2,3-Bis(acetylmercaptomethyl)quinoxaline

2,3-Bis(acetylmercaptomethyl)quinoxaline.svg 2,3-Bis(acetylmercaptomethyl)quinoxaline S,S′-[Quinoxaline-2,3-diylbis(methylene)] diethanethioate 36014-40-1 correct FDA 8D6GD5CB5H 188227 CC(=O)SCC1=NC2=CC=CC=C2N=C1CSC(=O)C 163612 1/C14H14N2O2S2/c1-9(17)19-7-13-14(8-20-10(2)18)16-12-6-4-3-5-11(12)15-13/h3-6H,7-8H2,1-2H3 KIYGADXCTZZZDG-UHFFFAOYAA 1S/C14H14N2O2S2/c1-9(17)19-7-13-14(8-20-10(2)18)16-12-6-4-3-5-11(12)15-13/h3-6H,7-8H2,1-2H3 KIYGADXCTZZZDG-UHFFFAOYSA-N 14 14 2 2 2 2,3-Bis(acetylmercaptomethyl)quinoxaline (BAMMQ) is an antiviral agent which inhibits poliovirus RNA synthesis in vitro and in vivo and inhibits human herpesvirus 1 multiplication in vitro. It does not interfere with attachment, penetration or DNA synthesis, but interrupts a late stage in virus assembly and/or maturation. BAMMQ was first identified as an antiviral agent in 1974, when it was shown to inhibit poliovirus growth by 99.8% or more at concentrations as low as 10−5 M. That same year, a patent was filed for BAMMQ and related quinoxaline compounds as antiviral agents, particularly noting their effectiveness against herpes simplex virus. The compound acts by specifically inhibiting viral RNA synthesis, with inhibition occurring within 30–60 minutes after addition of the drug. Studies demonstrated that while BAMMQ inhibited viral RNA replication, it did not directly affect viral protein synthesis. The compound's antiviral activity was found to be somewhat dependent on the culture medium composition and viral infection levels. This initial research also suggested that BAMMQ may act by preventing the reinitiation of viral RNA synthesis rather than blocking ongoing RNA synthesis. BAMMQ has demonstrated broad-spectrum antiviral activity against multiple viruses. In addition to poliovirus, early studies showed it was effective against vesicular stomatitis virus, human parainfluenza virus type 3, Rous sarcoma virus, and herpes simplex virus. However, the compound's basic cytotoxicity and the fact that its antiviral efficiency could be partly reversed by increasing viral infection levels or using enriched medium limited its practical applications. The compound has also shown activity against plant viruses. It effectively inhibits both tobacco mosaic virus (TMV) and cowpea chlorotic mottle virus (CCMV) at relatively low concentrations, requiring only 0.015 millimolar (mM) for 90% inhibition of TMV and 0.03 mM for CCMV in leaf disk experiments. While the compound shows promise in leaf disk studies, research has shown that it does not reduce TMV accumulation in tobacco tissue cultures containing the compound. BAMMQ has also been studied as an inhibitor of encephalomyocarditis (EMC) virus. While it allowed plating of high virus concentrations without causing extensive cell damage, no resistant viral mutants were observed in these studies. References 30em Bucchini Danielle Fiszman Marc Girard Marc 1974 On a new inhibitor of poliovirus RNA replication Intervirology 3 5–6 281–291 10.1159/000149766 4374448 Bucchini Danielle Girard Marc 1975 Inhibition of herpes simplex virus multiplication by 2,3-bis(acetyl mercaptomethyl)-quinoxalin Intervirology 6 4–5 285–295 10.1159/000149482 186437 International Grain Legume Information Center 1987 Cowpeas (Vigna unguiculata L. Walp): Abstracts of world literature, Vol. V, 1983–1985 5 International Institute of Tropical Agriculture Idaban 125 Dawson W.O. 1984 Effects of animal antiviral chemicals on plant viruses Phytopathology 74 2 211–213 10.1094/Phyto-74-211 https://www.apsnet.org/publications/phytopathology/backissues/Documents/1984Articles/Phyto74n02_211.pdf US 3845047 Christian Egli 2,3-Bis-(acylmercaptomethyl)-quinoxalines 29 October 1974 6 July 1971 https://patentimages.storage.googleapis.com/d1/96/d6/81552e24a7e345/US3845047.pdf Galabov A.S. Dmitrieva T.M. 1983 Inhibitory effect of N-phenyl-N'-3-hydroxyphenylthiourea (PTU-23) on the reproduction of encephalomyocarditis virus in Krebs-II cells Zentralblatt für Bakteriologie, Mikrobiologie und Hygiene. 1. Abt. Originale. A, Medizinische Mikrobiologie, Infektionskrankheiten und Parasitologie 254 3 10.1016/S0174-3031(83)80110-3 291–305 6326421 Mahy Brian W.J. A Dictionary of Virology https://archive.org/details/dictionaryofviro0000mahy registration 2001 Academic Press San Diego, Calif. [u.a.] 0-12-465327-8 2 3 Rabinovitch Peter S. Martin George M. 1982 Encephalomyocarditis virus as a probe of errors in macromolecular synthesis in aging mice Mechanisms of Ageing and Development 20 2 155–163 10.1016/0047-6374(82)90066-5 6294419 Category:Quinoxalines Category:Thioesters Category:Antiviral drugs Category:Acetyl compounds