Condensed Ring Compounds Research Articles

The Crystal Structure of condensed Ring Compounds, III:

The Crystal Structure of condensed Ring Compounds, III:

The Crystal Structure of Condensed Ring Compounds II 7-Methoxy-3': 3'-dimethyl-1:2-cyclopentenophenanthrene and 7-Methoxy-1:2-cyclopentenophenanthrene

Article The Crystal Structure of Condensed Ring Compounds II 7-Methoxy-3': 3'-dimethyl-1:2-cyclopentenophenanthrene and 7-Methoxy-1:2-cyclopentenophenanthrene was published on October 1, 1936 in the journal Zeitschrift für Kristallographie - Crystalline Materials (volume 93, issue 1-6).

STUDIES OF THE RAMAN EFFECT OF ORGANIC SUBSTANCES. V. RAMAN EFFECT OF HOMO-CYCLIC COMPOUNDS

Abstract 1. The Raman spectra of the following substances have been measured: benzene, cyclohexane, phenyl-cyclohexane, di-cyclohexyl, indene, naphthalene, tetrahydro-naphthalene, decahydro-naphthalene, tetrahydro-acenaphthene, decahydro-acenaphthene, decahydro-pyrene, and perhydro-pyrene. 2. A complete Raman spectrum of cyclohexane has been obtained. 3. Considering phenyl-cyclohexane, tetrahydro-naphthalene, tetrahydroacenaphthene, and decahydro-pyrene as the substitution products of benzene as well as of cyclohexane, the Raman frequencies of these substances have been classified into three groups, i. e., the first due to the benzene ring, the second due to the cyclohexane ring, and the third due to the combination of the two. 4. The disappearance of Δν and 1000 cm−1. in the di-derivatives (ortho) of benzene has been confirmed even in the case of the condensed ring compounds, such as indene, naphthalene, and tetrahydro-naphthalene. 5. The oscillation of the two forms of indene, i. e. (Remark: Graphics omitted.), has been explained.

The Crystal Structure of Condensed Ring Compounds I

The Crystal Structure of Condensed Ring Compounds I

The œstrogenic activity of some condensed-ring compounds in relation to their other biological activities

The very rapid progress which has been made recently in the chemistry of the œstrogenic hormones, of which an excellent has been given by Girard (1933) has established that these substances are hydrogenated phenanthrene derivatives containing oxygen in the molecule ( cf . Butenandt, Weidlich, and Thompson, 1933). On the assumption of a biological relationship between these hormones and the sterols and bile acids, an assumption which seems justifiable, although it cannot yet be regarded as rigidly proved, œstrone (= ketohydroxyœstratriene) is probably represented by formula I or II. The present communication describes the examination for œstrogenic properties of a number of condensed carbon-ring compounds of somewhat analogous structure in an attempt to elucidate the molecular conditions necessary for œstrogenic activity. A preliminary account of some of these experiments has already been given (cook, Dodds, and Hewett, 1933; cook and Dodds, 1933). Our investigations have brought to light a number of pure synthetic compounds, of known molecular structure, which show this physiological activity, and in some of the compounds studied the activity is of a very high order. It will be observed that one of two oxygen atoms in œstrone is ketonic and the other hydroxylic. Girard (1933) has suggested that these two types of oxygen-containing groups are biologically equivalent, and our own experiments group but no hydroxyl group, whereas others contain only hydroxyl groups in a similar type of molecule.

Societies and Academies

LONDON Royal Society, November 16. J. W. COOK, E. C. DODDS, C. L. HEWETT and W. LAWSON: The oestrogenic activity of some condensed-ring compounds in relation to their other biological activities. In all experiments 100 mgm. of substance was administered to ovariectomised rats, and the doses were afterwards decreased if positive results were obtained. Certain di-alkyl derivatives of 1: 2: 5: 6-dibenz- 9: 10-dihydroanthraquinol, 1-keto-l: 2: 3: 4-tetrahydrophenanthrene, neo-ergosterol, calciferol, ergosterol, 5: 6-c?/cZopenteno-l: 2-benzanthracene, 1: 2-benzpyrene and 1: 9-dimethylphenanthrene were found to be active. Two interesting features of the results are (a) the remarkable fact that the oastrus phenomena may be produced by compounds which differ relatively widely in molecular structure from the natural product, and (6) that it is possible to have apparently unconnected biological activities associated with the same molecular structure, for two of the substances now shown to be cestrogenic have powerful cancer-producing activity, and another one is the antirachitic vitamin, calciferol. Some degree of unsaturation seems necessary for oestrus-producing activity, as was shown by an examination of several compounds related to the sterols, some saturated, some ethylenic, and some aromatic in type. J. W. COOK, E. C. DODDS and A. GREENWOOD: Sex change in the plumage of brown Leghorn capons following the injection of certain synthetic oestrus-producing compounds. Intramuscular injection of o 1-keto, 1:2:3: 4-tetrahydrophenanthrene, and 9: 10-dihydroxy-9: 10-di-n-butyl-9: 10 dihydro-1: 2: 5: 6-dibenzanthracene was followed by a definite appearance of isolated patches of red pigment on the feathers. Later this developed into a definite band across the feather, producing unmistakable demonstration of change from male to female characteristics, as is seen after administration of oestrin. W. E. LE G. CLARK and G. G. PENMAN: The pio-jection of the retina in the lateral geniculate body. The localisation of the retina in the lateral geniculate body of monkeys has been studied by reference to the cellular atrophy which occurs in the nucleus after retinal lesions. Atrophy in the geniculate body is always found to be quite localised and sharply defined after small peripheral lesions. The termination of crossed and uncrossed optic fibres in different cell laminae is confirmed. The macular area of the geniculate body is more restricted than previous observations have suggested, and is represented by a median sector which is definitely limited to the caudal two-thirds of the nucleus. It involves all the cell laminae. Fibres from the nasal half of the macula undergo complete decussation in the chiasma, while those from the temporal half remain uncrossed. The whole width of the cell laminae in the rostral third of the nucleus is concerned with peripheral vision.