How to cite this paper
Lelyukh, M., Halevych, H., Zhukrovska, M., Semiion-Luchyshyn, O & Kalytovska, M. (2023). Synthesis of 5-aryl/heterylidene substituted 2-imino-4-thiazolidinones possessing 1,3,4-thiadiazole moiety and their antitrypanosomal activity.Current Chemistry Letters, 12(2), 413-420.
Refrences
1. Patil V., Tilekar K., Mehendale-Munj S., Mohan R., and Ramaa C.S. (2010) Synthesis and primary cytotoxicity evaluation of new 5-benzylidene-2,4-thiazolidinedione derivatives. Eur. J. Med. Chem., 45 (10) 4539-4544.
2. Iqbal M.A., Husain A., Alam O., Khan S.A., Ahmad A., Haider M.R., and Alam M.A. (2020) Design, synthesis, and biological evaluation of imidazopyridine-linked thiazolidinone as potential anticancer agents. Arch. Pharm., 353 (10) e2000071.
3. Liu X.-F., Zheng C.-J., Sun L.-P., Liu X.-K., and Piao H.-R. (2011) Synthesis of new chalcone derivatives bearing 2,4-thiazolidinedione and benzoic acid moieties as potential anti-bacterial agents. Eur. J. Med. Chem., 46 (8) 3469-3473.
4. Patel N.B., and Patel M.D. (2017) Synthesis and evaluation of antibacterial and antifungal activities of 4-thiazolidinones and 2-azetidinones derivatives from chalcone. Med. Chem. Res., 26 (8) 1772-1783.
5. Nitsche C., Schreier V., Behnam M.A.M., Kumar A., Bartenschlager R., and Klein C.D.P. (2013) Thiazolidinone-peptide hybrids as Dengue virus protease inhibitors with antiviral activity in cell culture. J. Med. Chem., 56 (21) 8389-8403.
6. Apaydin Ç.B., Loy B.V., Stevaert A., and Naesens L. (2020) New spirothiazolidinone derivatives: Synthesis and antiviral evaluation. Phosphorus Sulfur Silicon Relat. Elem., 196 (3) 294-299.
7. Pandey S., Pandey P., Gautam S.S., and Singh J. (2021) Synthesis, characterization and antifungal evaluation of substituted pyrimidin-2-thione derivatives. Research J. Pharm. and Tech., 14 (1) 275-279.
8. Yang B., Si H., and Zhai H. (2021) QSAR Studies on the IC50 of a class of thiazolidinone/thiazolide based hybrids as antitrypanosomal agents. Lett. Drug. Des. Discov., 18 (4) 406-415.
9. El-Karim S.S.A., Mohamed H.S., Abdelhameed M.F., Amr A.E.-G.E., Almehizia A.A., and Nossier E. (2021) Design, synthesis and molecular docking of new pyrazole-thiazolidinones as potent anti-inflammatory and analgesic agents with TNF-α inhibitory activity. Bioorg. Chem., 111, Article ID 104827.
10. Abdellatif K.R.A., Abdelgawad M.A., Elshemy H.A.H., and Alsayed S.S.R. (2016) Design, synthesis and biological screening of new 4-thiazolidinone derivatives with promising COX-2 selectivity, anti-inflammatory activity and gastric safety profile. Bioorg. Chem., 64 1-12.
11. Mavrova A.Ts., Wesselinova D., Tsenov J.A., and Lubenov L.A. (2014) Synthesis and antiproliferative activity of some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety. Eur. J. Med. Chem., 86 (30) 676-683.
12. Wu W.-N., Tai A.-Q., Chen Q., and Ouyang G.-P. (2016) Synthesis and antiviral bioactivity of novel 2-substituted methylthio-5-(4-amino-2-methylpyrimidin-5-yl)-1,3,4-thiadiazole derivatives. J. Het Chem., 53 (2) 626-632.
