Rhodanine Explained

Rhodanine should not be confused with rhodamine.

Rhodanine is a 5-membered heterocyclic organic compound possessing a thiazolidine core. It was discovered in 1877 by Marceli Nencki who named it "Rhodaninsaure" in reference to its synthesis from ammonium rhodanide (known as ammonium thiocyanate to modern chemists) and chloroacetic acid in water.^[1]

Rhodanines can also be prepared by the reaction of carbon disulfide, ammonia, and chloroacetic acid, which proceeds via an intermediate dithiocarbamate.

Derivatives

Some rhodanine derivatives have pharmacological properties; for instance, epalrestat is used to treat diabetic neuropathy. However, most are promiscuous binders with poor selectivity; as a result, this class of compounds is viewed with suspicion by medicinal chemists.^{[2] [3] [4]} Differing academic opinions exist concerning the correct use of PAINS filters, the necessity of the experimental confirmations of such properties, and many useful features of rhodanine derivatives.^{[5] [6]}

Notes and References

1. Nencki. M.. Ueber die Einwirkung der Monochloressigsäure auf Sulfocyansäure und ihre Salze. Journal für Praktische Chemie. 10 July 1877. 16. 1. 1–17. 10.1002/prac.18770160101.
2. J. Med. Chem. . 2010 . 53 . 2719–2740 . 10.1021/jm901137j . 20131845 . New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays . 7. Baell . J. B . Holloway . G. A . 10.1.1.394.9155 .
3. 10.1517/17460441.2012.688743 . 22607309 . Rhodanine as a scaffold in drug discovery: A critical review of its biological activities and mechanisms of target modulation . 2012 . Tomašić . Tihomir . Peterlin Mašič . Lucija . Expert Opinion on Drug Discovery . 549–60 . 7. 7 . 3401210 .
4. Pouliot. Martin. Jeanmart. Stephane. Pan Assay Interference Compounds (PAINS) and Other Promiscuous Compounds in Antifungal Research. Journal of Medicinal Chemistry. 8 September 2015. 497–503. 10.1021/acs.jmedchem.5b00361. 59. 2. 26313340.
5. Expert Opinion on Drug Discovery . 2017 . 12 . 1233–1252 . 10.1080/17460441.2017.1388370 . 29019278 . Recent developments with rhodanine as a scaffold for drug discovery . 12. Kaminskyy . D . Kryshchyshyn . A . Lesyk . R . 3514481 .
6. Eur. J. Med. Chem. . 2017 . 140 . 542–594 . 10.1016/j.ejmech.2017.09.031 . 28987611 . 5-Ene-4-thiazolidinonese An efficient tool in medicinal chemistry . 10. Kaminskyy . D . Kryshchyshyn . A . Lesyk . R . 7111298 .