78231-83-1Relevant academic research and scientific papers
Deacetylcolchicine deriv.
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Paragraph 0316, (2016/10/08)
Provided are 4-modified colchicine compounds and medicines using the same. Specifically provided are colchicine derivatives represented by general formula (1), salts thereof, and solvates of the same. In general formula (1), R1 is a halogen atom, a hydroxyl group, a nitro group, an amino group, or a mono-, di- or tri-fluoromethyl group; R2, R3 and R4 are each a methoxy group or a hydroxyl group, or alternatively R2 and R3, or R3 and R4 together represent a methylenedioxy group; R5 and R6 may be the same or different and are each a hydrogen atom, a C1-6 alkyl group, an arylalkyl group, a C2-6 alkenyl group, -COR7, -COOR8, -SO2R9, -CONR10R11, or -CSNR12R13, or alternatively R5 and R6 together with the nitrogen atom to which R5 and R6 are bonded may form a three- to seven-membered cyclic amino group; R7 is a C1-6 alkyl group or the like; R8 is a C1-6 alkyl group or the like; R9 is a C1-6 alkyl group or the like; R10 and R11 may be the same or different and are each a hydrogen atom, a C1-6 alkyl group, or the like; and R12 and R13 may be the same or different and are each a hydrogen atom, an alkyl group, or the like.
Four new colchicinoids, gloriosamines A-D, from Gloriosa rothschildiana
Kitajima, Mariko,Tanaka, Akiko,Kogure, Noriyuki,Takayama, Hiromitsu
, p. 257 - 260 (2008/03/30)
Four new colchicinoids, gloriosamines A-D, were isolated from the aerial parts of Gloriosa rothschildiana. The structure of gloriosamine A, including the absolute configuration, was determined by chemical conversion from colchicine.
PHENOLIC CONGENERS OF COLCHICINE: PREPARATION AND CHARACTERIZATION OF PHENOLIC AND CATECHOLIC ANALOGUES OF COLCHICINE, COLCHICEINE AND THIOCOLCHICINE
Muzaffar, Anjum,Chrzanowska, Maria,Brossi, Arnold
, p. 365 - 372 (2007/10/02)
Treatment of 2-demethylcolchicine (2) with sulfuric acid afforded 1,2-didemethylcolchicine (6) as the major, and 2,3-didemethylcolchicine (8) as the minor product. 2,3-Didemethylcolchicine (8) was prepared from 3-ethoxycarbonyl-3-demethylcolchicine by sulfuric acid treatment.Hydrolysis of catecholic compounds 6 and 8 with 0.1 N hydrochloric acid afforded colchiceines 13 and 14, respectively.Ester derivatives of 2-demethyl- and 3-demethylcolchicine, and of catechols 6 and 8 were prepared.A direct conversion of 3 into 3-demethylthiocolchicine (15) and conversion of 15 into ester derivatives is described.Cleavage of the ether groups of colchicine by boron tribromide is also reported.
Synthesis of Two Aromatic Methylenedioxy-Substituted Colchicine Congeners: Elucidation of the Structure of Cornigerine as 2,3-(Methylenedioxy)-2,3-Didemethoxycolchicine
Roesner, Manfred,Hsu, Fu-Lian,Brossi, Arnold
, p. 3686 - 3688 (2007/10/02)
Treatment of colchicine with concentrated sulfuric acid at 80-90 deg C afforded besides 2-demethylcolchicine a mixture of catecholic colchicines which could be separated and identified.Similar treatment of 1-demethyl- and 3-demethylcolchicine gave predominantly the 1,2-catechol or its 2,3 isomer.Methylenation of these catechols afforded the colchicine congeners 1 and 10.A comparison with natural cornigerine revealed that the alkaloid was identical with the 2,3-methylenedioxy compound 10 and not with 1, as formerly proposed.
