{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,27]],"date-time":"2026-10-27T22:50:57Z","timestamp":1793141457970,"version":"4.5.0"},"reference-count":29,"publisher":"Walter de Gruyter GmbH","issue":"3-4","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2023,3,28]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    A new series of aminoacetylenic nitroimidazole piperazine hybrid compounds were prepared\n                    <jats:italic>via<\/jats:italic>\n                    three-component reaction. Mannich-type reaction was utilized to couple the nitroimidazole containing propargylic moiety with secondary amines and formaldehyde in the presence of Cu (I)\u00a0catalyst. The newly synthesized molecules\n                    <jats:bold>10a\u201310w<\/jats:bold>\n                    , were characterized an ambiguously through NMR and mass spectrometry. The prepared compounds were assessed\n                    <jats:italic>in vitro<\/jats:italic>\n                    for their antibacterial activity against selected gram-positive and gram-negative bacteria. All of the compounds had shown insignificant activities toward gram-negative bacteria. While compounds\n                    <jats:bold>10m<\/jats:bold>\n                    ,\n                    <jats:bold>10q<\/jats:bold>\n                    ,\n                    <jats:bold>10s<\/jats:bold>\n                    and\n                    <jats:bold>10t<\/jats:bold>\n                    had shown moderate activities against the gram\u2013positive bacteria\n                    <jats:italic>Staphylococcus aureus<\/jats:italic>\n                    ,\n                    <jats:italic>Bacillus subtilis<\/jats:italic>\n                    and against fungi\n                    <jats:italic>Escherichia coli<\/jats:italic>\n                    and\n                    <jats:italic>Proteus vulgaris<\/jats:italic>\n                    .\n                  <\/jats:p>","DOI":"10.1515\/znc-2022-0043","type":"journal-article","created":{"date-parts":[[2022,8,9]],"date-time":"2022-08-09T05:23:08Z","timestamp":1660022588000},"page":"113-121","source":"Crossref","is-referenced-by-count":19,"title":["Design, synthesis and antimicrobial assessments of aminoacetylenic-piperazine nitroimidazole hybrid compounds"],"prefix":"10.1515","volume":"78","author":[{"given":"Anas J.","family":"Rasras","sequence":"first","affiliation":[{"name":"Faculty of Science, Department of Chemistry , Al-Balqa Applied University , P.O. Box\u00a019117 , Al-Salt , Jordan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raed A.","family":"Al-Qawasmeh","sequence":"additional","affiliation":[{"name":"Pure and Applied Chemistry Group, Department of Chemistry, College of Sciences , University of Sharjah , 27272 , Sharjah , UAE"},{"name":"Department of Chemistry , The University of Jordan , 11942 , Amman , Jordan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohamed","family":"El-Naggar","sequence":"additional","affiliation":[{"name":"Pure and Applied Chemistry Group, Department of Chemistry, College of Sciences , University of Sharjah , 27272 , Sharjah , UAE"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ihsan","family":"Shehadi","sequence":"additional","affiliation":[{"name":"Pure and Applied Chemistry Group, Department of Chemistry, College of Sciences , University of Sharjah , 27272 , Sharjah , UAE"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mahmoud M.","family":"Elaasser","sequence":"additional","affiliation":[{"name":"The Regional Center for Mycology and Biotechnology , Al-Azhar University , 11371 Nasr City , Cairo , Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3357-3801","authenticated-orcid":false,"given":"Yaseen A.","family":"Al-Soud","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science , Al al-Bayt University , Al-Mafraq , Jordan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"374","published-online":{"date-parts":[[2022,8,10]]},"reference":[{"key":"2023040103535326688_j_znc-2022-0043_ref_001","doi-asserted-by":"crossref","unstructured":"Al-Soud, YA, Al-Ahmad, AH, Abu-Qatouseh, L, Shtaiwi, A, Alhelal, KAS, Al-Suod, HH, et al.. Nitroimidazoles part 9. Synthesis, molecular docking, and anticancer evaluations of piperazine-tagged imidazole derivatives. Z Naturforsch B 2021;76b:293\u2013302. https:\/\/doi.org\/10.1515\/znb-2020-0200.","DOI":"10.1515\/znb-2020-0200"},{"key":"2023040103535326688_j_znc-2022-0043_ref_002","doi-asserted-by":"crossref","unstructured":"Elejalde, NR, Mac\u00edas, M, Castillo, JC, Sortino, M, Svetaz, L, Zacchino, S, et al.. Synthesis and in\u00a0vitro antifungal evaluation of novel N\u00a0\u2013 substituted 4-aryl-2-methylimidazoles. ChemistrySelect 2018;3:5220\u20137. https:\/\/doi.org\/10.1002\/slct.201801238.","DOI":"10.1002\/slct.201801238"},{"key":"2023040103535326688_j_znc-2022-0043_ref_003","doi-asserted-by":"crossref","unstructured":"Nandwana, NK, Singh, RP, Patel, OPS, Dhiman, S, Saini, HK, Jha, PN, et al.. Design and synthesis of imidazo\/benzimidazo[1, 2-c]quinazoline derivatives and evaluation of their antimicrobial activity. ACS Omega 2018;3:16338\u201346. https:\/\/doi.org\/10.1021\/acsomega.8b01592.","DOI":"10.1021\/acsomega.8b01592"},{"key":"2023040103535326688_j_znc-2022-0043_ref_004","doi-asserted-by":"crossref","unstructured":"Al-Qawasmeh, RA, Huesca, M, Nedunuri, V, Peralta, R, Wright, J, Lee, Y, et al.. Potent antimicrobial activity of 3-(4, 5-diaryl-1H-imidazol-2-yl)-1H-indole derivatives against methicillin-resistant staphylococcus aureus. Bioorg Med Chem Lett 2010;20:3518\u201320. https:\/\/doi.org\/10.1016\/j.bmcl.2010.04.137.","DOI":"10.1016\/j.bmcl.2010.04.137"},{"key":"2023040103535326688_j_znc-2022-0043_ref_005","doi-asserted-by":"crossref","unstructured":"Liu, F, Dawadi, S, Maize, KM, Dai, R, Park, SW, Schnappinger, D, et al.. Structure-based optimization of pyridoxal 5\u2019-Phosphate-dependent transaminase enzyme (BioA) inhibitors that target biotin biosynthesis in mycobacterium tuberculosis. J Med Chem 2017;60:5507\u201320. https:\/\/doi.org\/10.1021\/acs.jmedchem.7b00189.","DOI":"10.1021\/acs.jmedchem.7b00189"},{"key":"2023040103535326688_j_znc-2022-0043_ref_006","doi-asserted-by":"crossref","unstructured":"Kumar, PP, Siva, B, Rao, BV, Kumar, GD, Nayak, VL, Jain, SN, et al.. Synthesis and biological evaluation of bergenin-1, 2, 3-triazole hybrids as novel class of anti-mitotic agents. Bioorg Chem 2019;91:103161. https:\/\/doi.org\/10.1016\/j.bioorg.2019.103161.","DOI":"10.1016\/j.bioorg.2019.103161"},{"key":"2023040103535326688_j_znc-2022-0043_ref_007","doi-asserted-by":"crossref","unstructured":"Yakovenko, EA, Baimurzina, YL, Raskil\u2019dina, GZ, Zlotskii, SS. Synthesis and herbicidal and antioxidant activity of a series of hetero\u00a0\u2013 and carbocyclic derivatives of monochloroacetic acid. Russ J Appl Chem 2020;93:712\u201320. https:\/\/doi.org\/10.1134\/s1070427220050122.","DOI":"10.1134\/S1070427220050122"},{"key":"2023040103535326688_j_znc-2022-0043_ref_008","unstructured":"Goldfarb, DS. Method for altering the lifespan of eukaryotic organisms. USA: University of Rochester; 2009. US. PCT Pub. No US20090163545 A1."