2-Thioxothiazolidin-4-one (Rhodanine)

Introduction

2-Thioxothiazolidin-4-one, commonly known as rhodanine, is an organic compound derived from thiazolidine. It is an interesting organic molecule with potential biological activities and pharmacological properties.[1] [2] [3] However, the biological activity of compounds possessing a rhodanine moiety should be considered critically.[4] Rhodanine is commercially available and has been synthesized by the reaction of carbon disulfide, ammonia, and chloroacetic acid (Scheme [1]).[5]

Scheme 1

Rhodanine has a wide variety of applications in organic syntheses due to the presence of some active centers. Two nucleophilic centers in rhodanine are localized on the sulfur and nitrogen. The methylene part of the rhodanine can act as a nucleophilic center in organic syntheses. An electrophilic center is also associated with the thiocarbonyl carbon atom (Figure [1]).

Figure 1

• References

• 1 Andres CJ, Bronson JJ, D’Andrea SV, Deshpande MS, Falk PJ, Grant-Young KA, Harte WE, Ho HT, Misco PF, Robertson JG, Stock D, Sun Y, Walsh AW. Bioorg. Med. Chem. Lett. 2000; 10: 715
• 2 Baell JB, Holloway GA. J. Med. Chem. 2010; 7: 2719
• 3 Tomašić T, Peterlin ML. Expert Opin. Drug Discov. 2012; 7: 549
• 4 Please see: http://pipeline.corante.com/archives/2012/05/23/another_vote_against_rhodanines.php, http://pipeline.corante.com/archives/2011/09/07/get_yer_rhodanines_here.php, http://pipeline.corante.com/archives/2011/12/06/riding_to_the_rescue_of_rhodanines.php
• 5 Redemann EC, Icke RN, Alles GA. Org. Synth. Coll. 1935; 3: 763
• 6 Anderluh M, Jukič M, Petrič R. Tetrahedron 2009; 65: 344
• 7 Ray S, Bhaumik A, Dutta A, Butcher RJ, Mukhopadhyay C. Tetrahedron Lett. 2013; 54: 2164
• 8 Zhang Y, Wang S, Wu S, Zhu S, Dong G, Miao Z, Yao J, Zhang W, Sheng C, Wang W. ACS Comb. Sci. 2013; 15: 298
• 9 Lakshmi NV, Selvarangam EK, Perumal PT. Can. J. Chem. 2013; 6: 479
• 10 Hassanabadi A, Mosslemin MH, Salari S, Momeni LM. Synth. Commun. 2012; 42: 2309
• 11 Abdel-Malek HA. Phosphorus Sulfur Silicon Relat. Elem. 2012; 187: 506
• 12 Pokhodylo NT, Matiychuk VS, Obushak ND. Chem. Heterocycl. Compd. 2009; 45: 121