Discovery of human CCR5 antagonists containing hydantoins for the treatment of HIV-1 infection

Synthesis and Evaluation of 3‐[(2,4‐Dioxo‐1,3,8‐triazaspiro[4.6]undec‐3‐yl)methyl]benzonitrile Derivatives as Potential Anticonvulsants

“…Compounds 16,19, and 33 offered 66% protection. Compounds 8,9,10,12,13,15,16,17,19,20,25,26,27,28,30,32,33, and 35 showed moderate protective effect in the MES and compounds 11, 18, and 31 were found to be 100% protective. Majority of the compounds, except 22,23,24,29,34, and 36, were active in MES tests making them useful for a broad spectrum of seizure types.…”

“…Dried over Na 2 SO 4 and concentrated in vacuo to get pure product 7. General procedure for the synthesis of triazaspiro sulfonamides (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22) The reactants such as 3-[ (2,4-dioxo-1,3,8-triazaspiro[4.6]undec-3-yl)methyl]benzonitrile 7 (100 mg 0.33 mmol), triethylamine (50.88 mg, 0.50 mmol), and sulfonyl chloride (0.37 mmol) in dichloromethane (4 mL) were mixed and stirred at room temperature for 16 h. After completion of the reaction (TLC), it was quenched with saturated sodium bicarbonate solution, extracted with dichloromethane (3 Â 4 mL), dried over Na 2 SO 4 and concentrated in vacuo to give the crude product which was purified by column chromatography on silica employing dichloromethane/methanol (9:1) as an eluent to obtain pure white solid (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22).…”

“…Depending on the nature of substitution on the hydantoin ring, a wide range of other pharmacological properties, e.g., antihypertensive [11], herbicidal [12], antitumor [13], anti-HIV [14], antibacterial [15] and antiviral [16] activities, have also been identified.…”

New platinum(II) complexes of cycloalkanespiro-5-(2-thiohydantoins). Synthesis and quantum chemical investigation

“…as antiepileptic drugs. 18,19 Antiproliferative effects, 20,21 inhibition of aldosoreductase 22 and potential application for treatment of HIV-1 infections 23,24 were also described. Recently, we reported the synthesis of various thioanalogues of cycloalkanespiro-5-hydantoins.…”

Synthesis and anticonvulsant activity of N-3-arylamide substituted 5,5-cyclopropanespirohydantoin derivatives

“…Hydantoins, a class of cyclic imides, have been demonstrated to possess good anticonvulsant property [7,8]. Depending on the nature of substitution on the hydantoin ring, a wide range of other pharmacological properties, e.g., antihypertensive [9], herbicidal [10], antitumor [11], anti-HIV [12], antibacterial [13] and antiviral [14] activities, have also been identified. Spirohydantoin analogs, such as 5,5-cyclohexanespirohydantoins [15], 5,5-cycloheptanespirohydantoins [15], and 5,5-cyclooctanespirohydantoins [15], have been synthesized and shown to have anticonvulsant activity.…”