Razoxane

Razoxane is a N-alkylpiperazine.|An antimitotic agent with immunosuppressive properties.

The racemic form of ADR- 925 (ICRF-198) (MW = 304 g/mol) was prepared in house according to the procedure described previously (Kovarikova et al., 2011). Briefly, At the beginning of each working day the capillary was flushed with NaOH 0.1M for 10min, 5min with Milli-Q water and 40min with the buffer in basic conditions and with MeOH for 5min, NaOH 1M for 25min, 5 min with Milli-Q water, 5min with HCl 0.1M and 30min with the buffer in acid conditions. In order to ensure the repeatability between injections, the capillary was flushed with NaOH 0.1M for 5min, 5min with the buffer and 2min with the BGE in basic or acid conditions. Buffer solutions were prepared by dissolving the appropriate amount of formic acid, acetic acid, ammonium bicarbonate or boric acid in Milli-Q water, adjusting the pH to the desired value (pH 2.5, 5.0, 7.0, or 9.0, respectively) with 0.1 or 1M NaOH before completing the volume with water to get the desired buffer concentration. Finally, BGEs were prepared by dissolving the appropriate amount of the chiral selectors in the buffer solution. Stock standard solutions of racemic captopril, econazole and clenbuterol were prepared by dissolving the appropriate amount of these drugs in MeOH and EXAMPLE 8 dl-1, 2-bis(3, 5-Dioxopiperazin-1-yl)propane N, N, N', N'-Tetracarboxamidomethyl-1, 2-diaminopropane (0.5 g.), prepared essentially by the method of Badinard et al. (loc. cit.), and phenol (10 g.) are heated together under nitrogen at 165C for 20 hours. The phenol is removed by evaporation under reduced pressure and the residue triturated with methanol, cooled in ice and filtered to give dl-1, 2-bis(3, 5-dioxopiperazin-1-yl) propane (0.44 g., 82%) m.p. 235-236C.dl-1, 2-bis(3, 5-Dioxopiperazin-1-yl)propane 1, 2-Diaminopropane tetra-acetic acid (100 g.) and formamide (400 ml.) are heated together at reduced pressure under nitrogen at 100-110C for 1 hour, and then at 150-155C for 4 hours. The brown solution is evaporated under reduced pressure at 80-90C and the residue taken up in methanol (120 ml.) and cooled in the refrigerator overnight. Filtration, followed by washing with cold methanol and vacuum drying at 65C gives dl-EXAMPLE 3 d-1, 2-bis(3, 5-Dioxopiperazin-1-yl)propane d-1, 2-Diaminopropane tetra-acetic acid monohydrate, [alpha]D + 47.1 (c. 0.5% in water), prepared essentially by the method of Dwyer and Garvan, J. Amer. Chem. Soc., 1959, 81, 2956, is reacted with formamide by the method described in to give a 43% yield of d-EXAMPLE 4 l-1, 2-bis(3, 5-Dioxopiperazin-1-yl)propane l, 1, 2-Diaminopropane tetra-acetic acid monohydrate, [alpha]D - 44.2 (c. 0.5% in water), prepared essentially by the method of Dwyer and Garvan (loc. cit.), is reacted with formamide by the method described in to give a 36% yield of l-EXAMPLE 8 dl-1, 2-Bis[4-(N-methylpiperazinomethyl)-3, 5-dioxopiperazin-1-yl]-propane A mixture of N-methylpiperazine (2.21 ml, 20.0 m mole), DMF (25 ml), chloroform (6 ml) and EXAMPLE 6 dl-1, 2-Bis[4-(3, 5-dimethylpiperidinomethyl)-3, 5-dioxopiperazin-1-yl]-propan A mixture of 3, 5-dimethylpiperidine (2.8 ml, 21 m mole), DMF (15 ml), 1, 4-dioxane (15 ml) and dl-1, 2-Bis(4-morpholinomethyl-3, 5-dioxopiperazin-1-yl)-propane A mixture of EXAMPLE 7 dl-1, 2-Bis[4-(N-phenylpiperazinomethyl)-3, 5-dioxopiperazin-1-yl]-propane A mixture of N-phenylpiperazine (2.9 g, 17.7 m mole), DMF (20 ml), absolute ethanol (5 ml) and

Molecular Weight:268.27
XLogP3:-1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:268.11715500
Monoisotopic Mass:268.11715500
Topological Polar Surface Area:98.8
Heavy Atom Count:19
Complexity:404
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes