The Synthesis of Potential Anabolic Agents. Steroidal Oxadiazoles<sup>1</sup>

Re, Havranek; Gb, Hoey; Dh, Baeder

doi:10.1021/jm00321a014

J. Med. Chem.

1966

DOI: 10.1021/jm00321a014

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The Synthesis of Potential Anabolic Agents. Steroidal Oxadiazoles¹

Havranek Re¹,

Hoey Gb²,

Baeder Dh³

Abstract: Vol. <1 nearly a quantitative yield of which was suitable for subsequent reduction. Recrystallization from acetone, however, gave lib (8.9 g), mp 168-169.5°, [a]2h> -75°.

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Wege zur Totalsynthese heterocyclischer Steroidsysteme

Huisman

1971

Angewandte Chemie

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Bei heterocyclischen Steroiden sind die Kohlenstoff-Atome des Kerns (Positionen 1-17) zum Teil durch Heteroatome ersetzt. Meist handelt es sich um Verbindungen mit ein oder zwei Stickstofl-, Sauerstofl-undloder Schwefel-Atomen. Der heteroatomhaltige Molekiilteil wird entweder als solcher eingesetzt oder durch schrittweise Synthese aufgebaut. Bei den mitgeteilten Beispielen befinden sich die Heteroatome in Ring A, Ring B, zwischen den Ringen A und B undloder zwischen den Ringen C und D.[**I Nach einem Vortrag beim 2. Internationalen KongreD uher Heterocyclische Chemie, Montpellier, 7.-11. Juli 1969.Schwefel. Einige dieser Verbindungen, die durch Teil-oder Vollsynthese hergestellt wurden, haben interessante pharmakologische Eigenschaften.Beispiele sind die Verbindungen (1) *I und (2) I3 -6], die Stickstoff in der Seitenkette tragen. Diese Aza-steroide zeigen eine hypercholesterinamische Wirkungr7 -131. ' ' I und (6) enthalten einen ankondensierten Pyrazol-, Isoxazol-, Oxadiazol-bzw. einen Lactonring. Typisch fur diese Verbindungen ist die deutliche Trennung der anabolischen von den androgenen Eigenschaften. Die modifizierten Steroide (3)['"], (4)Il5], (5)116,Heterocyclische Steroide mit stark entziindungshemmender Wirkung sind die Pyrazol-Derivate, die sich vom 9-Fluor-cortisol-System ableiten, z. B. Verbindung (7) [191.

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Wege zur Totalsynthese heterocyclischer Steroidsysteme

Huisman

1971

Angewandte Chemie

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Approaches to Total Synthesis of Heterocyclic Steroidal Systems

Huisman

1971

Angew. Chem. Int. Ed. Engl.

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In heterocyclic steroids the carbon atoms of the steroid skeleton (positions I to 17) are replaced in part by hetero atoms. The term generally denotes compounds containing one or two nitrogen, oxygen, andlor sulfur atoms. The part of the molecule containing the hetero atom is either introduced as a preformed unit or is constructed by stepwise synthesis. The examples given in the present article contain the hetero atoms in ring A, ring B, between rings A and B, andlor between rings C and D.

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2‐Phenyl‐5‐(trichloromethyl)‐1,3,4‐oxadiazoles, A new class of antimalarial substances

Hutt¹,

Elslager²,

Werbel³

1970

Journal of Heterocyclic Chem

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An investigation of hybrids of 2,5‐dimethyl‐1,3,4‐oxadiazole (I) and α,α,α,α',α',α'‐hexachloro‐p‐xylene (Hetol®) (II) as potential antimalarial agents led to the synthesis of representative 2‐phenyI‐5‐(trichloromethyl)‐1,3,4‐oxadiazoles (VIa‐f, VIII‐X) and related trichloromethyl 1,2,4‐oxadiazole, 1,3,4‐oxadiazoles, and 1,3,4‐thiadiazole (VII, XIII‐XV). Treatment of the appropriately substituted benzoic: acid hydrazides (IVa‐f) with trichloroacetic anhydride afforded the intermediate 1‐benzoyl‐2‐(triehloroacetyl)hydrazines (Va‐f) which were cyclized to the desired 5‐(chlorophenyl, tolyl, or α,α,α‐trifluorotolyl)‐2‐(trichloromethyl)‐1,3,4‐oxadiazoles (VIa‐f) (44–66%) in situ utilizing phosphorous oxychloride. Chlorination of the 5‐tolyl‐2‐(trichloromethyl)‐1,3,4‐oxadiazoles (VId‐f) afforded 2‐(trichloromethyl)‐5‐(α,α,α‐trichloro‐m‐ and p‐tolyl)‐1,3,4‐oxadiazole (VIII and IX) and 2‐(α,α,α,α',α',α'‐hexachloro‐3,5‐xylyl)‐5‐(trichloromethyl)‐1,3,4‐oxadiazole (X) in 23–56% yield. Each of the 2‐phenyl‐5‐(trichloromethyl)‐1,3,4‐oxadiazoles (VIa‐f, VIII‐X) was active against Plasmodium berghei in mice when administered in single 160 or 640 mg./kg. subcutaneous doses or given orally by drug‐diet for 6 days at doses of 29–336 mg./kg./day. The 2‐(trichloromethyl)‐5‐(α,α,α‐trichlorotolyl)‐1,3,4‐oxadiazoles (VIII‐X) were the most active compounds prepared and exhibited activity against P. berghei comparable with Hetol®. Structure‐activity relationships are discussed.

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The Synthesis of Potential Anabolic Agents. Steroidal Oxadiazoles¹

Abstract: Vol. <1 nearly a quantitative yield of which was suitable for subsequent reduction. Recrystallization from acetone, however, gave lib (8.9 g), mp 168-169.5°, [a]2h> -75°.

Cited by 11 publications

References 0 publications

Wege zur Totalsynthese heterocyclischer Steroidsysteme

Wege zur Totalsynthese heterocyclischer Steroidsysteme

Approaches to Total Synthesis of Heterocyclic Steroidal Systems

2‐Phenyl‐5‐(trichloromethyl)‐1,3,4‐oxadiazoles, A new class of antimalarial substances

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The Synthesis of Potential Anabolic Agents. Steroidal Oxadiazoles1

Abstract: Vol. <1 nearly a quantitative yield of which was suitable for subsequent reduction. Recrystallization from acetone, however, gave lib (8.9 g), mp 168-169.5°, [a]2h> -75°.

Cited by 11 publications

References 0 publications

Wege zur Totalsynthese heterocyclischer Steroidsysteme

Wege zur Totalsynthese heterocyclischer Steroidsysteme

Approaches to Total Synthesis of Heterocyclic Steroidal Systems

2‐Phenyl‐5‐(trichloromethyl)‐1,3,4‐oxadiazoles, A new class of antimalarial substances

Contact Info

Product

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The Synthesis of Potential Anabolic Agents. Steroidal Oxadiazoles¹