},{"key":"2023040103535326688_j_znc-2022-0043_ref_009","doi-asserted-by":"crossref","unstructured":"Medina, RA, Sallander, J, Benham\u00fa, B, Porras, E, Campillo, M, Pardo, L, et al.. Synthesis of new serotonin 5-HT7 receptor ligands. Determinants of 5-HT7\/5-HT1A receptor selectivity. J Med Chem 2009;52:2384\u201392. https:\/\/doi.org\/10.1021\/jm8014553.","DOI":"10.1021\/jm8014553"},{"key":"2023040103535326688_j_znc-2022-0043_ref_010","doi-asserted-by":"crossref","unstructured":"Enrique, R, Christian, FM. Conformationally constrained butyrophenones. Synthesis and evaluation as antipsychotics. Cent Nerv Syst Agents Med Chem 2001;1:43\u201362.","DOI":"10.2174\/1568015013358699"},{"key":"2023040103535326688_j_znc-2022-0043_ref_011","doi-asserted-by":"crossref","unstructured":"Foroumadi, A, Emami, S, Mehni, M, Moshafi, MH, Shafiee, A. Synthesis and antibacterial activity of N-[2-(5-bromothiophen-2-yl)-2-oxoethyl] and N-[(2-5-bromothiophen-2-yl)-2-oximinoethyl] derivatives of piperazinyl quinolones. Bioorg Med Chem Lett 2005;15:4536\u20139. https:\/\/doi.org\/10.1016\/j.bmcl.2005.07.005.","DOI":"10.1016\/j.bmcl.2005.07.005"},{"key":"2023040103535326688_j_znc-2022-0043_ref_012","doi-asserted-by":"crossref","unstructured":"Osa, Y, Kobayashi, S, Sato, Y, Suzuki, Y, Takino, K, Takeuchi, T, et al.. Structural properties of dibenzosuberanylpiperazine derivatives for efficient reversal of chloroquine resistance in plasmodium chabaudi. J Med Chem 2003;46:1948\u201356. https:\/\/doi.org\/10.1021\/jm020379v.","DOI":"10.1021\/jm020379v"},{"key":"2023040103535326688_j_znc-2022-0043_ref_013","unstructured":"Park, SW, Lee, HS, Min, DK, Lee, NR, Lee, CJ, Yang, GE. Industry-Academic Cooperation Foundation. S. Korea: Yonsei University; 2016. Int. PCTPub. No WO2016108572 A2."},{"key":"2023040103535326688_j_znc-2022-0043_ref_014","doi-asserted-by":"crossref","unstructured":"Davis, KL, Hollander, E, Davidson, M, Davis, BM, Mohs, RC, Horvath, TB. Induction of depression with oxotremorine in patients with Alzheimer\u2019s disease. Am J Psychiatry 1987;144:468\u201371.","DOI":"10.1176\/ajp.144.4.468"},{"key":"2023040103535326688_j_znc-2022-0043_ref_015","doi-asserted-by":"crossref","unstructured":"Al-Qaisi, JA, Alhussainy, TM, Qinna, NA, Matalka, KZ, Al-Kaissi, EN, Muhi-Eldeen, ZA. Synthesis and pharmacological evaluation of aminoacetylenic isoindoline-1, 3-dione derivatives as anti-inflammatory agents. Arab J Chem 2014;7:1024\u201330.","DOI":"10.1016\/j.arabjc.2010.12.030"},{"key":"2023040103535326688_j_znc-2022-0043_ref_016","unstructured":"Salama, ZB. New York, USA: Joyce Von Natzmer Pequignot + Meyers LLC; 2007. US. PCT Pub. No US 20070265269 A1."},{"key":"2023040103535326688_j_znc-2022-0043_ref_017","doi-asserted-by":"crossref","unstructured":"Al-Soud, YA, Alhelal, KAS, Saeed, BA, Abu-Qatouseh, L, Al-Suod, HH, Al-Ahmad, AH, et al.. Synthesis, anticancer activity and molecular docking studies of new 4-nitroimidazole derivatives. Arkivoc 2021:296\u2013309. part viii. https:\/\/doi.org\/10.24820\/ark.5550190.p011.479.","DOI":"10.24820\/ark.5550190.p011.479"},{"key":"2023040103535326688_j_znc-2022-0043_ref_018","doi-asserted-by":"crossref","unstructured":"Al-Masoudi, NA, Al-Soud, YA, Kalogerakis, A, Pannecouque, C, De Clercq, E. Nitroimidazoles, Part 2. Chem Biodivers 2006;3:515\u201326\u200f.","DOI":"10.1002\/cbdv.200690055"},{"key":"2023040103535326688_j_znc-2022-0043_ref_019","doi-asserted-by":"crossref","unstructured":"Al-Masoudi, NA, Al-Soud, YA, De Clercq, E, Pannecouque, C. Nitroimidazoles Part 6. synthesis, structure andin vitroanti-HIV activity of new 5-substituted piperazinyl-4-nitroimidazole derivatives. Antivir Chem Chemother 2007;18:191\u2013200\u200f.","DOI":"10.1177\/095632020701800403"},{"key":"2023040103535326688_j_znc-2022-0043_ref_020","doi-asserted-by":"crossref","unstructured":"Al-Soud, YA, Al-Masoudi, NA, Hassan, H, De Clercq, E, Pannecouque, C. Nitroimidazoles. V. Synthesis and anti-HIV evaluation of new 5-substituted piperazinyl-4-nitroimidazole derivatives. Acta Pharm 2007;57:379\u201393\u200f. https:\/\/doi.org\/10.2478\/v10007-007-0031-7.","DOI":"10.2478\/v10007-007-0031-7"},{"key":"2023040103535326688_j_znc-2022-0043_ref_021","doi-asserted-by":"crossref","unstructured":"Al-Soud, YA, Al-Sa\u2019doni, H, Amajaour, HA, Al-Masoudi, NA. Nitroimidazoles, part 3. synthesis and anti-HIV activity of new N-alkyl-4-nitroimidazoles bearing benzothiazole and benzoxazole backbones. Z