13. Barbuceanu S.-F., Saramet G., Almajan G.L., Draghici C., Barbuceanu F., and Bancescu G. (2012) New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characteriazation and antimicrobial activity evaluation. Eur. J. Med. Chem., 49 417-423.
14. Harish K.P., Mohana K.N., and Mallesha L. (2013) Synthesis of indazole substituted-1,3,4-thiadiazoles and their anticonvulsant activity. Drug Invent Today, 5 92-99.
15. Zhang Y.-B., Wang X.-L., Liu W., Yang Y.-S., Tang J.-F., and Zhu H.-L. (2012) Design, synthesis and biological evaluation of heterocyclic azoles derivatives containing pyrazine moiety as potential telomerase inhibitors. Bioorg. Med. Chem., 20 6356-6365.
16. Tu G.G., Li S.H., Huang H.M., Li G., Xiong F., Mai X., Zhu H.W., Kuang B.H., and Xu W.F. (2008) Novel aminopeptidase N inhibitors derived from 1,3,4-thiadiazole scaffold. Bioorg. Med. Chem., 16 (14) 6663-6668.
17. Kumudha D., Reddy R.R., and Kalavathi T. (2014) Synthesis and evaluation of some 1,3,4-thiadiazoles having substituted 1,2,4-triazole moiety for anticonvulsant and CNS depressant activity. World J. Pharm. Pharm. Sci., 3 (9) 728-740.
18. Lelyukh M., Adamchuk S., Harkov S., Chaban I., Demchuk I., Shelepeten L, and Chaban T. (2018) Synthetic approaches, chemical modification and biological activity of non-condensed 1,3,4-thiadiazole derivatives: A review. Pharmacia, 65 (4) 72-88.
19. Patel H., Mishra L., Noolvi M., Karpoormath R., and Cameotra S.S. (2014) Synthesis, in vitro evaluation, and molecular docking studies of azetidinones and thiazolidinones of 2-amino-5-cyclopropyl-1,3,4-thiadiazole as antibacterial agents. Arch. Pharm. Chem. Life Sci., 347 668-684.
20. Sahu R., Tiwari S., and Kalyani G. (2013) Thiazolidinone based 2,5-disubstituted-1,3,4-thiadiazole: Synthesis and antimicrobial evaluation. Int. J. Pharm. Pharm. Sci., 5 (1) 290-291.
21. Rawal R.K., Tripathi R., Katti S.B., Pannecouque C., and De Clercq E. (2007) Design, synthesis, and evaluation of 2-aryl-3-heteroaryl-1,3-thiazolidin-4-ones as anti-HIV agents. Bioorg. Med. Chem., 15 1725-1731.
22. Küçükgüzel I., Satılmış G., Gurukumar K.R., Basu A., Tatar E., Nichols D.B., Talele T.T., and Kaushik-Basu N (2013) 2-Heteroarylimino-5-arylidene-4-thiazolidinones as a new class of non-nucleoside inhibitors of HCV NS5B polymerase. Eur. J. Med. Chem., 69 931-941.
23. Joseph A., Shah C.S., Kumar S.S., Alex A.T., Maliyakkal N., Moorkoth S.,and Mathew J.E. (2013) Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones. Acta Pharm., 63 397-408.
24. Lelyukh M., Matiichuk Yu., Flud V., Chaban I., and Ogurtsov V. (2022) Synthesis and antioxidant properties of novel 2-(2,4-dioxothiazolidin-5-ylidene)-acetamides containing 1,3,4-thia/oxadiazole moieties. Biointerface Res. Appl. Chem., 12 (5) 6710-6722.
25. Omar Y.M., Abdel-Moty S.G., and Abdu-Allah H.H.M. (2020) Further insight into the dual COX-2 and 15-LOX anti-inlammatory activity of 1,3,4-thiadiazole-thiazolidinone hybrids: The contribution of the substituents at 5th positions is size dependent. Bioorg. Chem., 97 Article 103657.
