1.
2.
R
N N O
N N
N N
Ar
N
N
N
S
(Ia)
Ar
N
(Ib)
S
R
1
Ar
N
N
N
S
CH Ar
1
(II)
Ar
N
N
S
Ar
N
N
S
R
1
(IV)
Ar
2
N N
(III)
Ar
O
N
S
Ar = X S ; X= H, Cl, Br
HN
R
3 O
O
(V)
[1] Saramet I., Banciu M.D., Draghici C. – „Synthesis and characterization of some 5-substituted-3-mercapto-1,2,4triazoles”, Rev. Roum. Chim ., 1991, 36 (1-3), 135-143
[2] Almajan G.L., Barbuceanu S.F., Saramet I., Draghici C. – „Noi compusi heterociclici obtinuti din hidrazidele acizilor benzensulfonilbenzoici-4-substituiti”, Rev. Chim. (Bucuresti) , 2005 , 56 (11), 1182-1187
[3] Potts K.T., Husain S. – „1,2,4-Triazoles. XXVII. Synthesis of the thiazolo[2,3-c]-s-triazole and the thiazolo[3,2-b]-striazole systems”, J. Org. Chem ., 1971 , 36 (1), 10-13
[4] Pignatello R., Mazzone S., Panico A.M., Mazzone G., Pennisi G., Castana R., Matera M., Blandino G. – „Synthesis and biological evaluation of thiazolo-triazole derivatives”, Eur. J. Med. Chem ., 1991 , 26, 929-938
[5] Yathirajan H.S., Vijaya Raj K.K.., Narayana B., Sarojini B.K., Bolte M. – „2-(2-Bromo-5-methoxyphenyl)-6-phenyl-1,3thiazolo[3,2-b][1,2,4]triazole”, Acta Crystalogr . Sect.E
, 2006 , 62, 4444-4445
[6] Roy P., Leblanc Y, Ball R.G., Brideau C., Chan C.C., Chauret N., Cromlish W., Ethier D., Gauthier J.Y., Gordon R.,
Greig G., Guay J., Kargman S., Lau C.K., O’Neil G., Silva J., Thérien M., van Staden C., Wong E., Xu L., Prasit P. – „A new series of selective COX-2 inhibitors: 5,6-diarylthiazolo[3,2-b][1,2,4]triazoles”, Bioorg. Med. Chem. Lett., 1997 , 7, 1, 57-62
[7] Crişan O., Bojiţă M., Muñoz V. T., Terencio M.C., Aguilar G.A., Zaharia – „Synthesis, characterization and pharmacological activity of some thiazolo[3,2-b]1,2,4-triazoles derivatives”, Farmacia, 2001 , vol.XLIX, 5, 15-22
[8] Zaharia V., Chirtoc I. – „Heterocycles 20. Synthesis and characterization of some 2-amino-5-methyl-thiazol-5-yl)-[1,3,4]thiadiazole and 5-(2-phenyl-5-methyl-thiazol-5-yl)-[1,2,4]-triazol-[2 H ,4 H ]-3-thione”, Farmacia , 2002 , vol.L, 1, 38-43
[9] Zaharia V., Chirtoc I. – „Heterocycles 16. Synthesis and characterization of some thiazolo[2,3-c] [1,2,4]triazoles”,
Farmacia , 2001 , XLIX (6), 24-31
[10] Erol D.D., Çaliş Ü., Demirdamar R., Yuluğ N., Ertan M. – „Synthesis and biological activities of some 3,6-disubstituted thiazolo[3,2-b][1,2,4]triazoles”, J. Pharm. Sci ., 1995 , 84, 4, 462-465
[11] El-Sherif H.A.H., Mahmoud A.M., Sarhan A.A.O., Hozien Z.A., Habib O.M.A. – „One pot synthesis of novel thiazolo[3,2-b][1,2,4]triazoles: A useful synthetic application of the acidified acetic acid method”, J. Sulfur Chem ., 2006 , 27
(1), 65-85
[12] Zakaria K., El-Samii A., El-Feky S.A. – „Synthesis of some new 3-mercapto-5-substituted-1,2,4-triazine-s-triazoles for evaluation as antimicrobial agents”, J. Chem.
Tech. Biotechnol.
