Fifteen new formazans were synthesized by the condensation of the 4-nitrophenylhydrazone of 3-nitro-anisaldehyde with the appropriate phenyldiazonium salts. Their in vivo an!iviral activity was evaluated against Ranikhet disease virus (RDV) in chick embryos. Out of the compounds screened, (8) showed maximum (62.5 %) protection against RDV. The structure activity relationship has further been studied and is discussed. 1-[4'-carboxyphenyl]-3-[3-nitro4methoxyphenyl]-S-[4-nitrophenyl]formazan Synthese e w e r nenen Fonnmne Pls potentielle antivlrnle AgentienFunfzehn neue Formazane wurden durch Kondensation des 4-Nitrophenylhydrazons des 3-Nitroanisaldehydes mit Phenyldiazoniumsalzen synthetisiert und ihre in-vivo antivirale Wirksamkeit gegen Ranikhet-disease-Virus (RDV) in Huhnerembryonen gepriift. Unter diesen Verbindungen, wurde die starkste signifikante Schutzwirkung (bis zu 62.5 %) nit 1-(4'-Carboxyphenyl]-3-[3'-nitro-4'-methoxyphenyl]-5-[4'-nitrophenyl] formazan (8) erzielt. Die Struktur-Aktivitatsbeziehungen werden studiert und diskutiert. The biological utility of formazans for staining tissues and visualization of reducing enzymes in normal neoplastic are known for a long time. Their antibacterial') activity has come to light when Kuhn undJerchel screened them against various strains of bacteria. Libman et al." reported the antiviral activity of p-aminophenyl-2,5-diphenyltetrazolium chloride against influenza A and Nigg mouse pneumonitic virus. Recently Misra et al.') have synthesized a number of formazans and their tetrazolium salts and observed some of them to be active against RDV. In view of these observations of a broad spectrum of antiviral properties associated with formazan derivatives, it was thought of interest to synthesize some new formazan derivatives as potential antiviral agents. 0365-6233/81/1212-0991 I 0Z.Mm

The synthesis of 11-oxaestradiol, a product with antifertility actlvity but very low uterotropic potency, 1s reported. It was first prepared in moderate yield by a Dryden aramatizatmn from 118-acetoxy-11-oxaandrosta-1.4-dien-3-one and, secondly, from estrone or dehydroestrone, by a new and efficient route involvrng a photolytic chlorinating decarboxyiation of a 9-0x0-9.11-seco-11-acid and cyclization of the 98-hydroxy-9.11-seco-11-nor-12-chlor~de derived from the degradation product. By the latter procedure, 11-oxa-I-dehydro-11-deo~~cortisol and its acetate, antiinfl-atory agents with no mmeralocorticoid and, at the dose levels to be considered, insignificant glucocorticoid responses, were also prepared from 17.21-dlhydroxylated 5a-pregnan-20-ones.Among the various hormonal 11-oxasteroids which we ~ynthesized,"'."~ two products seemed of particular blolqical interest. The first of them, 11-oxaestradiol ( 5 , Scheme I) showed only extremely l o w estrogenic (uterotropic) activity, but still significant antifertility potency m a post-coltal test in rats, the ratlo of antifertility to estrogenic activity being increased by a factor of 10."In our first synthesis of thls hormone analogue (5), already reported in a preliminary fashion," the 11-oxa structure was elaborated by our original method,.' consisting in the ozanolysis of a r(l1)-unsaturated 12-ketone of the A/B-trans series, reduction of the resulting ll-nor-9.12seco-9-0x0-12-acid to the corresponding 90.12-did, and cyclization with p-toluenesulfonlc acid, hecogenln (1) having served es starting materral. The synthetic precursor of " Dedicated with admiration to Professor Sir Derek Barton on the occasion of his 7 0 ' " brrthday.

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Aus dem p‐Nitrophenylhydrazon (III) des durch Nitrierung von (I) erhaltenen Nitroanisaldehyds (II) werden mit den Diazoniumsalzen (IV) die Formazane (V) hergestellt, die z.Tl. antivirale Aktivität besitzen.