{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,29]],"date-time":"2026-07-29T23:09:24Z","timestamp":1785366564752,"version":"3.55.0"},"reference-count":32,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2008,7,29]],"date-time":"2008-07-29T00:00:00Z","timestamp":1217289600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Hydrazonyl bromides 2a,b reacted with active methylene compounds (dibenzoylmethane, acetylacetone, ethyl acetoacetate, phenacyl cyanide, acetoacetanilide, ethyl cyanoacetate, cyanoacetamide and malononitrile) to afford the corresponding 1,3,4,5- tetrasubstituted pyrazole derivatives 5-12a,b. Reaction of 12a,b with formamide, formic acid and triethyl orthoformate give the pyrazolo[3,4-d]pyrimidine, pyrazolo[3,4- d]pyrimidin-4(3H)one and 5-ethoxymethylene-aminopyrazole-4-carbo-nitrile derivatives 13-15a,b, respectively. Compounds 15a,b reacted with benzhydrazide and hydrazine hydrate to afford pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine and [4-iminopyrazolo- [3,4-d]pyrimidin-5-yl]amine derivatives 16a,b and 17a,b. Reactions of compounds 17a,b with triethyl orthoformate and carbon disulfide give the corresponding pyrazolo[4,3-e]- [1,2,4]triazolo[1,5-c]pyrimidine derivatives 18a,b and 19a,b, respectively.<\/jats:p>","DOI":"10.3390\/molecules13071501","type":"journal-article","created":{"date-parts":[[2008,8,2]],"date-time":"2008-08-02T07:26:38Z","timestamp":1217661998000},"page":"1501-1517","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":83,"title":["Synthesis and Antimicrobial Activity of Some New Pyrazole, Fused Pyrazolo[3,4-d]-pyrimidine and Pyrazolo[4,3-e][1,2,4]- triazolo[1,5-c]pyrimidine Derivatives"],"prefix":"10.3390","volume":"13","author":[{"given":"Nada M.","family":"Abunada","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Applied Sciences, Al-Aqsa University, 76888 Gaza, Palestine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hamdi M.","family":"Hassaneen","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Cairo University, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nadia G.","family":"Kandile","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University College for Women, Ain Shams University, Heliopolis, Cairo, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Omar A.","family":"Miqdad","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Applied Sciences, Al-Aqsa University, 76888 Gaza, Palestine"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2008,7,29]]},"reference":[{"key":"ref_1","first-page":"111","article-title":"Synthesis and Antimicrobial Evaluation of New Isoxazole and Pyrazole Derivatives","volume":"11","author":"Goda","year":"2003","journal-title":"Saudi Pharm. J."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"391","DOI":"10.1002\/jccs.200600050","article-title":"Synthesis and Biological Activity of Some New Pyrazolo[3,4-b]pyrazines","volume":"53","year":"2006","journal-title":"J. Chin. Chem. Soc."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"744","DOI":"10.3390\/81000744","article-title":"Synthesis and Reactions of Some New Heterocyclic Carbohydrazides and Related Compounds as Potential Anticancer Agents","volume":"8","author":"Mansour","year":"2003","journal-title":"Molecules"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"439","DOI":"10.1002\/jhet.5570270262","article-title":"Synthesis of Certain Pyrazolo[3,4-d]pyrimidin-3-one Nucleosides","volume":"27","author":"Anderson","year":"1990","journal-title":"J. Heterocycl. Chem."},{"key":"ref_5","first-page":"285","article-title":"Action of Pyrazolopyrimidine Derivatives on American Leiishmania SPP Promastigotes","volume":"83C","author":"Avila","year":"1986","journal-title":"Comp. BiocHem. Physiol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1165","DOI":"10.1021\/jm00142a009","article-title":"Pyrazolopyrimidine nucleosides. 12 Synthesis and biological activity of certain pyrazolo[3,4-d]pyrimidine nucleosides related to adenosine","volume":"24","author":"Bhat","year":"1981","journal-title":"J. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1010","DOI":"10.1021\/jm00146a007","article-title":"Synthesis and biological activity of 6-azacadeguomycin and certain 3,4,6-trisubstituted pyrazolo[3,4-d]pyrimidine ribonucleosides","volume":"28","author":"Petrie","year":"1985","journal-title":"J. Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"770","DOI":"10.1021\/jm0109614","article-title":"Synthesis, biological activity, and molecular modeling investigation of new pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives as human A(3) adenosine receptor antagonists","volume":"45","author":"Baraldi","year":"2002","journal-title":"J. Med. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1319","DOI":"10.2174\/0929867054020963","article-title":"Pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine ligands, new tools to characterize A3 adenosine receptors in human tumor cell lines","volume":"12","author":"Baraldi","year":"2005","journal-title":"Curr. Med. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1229","DOI":"10.1021\/jm021023m","article-title":"Design, synthesis, and biological evaluation of C9- and C2-substituted pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as new A2A and A3 adenosine receptors antagonists","volume":"46","author":"Baraldi","year":"2003","journal-title":"J. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"4287","DOI":"10.1021\/jm030852k","article-title":"Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives as adenosine receptor antagonists. Influence of the N5 substituent on the affinity at the human A3 and A2B adenosine receptor subtypes: a molecular modeling investigation","volume":"46","author":"Pastorin","year":"2003","journal-title":"J. Med. Chem."},{"key":"ref_12","unstructured":"Emmel, L., and Heubach, G. (1972). Acaricidal Phenylhydrazones of Dicarbonyl Compounds. Farbwerke Hoechet Ger Offen, 2,017,761. [Chem. Abstr.. 