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Indomycins and Indomycinones.

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crystalline claudetite is formed only under special experimental conditions.
The modifications of arsenic oxide provide a clear model
system for the study of phase transitions that are influenced
by structure.
The constitution of the yellow crystalline, optically inactive
r-indomycinone ( I ) was proved by K. H . Dahm [21, by ozone
degradation of dihydro- and tetrahydro-a-indomycinone
(2) to 9,10-dihydro-l,8-dihydroxy-3-methy1-9,1O-dioxo-2anthracenecarboxylic acid, chrysophanic acid ( 3 b ) , and
Lecture at Hamburg (Germany) on February 2, 1968 [VB 148 IEl
German version: Angew. Chem. 80, 495 (1968)
[*I Prof. Dr. I. N. Stranski
Fritz-Haber-Institut der Max-Planck-Gesellschaft
1 Berlin 33, Faradayweg 4-6 (Germany)
[l] K. A . Becker, K. Plieth, and I . N . Stranski, Progr. inorg.
Chem. 4,1 (1962).
[2] K. A . Becker, W. Kollmitt, and I. N . Stranski, Z . physik.
Chem. N.F. 37, 314 (1963).
[3] K. A . Becker, H . Karge, and I. N . Stranski, Z . physik. Chem.
N.F. 44, 1 (1965).
[4] K. A . Becker, H . Karge, and I. N . Stranski, 2. physik. Chem.
N.F. 44, 7 (1965).
151 I . Klipping, 2. physik. Chem. N.F. 54, 68 (1967).
Indomycins and Indomycinones
By H. Brockmann [*I
From the mycelium of Streptomyces sp. Ind. 927, J. SchneN[ll
has isolated: indomycin A, yellowish-red, provisional molecular formula C40H52N2010 [6 C-CH3, NH-CH3, N(CH3)z.
5 active H atoms], [a]’,” = +345 (CHC13), bacteriostatic
against B . subtilis t o a dilution of 1:2.5 x 105, carcinostatic
against Ehrlich ascites tumor at 2 mg/kg mouse; indomycin
B, brownish-yellow, provisional formula C3gH4&010
[5 C-CH3, NH-CH3, N(CH&, 5 active H atoms], [a]: =
+319 (CHCI3), bacteriostatic against B. subtilis t o 1 : 2.5 x
106, carcinostatic against Ehrlich ascites tumor at 2 mg/kg
mouse; and indomycin C, brownish-red crystals, provisional
formula C41H52N2011 [6 C-CH3, NH-CH3, N(CH3)2,
7 active H atoms], [a]; = +254 (CHCI3), carcinostatic
against Ehrlich ascites tumor at 30 mg/kg mouse.
The indomycins have a bitter taste, are yellowish-red in
organic solvents, violet in methanolic alkali hydroxide, and
red in concentrated sulfuric acid, give a red vat with dithionite, and contain a quinone group with a chelated hydroxyl
group. Further, biologically inactive, yellow indomycinones
were also isolated from the mycellium; these are either the
indomycin chromophores or compounds resembling them
very greatly in structure.
(30): R = COzH
(3b): R = H
2-methylhexanoic ( 4 ) or butyric acid respectively, supplemented by 1H-NMR and mass spectra of (21,of dihydroa-indomycinone, and of their acetates. The configuration of
the side chain has not yet been established.
Lecture at Clausthal-Zellerfeld (Germany) on January 26, 1968
[VB 156 1El
German version: Angew. Chem. 80, 493 (1968)
[*] Prof. Dr. H. Brockmann
Organisch-Chemisches Institut der Universitat
34 Gottingen, Windausweg 2 (Germany)
[l] J. Schnell, Dissertation, Universitat Gottingen, 1963; in the
present report, the indomycins are designated A, B, C and n o t
a-, fL,
y-, as they are in Schnell’s work.
[2] K . H. Dahm, unpublished
Olefins were converted into aldehydes by H . C . Brown,
R. A . Coleman, and M. W. Rathke by hydroboronation of the
olefins, treatment of the trialkylboranes with C O and
LiAIH(OCH& at atmospheric pressure and room temperature, a n d subsequent careful oxidation. Examples: 1 hexene + heptanal (yield 98 %); isobutene + 3-methylbutyraldehyde (91 %) ; norbornene -+ 2-norbornanecarbaldehyde (87 %). / J. Amer. chem. SOC.90, 499 (1968)/ -Kr.
[Rd 840 IE]
Microbiological conversion of 3-methylpyrocatechol into 2hydroxy-6-oxo-trans-Z-trans-4-heptadienoic acid ( I ) is described by D . Catelani, A . Fiecchi, and E. Galli. After incubation of 3-methylpyrocatechol with a Pseudomonas desmolyticum culture in phosphate buffer of p H = 7, a yellow
Angew. Chem. internat. Edit. / Vol. 7 (1968)
/ No. 6
rI’ c - o r r
compound of m.p. 122-124OC (decomp.) could be isolated
from the culture liquid; this product was identified as ( I ) . /
Experientia 24, 113 (1968) / -Ma.
[Rd 850 IE]
Exchange of oxygen and hydrogen atoms of o-nitrotoluene was
observed by E. K. Fields and S . Meyerson. On pyrolysis of
a solution of o-nitrotoluene in methanol at 6OO0C (11 sec
contact time) methyl anthranilate was formed as principal
48 1
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indomycins, indomycinones
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