, 1995 , 63, 135-140
[13] Heravi M.M., Kivanloo A., Rahimzadeh M., Bakavoli M., Ghassemzadeh M., Neumüller B. – „Regioselective synthesis of 6-benzylthiazolo[3,2-b][1,2,4]-triazoles during Sonogashira coupling”, Tetrahedron Lett ., 2005 , 46, 1607-1610
[14] Mogilaiah K., Prashanthi M., Kavitha S., Babu H.S. – „Microwave assisted synthesis of thiazolo[3,2-b][1,2,4]-triazoles containing 1,8-naphthyridine moiety”, J. Heterocycl . Chem.
, 2007 , 44, 1161-1163
[15] Tozkoparan B., KilcigilG.A., Ertan R. Ertan M.
, Kelicen P., Demirdamar R., - “Synthesis and evaluation of antiinflammatory activity of some thiazolo[3,2-b]-1,2,4-triazole-5(6H)-ones and their Michael addition products, Arzneim.-
Forsch./Drug Res ., 1999 , 49 (12), 1006-1011
[16] Tozkoparan B., Aktay G., Yesilada E., Ertan M. – „Syhthesis of some thiazolo[3,2-b]-1,2,4-triazole-5(6H)-ones and their novel Michael addition products with anti-inflammatory activities”, Arzneim.-Forsch./Drug. Res.
, 2001 , 51 (6), 470-477
[17] Doğdaş E; Tozkoparan B; Kaynak F.B., ErikssonL., Küpeli E; Yeşilada E., Ertan M.
–
„Design and synthesis of some new thiazolo [3,2-b]-1,2,4-triazole-5(6H)-ones substituted with flurbiprofen as anti-inflammatory and analgesic agents”,
Arzneim.-Forsch./Drug. Res.
, 2007 , 57 (4), 196-202
[18] Tozkoparan B., Gökhan N., Aktay G., Yeşilada E., Ertan M. – „6-Benzylidene-thiazolo[3,2-b]-1,2,4-triazole-5(6 H )-ones substituted with ibuprofen: synthesis, characterization and evaluation of anti-inflammatory activity”, Eur. J. Med. Chem .,
2000 , 35, 743-750
[19] Berk B., Aktay G., Yesilada E., Ertan M. – „Synthesis and pharmacological activities of some new 2-[1-(6-methoxy-2naphtyl)ethyl]-6(substituted)benzylidene-thiazolo[3,2-b]-1,2,4-triazolole-5(6 H )-one derivatives”, Pharmazie , 2001 , 56 (8),
613-616
[20] Tozkoparan B., Gökhan N., Küpeli E., Yeşilada E., Ertan M. – „Synthesis, characterization and antiinflammatoryanalgesic properties of some 6-(α-amino-4-chlorobenzyl)tiazolo[3,2-b]-1,2,4-triazol-5-ols”, Arzneim.-Forsch./Drug Res .,
2004 , 54 (1), 35-41
[21]
Mekuškiene G., Gaidelis P., Vainilavičius P. – „Synthese und eigenschaften von 5-(4,6-diphenyl-pyrimidin-2-yl)-1,2,4triazolin-3-thion und seinen derivaten”, Pharmazie , 1998 , 53 (2), 94-96
[22] Köysal Y., Işik Ş., Doğdaş E., Tozkoparan B., Ertan M. – „6-(2-Fluorobenzylidene)-2-[1-(2-fluoro-4biphenyl)ethyl]thiazolo[3,2-b][1,2,4]triazol-5(6 H )-one”, Acta Cryst., 2004 , C60, 356-357
[23] Lesyk R., Vladzimirska O., Holota S., Zaprutko L., Gzella A. – „New 5-substituted thiazolo[3,2-b][1,2,4]triazol-6-ones:
Synthesis and anticancer evaluation”, Eur. J. Med. Chem.
, 2007 , 42, 641-648
[24] Burbuliene M.M., Jakubkiene V., Mekuskiene G., Vainilavicius P. – „Synthesis of novel derivatives of 5-(4,6-dimethyl-
2-pyrimidinylsulfanyl)methyl-1,2,4-triazole-3-thione”, Phosphorus, Sulfur Silicon , 2003 , 178, 2431-2440
[25] Vinod Mathew, J. Keshavayya, V.P. Vaidya, D. Giles – „Studies on synthesis and pharmacological activities of 3,6disubstituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and their dihydro analogues”, Eur. J. Med. Chem , 2007 , 42, 823-840
[26] . Mohammad Amir, Harish Kumar, Sadique A. Javed – „Synthesis and pharmacological evaluation of condensed heterocyclic 6-substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives of naproxen”, Bioorg. Med. Chem. Lett ., 2007,
17, 4504-4508
[27] T. Karabasanagouda, Airody Vasudeva Adhikari, N. Suchetha Shetty – „Synthesis and antimicrobial activities of some novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines carrying thioalkyl and sulphonyl phenoxy moieties”, Eur. J. Med. Chem., 2007 , 42, 521-529
[28] V. Padmavathi, P. Thriveni, G. Sudhakar Reddy, D. Deepti – „Synthesis and antimi-microbial activity of novel sulfonelinked bis heterocycles”, Eur. J. Med. Chem ., 2007 , doi:10.1016/j.ejmech.2007.06.011
[29] V. Mathew, J. Keshavayy, V.P. Vaidy – „Heterocyclic system containing bridgehead nitrogen atom: synthesis and pharmacological activities of some substituted 1,2,4-triazolo [3,4-b]-1,3,4-thiadiazoles”, Eur. J. Med. Chem , 2006 , 41, 1048-
1058
[30] Peng-Fei Xua, Zhi-Hui Zhanga, Xin-Ping Huia, Zi-Yi Zhanga, Rong-Liang Zhengb – „Synthesis of triazoles, oxadiazoles and condensed heterocyclic compounds containing cinchopheny and studies on biological activity of representative compounds”, J. Chin. Chem. Soc ., 2004 , 51, 315-319
[31] K. Subrahmanya Bhat, D. Jagadeesh Prasad, Boja Poojary, B. Shivarama Holla – „Synthesis of some new 1,2,4triazolo[3,4-b]-thiadiazole derivatives as possible anticancer agents”, Phosphorus, Sulfur Silicon Relat. Elem ., 2004 , 179,
1595-1603
[32] Heng-Shan Donga, Bin Wangb – „Synthesis of some novel 3,6-bis(1,2,3-triazolyl)s -triazolo[3,4-b]-1,3,4-thiadiazole derivatives”, J. Chin. Chem. Soc ., 2005 , 52, 103-108
[33] M.M. Heraw, M. Rahimizadeh, M. Seyf, A. Davoodnia, M. Ghassemzadeh – „Bicyclic compounds derived from 4amino-3-mercapto-1,2,4-triazoles: A facile routes to 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 1,2,4-triazolo[3,4b][1,3,4]thiadiazines”, Phosphorus, Sulfur Silicon Relat. Elem ., 2000 , 167, 211-217
[34] E. S. H. El Ashry, A. A. Kassem, H. Abdel-Hamid, F. F. Louis, Sh. A. N. Khattab,M. R. Aouad – „ “Synthesis of 4amino-5-(3-chlorobenzo[ b ]thien-2-yl)-3-mercapto-1,2,4-triazolo [3,4b ][1,3,4]thiadiazoles and triazolo[3,4, b ] [1,3,4]thiadiazines under classical and micro-wave conditions”, Arkivoc , 2006 , (xiv), 119-132
[35] Abdel-Rahman Farghaly, Erik De Clercq, Hussein El-Kashefa – „Synthesis and antiviral activity of novel
[1,2,4]triazolo[3,4b ][1,3,4]thiadiazoles, [1,2,4]triazolo[3,4b ][1,3,4]thiadia-zines and [1,2,4]triazolo[3,4b ][1,3,4] thiadiazepines”, Arkivoc , 2006 , (x), 137-151
