Synthesis, Reactions and Characterization of 1,1’-(1,4-Phenylenebis(3-amino-6-methyl-1H-pyrazolo[3,4-b]pyridine-4,5-diyl))bis(ethan-1-one) — Oak Academic Publishing
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Synthesis, Reactions and Characterization of 1,1’-(1,4-Phenylenebis(3-amino-6-methyl-1H-pyrazolo[3,4-b]pyridine-4,5-diyl))bis(ethan-1-one)
Basic-Applied Science Department, Faculty of Oral and Dental Medicine, Nahda University, Beni-Suef, Egypt
,
College of Science for Women, Baghdad University, Baghdad, Iraq
,
Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt
1 Basic-Applied Science Department, Faculty of Oral and Dental Medicine, Nahda University, Beni-Suef, Egypt
2 College of Science for Women, Baghdad University, Baghdad, Iraq
3 Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt
Reaction of 4,4’-(1,4-phenylene)bis(5-acetyl-6-methyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile) (1) with methyl iodide afforded the 4,4’-(1,4-phenylene)bis(5-acetyl-6-methyl-2-(methylthio)nicotinonitrile) (2). The reaction of 2 with hydrazine hydrate followed by diazotization reaction af-forded the 1,1’-(1,4-phenylenebis(3-amino-6-methyl-1H-pyrazolo[3,4-b]pyridine-4,5-diyl))bis(e-than-1-one) (3) and 1,1’-(1,4-phenylenebis(3-(chlorodiazenyl)-6-methyl-1H-pyrazolo[3,4-b]-pyridine-4,5-diyl))bis(ethan-1-one) (4) respectively. On the other hand, reaction of 4 with malononitrile, 2-cyanoethanethioamide, ethyl acetoacetate, acetyl acetone, ethyl benzoylacetate, diethylmalonate, ethyl cyanoacetate and phenacylbromide aiming to build up pyrazolotriazine or pyrazole ring on the ring system of 4. Structures of all newly synthesized heterocyclic compounds in the present study were confirmed by considering the data of IR, 1H NMR, mass spectra as well as that of elemental analyses.
Singh, H., Yadav, L.D.S. and Bhattacharya, B.K. (1979) Synthesis of Some New Bis(1,2,4-triazol-3-yl)disulfides, Sulfides and Sulfones as Potential Pesticides. J. Indian. Chem. Soc., 56, 1013.
Desai, N.C. (1993) Synthesis and Antimicrobial Activity of Some Dithiocarbamates, 2-Arylamino-4-oxothiazoles and Their 5-Arylidine Derivatives. Indian Journal of Chemistry—Section B, 32, 343.
Yahia, N.M., Assem, B., Abdullah, M., Saeed, A., Sammer, Y. and Choudhary, M. (2013) Synthesis, Reactions and Biological Activity of Some New Bis-Heterocyclic Ring Compounds Containing Sulphur Atom. Chemistry Central Journal, 7, 112.
Upadhyay, P.S., Vansdadia, R.N. and Baxi, A.J. (1990) Studies on Sulphone Derivatives: Preparation and Antimicrobial Activity of Thiosemicarbazides, Thiazolidones, Triazoles, Oxadiazoles and Thiadiazoles. Indian Journal of Chemistry—Section B, 29, 793.
Zhang, Z.Y., Chen, X., Wei, L.L. and Ma, Z.L. (1991) Studies on Condensed Heterocyclic Compounds (Ⅲ) Synthesis and Antibacterial Activity of 3-(4-Pyridyl)-6-Alkyl/Aromatic Heterocyclyl-s-Tri-azolo[3,4-b]-1,3,4-Thiadiazoles and 1,4-Bis [6-(4-Pyridyl)-s-Triazolo[3,4-b]-1, 3,4-Thiadiazol-3-yl]-n-Bu. Chem. Res. Chin. Univ., 7, 129.
Bhat, A.R., Athar, F. and Azam, A. (2009) Bis-Pyrazolines: Synthesis, Characterization and Antiamoebic Activity as Inhibitors of Growth of Entamoeba histolytica. European Journal of Medicinal Chemistry, 44, 426-431. http://dx.doi.org/10.1016/j.ejmech.2007.11.005
Kerru, N., Nallapaneni, H., Kasturi, V. and Rao, C.V. (2015) Synthesis and Biological Activity of Novel Bis and Mono Heterocycles of Thienopyrimidine Derivatives. Indo American Journal of Pharmaceutical Research, 5, 1604.
Iqbal, P.F., Parveen, H., Bhat, A.R., Hayat, F. and Azam, A. (2009) Synthesis, Characterization, Antiamoebic Activity and Toxicity of Novel Bisdioxazole Derivatives. European Journal of Medicinal Chemistry, 44, 4747-4751. http://dx.doi.org/10.1016/j.ejmech.2009.06.016
Dawoud, N.T.A. (2011) Synthesis, Reactions and Antimicrobial Activity of Some Substituted 4,6-Diphenyl Pyridine 2-Thione Derivatives. Nature and Science, 9, 202.
Madkour, H.M.F., Salem, M.A.L., Marzouk, M.L., Azab, M.E. and Mahmoud, N.F.H. (2007) Utility of Cyanothioacetamide in the Synthesis of Pyrazolo[4,3-c], Isoxazolo[4,5-c], Thieno[2,3-b] and Furo[2,3-c] of Thioxopyridine Derivatives and their Antibacterial Activities. American-Eurasian Journal of Scientific Research, 2, 161-169.
4-b]pyridine
Paronikyan, E.G., Akopyan, Sh.F., Noravyan, A.S., Dzhagatspanyan, L.A., Nazaryan, L.M. and Akopyan, A.G. (2010) Synthesis and Neurotropic Activity of 6-Thio-Substituted Pyrano[3,4-c]pyridine and 1-Aminopyrano[4,3-d]-thieno [2,3-b]pyridine Derivatives and 9-Substituted Pyrido[2,3-b]thieno[3,2-d]pyrimidines. Pharmaceutical Chemistry Journal, 44, 183-185. http://dx.doi.org/10.1007/s11094-010-0426-5
Abbas, A.A., Elneairy, M.A.A. and Mabkhot, Y.N. (2001) Versatile Starting Materials for Novel 1,ω-Bis(pyridin-4-ylphenoxy)alkanes, and Their Corresponding Bis-(thieno[2,3-b]pyridin-4-ylphenoxy) Derivatives. Journal of Chemical Research, 4, 124-126. http://dx.doi.org/10.3184/030823401103169388
Bhat, A.R., Ather, F. and Azam, A. (2009) Bis-Pyrazolines: Synthesis, Characterization and Antiamoebic Activity as Inhibitors of Growth of Entamoeba histolytica. European Journal of Medicinal Chemistry, 44, 426-431. http://dx.doi.org/10.1016/j.ejmech.2007.11.005
Griffin, A.C. and Britt, T.R. (1981) Effect of Molecular Structure on Mesomorphism. 12. Flexible-Center Siamese- Twin Liqiud Crystalline Diesters-a “Prepolymer” Model. Journal of the American Chemical Society, 103, 4957-4959. http://dx.doi.org/10.1021/ja00406a056
Galli, G., Laus, M. and Angeloni, A.S. (1986) Synthesis and Thermotropic Properties of New Mesogenic Diacrylate Monomers. Die Makromolekulare Chemie, 187, 289-296. http://dx.doi.org/10.1002/macp.1986.021870206
Ringsdorf, H., Schlarb, B. and Venzmer, J. (1988) Molecular Architecture and Function of Polymeric Oriented Systems: Models for the Study of Organization, Surface Recognition, and Dynamics of Biomembranes. Angewandte Chemie International Edition in English, 27, 113-158. http://dx.doi.org/10.1002/anie.198801131
Finkelman, H. (1987) Liquid Crystalline Polymers. Angewandte Chemie International Edition in English, 26, 816-824. http://dx.doi.org/10.1002/anie.198708161
Aguilera, C., Parra, M. and Fuentes, G.Z. (1998) Synthesis and Mesomorphic Properties of Polymethylene-bis[2-thio- 5-(4’,4’’n-alcoxybenzoyloxy)phenyl]-1,3,4-oxadiazole. Zeitschrift für Naturforschung, 53b, 367-370.
Braun, D. and Langendorf, R. (1999) Vitrigens. I. Synthesis and Characterization of Low Molecular Weight Organic Glasses. Journal für Praktische Chemie, 341, 128-137. http://dx.doi.org/10.1002/(SICI)1521-3897(199902)341:2 3.0.CO;2-M
Abdel-Fattah, A.M. and Elsayed, M.M. (2009) Novel Synthesis, Reactions and Anti-Cancer Activities of 4,4’-Ben- zene-1,4-diylbis(6-phenyl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile). Current Organic Chemistry, 13, 1751-1757. http://dx.doi.org/10.2174/138527209789578036
Shestopalov, A.M., Nikishin, K.G., Gromova, A.V. and Rodinovskaya, L.A. (2003) One-Pot Synthesis of 4,6-Diaryl-3-cyanopyridine-2(1H)-thiones and Their Transform-Ation to Substituted Thieno[2,3-b;4,5-b]dipyridines and Pyrido[3’’,2’’:4,5]thieno-[3,2-d]pyrimidines. Russian Chemical Bulletin, 52, 2203-2206.
