{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,5,20]],"date-time":"2025-05-20T11:56:47Z","timestamp":1747742207850,"version":"3.37.3"},"reference-count":27,"publisher":"International Union of Crystallography (IUCr)","issue":"1","license":[{"start":{"date-parts":[[2019,12,12]],"date-time":"2019-12-12T00:00:00Z","timestamp":1576108800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2019,12,12]],"date-time":"2019-12-12T00:00:00Z","timestamp":1576108800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"accepted":{"date-parts":[[2019,11,30]]},"published-print":{"date-parts":[[2020,1,1]]},"abstract":"<jats:p>1,3-Enyne structural motifs are versatile building blocks in organic synthesis and occur widely in various natural products with many of them being highly active as cytotoxic macrolides and antitumour antibiotics. This article presents the crystal structure of three 1,1,4-triphenyl-substituted 1,3-enynes, <jats:italic>viz<\/jats:italic>. 4-(2-methylphenyl)-1,1-diphenylbut-1-en-3-yne, C<jats:sub>23<\/jats:sub>H<jats:sub>18<\/jats:sub> (<jats:bold>1<\/jats:bold>), 4-(2-methoxyphenyl)-1,1-diphenylbut-1-en-3-yne, C<jats:sub>23<\/jats:sub>H<jats:sub>18<\/jats:sub>O (<jats:bold>2<\/jats:bold>), and 4-(4-nitrophenyl)-1,1-diphenylbut-1-en-3-yne, C<jats:sub>22<\/jats:sub>H<jats:sub>15<\/jats:sub>NO<jats:sub>2<\/jats:sub> (<jats:bold>3<\/jats:bold>). The benzene ring at position 4 of the but-1-en-3-yne group bears a weakly activating methyl group in compound <jats:bold>1<\/jats:bold>, a moderately activating methoxy group in <jats:bold>2<\/jats:bold> and a strongly deactivating nitro group in <jats:bold>3<\/jats:bold>. The crystal structures of <jats:bold>1<\/jats:bold> and <jats:bold>3<\/jats:bold> both have monoclinic symmetry, while that of <jats:bold>2<\/jats:bold> is orthorhombic, and all of them have one molecule in the asymmetric unit. All three compounds were investigated for their antibacterial and antifungal activities. Interestingly, enyne <jats:bold>2<\/jats:bold> is the only compound tested that inhibited the growth of <jats:italic>Aspergillus niger<\/jats:italic>.<\/jats:p>","DOI":"10.1107\/s2053229619016127","type":"journal-article","created":{"date-parts":[[2019,12,12]],"date-time":"2019-12-12T14:30:44Z","timestamp":1576161044000},"page":"87-92","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Crystal structures and biological activity of 1,1,4-triphenyl-substituted 1,3-enyne compounds"],"prefix":"10.1107","volume":"76","author":[{"given":"Leslie W.","family":"Pineda","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mar\u00eda Laura","family":"Arias","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7571-6914","authenticated-orcid":true,"given":"Jorge A.","family":"Cabezas","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2019,12,12]]},"reference":[{"key":"qs3087_bb1","doi-asserted-by":"crossref","first-page":"1254","DOI":"10.1016\/0006-291X(74)90449-5","volume":"59","author":"Beerman","year":"1974","journal-title":"Biochem. 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