Naturforsch 2007;62b:523\u20138\u200f.","DOI":"10.1515\/znb-2007-0406"},{"key":"2023040103535326688_j_znc-2022-0043_ref_022","doi-asserted-by":"crossref","unstructured":"Al-Soud, YA, Al-Masoudi, NA, De Clercq, E, Paneccoque, C. Nitroimidazoles, part 4: synthesis and anti-HIV activity of new 5-alkylsulfanyl and 5-(4\u2019-arylsulfonyl) piperazinyl-4-nitroimidazole derivatives. Heteroat Chem 2007;18:333\u201340.","DOI":"10.1002\/hc.20301"},{"key":"2023040103535326688_j_znc-2022-0043_ref_023","doi-asserted-by":"crossref","unstructured":"Al-Soud, YA, Al-Masoudi, NA, Al-Suod, HH, Pannecouque, C. Nitroimidazoles part 8. synthesis and anti-HIV activity of New 4-Nitroimidazole derivatives using the suzuki cross-coupling reaction. Z Naturforsch 2012;67b:925\u201334.","DOI":"10.5560\/znb.2012-0185"},{"key":"2023040103535326688_j_znc-2022-0043_ref_024","unstructured":"Al-Qawasmeh, RA, Young, AH, Huesca, M, Lee, Y. 2, 4, 5-trisubstituted imidazoles and their use as anti-microbial agents. USA: USP 7884120 B2; 2011."},{"key":"2023040103535326688_j_znc-2022-0043_ref_025","doi-asserted-by":"crossref","unstructured":"Al-Qawasmeh, RA, Hussein, NH, Shehadi, I, Khanfar, MA, Salameh, BA. Design and synthesis of aminoacetylenic indole and carbazole hybrid compounds. ChemistrySelect 2020;22:6834\u20139. https:\/\/doi.org\/10.1002\/slct.202001146.","DOI":"10.1002\/slct.202001146"},{"key":"2023040103535326688_j_znc-2022-0043_ref_026","doi-asserted-by":"crossref","unstructured":"Abdel-Jalil, RJ, Al-Qawasmeh, RA, Voelter, W, Heeg, P, El-Abadelah, MM, Sabri, SS. Synthesis and properties of some 2, 3-disubstituted 6-fluoro-7-(4-methyl-1-piperazinyl) quinoxalines. J Heterocycl Chem 2000;37:1273\u20135. https:\/\/doi.org\/10.1002\/jhet.5570370541.","DOI":"10.1002\/jhet.5570370541"},{"key":"2023040103535326688_j_znc-2022-0043_ref_027","doi-asserted-by":"crossref","unstructured":"Al-Aboudi, A, Al-Qawasmeh, RA, Shahwan, A, Uzma, M, Asaad, K, Ul-Haq, Z. In-silico identification of the binding mode of synthesized adamantyl derivatives inside cholinesterase enzymes. Acta Pharmacol Sin 2015;36:879\u201386. https:\/\/doi.org\/10.1038\/aps.2014.173.","DOI":"10.1038\/aps.2014.173"},{"key":"2023040103535326688_j_znc-2022-0043_ref_028","doi-asserted-by":"crossref","unstructured":"Liu, ZZ, Chen, HC, Cao, SL, Li, RT. Solid\u00a0\u2013 liquid phase\u00a0\u2013 transfer catalytic method for N-alkylation of nitroimidazole. Synth Commun 1993;23:2611\u20135. https:\/\/doi.org\/10.1080\/00397919308012596.","DOI":"10.1080\/00397919308012596"},{"key":"2023040103535326688_j_znc-2022-0043_ref_029","doi-asserted-by":"crossref","unstructured":"Abo-Ashour, MF, Eldehna, WFGRF, Abdel-Aziz, MM, Elaasser, MM, Mahmoud, F, Wagdy, M, et al.. Novel indole-thiazolidinone conjugates: design, synthesis and whole-cell phenotypic evaluation as a novel class of antimicrobial agents. Eur J Med Chem 2018;160:49\u201360. https:\/\/doi.org\/10.1016\/j.ejmech.2018.10.008.","DOI":"10.1016\/j.ejmech.2018.10.008"}],"container-title":["Zeitschrift f\u00fcr Naturforschung C"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1515\/znc-2022-0043\/xml","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1515\/znc-2022-0043\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,2]],"date-time":"2023-04-02T12:48:41Z","timestamp":1680439721000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1515\/znc-2022-0043\/html"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,8,10]]},"references-count":29,"journal-issue":{"issue":"3-4","published-online":{"date-parts":[[2022,3,18]]},"published-print":{"date-parts":[[2023,3,28]]}},"alternative-id":["10.1515\/znc-2022-0043"],"URL":"https:\/\/doi.org\/10.1515\/znc-2022-0043","relation":{},"ISSN":["0939-5075","1865-7125"],"issn-type":[{"value":"0939-5075","type":"print"},{"value":"1865-7125","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,8,10]]}}}