TY - DATA T1 - Synthesis and Biological Evaluation of Aromatic Analogues of Conduritol F, l-chiro-Inositol, and Dihydroconduritol F Structurally Related to the Amaryllidaceae Anticancer Constituents PY - 2006/07/21 AU - Artem S. Kireev AU - Oleg N. Nadein AU - Vincent J. Agustin AU - Nancy E. Bush AU - Antonio Evidente AU - Madhuri Manpadi AU - Marcia A. Ogasawara AU - Shiva K. Rastogi AU - Snezna Rogelj AU - Scott T. Shors AU - Alexander Kornienko UR - https://acs.figshare.com/articles/journal_contribution/Synthesis_and_Biological_Evaluation_of_Aromatic_Analogues_of_Conduritol_F_l_i_c_i_i_hiro_i_Inositol_and_Dihydroconduritol_F_Structurally_Related_to_the_Amaryllidaceae_Anticancer_Constituents/3069583 DO - 10.1021/jo0607562.s001 L4 - https://ndownloader.figshare.com/files/4775353 KW - phenanthridone skeleton KW - C 10a bond KW - Conduritol F KW - inositol analogues KW - lactam ring B KW - Biological Evaluation KW - pancratistatin stereocenters KW - chemical preparation KW - pancratistatin analogues KW - Dihydroconduritol F Structurally Related KW - compound KW - Amaryllidaceae Anticancer ConstituentsPancratistatin KW - Aromatic Analogues KW - conduritol F KW - dihydroconduritol F KW - anticancer activity N2 - Pancratistatin is a potent anticancer natural product, whose clinical evaluation is hampered by the limited natural abundance and the stereochemically complex structure undermining practical chemical preparation. Fifteen aromatic analogues of conduritol F, l-chiro-inositol, and dihydroconduritol F that possess four of the six pancratistatin stereocenters have been synthesized and evaluated for anticancer activity. These compounds serve as truncated pancratistatin analogues lacking the lactam ring B, but retaining the crucial C10a−C10b bond with the correct stereochemistry. The lack of activity of these compounds provides further insight into pancratistatin's minimum structural requirements for cytotoxicity, particularly the criticality of the intact phenanthridone skeleton. Significantly, these series provide rare examples of simple aromatic conduritol and inositol analogues and, therefore, this study expands the chemistry and biology of these important classes of compounds. ER -