{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,7]],"date-time":"2026-07-07T08:47:09Z","timestamp":1783414029920,"version":"3.54.6"},"reference-count":33,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2014,1,17]],"date-time":"2014-01-17T00:00:00Z","timestamp":1389916800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>This study aimed for the synthesis of new heterocyclic compounds incorporating  sulfamoyl moiety suitable for use as antimicrobial agents via a versatile, readily accessible N-[4-(aminosulfonyl)phenyl]-2-cyanoacetamide (3). The 2-pyridone derivatives were obtained via reaction of cyanoacetamide with acetylacetone or arylidenes malononitrile. Cycloaddition reaction of cyanoacetamide with salicyaldehyde furnished chromene derivatives. Diazotization of 3 with the desired diazonium chloride gave the hydrazone derivatives 13a\u2013e. Also, the reactivity of the hydrazone towards hydrazine hydrate to give Pyrazole derivatives was studied. In addition, treatment of 3 with elemental sulfur and phenyl isothiocyanate or malononitrile furnished thiazole and thiophene derivatives respectively. Reaction of 3 with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt 17 which reacted in situ with 3-(2-bromoacetyl)-2H-chromen-2-one  and methyl iodide afforded the thiazole and ketene N,S-acetal derivatives respectively. Finally, reaction of 3 with carbon disulfide and 1,3-dibromopropane afforded the N-[4-(aminosulfonyl) phenyl]-2-cyano-2-(1,3-dithian-2-ylidene)acetamide product 22.  All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis. The compounds were evaluated for both their in vitro antibacterial and antifungal activities and showed promising results.<\/jats:p>","DOI":"10.3390\/ijms15011237","type":"journal-article","created":{"date-parts":[[2014,1,17]],"date-time":"2014-01-17T12:48:09Z","timestamp":1389962889000},"page":"1237-1254","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":52,"title":["Synthesis and Antimicrobial Evaluation of Some Novel Thiazole, Pyridone, Pyrazole, Chromene, Hydrazone Derivatives Bearing a Biologically Active Sulfonamide Moiety"],"prefix":"10.3390","volume":"15","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6058-7320","authenticated-orcid":false,"given":"Elham","family":"Darwish","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Cairo University, Giza  12613, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Azza","family":"Fattah","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Cairo University, Giza  12613, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fawzy","family":"Attaby","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Cairo University, Giza  12613, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oqba","family":"Al-Shayea","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Cairo University, Giza  12613, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2014,1,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"596","DOI":"10.1016\/S0014-827X(00)00079-3","article-title":"Studies on aminopyrazoles: Antibacterial activity of some novel pyrazolo[1,5-a]pyrimidines containing sulfonamido moieties","volume":"55","author":"Atalla","year":"2000","journal-title":"Il Farm"},{"key":"ref_2","first-page":"159","article-title":"Preparation of some novel 3, 5-diaminopyrazole, pyrazolo [1,5-a][1,3,5]triazine and pyrazolo [1,5-a]pyrimidine derivatives containing sulfonamido moieties as antimicrobial agents","volume":"49","author":"Taha","year":"2002","journal-title":"Acta Chim. Slov"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"613","DOI":"10.1016\/S0014-827X(01)01178-8","article-title":"Novel synthesis and antifungal activity of pyrrole and pyrrolo[2,3-d]pyrimidine derivatives containing sulfonamido moieties","volume":"57","author":"Gaber","year":"2002","journal-title":"Il Farm"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1146\/annurev.pa.16.040176.001521","article-title":"Relations between structure and biological activity of sulfonamides","volume":"16","author":"Maren","year":"1976","journal-title":"Annu. Rev. Pharmacol. Toxicol"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1396","DOI":"10.1016\/j.bmc.2012.12.004","article-title":"Carbonic anhydrase inhibitors: Benzenesulfonamides incorporating cyanoacrylamide moieties are low nanomolar\/subnanomolar inhibitors of the tumor-associated isoforms IX and XII","volume":"21","author":"Alafeefy","year":"2013","journal-title":"Bioorg. Med. Chem"},{"key":"ref_6","unstructured":"Roifman, C.M., Aviv, G., and Alexander, L. (2000). Preparation of N-benzyl-3-aryl-2-cyanoacrylamides activity for treatment of neoplastic disorders. (0055, 128), PCT. Int. Appl. WO Patent."