Stewart FHC. The chemistry of the sydnones. Chem Rev. 1964;64:129–47. https://doi.org/10.1021/cr60228a004

Article  CAS  Google Scholar 

Mummel S, Lederle F, Hübner EG, Namyslo JC, Nieger M, Schmidt A. Sydnone methides: intermediates between mesoionic compounds and mesoionic N-heterocyclic olefins. Eur J Org Chem. 2023;26:e202300216. https://doi.org/10.1002/ejoc.202300216

Article  CAS  Google Scholar 

Cherepanov IYA, Moiseev SK. Recent developments in the chemistry of sydnones and sydnone imines. Adv Heterocycl Chem. 2020;131:49–164. https://doi.org/10.1016/bs.aihch.2019.11.003

Article  CAS  Google Scholar 

Earl JC, Mackney AW. The action of acetic anhydride on N-nitrosophenylglycine and some of its derivatives. J Chem Soc. 1935:899–900. https://doi.org/10.1039/JR9350000899

Gimadiev TR, Klimchuk O, Nugmanov RI, Madzhidov TI, Varnek A. Sydnone-alkyne cycloaddition: which factors are responsible for reaction rate? J Mol Struct. 2019;1198:126897. https://doi.org/10.1016/j.molstruc.2019.126897

Article  CAS  Google Scholar 

Decuypère E, Plougastel L, Audisio D, Taran F. Sydnone–alkyne cycloaddition: applications in synthesis and bioconjugation. Chem Commun. 2017;53:11515–27. https://doi.org/10.1039/C7CC06405E

Article  Google Scholar 

Zerbib S, Khouili M, Catto M, Bouissane L. Sydnone: synthesis, reactivity and biological activities. Curr Med Chem. 2023;30:1122–44. https://doi.org/10.2174/0929867329666220620123050

Article  CAS  PubMed  Google Scholar 

Patel YM, Patel KC. Synthesis and biological evaluation of new sydnone-based derivatives. J Saudi Chem Soc. 2015;19:193–9. https://doi.org/10.1016/j.jscs.2012.02.005

Article  Google Scholar 

Cherevatskaya M, Cherepanov I, Kalganova N, Erofeeva N, Romanovskaya E, Frolov A, et al. Sydnone imines as a new class of promising plant growth and stress tolerance modulators—a first experimental structure–activity overview. Stresses. 2024;4:133–54. https://doi.org/10.3390/stresses4010008

Article  Google Scholar 

Pétry N, Luttringer F, Bantreil X, Lamaty F. A mechanochemical approach to the synthesis of sydnones and derivatives. Faraday Discuss. 2023;241:114–27. https://doi.org/10.1039/D2FD00096B

Article  PubMed  Google Scholar 

Chandrasekhar R, Nanjan MJ. Sydnones: a brief review. Mini-Rev Med Chem. 2012;12:1359–65. https://doi.org/10.2174/13895575112091359

Article  CAS  PubMed  Google Scholar 

Gireesh T, Kamble RR, Kattimani PP, Dorababu A, Manikantha M, Hoskeri JH. Synthesis of sydnone substituted biginelli derivatives as hyaluronidase inhibitors. Arch Pharm. 2013;346:645–53. https://doi.org/10.1002/ardp.201300118

Article  CAS  Google Scholar 

Hossain SL, Mathews M, Bhyranalyar Nagarajappa VS, Kumar BK, Veerappa Yelamaggad CV. Antiproliferative CRS apoptosis-inducing activity and molecular docking studies of sydnones compounds. J Cancer Res Ther. 2022;18:681–90. https://doi.org/10.4103/jcrt.JCRT_1614_20.

Article  PubMed  Google Scholar 

Galuppo LF, dos Reis Lívero FA, Martins GG, Cardoso CC, Beltrame OC, Klassen LMB, et al. Sydnone 1: a mesoionic compound with antitumoral and haematological effects in vivo. Basic Clin Pharmacol Toxicol. 2016;119:41–50. https://doi.org/10.1111/bcpt.12545

Article  CAS  PubMed  Google Scholar 

Dorababu A, Kamble RR, Shaikh SKJ, Somagond SM, Bayannavar PK, Joshi SD. Synthesis, docking, and pharmacological evaluation of derivatives of α-aminoketones appended to sydnones as potent antitubercular and antifungal scaffolds. J Heterocycl Chem. 2019;56:2430–41. https://doi.org/10.1002/jhet.3630

Article  CAS  Google Scholar 

Shih M-H, Su Y-S, Wu C-L. Syntheses of aromatic substituted hydrazino-thiazole derivatives to clarify structural characterization and antioxidant activity between 3-arylsydnonyl and aryl substituted hydrazino-thiazoles. Chem Pharm Bull. 2007;55:1126–35. https://doi.org/10.1248/cpb.55.1126

Article  CAS  Google Scholar 

Deshpande SR, Pai KV. Synthesis, antibacterial and analgesic activities of 4-[1-Oxo-3-(substituted aryl)-2-propenyl]-3-(4-methylphenyl) sydnones. J Chem. 2010;7:237473. https://doi.org/10.1155/2010/237473.

Article  Google Scholar 

Savaliya PP, Akbari VK, Modi JA, Patel KC. Synthesis, characterization, and antimicrobial screening of some Mannich base sydnone derivatives. Med Chem Res. 2013;22:5789–97. https://doi.org/10.1007/s00044-013-0568-6

Article  CAS  Google Scholar 

Du S, Hu X, Shao X, Qian X. Novel trifluoromethyl sydnone derivatives: design, synthesis and fungicidal activity. Bioorg Med Chem Lett. 2021;44:128114. https://doi.org/10.1016/j.bmcl.2021.128114

Article  CAS  PubMed  Google Scholar 

Yeh M-Y, Tien H-J, Huang L-Y, Chen M-H. Sydnone compounds. XX. The synthesis and the schmidt reaction of 4-formyl-3-arylsydnone. J Chin Chem Soc. 1983;30:29–37. https://doi.org/10.1002/jccs.198300005

Article  CAS  Google Scholar 

Shih M-H, Ke F-Y. Syntheses and evaluation of antioxidant activity of sydnonyl substituted thiazolidinone and thiazoline derivatives. Bioorg Med Chem. 2004;12:4633–43. https://doi.org/10.1016/j.bmc.2004.06.033

Article  CAS  PubMed  Google Scholar 

Thoman CJ, Voaden DJ, Hunsberger IM. Direct formylation of sydnones1a,b. J Org Chem. 1964;29:2044–5. https://doi.org/10.1021/jo01030a525

Article  CAS  Google Scholar 

Asundaria ST, Pannecouque C, De Clercq E, Supuran CT, Patel KC. Synthesis of novel biologically active methylene derivatives of sydnones. Med Chem Res. 2013;22:5752–63. https://doi.org/10.1007/s00044-013-0567-7

Article  CAS  Google Scholar 

Mummel S, Lederle F, Hübner EG, Namyslo JC, Nieger M, Schmidt A. Sydnone methides—a forgotten class of mesoionic compounds for the generation of anionic N-heterocyclic carbenes. Angew Chem Int Ed. 2021;60:18882–7. https://doi.org/10.1002/anie.202107495

Article  CAS  Google Scholar 

Choudhury LH, Parvin T. Recent advances in the chemistry of imine-based multicomponent reactions (MCRs). Tetrahedron 2011;67:8213–28. https://doi.org/10.1016/j.tet.2011.07.020

Article  CAS  PubMed  PubMed Central  Google Scholar 

Yang L, Liu H, Xia D, Wang S. Antioxidant properties of camphene-based thiosemicarbazones: experimental and theoretical evaluation. Molecules 2020;25:1192. https://doi.org/10.3390/molecules25051192

Article  CAS  PubMed  PubMed Central  Google Scholar 

Govender H, Mocktar C, Kumalo HM, Koorbanally NA. Synthesis, antibacterial activity and docking studies of substituted quinolone thiosemicarbazones. Phosphorus Sulfur Silicon Relat Elem. 2019;194:1074–81. https://doi.org/10.1080/10426507.2019.1618298

Article  CAS  Google Scholar 

Bai X-G, Zheng Y, Qi J. Advances in thiosemicarbazone metal complexes as anti-lung cancer agents. Front Pharmacol. 2022;13. https://doi.org/10.3389/fphar.2022.1018951

Bajaj K, Buchanan RM, Grapperhaus CA. Antifungal activity of thiosemicarbazones, bis(thiosemicarbazones), and their metal complexes. J Inorg Biochem. 2021;225:111620. https://doi.org/10.1016/j.jinorgbio.2021.111620

Article  CAS  PubMed  Google Scholar 

Benmohammed A, Rekiba N, Sehanine Y, Louail AA, Khoumeri O, Kadiri M, et al. Synthesis and antimicrobial activities of new thiosemicarbazones and thiazolidinones in indole series. Chem Mon. 2021;152:977–86. https://doi.org/10.1007/s00706-021-02823-6

Article  CAS  Google Scholar 

Fonseca NC, da Cruz LF, da Silva Villela F, do Nascimento Pereira GA, de Siqueira-Neto JL, Kellar D, et al. Synthesis of a sugar-based thiosemicarbazone series and structure-activity relationship versus the parasite cysteine proteases Rhodesian, Cruzain, and Schistosoma mansoni cathepsin B1. Antimicrob Agents Chemother. 2015;59:2666–77. https://doi.org/10.1128/aac.04601-14

Article  CAS  PubMed  PubMed Central  Google Scholar 

Thanh DN, Duc TH, Hue HMN, Van TKH. Reaction of some substituted 3-aryl-4-formylsydnones with tetra-O-acetyl-β-D-galactopyranosyl) thiosemicarbazide. Lett Org Chem. 2016;13:541–6. https://doi.org/10.2174/1570178613666160824104037.

Article  CAS  Google Scholar 

Thoman CJ, Voaden DJ. 3-Phenylsydnone. Org Synth. 1965;45:96.

Lemieux R. Tetra-O-acetyl-β-D-glucopyranosyl bromide. Methods in carbohydrate chemistry. New York: Academic Press; 1963. pp. 221-222.

Tashpulatov AA, Afanas’ev VA, Lidak MY, Sukhova NM, Popelis YY, Rakhmatullaev I. Synthesis and transformations