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Organic Phosphorus Compounds. 5. (4-Benzothiazol-2-ylbenzyl)amidophosphonate as Potent Calcium Antagonistic Vasodilators

Structural modification of the calcium antagonist fostedil (KB-944) and their coronary vasodilator activity are described.Amidophosphonate 4a-m, lactam amidophosphonate 7a-l, and diamide dilactam 10 were prepared, and their coronary vasodilator activity was assessed in dogs.Many compounds exhibited coronary vasodilator activity superior to that of fostedil.Among them, the 2-oxopyrrolidine derivative 7a was the most effective compound.Its action as a coronary vasodilator was 3 and 2 times more potent than that of fostedil and diltiazem hydrochloride, respectively.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1183NO – PubChem

 

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Hydrolytic deallylation of N-allyl amides catalyzed by PdII complexes

Hydrolytic deallylation of N-allyl amides to give amides and propanal can be achieved with PdII catalysts. The optimized catalyst consists of Pd(OCOCF3)2 and 1,3-bis(diphenylphosphanyl) propane (DPPP). Several kinds of open-chain N-allyl amides and N-allyl lactams undergo hydrolytic deallylation to give the corresponding amides and lactams in good to high yield. A mechanism which includes isomerization to enamides and subsequent hydrolysis is proposed. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H869NO – PubChem

 

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Copper-catalyzed intermolecular amidation and imidation of unactivated alkanes

We report a set of rare copper-catalyzed reactions of alkanes with simple amides, sulfonamides, and imides (i.e., benzamides, tosylamides, carbamates, and phthalimide) to form the corresponding N-alkyl products. The reactions lead to functionalization at secondary C-H bonds over tertiary C-H bonds and even occur at primary C-H bonds. [(phen)Cu(phth)] (1-phth) and [(phen)Cu(phth)2] (1-phth2), which are potential intermediates in the reaction, have been isolated and fully characterized. The stoichiometric reactions of 1-phth and 1-phth2 with alkanes, alkyl radicals, and radical probes were investigated to elucidate the mechanism of the amidation. The catalytic and stoichiometric reactions require both copper and tBuOOtBu for the generation of N-alkyl product. Neither 1-phth nor 1-phth2 reacted with excess cyclohexane at 100 C without tBuOOtBu. However, the reactions of 1-phth and 1-phth2 with tBuOOtBu afforded N-cyclohexylphthalimide (Cy-phth), N-methylphthalimide, and tert-butoxycyclohexane (Cy-OtBu) in approximate ratios of 70:20:30, respectively. Reactions with radical traps support the intermediacy of a tert-butoxy radical, which forms an alkyl radical intermediate. The intermediacy of an alkyl radical was evidenced by the catalytic reaction of cyclohexane with benzamide in the presence of CBr4, which formed exclusively bromocyclohexane. Furthermore, stoichiometric reactions of [(phen)Cu(phth)2] with tBuOOtBu and (Ph(Me)2CO) 2 at 100 C without cyclohexane afforded N-methylphthalimide (Me-phth) from beta-Me scission of the alkoxy radicals to form a methyl radical. Separate reactions of cyclohexane and d12-cyclohexane with benzamide showed that the turnover-limiting step in the catalytic reaction is the C-H cleavage of cyclohexane by a tert-butoxy radical. These mechanistic data imply that the tert-butoxy radical reacts with the C-H bonds of alkanes, and the subsequent alkyl radical combines with 1-phth2 to form the corresponding N-alkyl imide product.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1067NO – PubChem

 

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N-cyclopropylation of indoles and cyclic amides with copper(II) reagent

Copper-mediated coupling reactions of cyclopropylboronic acid with indoles and cyclic amides are described. The process utilizes catalytic or stoichiometric amounts of copper(ll) acetate, DMAP, and NaHMDS at 95 C under an atmosphere containing oxygen. A variety of functional groups remain intact throughout the reaction.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1074NO – PubChem

 

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Anilide derivative herbicides

New herbicidally active compounds have the formula STR1 wherein R1 is H, alkyl, alkenyl, cycloalkyl, R2 is CF3, NO2, CN, halogen, alkyl, alkoxy or alkyl, and –X–Y–Z– is STR2 in which R3 is H, or alkyl, R4 is H, alkyl or cycloalkyl, R5 is H or alkyl or when –Y–Z– contains two vicinal R4 groups then these R4 groups taken together with the ring carbon atoms to which they are attached form a saturated or unsaturated hydrocarbyl ring containing 5 or 6 carbon atoms.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H199NO – PubChem

 

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beta-Amino phosphine mn catalysts for 1,4-transfer hydrogenation of chalcones and allylic alcohol isomerization

Mn complexes with amino acid derived PN ligands were used in the catalytic transfer hydrogenation (TH) of ketone and chalcone substrates in 2-propanol with mild heating. Moreover, chalcones are reduced selectively to the saturated ketone at short times and can be fully converted to the alcohol when reactions are prolonged. The mechanism of chalcone reduction was briefly considered. Allylic alcohols are not reactive in 2-propanol, but quantitative isomerization occurs in toluene. Thus, we suspect that the allylic alcohols are dehydrogenated and the resulting ketone is formed through a direct 1,4-hydrogenation of the chalcone. Finally, several other related ligands that have been used in Mn-based TH reactions were explored to test the viability of ligand design in favoring chemoselectivity. The beta-amino phosphine ligands proved most effective in this regard.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1099NO – PubChem

 

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Arylaminoethyl amides as inhibitors of the cysteine protease cathepsin K – Investigating P1? substituents

Modeling, synthesis and in vitro activities of a series of arylaminoethyl amide based inhibitors of the cysteine protease cathepsin K are described.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H292NO – PubChem

 

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DCC/DMAP-Mediated Coupling of Carboxylic Acids with Oxazolidinones and Thiazolidinethiones

Dicyclohexylcarbodiimide and catalytic dimethylaminopyridine were successfully used in the coupling of carboxylic acids with oxazolidinones and thiazolidinethiones. The acylated products were obtained in good yields.

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Oxazolidine – Wikipedia,
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Heterobiaryl human immunodeficiency virus entry inhibitors

Previously disclosed HIV (human immunodeficiency virus) attachment inhibitors, exemplified by BMS 806 (formally BMS378806, 1), are characterized by a substituted indole or azaindole ring linked to a benzoylpiperazine via a ketoamide or sulfonamide group. In the present report, we describe the discovery of a novel series of potent HIV entry inhibitors in which the indole or azaindole ring of previous inhibitors is replaced by a heterobiaryl group. Several of these analogues exhibited IC50 values of less than 5 nM in a pseudotyped antiviral assay, and compound 13k was demonstrated to exhibit potency and selectivity similar to those of 1 against a panel of clinical viral isolates. Moreover, current structure-activity relationship studies of these novel biaryl gp120 inhibitors revealed that around the biaryl, a fine crevice might exist in the gp120 binding site. Taken in sum, these data reveal a hitherto unsuspected flexibility in the structure-activity relationships for these inhibitors and suggest new avenues for exploration and gp120 inhibitor design. 2009 American Chemical Society.

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Oxazolidine – Wikipedia,
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Substituted aryl piperazines as neurokinin antagonists

Disclosed are substituted aryl piperazines of Formula I STR1 are tachykinin receptor antagonists useful in the treatment of inflammatory diseases, pain or migraine, asthma and emesis. In particular compounds of Formula I are shown to be neurokinin antagonists.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H63NO – PubChem