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"32","DOI":"10.5923\/j.ajoc.20120202.06","article-title":"Utility of activated nitriles in the synthesis of some new heterocyclic compounds","volume":"2","author":"Fadda","year":"2012","journal-title":"Am. J. Org. Chem"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"319","DOI":"10.2165\/00003495-199345030-00001","article-title":"Immunomodulation by antibacterial agents: Is it clinically relevant","volume":"45","author":"Labro","year":"1993","journal-title":"Drugs"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"832","DOI":"10.3390\/molecules18010832","article-title":"Synthesis and antibacterial evaluation of novel heterocyclic compounds containing a sulfonamido moiety","volume":"18","author":"Azab","year":"2013","journal-title":"Molecules"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1976","DOI":"10.1016\/j.ejmech.2010.01.042","article-title":"Synthesis of some new pyrimido [2\u2032,1\u2032:2,3] thiazolo[4,5-b]quinoxaline derivatives as anti-inflammatory and analgesic agents","volume":"45","author":"Gouda","year":"2010","journal-title":"Eur. J. Med. Chem"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1338","DOI":"10.1016\/j.ejmech.2009.12.020","article-title":"Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzo thiophene moiety","volume":"45","author":"Gouda","year":"2010","journal-title":"Eur. J. Med. Chem"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4434","DOI":"10.1016\/j.ejmech.2009.06.002","article-title":"Synthesis and antibacterial activity of some new thiazole and thiophene derivatives","volume":"44","author":"Khalil","year":"2009a","journal-title":"Eur. J. Med. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1658","DOI":"10.1080\/00397910903161652","article-title":"Synthesis and antimicrobial evaluation of some new thiophene derivatives","volume":"40","author":"Khalil","year":"2010a","journal-title":"Synth. Commun."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1455","DOI":"10.1080\/10426500903074858","article-title":"Synthesis and antimicrobial of certain new thiazolidinone, thiazoline, and thiophene derivatives","volume":"185","author":"Khalil","year":"2010b","journal-title":"Phosphorus Sulfur Silicon"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1111\/j.1527-3458.2004.tb00028.x","article-title":"The pharmacology of chlormethiazole: A potential neuroprotective agent?","volume":"10","author":"Wilby","year":"2004","journal-title":"CNS Drug Rev"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1016\/j.bmcl.2003.09.077","article-title":"Phenolic thiazoles as novel orally-active neuroprotective agents","volume":"14","author":"Harnett","year":"2004","journal-title":"Bioorg. Med. Chem. Lett"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1667","DOI":"10.1021\/jm00168a021","article-title":"Synthesis, chemistry, and antineoplastic activity of \u03b1-halopyridinium salts: Potential pyridone prodrugs of acylated vinylogous carbinolamine tumor inhibitors","volume":"33","author":"Anderson","year":"1990","journal-title":"J. Med. Chem"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"231","DOI":"10.1002\/1098-1128(200007)20:4<231::AID-MED1>3.0.CO;2-N","article-title":"The 2-pyridone antibacterial agents: Bacterial topoisomerase inhibitors","volume":"20","author":"Li","year":"2000","journal-title":"Med. Res. Rev"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1607","DOI":"10.1021\/jm010469k","article-title":"Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 6: Structure\u2013activity studies of orally bioavailable, 2-pyridone-containing peptidomimetics","volume":"45","author":"Dragovich","year":"2002","journal-title":"J. Med. Chem"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"733","DOI":"10.1016\/S0960-894X(02)00008-2","article-title":"Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. Part 