26. Lelyukh M., Pylypchuk I., Kalytovska M., Harkov S., Kostyshyn L., and Drapak I. (2022) Synthesis and anti-cancer activity evaluation of novel 1,3,4-oxadiazole substituted 5-arylidene/isatinylidene-2-iminothiazolidin-4-ones. Biointerface Res. Appl. Chem., 12 (1) 1161-1173.
27. Popov-Pergal K., Cekovic Z., and Pergal M. (1991) Condensation of 2,4-dioxotetrahydro-1,3-thiazole with aromatic aldehydes. J. Gen. Chem. USSR., 61 1958-1962.
28. Bruno G., Costantino L., Curinga C., Maccari R., Monforte F., Nicolo F., Ottana R., and Vigorita M.G. (2002) Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones. Bioorg. Med. Chem., 10 (4) 1077-1084.
29. Vicini P., Geronikaki A., Incerti M., Zani F., Dearden J., and Hewitt M. (2008) 2-Heteroarylimino-5-benzylidene-4-thiazolidinones analogues of 2-thiazolylimino-5-benzylidene-4-thiazolidinones with antimicrobial activity: Synthesis and structure-activity relationship. Bioorg. Med. Chem., 16 (7) 3714-3724.
30. Bacchi A., Carcelli M., Pelizzi G., and Vicini P. (1995) Investigation on the amidine systems in amidinobenzisothiazole derivatives. Arch. Pharm. Chem. Life Sci., 328 (3) 217-221.
31. Vicini P., Geronikaki A., Anastasia K., Incerti M., and Zani, F. (2006) Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones. Bioorg. Med. Chem., 14 (11) 3859-3864.
32. Lutje V., Seixas J., and Kennedy A. (2013) Chemotherapy for second-stage human African trypanosomiasis. Cochrane Database Syst. Rev., 6 CD006201.
33. Seebacher W., Brun R., Weis R. (2004) New 4-aminobicyclo[2.2.2]octane derivatives and their activities against Plasmodium falciparum and Trypanosoma b. rhodesiense. Eur. J. Pharm. Sci., 21 (2-3) 225-233.
34. Haroon M., de Barros Dias M.C.H., da Silva Santos A.C., Pereira V.R.A., Freitas L.A.B., Balbinot R.B., Kaplum V., Nahamura C.V., Alves L.C., Brayner F.A., Leite A.C.L., Akhtar T. (2021) The design, synthesis, and in vitro trypanocidal and leishmanicidal activities of 1,3-thiazole and 4-thiazolidinone ester derivatives. RSC Adv., 11 2487-2500.
35. Leite A.C.L., Moreira D.R.M., Cardoso M.V.O., Hernandes M.Z., Pereira V.R.A., Silva R.O., Kiperstok A.C., Lima M.S., Soares M.B.P. (2007) Synthesis, cruzain docking, and in vitro studies of aryl-4-oxothiazolylhydrazones against Trypanosoma cruzi. Chem. Med. Chem., 2 (9) 1339-1345.
36. Pizzo C., Saiz C., Talevi A., Gavernet L., Palestro P., Bellera C., Blanch L.B., Benitez D., Cazzulo J.J., Chidichimo A., Wipf P., Mahler S.G. (2011) Synthesis of 2-hydrazolyl-4-thiazolidinones based on multicomponent reactions and biological evaluation against Trypanosoma cruzi. Chem. Biol. Drug Des., 77 (3) 166-172.
37. Smith T.K., Young B.L., Denton H., Hughes D.L., Wagner G.K. (2009) First small molecular inhibitors of T. brucei dolicholphosphate mannose synthase (DPMS), a validated drug target in African sleeping sickness. Bioorg. Med. Chem. Lett., 19 (6) 1749-1752.