Prachayasittikul, S., Treeratanapiboon, L., Ruchirawat, S. and Prachayasittikul, V. (2009) Novel Activities of 1-Ada-mantylthiopyridines as Antibacterials, Antimalarials and Anticancers. EXCLI Journal, 8, 121-129.
Al-Abdullah, E.S. (2011) Synthesis and Anticancer Activity of Some Novel Tetralin-6-yl-pyrazoline, 2-Thioxopyrimi- dine, 2-Oxopyridine, 2-Thioxopyridine and 2-Iminopyridine Derivatives. Molecules, 16, 3410.
Attaby, F.A. and Alkubaisi, H.M. (2015) Synthesis, Reactions and Characterization of 6-Thioxo-1,6-dihydro-2,3’-bi- pyridine-5-carbonitrile. Journal of Purity, Utility Reaction and Environment, 4, 1-15.
Attaby, F.A., Abdel-Fattah, A.M., Shaif, L.M. and Elsayed, M.M. (2010) Anti-Alzheimer and Anti-COX-2 Activities of the Newly Synthesized 2,3’-Bipyridine Derivatives (II). Phosphorus, Sulfur and Silicon and the Related Elements, 185, 668-679. http://dx.doi.org/10.1080/10426500902917644
Attaby, F.A., Abdel-Fattah, A.M., Shaif, L.M. and Elsayed, M.M. (2010) Anti-Alzheimer and Anti-COX-2 Activities of the Newly Synthesized 2,3’-Bipyridine Derivatives (I). Phosphorus, Sulfur and Silicon and the Related Elements, 185, 129-139. http://dx.doi.org/10.1080/10426500902717333
Attaby, F.A., Elghandour, A.H., Ali, M.A. and Ibrahem, Y.M. (2007) Synthesis, Characterization and Antiviral Activities of Pyridopyrazolotriazines. Phosphorus, Sulfur and Silicon and the Related Elements, 182, 133-149. http://dx.doi.org/10.1080/10426500600887313
Attaby, F.A., Elghandour, A.H.H., Ali, M.A. and Ibrahem, Y.M. (2007) Synthesis, Reactions and Antiviral Activity of 6’-Amino-2’-thioxo-1’,2’-dihydro-3,4’-bipyridine-3’,5’-dicarbonitrile. Phosphorus, Sulfur and Silicon and the Related Elements, 182, 695-709. http://dx.doi.org/10.1080/10426500601087277
Attaby, F.A., Ramla, M.M. and Gouda, E.M. (2007) Synthesis, Reactions, and Biological Activity of 4(1H-Indol-3-yl)-2-Thioxopyridine Derivatives. Phosphorus, Sulfur and Silicon and the Related Elements, 182, 517-528. http://dx.doi.org/10.1080/10426500601013216
Attaby, F.A., Abdel-Fattah, A.M., Shaif, L.M. and Elsayed, M.M. (2009) Anti-Alzheimer and Anti-COX-2 Activities of the Newly 2-Substituted thienopyridines. Current Organic Chemistry, 14, 1654-1663. http://dx.doi.org/10.2174/138527209789578135
Attaby, F.A., Abdel-Fattah, A.M., Shaif, L.M. and Elsayed, M.M. (2010) Reactions, Anti-Alzheimer and Anti COX-2 Activities of 6-Pyridin-3-yl-1H-pyrazolo[3,4-b]pyridin-3-amines. Current Organic Chemistry, 14, 2522-2530. http://dx.doi.org/10.2174/138527210793358303
Attaby, F.A., Said, M.M. and Bakr, S.A.M. (2013) Synthesis, Reactions and Characterization of 4,4’-Benzene-1,4-diylbis(5-Acetyl-6-methyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile). Egyptian Journal of Chemistry, 56, 127-140.
Attaby, F.A. and Elreedy, A.A.M. (2014) Synthesis, Reactions and Characterization of Bisthieno[2,3-b]pyridine-2- carbohydrazide Derivative. International Journal of Scientific & Engineering Research, 5, 662-671.