7: Structure\u2013activity studies of bicyclic 2-pyridone-containing peptidomimetics","volume":"12","author":"Dragovich","year":"2002","journal-title":"Bioorg. Med. Chem. Lett"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2247","DOI":"10.3987\/COM-10-11999","article-title":"Synthesis and antimicrobial evaluation of some new pyridine based heterocycles","volume":"81","author":"Darwish","year":"2010","journal-title":"Heterocycles"},{"key":"ref_22","unstructured":"Darwish, E.S., Mahmoud, F.F., Hussein, A.M., and Altalbawy, F.M. (2013). \u03b2-Oxoanilides in heterocyclic: Synthesis of som new pyridazine and polyfunctionally substituted heterocyclic compounds. Arab. J. Chem, in press."},{"key":"ref_23","first-page":"2203","article-title":"Activated nitriles in heterocyclic chemistry: Facile synthesis and antimicrobial activity of some pyrimidine, pyrazolopyrimidine and pyrazolotriazinederivatives containing sulfonamido moiety","volume":"43B","author":"Ammar","year":"2004","journal-title":"Indian J. Chem"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"455","DOI":"10.5155\/eurjchem.2.4.455-462.171","article-title":"Novel 4(3H)-quinazolinones containing biologically active thiazole, pyridinone and chromene of expected antitumor and antifungal activities","volume":"2","author":"Basyouni","year":"2011","journal-title":"Eur. J. Chem"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"8633","DOI":"10.1016\/j.tet.2004.05.100","article-title":"Rapid microwave-assisted solution phase synthesis of substituted 2-pyridone libraries","volume":"60","author":"Gorobets","year":"2004","journal-title":"Tetrahedron"},{"key":"ref_26","first-page":"1787","article-title":"Heterocyclic compounds from urea derivatives. Part XXIII. Thiobenzoylated thiocarbonohydrazides and their cyclization","volume":"18","author":"Esmail","year":"1975","journal-title":"J. Chem. Soc"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"337","DOI":"10.3109\/13880209409083012","article-title":"Antibacterial and antifungal activities of nine medicinal plants from Zaire","volume":"32","author":"Muanz","year":"1994","journal-title":"Int. J. Pharmacogn"},{"key":"ref_28","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, 1982\u20131993","volume":"37","author":"Harborne","year":"1994","journal-title":"Phytochemistry"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2993","DOI":"10.1021\/ja01163a053","article-title":"Bromination of acetocoumarin","volume":"72","author":"Koelsch","year":"1950","journal-title":"J. Am. Chem. Soc"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1002\/prac.19833250405","article-title":"3-\u03b1-Bromoacetyl-coumarines as synthones for heterocyclic substituted coumarines","volume":"325","author":"Czerney","year":"1983","journal-title":"J. Prakt. Chem"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1710","DOI":"10.1080\/10426500701729554","article-title":"Cyanoacetanilides intermediates in heterocyclic synthesis. Part 4: Preparation of some hitherto unknown thiazolidine and bisthiazolidine derivatives","volume":"183","author":"Ammar","year":"2008","journal-title":"Phosphorus Sulfur Silicon"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1021\/cr60294a004","article-title":"The diazotization of heterocyclic primary amines","volume":"75","author":"Butler","year":"1975","journal-title":"Chem. Rev"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1064","DOI":"10.1002\/jccs.200900154","article-title":"Cyanoacetanilides intermediates in heterocyclic synthesis. Part 5: Preparation of hitherto unknown 5-aminopyrazole and pyrazolo[1,5-a]pyrimidine derivatives containing sulfamoyl moiety","volume":"56","author":"Ammar","year":"2009","journal-title":"J. Chin. Chem. Soc"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/15\/1\/1237\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:07:26Z","timestamp":1760216846000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/15\/1\/1237"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,1,17]]},"references-count":33,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2014,1]]}},"alternative-id":["ijms15011237"],"URL":"https:\/\/doi.org\/10.3390\/ijms15011237","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,1,17]]}}}