[36] Abu Zeid Abd El-Baset Hassanien – „Phthalazinone in heterocyclic synthesis: Synthesis of some s-tiazole, striazolothiadiazine, s-triazolothiadiazole derivatives as pharmaceutical interest”, Phosphorus, Sulfur Silicon Relat. Elem .,
2003 , 178, 1987-1997
[37] G. Turan-Zitouni, Z.A. Kaplancikli, K. Erol, F.S. Kilic – „Synthesis and analgesic activity of some triazoles and triazolothiadiazines”, Il Farmaco , 1999 , 54, 218–223
[38] Yi Xiong, Lixue Zhang, Anjiang Zhang, Duanjun Xu – „Synthesis of 6-aryl-3-(D-glucopentitol-1-yl)-7 H -1,2,4-triazolo-
[3,4-b][1,3,4]thiadiazines”, Synth. Comm ., 2002 , 32 (22), 3455-3459
[39] Zafer Asım Kaplancıklı, Gulhan Turan-Zitouni, Ahmet Ozdemir, Gilbert Revial – „New triazole and triazolothiadiazine derivatives as possible antimicrobial agents”, Eur. J. Med. Chem ., 2007 , doi:10.1016/j.ejmech.2007.03.019
[40] El Sayed H. El Ashry, Laila F. Awad – „Novel synthesis of seco type of acyclo C -nucleosides of 1,2,4-triazole and
1,2,4-triazolo[3,4-b][1,3,4]thiadiazine”, Nucleosides, Nucleotides, Nucleic Acids , 2001 , 20 (1-2), 103-116
[41] Guo Qiang Hu, Wen Long Huang, Hai Wang – „Synthesis of tetrahydro-pyridinyltriazolothiadiazines as possible muscarinic agonists”, Chin. Chem. Lett ., 2005 , 16 (1), 1-3
[42] B. Shivarama Holla, P.M. Akberali, M.K. Shivananda – „Studies on nitrophenylfuran derivatives. Part XII. Synthesis, characterization, antibacterial and antiviral activities of some nitrophenylfurfurylidene-1,2,4-triazolo[3,4b ]-1,3,4thiadiazines”, Il Farmaco , 2001 , 56, 919–927
[43] Xin-Ping Huia, Heng-Shan Donga, Peng-Fei Xua, Zi-Yi Zhang, Qin Wangb, Yan-Ni Gong – „Heterocyclic systems containing bridged nitrogen atom: Synthesis and antibacterial activity of 3-(2-phenylquinolin-4-yl)/3-(1p -Chlorophenyl-5methyl-1,2,3-triazol-4-yl)s -triazolo[3,4-b]-1,3,4-thiadiazine derivatives”, J. Chin. Chem, Soc ., 2000 , 47, 1115-1119
[44] A. H. Moustafa, R. A. Haggam, M. E. Younes , E. S. H. El Ashry – „Double-headed acyclo C-nucleoside analogues.
Functionalized 1,2bis -(1,2,4-Triazol-3-yl)ethane-1,2-diol”, Nucleosides, Nucleotides, Nucleic Acids , 2005 , 24, 1885–1894,
[45] Jian-yu Jin, Li-xue Zhang, Xian-xing Chen, An-jiang Zhang, Hai-le Zhang – „Syntheses and biological activities of 6aryl-3-(3-hydroxypropyl)-7 H -1,2,4-triazolo[3,4b ][1,3,4]thia- diazines”, Molecules, 2007 , 12 , 297-303
[46] M. M. Heravi, M. Bakherad, M. Rahimzadeh, M. Bakavolib – „Solid acid induced cyclocondensation: A facile synthesis of 7 H -1,2,4-triazolo[3,4b ][1,3,4]thiadiazines”, Phosphorus, Sulfur Silicon Relat. Elem ., 2002 , 177, 2403-2407
[47] A. M. Demchenko, V. A. Yanchenko, M. O. Lozinskii – „Synthesis of 3-alkyl-6-aryl (arylamino)-7 H -
[1,2,4]triazolo[3,4b ][1,3,4]thiadiazines”, Russian J. Org. Chem ., 2003 , 39 (7), 1025-1028
[48] V. A. Yanchenko, A. M. Demchenko, M. O. Lozinskii – „6-Arylamino-3-methyl-7 H -[1,2,4]triazolo[3,4b ][1,3,4] thiadiazines: Novel N-arylamidine structures”, Chem. Het. Compd ., 2004 , 40 (4), 516-518
[49] Vainilavicius P., Smicius R., Jakubkiene V., Tumkevicius S. – „Synthesis of 5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-
3-pyrimidinyl)-methyl-4-amino-1,2,4-triazole-3-thione and its reactions with polyfunctional electrophiles”, Monatsh. Chem .,
2001 , 132 (7), 825-831
Project Director,
Prof Dr IOANA SARAMET