38. Carvalho S.A., da Silva E.F., Santa-Rita R.M., de Castro S.L., Fraga C.A.M. (2004) Synthesis and antitrypanosomal profile of new functionalized 1,3,4-thiadiazole-2-arylhydrazone derivatives, designed as non-mutagenic megazol analogues. Bioorg. Med. Chem. Lett., 14 5967-5970.
39. Liesen A.P., de Aquino T.M., Carvalho C.S., Lima V.T., de Araujo J.M., de Lima J.G., de Faria A.R., de Melo E.J.T., Alves A.J., Alves E.W., Alves A.Q., Goes A.J.S. (2010) Synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities of thiosemicarbazides, 4-thiazolidinones and 1,3,4-thiadiazoles. Eur. J. Med. Chem., 45 3685-3691.
40. Martins S.C., Desoti V.C., Lazarin-Bidoia D., Vandresen F., da Silva C.C., Ueda-Nakamiura T., Silva S.O., Nakamura C.V. (2016) Synthesis and evaluation of the trypanocidal activity of a series of 1,3,4-thiadiazoles derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones. Med. Chem. Res., 25 1193-1203.
41. Serban G. (2020) 2-Amino-1,3,4-thiadiazoles as prospective agents in trypanosomiasis and other parasitoses. Acta Pharm., 70 259-290.
42. Petrow V., Stephenson O., Thomas A.J., and Wild A.M. (1958) 302. Preparation and hydrolysis of some derivatives of 1:3:4-thiadiazole. J. Chem. Soc., 0 1508-1513.
43. Rubtsov N., Baichykov A. (1971) [Synthetic chemical and pharmaceutical drugs]. Publishing House «Medicine», Moscow, 126-127. [available in Russian]
44. Bastos I.M.D., Motta F.N., Charneau S., Santana J.M., Dubost L., Augustynus K., and Grellier P. (2010) Prolyl oligopeptidase of Trypanosoma brucei hydrolyzes native collagen, peptide hormones and is active in the plasma of infected mice. Microb. Infect., 12 (6) 457-466.
45. Lethu S., Bosc D., Mouray E., Grellier P., and Dubois J. (2013) New protein farnesyltransferase inhibitors in the 3-arylthiophene 2-carboxylic acid series: Diversification of the aryl moiety by solid-phase synthesis. J. Enzyme Inhib. Med. Chem., 28 (1) 163-171.
2. Iqbal M.A., Husain A., Alam O., Khan S.A., Ahmad A., Haider M.R., and Alam M.A. (2020) Design, synthesis, and biological evaluation of imidazopyridine-linked thiazolidinone as potential anticancer agents. Arch. Pharm., 353 (10) e2000071.
3. Liu X.-F., Zheng C.-J., Sun L.-P., Liu X.-K., and Piao H.-R. (2011) Synthesis of new chalcone derivatives bearing 2,4-thiazolidinedione and benzoic acid moieties as potential anti-bacterial agents. Eur. J. Med. Chem., 46 (8) 3469-3473.
4. Patel N.B., and Patel M.D. (2017) Synthesis and evaluation of antibacterial and antifungal activities of 4-thiazolidinones and 2-azetidinones derivatives from chalcone. Med. Chem. Res., 26 (8) 1772-1783.
5. Nitsche C., Schreier V., Behnam M.A.M., Kumar A., Bartenschlager R., and Klein C.D.P. (2013) Thiazolidinone-peptide hybrids as Dengue virus protease inhibitors with antiviral activity in cell culture. J. Med. Chem., 56 (21) 8389-8403.
6. Apaydin Ç.B., Loy B.V., Stevaert A., and Naesens L. (2020) New spirothiazolidinone derivatives: Synthesis and antiviral evaluation. Phosphorus Sulfur Silicon Relat. Elem., 196 (3) 294-299.
7. Pandey S., Pandey P., Gautam S.S., and Singh J. (2021) Synthesis, characterization and antifungal evaluation of substituted pyrimidin-2-thione derivatives. Research J. Pharm. and Tech., 14 (1) 275-279.
8. Yang B., Si H., and Zhai H. (2021) QSAR Studies on the IC50 of a class of thiazolidinone/thiazolide based hybrids as antitrypanosomal agents. Lett. Drug. Des. Discov., 18 (4) 406-415.
9. El-Karim S.S.A., Mohamed H.S., Abdelhameed M.F., Amr A.E.-G.E., Almehizia A.A., and Nossier E. (2021) Design, synthesis and molecular docking of new pyrazole-thiazolidinones as potent anti-inflammatory and analgesic agents with TNF-α inhibitory activity. Bioorg. Chem., 111, Article ID 104827.
10. Abdellatif K.R.A., Abdelgawad M.A., Elshemy H.A.H., and Alsayed S.S.R. (2016) Design, synthesis and biological screening of new 4-thiazolidinone derivatives with promising COX-2 selectivity, anti-inflammatory activity and gastric safety profile. Bioorg. Chem., 64 1-12.
11. Mavrova A.Ts., Wesselinova D., Tsenov J.A., and Lubenov L.A. (2014) Synthesis and antiproliferative activity of some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety. Eur. J. Med. Chem., 86 (30) 676-683.
12. Wu W.-N., Tai A.-Q., Chen Q., and Ouyang G.-P. (2016) Synthesis and antiviral bioactivity of novel 2-substituted methylthio-5-(4-amino-2-methylpyrimidin-5-yl)-1,3,4-thiadiazole derivatives. J. Het Chem., 53 (2) 626-632.
13. Barbuceanu S.-F., Saramet G., Almajan G.L., Draghici C., Barbuceanu F., and Bancescu G. (2012) New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characteriazation and antimicrobial activity evaluation. Eur. J. Med. Chem., 49 417-423.
14. Harish K.P., Mohana K.N., and Mallesha L. (2013) Synthesis of indazole substituted-1,3,4-thiadiazoles and their anticonvulsant activity. Drug Invent Today, 5 92-99.
15. Zhang Y.-B., Wang X.-L., Liu W., Yang Y.-S., Tang J.-F., and Zhu H.-L. (2012) Design, synthesis and biological evaluation of heterocyclic azoles derivatives containing pyrazine moiety as potential telomerase inhibitors. Bioorg. Med. Chem., 20 6356-6365.
16. Tu G.G., Li S.H., Huang H.M., Li G., Xiong F., Mai X., Zhu H.W., Kuang B.H., and Xu W.F. (2008) Novel aminopeptidase N inhibitors derived from 1,3,4-thiadiazole scaffold. Bioorg. Med. Chem., 16 (14) 6663-6668.
17. Kumudha D., Reddy R.R., and Kalavathi T. (2014) Synthesis and evaluation of some 1,3,4-thiadiazoles having substituted 1,2,4-triazole moiety for anticonvulsant and CNS depressant activity. World J. Pharm. Pharm. Sci., 3 (9) 728-740.
18. Lelyukh M., Adamchuk S., Harkov S., Chaban I., Demchuk I., Shelepeten L, and Chaban T. (2018) Synthetic approaches, chemical modification and biological activity of non-condensed 1,3,4-thiadiazole derivatives: A review. Pharmacia, 65 (4) 72-88.
19. Patel H., Mishra L., Noolvi M., Karpoormath R., and Cameotra S.S. (2014) Synthesis, in vitro evaluation, and molecular docking studies of azetidinones and thiazolidinones of 2-amino-5-cyclopropyl-1,3,4-thiadiazole as antibacterial agents. Arch. Pharm. Chem. Life Sci., 347 668-684.
20. Sahu R., Tiwari S., and Kalyani G. (2013) Thiazolidinone based 2,5-disubstituted-1,3,4-thiadiazole: Synthesis and antimicrobial evaluation. Int. J. Pharm. Pharm. Sci., 5 (1) 290-291.
21. Rawal R.K., Tripathi R., Katti S.B., Pannecouque C., and De Clercq E. (2007) Design, synthesis, and evaluation of 2-aryl-3-heteroaryl-1,3-thiazolidin-4-ones as anti-HIV agents. Bioorg. Med. Chem., 15 1725-1731.
22. Küçükgüzel I., Satılmış G., Gurukumar K.R., Basu A., Tatar E., Nichols D.B., Talele T.T., and Kaushik-Basu N (2013) 2-Heteroarylimino-5-arylidene-4-thiazolidinones as a new class of non-nucleoside inhibitors of HCV NS5B polymerase. Eur. J. Med. Chem., 69 931-941.
23. Joseph A., Shah C.S., Kumar S.S., Alex A.T., Maliyakkal N., Moorkoth S.,and Mathew J.E. (2013) Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones. Acta Pharm., 63 397-408.
24. Lelyukh M., Matiichuk Yu., Flud V., Chaban I., and Ogurtsov V. (2022) Synthesis and antioxidant properties of novel 2-(2,4-dioxothiazolidin-5-ylidene)-acetamides containing 1,3,4-thia/oxadiazole moieties. Biointerface Res. Appl. Chem., 12 (5) 6710-6722.
25. Omar Y.M., Abdel-Moty S.G., and Abdu-Allah H.H.M. (2020) Further insight into the dual COX-2 and 15-LOX anti-inlammatory activity of 1,3,4-thiadiazole-thiazolidinone hybrids: The contribution of the substituents at 5th positions is size dependent. Bioorg. Chem., 97 Article 103657.
26. Lelyukh M., Pylypchuk I., Kalytovska M., Harkov S., Kostyshyn L., and Drapak I. (2022) Synthesis and anti-cancer activity evaluation of novel 1,3,4-oxadiazole substituted 5-arylidene/isatinylidene-2-iminothiazolidin-4-ones. Biointerface Res. Appl. Chem., 12 (1) 1161-1173.
27. Popov-Pergal K., Cekovic Z., and Pergal M. (1991) Condensation of 2,4-dioxotetrahydro-1,3-thiazole with aromatic aldehydes. J. Gen. Chem. USSR., 61 1958-1962.
28. Bruno G., Costantino L., Curinga C., Maccari R., Monforte F., Nicolo F., Ottana R., and Vigorita M.G. (2002) Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones. Bioorg. Med. Chem., 10 (4) 1077-1084.
29. Vicini P., Geronikaki A., Incerti M., Zani F., Dearden J., and Hewitt M. (2008) 2-Heteroarylimino-5-benzylidene-4-thiazolidinones analogues of 2-thiazolylimino-5-benzylidene-4-thiazolidinones with antimicrobial activity: Synthesis and structure-activity relationship. Bioorg. Med. Chem., 16 (7) 3714-3724.
30. Bacchi A., Carcelli M., Pelizzi G., and Vicini P. (1995) Investigation on the amidine systems in amidinobenzisothiazole derivatives. Arch. Pharm. Chem. Life Sci., 328 (3) 217-221.
31. Vicini P., Geronikaki A., Anastasia K., Incerti M., and Zani, F. (2006) Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones. Bioorg. Med. Chem., 14 (11) 3859-3864.
32. Lutje V., Seixas J., and Kennedy A. (2013) Chemotherapy for second-stage human African trypanosomiasis. Cochrane Database Syst. Rev., 6 CD006201.
33. Seebacher W., Brun R., Weis R. (2004) New 4-aminobicyclo[2.2.2]octane derivatives and their activities against Plasmodium falciparum and Trypanosoma b. rhodesiense. Eur. J. Pharm. Sci., 21 (2-3) 225-233.
