RELATIVE EFFECTIVENESS OF VARIOUS STEROIDS IN AN ANDROGEN ASSAY USING THE EXORBITAL LACRIMAL GLAND OF THE CASTRATED RAT.

1967 ◽  
Vol 55 (1) ◽  
pp. 131-135 ◽  
Author(s):  
Cesare Cavallero ◽  
Peter Ofner
Keyword(s):  
Lacrimal Gland ◽  
Relative Effectiveness ◽  
Preceding Paper ◽  
Fold Increase ◽  
Morphological Transformation ◽  
Methyl Substitution ◽  
Androgenic Activity ◽  
Androstane Series ◽  
Derivatives Of ◽  
Androstane Derivatives

ABSTRACT The morphological transformation of the exorbital lacrimal gland of the castrated rat following subcutaneous injection of steroids, described in detail in the preceding paper, was employed as the end-point of androgenic activity. The relative effectiveness of androsterone and of thirteen derivatives of the 5α-androstane series was then determined using testosterone as reference standard. Androsterone proved one-half as active as the standard; 5α-androstan-17β-ol, 5α-androstane-3β,17β-diol and 5α-androst-1-ene-3,17-dione were much less active, whereas 5α-androstane-3α,17β-diol was 3 times as potent as testosterone. Introduction of a conjugated double bond at C 1,2 of 17β-hydroxy-5α-androstan-3-one produced a four-fold increase of activity from a level a little lower than that of testosterone; a further increase in androgenicity was obtained on methyl substitution at C 1 of the Δ1-5α-isomer of testosterone. Esterification consistently increased the activities of the 5α-androstane derivatives tested.

RELATIVE EFFECTIVENESS OF VARIOUS STEROIDS IN AN ANDROGEN ASSAY USING THE EXORBITAL LACRIMAL GLAND OF THE CASTRATED RAT.

1967 ◽  
Vol 55 (1) ◽  
pp. 119-130 ◽  
Author(s):  
Cesare Cavallero
Keyword(s):  
Lacrimal Gland ◽  
Relative Effectiveness ◽  
Sexually Dimorphic ◽  
Albino Rat ◽  
Steroid Nucleus ◽  
Morphological Studies ◽  
Assay Procedure ◽  
Androgenic Activity ◽  
Highly Sensitive ◽  
Reported Data

ABSTRACT Morphological studies have shown that the exorbital lacrimal gland of the albino rat is a sexually dimorphic structure highly sensitive to androgens. Testosterone treatment elicits a vesicular-mucous change in the glandular acini which can be quantitated histologically and appears to be closely related to the administered dose. An assay procedure using the vesicular change as the end-point of androgenic activity is described and the relative androgenic activities of twenty-one Δ4-3-keto- and Δ5-3β-hydroxysteroids are given. The effect of a variety of substitutions in the steroid nucleus on the activities of testosterone, 17α-methyl-testosterone and 19-nortestosterone is described and discussed with reference to previously reported data.

2,5-Dihydrophenylalanine as an inhibitor of microbial growth

1970 ◽  
Vol 16 (6) ◽  
pp. 545-547 ◽  
Author(s):  
Dorothy S. Genghof
Keyword(s):  
Synergistic Effect ◽  
Growth Inhibition ◽  
Filamentous Fungi ◽  
Molecular Basis ◽  
Microbial Growth ◽  
Relative Effectiveness ◽  
E Coli ◽  
Growth Of A Variety ◽  
Derivatives Of

DL-2,5-Dihydrophenylalanine (DHPA) inhibited the growth of a variety of bacteria representing 10 different genera. Three yeasts were also sensitive to DHPA but only two of nine filamentous fungi were inhibited. The relative effectiveness of DHPA isomers as growth antagonists for S. cerevisiae and E. coli has also been investigated, and, on a molecular basis, DL-DHPA was found to be half as effective as L-DHPA against both of these microorganisms. This DHPA inhibition was reversed by addition of equimolar amounts of phenylalanine. Acetyl derivatives of L-DHPA and DL-DHPA were only slightly inhibitory for S. cerevisiae. A synergistic effect on the DHPA-induced growth inhibition of S. cerevisiae was observed when tyrosine was added to the medium.

