulfonylamino-S-phenyl esters of N-substituted thiocarbamic acids. 2,2′-Bis(phenylsulfonylamino)diphenyl disulfide and the corresponding symmetrical ureas were obtained in the reaction with several primary amines.

D. Simov

Papers

Synthesis of 2-aminobenzoxazoles and 2-iminobenzoxazolines

Charge-transfer complexes of phenothiazine derivatives with π-electron acceptors

Reaction of N-phenylsulfonylbenzoxazolone with some amines

Reaction of 3-phenylsulfonylbenzothiazclone with amines