34. Haroon M., de Barros Dias M.C.H., da Silva Santos A.C., Pereira V.R.A., Freitas L.A.B., Balbinot R.B., Kaplum V., Nahamura C.V., Alves L.C., Brayner F.A., Leite A.C.L., Akhtar T. (2021) The design, synthesis, and in vitro trypanocidal and leishmanicidal activities of 1,3-thiazole and 4-thiazolidinone ester derivatives. RSC Adv., 11 2487-2500.
35. Leite A.C.L., Moreira D.R.M., Cardoso M.V.O., Hernandes M.Z., Pereira V.R.A., Silva R.O., Kiperstok A.C., Lima M.S., Soares M.B.P. (2007) Synthesis, cruzain docking, and in vitro studies of aryl-4-oxothiazolylhydrazones against Trypanosoma cruzi. Chem. Med. Chem., 2 (9) 1339-1345.
36. Pizzo C., Saiz C., Talevi A., Gavernet L., Palestro P., Bellera C., Blanch L.B., Benitez D., Cazzulo J.J., Chidichimo A., Wipf P., Mahler S.G. (2011) Synthesis of 2-hydrazolyl-4-thiazolidinones based on multicomponent reactions and biological evaluation against Trypanosoma cruzi. Chem. Biol. Drug Des., 77 (3) 166-172.
37. Smith T.K., Young B.L., Denton H., Hughes D.L., Wagner G.K. (2009) First small molecular inhibitors of T. brucei dolicholphosphate mannose synthase (DPMS), a validated drug target in African sleeping sickness. Bioorg. Med. Chem. Lett., 19 (6) 1749-1752.
38. Carvalho S.A., da Silva E.F., Santa-Rita R.M., de Castro S.L., Fraga C.A.M. (2004) Synthesis and antitrypanosomal profile of new functionalized 1,3,4-thiadiazole-2-arylhydrazone derivatives, designed as non-mutagenic megazol analogues. Bioorg. Med. Chem. Lett., 14 5967-5970.
39. Liesen A.P., de Aquino T.M., Carvalho C.S., Lima V.T., de Araujo J.M., de Lima J.G., de Faria A.R., de Melo E.J.T., Alves A.J., Alves E.W., Alves A.Q., Goes A.J.S. (2010) Synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities of thiosemicarbazides, 4-thiazolidinones and 1,3,4-thiadiazoles. Eur. J. Med. Chem., 45 3685-3691.
40. Martins S.C., Desoti V.C., Lazarin-Bidoia D., Vandresen F., da Silva C.C., Ueda-Nakamiura T., Silva S.O., Nakamura C.V. (2016) Synthesis and evaluation of the trypanocidal activity of a series of 1,3,4-thiadiazoles derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones. Med. Chem. Res., 25 1193-1203.
41. Serban G. (2020) 2-Amino-1,3,4-thiadiazoles as prospective agents in trypanosomiasis and other parasitoses. Acta Pharm., 70 259-290.
42. Petrow V., Stephenson O., Thomas A.J., and Wild A.M. (1958) 302. Preparation and hydrolysis of some derivatives of 1:3:4-thiadiazole. J. Chem. Soc., 0 1508-1513.
43. Rubtsov N., Baichykov A. (1971) [Synthetic chemical and pharmaceutical drugs]. Publishing House «Medicine», Moscow, 126-127. [available in Russian]
44. Bastos I.M.D., Motta F.N., Charneau S., Santana J.M., Dubost L., Augustynus K., and Grellier P. (2010) Prolyl oligopeptidase of Trypanosoma brucei hydrolyzes native collagen, peptide hormones and is active in the plasma of infected mice. Microb. Infect., 12 (6) 457-466.
45. Lethu S., Bosc D., Mouray E., Grellier P., and Dubois J. (2013) New protein farnesyltransferase inhibitors in the 3-arylthiophene 2-carboxylic acid series: Diversification of the aryl moiety by solid-phase synthesis. J. Enzyme Inhib. Med. Chem., 28 (1) 163-171.