Synthesis of 9α-chloro and Bromo-androstane Derivatives

2005 ◽  
Vol 2005 (7) ◽  
pp. 434-435 ◽  
Author(s):  
Mayra Reyes ◽  
Yoanna M. álvarez ◽  
Ariadna Fuente ◽  
José A. Ruiz ◽  
Hermán Vélez-Castro
Keyword(s):  
Bromine Atom ◽  
Androgenic Activity ◽  
Androstane Derivatives

New steroids derivatives having a chlorine and a bromine atom at 9α-position were obtained from a key intermediate 5α-9(11), 16-pregnadien-3β-ol-20-one acetate. These steroids have potential anabolic/androgenic activity.

Derivatives of the androstane series

1970 ◽  
Vol 6 (1) ◽  
pp. 28-29
Author(s):  
L. N. Volovel'skii ◽  
I. I. Kuz'menko
Keyword(s):  
Androstane Series ◽  
Derivatives Of

ANABOLIC, ANDROGENIC AND MYOTROPIC ACTIVITIES OF DERIVATIVES OF 7α-METHYL-19-NORTESTOSTERONE

1963 ◽  
Vol 43 (3) ◽  
pp. 399-411 ◽  
Author(s):  
Stanley C. Lyster ◽  
Gordon W. Duncan
Keyword(s):  
Oral Administration ◽  
Testosterone Propionate ◽  
Free Alcohol ◽  
Anabolic Agent ◽  
Androgenic Activity ◽  
Oral Activity ◽  
Derivatives Of

ABSTRACT Anabolic, myotropic and androgenic properties of a series of 7α=methyl-19-nortestosterone derivatives were compared using quantitative monkey anabolic and rat myotropic/androgenic assays. 7α-Methyl-19-nortestosterone acetate was found to be 6.5 times as potent an androgen as testosterone propionate, and 23 times as potent as a myotropic agent when parenterally administered. The cyclopentylpropionate ester, also more potent than testosterone propionate, possessed depot anabolic and androgenic activity. By oral administration, 7α,17α-dimethyl-19-nortestosterone was 14 times as potent as fluoxymesterone as an anabolic agent in monkeys and possessed a monkey anabolic/rat androgenic ratio of 7 : 1 relative to fluoxymesterone. The free alcohol parent of this series also had high oral activity and possessed a favorable anabolic/androgenic ratio.

Synthesis of derivatives of the androstane series. XXI. Synthesis and properties of some N-acylated androstano[3,2-c]pyrazoles

1981 ◽  
Vol 17 (1) ◽  
pp. 68-72
Author(s):  
L. N. Volovel'skii ◽  
N. M. Khvorova ◽  
I. I. Kuz'menko ◽  
S. N. Ushenko
Keyword(s):  
Androstane Series ◽  
Derivatives Of

scholarly journals Potent Antiplasmodial Derivatives of the Antitussive Drug Dextromethorphan Reveal the Ent-Morphinan Pharmacophore of Tazopsine-Type Alkaloids

2022 ◽  
Author(s):  
Antoinette Keita ◽  
Jean-François Franetich ◽  
Maelle Carraz ◽  
Loise Valentin ◽  
Mallaury Bordesoulles ◽  
...  
Keyword(s):  
Fold Increase ◽  
Structural Determinants ◽  
Prophylactic Drugs ◽  
Therapeutic Development ◽  
Ic50 Values ◽  
Phase Selectivity ◽  
Definition Of ◽  
Further Development ◽  
Derivatives Of

