Regioselective synthesis of 9,10-dihydro-2,5-dimethoxyphenanthrene-1,7-diol (1) and 9,10-dihydro-2,7-dimethoxyphenanthrene-1,5-diol (2) was achieved using regioselective methylation, Wittig reaction, intramolecular cyclization and hydrogenation as key steps. The synthesis was successfully completed in total of 15 steps with 3.3% overall yield in case of 1 and in total of 13 steps with 9.0% overall yield in case of 2. All compounds (1-4) showed good antioxidant and anti-inflammatory activity in in vitro assays and these activities were found to be due the presence of phenolic hydroxyl groups.
Keywords: AKQZCVGNQPNGCN-UHFFFAOYSA-N; AYNKAXMSZZZOKZ-UHFFFAOYSA-N; Anti-inflammatory; Anti-oxidant; BONZUBOOGNLLPJ-UHFFFAOYSA-N; CBGNWUINIDQCCM-UHFFFAOYSA-N; CDJDSQVTRDRYNP-UHFFFAOYSA-N; GBESWDWAYNNSLH-UHFFFAOYSA-N; GLJLCZSVSWEONA-UHFFFAOYSA-N; GWRPDZYHRFTJHI-UHFFFAOYSA-N; HDBBNMLLPKIKGK-UHFFFAOYSA-N; IOKUVQZOQGQLJX-UHFFFAOYSA-N; IUEQPFFUSKONCU-UHFFFAOYSA-N; JLYSWVJOEWQBMD-UHFFFAOYSA-N; JXHACMBYZZWSEG-UHFFFAOYSA-N; KCNZQSQLCOWRRP-UHFFFAOYSA-N; KHBXSVKLBOMJAD-UHFFFAOYSA-N; KRIPXDLNXPJDKZ-UHFFFAOYSA-N; KXBGOVZWCRLLOR-UHFFFAOYSA-N; LVUPFFBOVAMKQT-UHFFFAOYSA-N; LXOUJONCKZPDKA-UHFFFAOYSA-N; MKLFXDXNXORURG-MSUUIHNZSA-N; NRQGIQXMGQQHFZ-MSUUIHNZSA-N; ODJKEUWVBSQHIZ-UHFFFAOYSA-N; OKMISEPAUVGQMZ-UHFFFAOYSA-N; OQIGXCSBMYVDOZ-UHFFFAOYSA-N; PVWBMFLLBACRJL-UHFFFAOYSA-N; Regioselective synthesis; SOHTUOALNFQEMJ-UHFFFAOYSA-N; TNF-alpha; TZDOXAQDBDJUMB-UHFFFAOYSA-N; UUUWTNIEFNNIAF-UHFFFAOYSA-N; VHHUBNSVHIMJSD-UHFFFAOYSA-N; VUNWBEIDIFFPMG-UHFFFAOYSA-N; WPNXLBKYYDXMCX-UHFFFAOYSA-N; XCGSVZJXMLVULN-UHFFFAOYSA-N; XLLSFBFZOFIRBQ-UHFFFAOYSA-N; YSSFIGREEVEYNI-UHFFFAOYSA-N; ZUQDIPSVEZOOJE-UHFFFAOYSA-N.
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