634151-16-9Relevant articles and documents
SYNTHETIC METHOD FOR CERATAMINE A AND B AND ANALOGS THEREOF
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Page/Page column 10-11, (2010/09/18)
Methods are provided for preparing compounds of the general formula (I) wherein X1 is an aryl hydrocarbon group optionally substituted with one or more groups independently selected from —R, —NH2, —NHR, —NR2, —OH, —OR, —F, —Cl, —Br, —I, —CF3, —C(═O)OH, —C(═O)OR, —C(═O)NH2, —C(═O)NHR, and —C(═O)NR2; X2 is —H, —R, —NHR, —NR2, —OR, —F, —Cl, —Br, or —I; and R is C1 to C10 hydrocarbyl. The methods comprise a double-dehydrogenation reaction step in which a functionalized aminohydroazepinone skeleton comprising an aminoimidazole ring is reacted with 2-iodoxybenzene to form the imidazo[4,5-d]azepine ring system present in formula (I). Example methods comprising the double-dehydrogenation reaction step are provided as efficient synthetic routes to ceratamine A, ceratamine B, and the des-methyl analogs thereof.
A direct and efficient total synthesis of the tubulin-binding agents ceratamine A and B.; use of IBX for a remarkable heterocycle dehydrogenation
Coleman, Robert S.,Campbell, Erica L.,Carper, Daniel J.
supporting information; experimental part, p. 2133 - 2136 (2009/09/25)
The total synthesis of the tubulin-binding agents ceratamine A and B is reported, along with des-methyl analogs, via a synthetic route that is high-yielding and operationally efficient. The synthetic route involved a Beckmann rearrangement to form an azep
CERATAMINES A AND B, AND ANALOGUES, SYNTHESES AND PHARMACEUTICAL COMPOSITIONS THEREOF
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Page/Page column 15, (2008/06/13)
Antimitotic compounds and salts are provided in which the compound has the structure (formula (I)): wherein wherein X and Y are substituted or unsubstituted and are selected from carbon atoms and atoms of groups 15 and 16 of the periodic table; Z is selected from N-R, O and S; U is selected from CR1, N, NH, NR, S and O, R1, R2, and R3 are independently selected from H, NH2, NHR, NR2, SH, SR, SiR3, OH, OR, F, CI, Br, I,=O, =S and R; W is selected from O, S, and H2; R4 is selected from H, R, OH, OR, SH, SR, NH2, NHR, NR2 and halide; R is selected from H, substituted or unsubstituted aryl, and substituted or unsubstituted 1 to 20 carbon linear, branched, or cyclic, saturated or unsaturated alkyl, in which alkyl carbon atoms are replaced by 0 to 10 oxygen, 0 to 10 sulphur, and 0 to 10 N atoms; and wherein bonds to carbon atoms or to any of X, Y, Z and U are saturated or unsaturated; and providing that when W is H2, R4 is not H, OH, or unsubstituted phenyl.