The alkaloid tazopsine 1 was introduced in the late 2000's as a novel antiplasmodial hit compound active against Plasmodium falciparum hepatic stages, with potential to develop prophylactic drugs based on this novel chemical scaffold. However, the structural determinants of tazopsine 1 bioactivity, together with the exact definition of the pharmacophore, remained elusive, impeding further development. We found that the antitussive drug dextromethorphan (DXM) 3, although lacking the complex pattern of stereospecific functionalization of the natural hit, was harboring significant antiplasmodial activity in vitro despite suboptimal prophylactic activity in a murine model of malaria, which precluded its direct repurposing against malaria. The targeted N-alkylation of nor-DXM 15 delivered a small library of analogues with greatly improved activity over DXM 3 against P. falciparum asexual stages. Amongst these, N-2’-pyrrolylmethyl-nor-DXM 16i showed a 2- to 36-fold superior inhibitory potency compared to tazopsine 1 and DXM 3 against parasite liver and blood stages, with 760 ± 130 nM and 2.1 ± 0.4 µM IC50 values, respectively, as well as liver/blood phase selectivity of 2.8. Furthermore, cpd. 16i showed a 5 to 8-fold increase of activity relatively to DXM 3 against P. falciparum stages I-II and V gametocytes, with 18.5 µM and 13.2 µM IC50 values, respectively. Cpd. 16i can thus be considered a promising novel hit compound against malaria in the ent-morphinan series with putative pan-cycle activity, paving the way for further therapeutic development (e. g., investigation of its prophylactic activity in a mouse model of malaria).

Preparation of 3-(6-Deoxy-β-D-glucopyranosyloxy) and 3-(6-Deoxy-α-L-mannopyranosyloxy)androstane Derivatives with Unsaturated Side Chain in Position 17β

1993 ◽  
Vol 58 (12) ◽  
pp. 3000-3008 ◽  
Author(s):  
Hana Chodounská ◽  
Vladimír Pouzar
Keyword(s):  
Side Chain ◽  
Unsaturated Ester ◽  
Silver Silicate ◽  
Derivatives Of ◽  
Androstane Derivatives ◽  
Steroidal Derivatives ◽  
Ester Chain

In our previous papers we described the preparation of 3-β-D-glucopyranosyloxy) and 3-β-D-galactopyranosyloxy) derivatives of steroids with an α,β-unsaturated ester chain in position 17β of androstane skeleton. In conection with this project we have studied silver silicate promoted glycosylation of some of above mentioned steroidal derivatives with 2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyl bromide and 2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl bromide.

scholarly journals Synthesis and properties of peptidyl derivatives of arginylfluoromethanes

1988 ◽  
Vol 256 (2) ◽  
pp. 481-486 ◽  
Author(s):  
H Angliker ◽  
P Wikström ◽  
P Rauber ◽  
S Stone ◽  
E Shaw
Keyword(s):  
Amino Acid ◽  
Amino Acid Sequence ◽  
Active Site ◽  
Relative Effectiveness ◽  
Serine Proteinases ◽  
Cysteine Proteinases ◽  
Peptide Derivatives ◽  
Guanidino Group ◽  
Derivatives Of

Two peptide derivatives of arginylfluoromethane (Arg-CH2F), namely Bz(benzoyl)-Phe-ArgCH2F and D-Phe-Pro-Arg-CH2F, have been synthesized by extension of available methods, i.e. the Dakin-West reaction [Rasnick (1985) Anal. Biochem. 149, 461-465] or synthesis of a phthaloyl-blocked C-terminal fluoromethane [Rauber, Angliker, Walker & Shaw (1986) Biochem. J. 239, 633-640; Angliker, Wikström, Rauber & Shaw (1987) Biochem. J. 241, 871-875] with subsequent elongation. The guanidino group of arginine was protected as the bis-Cbz (benzyloxycarbonyl) derivative. The products were examined as active-site-directed inhibitors of some trypsin-related serine proteinases as well as a pair of cysteine proteinases. The results extend previous observations that the rate of alkylation of serine proteinases by fluoromethanes may be considerably slower than by chloromethanes. As expected, the amino acid sequence of the inhibitors influenced their relative effectiveness. Thus the rate of inactivation of a number of trypsin-like proteinases by D-Phe-Pro-Arg-CH2F varied by more than two orders of magnitude.

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