Synthesis of Some New Substituted Thiosemicarbazides as Potential Antiviral Agents

Abstract

The substituted thiosemicarbazides 1-15, synthesized by the condensation of substituted 5-chloro-diphenylamine-2-carboxylic acid hydrazides with appropriate arylisothiocyanates, have been tested for their antiviral activity against the plant virus, sunnhemp rosette virus, in vitro as well as in vivo and against the animal virus, ranikhet disease virus, in a stationary culture of chorioallantoic membranes of chick embryo. The majority of these compounds showed significant antiviral activity against both viruses. The structure-activity relationships have further been studied and are discussed. Synthese einiger neuer snbstituierter Tbiosemicarbazide als potentielle mtivirale AgentienDie substituierten Thiosemicarbazide 1-15, synthetisiert durch Kondensation substituierter 5-Chlordiphenylamin-2-carbonsaurehydrazide mit geeigneten Arylisothiocyanaten, wurden auf ihre Wirksamkeit gegen ein pflanzenpathogenes Virus, Sunnhemp-rosette-Virus, sowohl in vitro als auch in vivo und gegen ein tierpathogenes Virus, Ranikhet-disease-Virus, in einer stationaren Kultur der Chorionallantoismembran des Hiihnerembryos gepriift. Die meisten dieser Verbindungen zeigen signifikante antivirale Wirkswnkeit gegen beide Viren. Die Struktur-Aktivitatsbeziehungen wurden studiert und diskutiert.Diphenylamine-2-carboxylic acid derivatives have been reported to exhibit diverse biological properties such as anthelminthic'), antiba~terial~.~); antifunga14) and antiviral5,@. Further, a large number of thiosemicarbazides have also been found to be remarkably antiba~terially'.~), antifungally9) and antivirally"*") active. Our interest was thus arisen to synthesize the title compounds having both the diphenylamine-2-carboxylic acid nucleus and the thiosemicarbazide group and to see if these would be effective as antiviral agents.Substituted 5-chlorodiphenylamine-2-carboxylic acids, prepared by the Ullmann reaction of 2,4-dichlorobenzoic acid with substituted aromatic amines in presence of anhydrous K2CO3, Cu powder and amyl alcohol, were converted into methylesters by refluxing with thionyl chloride and absol. methanol. The methyl esters on reaction with +) Adress: 559K/22CHH,

Solvatochromic absorption and fluorescence studies of adenine, thymine and uracil thio-derived acyclonucleosides

“…Novel nucleosides with anticancer and/or antiviral activity, with modifications in the nucleobase and/or the sugar moiety have also increased considerably. Among sulfur and nitrogen containing nucleoside derivatives, thiosemicarbazide and thiourea derivatives demonstrate wide range of biological activities, including anticancer [6], anti-HIV [7], antibacterial [8], antiviral [9] and antifungal [10] owing to their ability of diffusion through semipermeable cell membrane [11,12].…”

The interaction between N‐n‐undecyl‐N′‐(sodium p‐aminobenzenesulfonate) thiourea and serum albumin studied using various spectroscopies and the molecular modeling method

“…6 They can be used as insecticides, herbicides, and plant-growth regulators. 7 In this article, N-nundecyl-N 0 -(sodium-p-aminobenzenesulfonate) thiourea (UPT) was synthesized from N-n-undecyl amine and p-aminobenzenesulfonic acid, which contained both a long-chain saturated fatty hydrocarbon substituting group and a water-soluble sulfonic group.…”

Transgenes as screening tools to probe and manipulate the zebrafish genome

“…As a new kind of drug, the derivatives of thiourea exhibited various biological activities such as antiviral and antifungal 6. They can be used as insecticides, herbicides, and plant‐growth regulators 7. In this article, N‐ n ‐undecyl‐N′‐(sodium‐ p ‐aminobenzenesulfonate) thiourea (UPT) was synthesized from N‐ n ‐undecyl amine and p ‐aminobenzenesulfonic acid, which contained both a long‐chain saturated fatty hydrocarbon substituting group and a water‐soluble sulfonic group.…”