7336-36-9Relevant academic research and scientific papers
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.
2,10-DIDEMETHYLCOLCHICINE - A NEW ALKALOID FROM MERENDERA ROBUSTA
Chommadov, B. Ch.,Yusupov, M. K.,Aslanov, Kh. A.
, p. 58 - 61 (2007/10/02)
The alkaloid complex of Merendera robusta Bge. (family Liliaceae) growing in the Tashkent province of the Uzbek SSR has been investigated.The main alkaloids of this plant are colchicine and colchamine.Eleven tropolone alkaloids and their photochemical isomers have been isolated and identified.A new alkaloid of phenolic nature has been isolated for which the structure of 2,10-didemethylcolchicine has been established.
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.
Biological Effects of Modified Colchicines. Improved Preparation of 2-Demethylcolchicine, 3-Demethylcolchicine, and (+)-Colchicine and Reassignment of the Position of the Double Bond in Dehydro-7-deacetamidocolchicines
Roesner, Manfred,Capraro, Hans-Georg,Jacobson, Arthur E.,Atwell, Louise,Brossi, Arnold,et al.
, p. 257 - 261 (2007/10/02)
A variety of colchicine, demecolcine, and isocolchicine derivatives were examined for their potency in the lymphocytic leukemia P388 screen in mice, for their toxicity in mice, and for their binding to microtubule protein.A qualitatively direct correlation was found between in vivo potency and toxicity; potency appeared to be less well correlated with tubulin binding.The most potent compounds were N-acylated analogues of colchicine and demecolcine.Among the monophenols, only 3-demethylcolchicine showed an appreciable effect in vitro and in vivo and was less toxic than colchicine.Improved methods were found for the preparation of 3- and 2-demethylcolchicine, which involved the use of 85percent phosphoric acid and concentrated sulfuric acid, respectively.Decoupling experiments with 1H NMR proved that the double bond of dehydro-7-deacetamidocolchiceine and its derived tropolonic methyl ethers 24 and 25 was in the 5,6 position, rather than the 6,7 position formerly tentatively assigned.