1972, 76p33935f]."},{"key":"ref_13","first-page":"33","article-title":"Antimicrobial Activity of Some Arylhydrazones of Acyl Halides and Arylhydrazides of Carboxylic Acids","volume":"14","author":"Molodykh","year":"1980","journal-title":"Khim Farm. Zh."},{"key":"ref_14","unstructured":"Kaugers, G. (1973). Combating Insects and Mits Using Alkanoyl Chloride Phenylhydrazone. (3,745,215), US Pat., [Chem. Abstr. 1973, 79, 78412m]."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1358","DOI":"10.1021\/jm00186a014","article-title":"Structure-Activity Relationships of Antibacterial 6,7- and 7,8-Disubstituted 1-Alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids","volume":"23","author":"Koga","year":"1980","journal-title":"J. Med. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"505","DOI":"10.1021\/cr00012a002","article-title":"Recent Advances in the Selective Formation of the Carbon-Fluorine Bond","volume":"92","author":"Wilkinson","year":"1992","journal-title":"Chem. Rev."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"559","DOI":"10.1128\/AAC.23.4.559","article-title":"In Vitro Activity of Bay 09867, a New Quinoline Derivative, Compared with Those of Other Antimicrobial Agents","volume":"23","author":"Wise","year":"1983","journal-title":"Antimicrb. Agents Chemother."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1155","DOI":"10.1021\/jm00107a040","article-title":"Synthesis and Biological Activity of 5-Alkyl-1,7,8-trisubstituted-6-fluoroquinoline-3-carboxylic Acids","volume":"34","author":"Hagen","year":"1991","journal-title":"J. Med. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"292","DOI":"10.1021\/jm00369a011","article-title":"Pyridonecarboxylic Acids As Antibacterial Agents. 2. Synthesis and Structure-Activity Relationships of 1,6,7-trisubstituted 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acids, Including Enoxacin, a New Antibacterial Agent","volume":"27","author":"Matsumoto","year":"1984","journal-title":"J. Med. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"4907","DOI":"10.1248\/cpb.32.4907","article-title":"Synthesis and Antibacterial Activities of Substituted 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic Acids","volume":"32","author":"Hayakawa","year":"1984","journal-title":"Chem. Pharm. Bull. (Tokyo)"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1007\/BF02876867","article-title":"Synthesis of C-(2-Furyl)-N-(4-nitrophenyl)methanohydrazonyl Bromide. Reactions with Nucleophiles and Active Methylene Compounds","volume":"14","author":"Hassaneen","year":"1991","journal-title":"Arch. Pharm. Res."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"247","DOI":"10.3987\/COM-89-5045","article-title":"Synthesis and cycloaddition reactions of N-phenyl-C-styrylmethanohydrazonyl bromide","volume":"31","author":"Hassaneen","year":"1990","journal-title":"Heterocycles"},{"key":"ref_23","first-page":"41","article-title":"A Facile Synthesis of Thiadiazolo[2,3-b]quinazoline, 2,3-Dihydro-1,3,4-thiadiazole and 2-Amino-5-arylazothiazole Derivatives","volume":"14","author":"Hassaneen","year":"1992","journal-title":"Sulfur Lett."},{"key":"ref_24","first-page":"273","article-title":"Reaction of 1-(2-Naphthoyl)methylsulfonium Bromide with N-Nitroso-N-arylacetamides and Reactions of The Products with Some Nucleophiles","volume":"13","author":"Hassaneen","year":"1992","journal-title":"Sulfur Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"739","DOI":"10.1002\/hlca.200390073","article-title":"Synthesis of 1,2,4-Triazolo[4,3-a]pyrimidine Derivatives by Cyclocondensation of a 2-Thioxopyrimidin-4(3H)-one with Hydrazonyl Halides","volume":"86","author":"Elwan","year":"2003","journal-title":"Helv. Chem. Acta"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"494","DOI":"10.3390\/70600494","article-title":"A Novel Synthesis of 1,2,4-Triazolopteridines","volume":"7","author":"Abdallah","year":"2002","journal-title":"Molecules"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"10133","DOI":"10.1016\/S0040-4020(01)01026-2","article-title":"Novel Synthesis of 1,2,4-triazolo[4,3-a]pyrimidin-5-one Derivatives","volume":"57","author":"Hassaneen","year":"2001","journal-title":"Tetrahedron"},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Hegarty, A. F., and Scott, F. L. (1966). The kinetics of Bromination of Hydrazones. J. Chem. Soc. (B), 672\u2013675.","DOI":"10.1039\/j29660000672"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/S0040-4020(01)99385-8","article-title":"Reaction of Carbanions of \u03b2\u2013Diketones and \u03b2\u2013Keto Esters with Hydrazidic Bromides","volume":"29","author":"Shawali","year":"1972","journal-title":"Tetrahedron"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1011","DOI":"10.3390\/molecules13041011","article-title":"Synthesis and Biological Activity of Some New Pyrazoline and Pyrrolo[3,4-c]pyrazole-4,6-dione Derivatives: Reaction of Nitrilimines with Some Dipolarophiles","volume":"13","author":"Abunada","year":"2008","journal-title":"Molecules"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1016\/0031-9422(94)85005-4","article-title":"A Survey of Antifungal Compounds from Higher Plants","volume":"37","author":"Grayer","year":"1994","journal-title":"PhytOCHemistry"},{"key":"ref_32","first-page":"87","article-title":"Antimicrobial Activity of Annatto Extract","volume":"34","author":"Irob","year":"1996","journal-title":"Int. J. Pharm."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/13\/7\/1501\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T22:20:48Z","timestamp":1760221248000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/13\/7\/1501"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,7,29]]},"references-count":32,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2008,7]]}},"alternative-id":["13071501"],"URL":"https:\/\/doi.org\/10.3390\/molecules13071501","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,7,29]]}}}