{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,19]],"date-time":"2026-02-19T12:35:39Z","timestamp":1771504539124,"version":"3.50.1"},"reference-count":35,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2003,6,16]],"date-time":"2003-06-16T00:00:00Z","timestamp":1055721600000},"content-version":"vor","delay-in-days":15,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2003,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The substituted ethyl\u20102\u2010phenacyl\u20103\u2010phenylpyrrole\u20104\u2010carboxylates were synthesized by a condensation of a beta\u2010chloroenal and an alpha\u2010aminoketone under neutral conditions. They proved to be potent cytotoxic agents against the growth of murine L1210 and P388 leukemias and human HL\u201060 promyelocytic leukemia, HuT\u201078 lymphoma, and HeLa\u2010S<jats:sup>3<\/jats:sup> uterine carcinoma. Selective compounds were active against the growth of Tmolt<jats:sub>3<\/jats:sub> and Tmolt<jats:sub>4<\/jats:sub> leukemias and THP\u20101 acute monocytic leukemia, liver Hepe\u20102, ovary 1\u2010A9, ileum HCT\u20108 adenocarcinoma, and osteosarcoma HSO. A mode of action study in HL\u201060 cells demonstrated that DNA and protein syntheses were inhibited after 60[TH]min at 100[TH]\u03bcM. DNA and RNA polymerases, PRPP\u2010amido transferase, dihydrofolate reductase, thymidylate synthase, and TMP kinase activities were interfered with by the agent with reduction of d[NTP] pools. Nonspecific interaction with the bases of DNA and cross\u2010linking of the DNA may play a role in the mode of action of these carboxylates.<\/jats:p>","DOI":"10.1002\/ardp.200390018","type":"journal-article","created":{"date-parts":[[2003,6,18]],"date-time":"2003-06-18T15:12:57Z","timestamp":1055949177000},"page":"181-190","source":"Crossref","is-referenced-by-count":16,"title":["Synthesis and Cytotoxicity of Substituted Ethyl 2\u2010Phenacyl\u20103\u2010phenylpyrrole\u20104\u2010carboxylates"],"prefix":"10.1002","volume":"336","author":[{"given":"Michael A.","family":"Evans","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Daniel C.","family":"Smith","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Justin M.","family":"Holub","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Anthony","family":"Argenti","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mafoloe","family":"Hoff","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gerard A.","family":"Dalglish","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Donna L.","family":"Wilson","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Brett M.","family":"Taylor","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Joshua D.","family":"Berkowitz","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bruce S.","family":"Burnham","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Keith","family":"Krumpe","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"John T.","family":"Gupton","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tanya C.","family":"Scarlett","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Richard W.","family":"Durham, Jr","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Iris H.","family":"Hall","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2003,6,16]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-4184(199811)331:11<337::AID-ARDP337>3.0.CO;2-R"},{"key":"e_1_2_1_3_2","first-page":"691","volume":"54","author":"Gupton J. T.","year":"1999","journal-title":"Pharmazie"},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-4184(200001)333:1<3::AID-ARDP3>3.0.CO;2-4"},{"key":"e_1_2_1_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(99)00926-6"},{"key":"e_1_2_1_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00247-6"},{"key":"e_1_2_1_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm960858s"},{"key":"e_1_2_1_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00367a026"},{"key":"e_1_2_1_9_2","unstructured":"A. J. Gordon R. A. Ford The Chemist's Companion: A Handbook of Practical Data Techniques and References. New York John Wiley and Sons 1972 pp. 429\u2013436."},{"key":"e_1_2_1_10_2","first-page":"9","volume":"3","author":"Geran R. J.","year":"1972","journal-title":"Cancer Chemo. Rep."},{"key":"e_1_2_1_11_2","first-page":"4562","volume":"36","author":"Leibovitz A. L.","year":"1976","journal-title":"Cancer Res."},{"key":"e_1_2_1_12_2","first-page":"167","volume":"12","author":"Liao L. L.","year":"1976","journal-title":"Mol. Pharmacol."},{"key":"e_1_2_1_13_2","doi-asserted-by":"crossref","first-page":"1695","DOI":"10.1016\/S0021-9258(19)69863-7","volume":"256","author":"Cadman E.","year":"1981","journal-title":"J. Biol. Chem."},{"key":"e_1_2_1_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2697(81)90560-1"},{"key":"e_1_2_1_15_2","first-page":"3341","volume":"34","author":"Sawada H.","year":"1974","journal-title":"Cancer Res."},{"key":"e_1_2_1_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(19)44934-X"},{"key":"e_1_2_1_17_2","doi-asserted-by":"crossref","first-page":"4011","DOI":"10.1016\/S0021-9258(17)40351-6","volume":"252","author":"Eichler D. C.","year":"1977","journal-title":"J. Biol. Chem."},{"key":"e_1_2_1_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/0005-2787(75)90245-2"},{"key":"e_1_2_1_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00258a004"},{"key":"e_1_2_1_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)99717-6"},{"key":"e_1_2_1_21_2","doi-asserted-by":"crossref","first-page":"1538","DOI":"10.1016\/S0021-9258(18)49368-4","volume":"233","author":"Maley F.","year":"1958","journal-title":"J. Biol. Chem."},{"key":"e_1_2_1_22_2","doi-asserted-by":"crossref","first-page":"1871","DOI":"10.1016\/S0021-9258(18)96716-5","volume":"241","author":"Kalman S. M.","year":"1966","journal-title":"J. Biol. Chem."},{"key":"e_1_2_1_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(17)41681-4"},{"key":"e_1_2_1_24_2","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1016\/S0021-9258(18)65539-5","volume":"209","author":"Koritz S. B.","year":"1954","journal-title":"J. Biol. Chem."},{"key":"e_1_2_1_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00229a009"},{"key":"e_1_2_1_26_2","first-page":"1023","volume":"32","author":"Ho Y. K.","year":"1971","journal-title":"Cancer Res."},{"key":"e_1_2_1_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(76)90316-6"},{"key":"e_1_2_1_28_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF01481491"},{"key":"e_1_2_1_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(19)52451-6"},{"key":"e_1_2_1_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2697(72)90004-8"},{"key":"e_1_2_1_31_2","doi-asserted-by":"crossref","first-page":"723","DOI":"10.1139\/o81-100","volume":"59","author":"Hunting D.","year":"1982","journal-title":"Can. J. Biochem."},{"key":"e_1_2_1_32_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.31.875"},{"key":"e_1_2_1_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/0005-2787(81)90005-8"},{"key":"e_1_2_1_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(81)90268-9"},{"key":"e_1_2_1_35_2","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.35.2052"},{"key":"e_1_2_1_36_2","first-page":"937","volume":"55","author":"Hall I. H.","year":"2000","journal-title":"Pharmazie"}],"container-title":["Archiv der Pharmazie"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fardp.200390018","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ardp.200390018","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,18]],"date-time":"2023-10-18T20:02:02Z","timestamp":1697659322000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/ardp.200390018"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2003,6]]},"references-count":35,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2003,6]]}},"alternative-id":["10.1002\/ardp.200390018"],"URL":"https:\/\/doi.org\/10.1002\/ardp.200390018","archive":["Portico"],"relation":{},"ISSN":["0365-6233","1521-4184"],"issn-type":[{"value":"0365-6233","type":"print"},{"value":"1521-4184","type":"electronic"}],"subject":[],"published":{"date-parts":[[2003,6]]}}}