Structure and chemistry of kidamycin

The Antibiotics of the Pluramycin Group (4 H-Anthra [1,2-b] pyran Antibiotics)

“…It is one of the best investigated puramycins and the first compound of this family of antibiotics whose structure was fully elucidated. The constitution and configuration were determined from chemical and NMR spectroscopical investigations (28) in conjunction with X-ray analyses of the bis(m-bromobenzoyl) and bis(m-iodobenzoyl) derivatives (28) and (29) of isokidamycin (26) (29) (see Scheme 1) as well as of the rather peculiar kidamycin derivative (30), where C(12) is in fact the acetylated methyl hemiketal of the parent quinone (30). The fact that the structure of kidamycin had been determined unambig- Kidamycin (1) is the only pluramycin antibiotic where an effort was made to reduce its toxicity and thus get a better therapeutic index by derivatization.…”

The structures of kidamycin derivatives: triacetylmethoxykidamycin bis(trimethylammonium) iodide and isokidamycin bis(m-bromobenzoate)

“…Copies may be obtained through The Executive Secretary, International Union of Crystallography, 5 Abbey Square, Chester CH 1 2HU, England. The atom numbering adopted here is, with the exception of Tables 2 and 3, identical with that given in the previous paper (Furukawa et al, 1975). sisting of four fused rings, A, B, C, D, and two tetrahydropyran rings, E and F, which are attached to ring D through C-glycosidic linkages.…”

“…A preliminary report of the structure of the methanolysis product of a kidamycin derivative, triacetylmethoxykidamycin bis(trimethylammonium) iodide (I) (Furukawa, Itai & Iitaka, 1973) and the structure of an isokidamycin derivative, isokidamycin bis(m-bromobenzoate) (II) (Furukawa & Iitaka, 1974), and a full account of the chemical study (Furukawa, Hayakawa, Ohta & Iitaka, 1975) have been published. The chemical structures of kidamycin and isokidamycin are shown in Fig.…”

Isolation and Structure Elucidation of Some Components of the Antitumor Antibiotic Mixture ‘Rubiflavin’

“…In fact, isokidamycin was prepared by Furukawa [8] by heating kidamycin (5) with p-toluenesulfonic acid in refluxing CHCl,.…”