Abstract5,5’-Dimethoxy-3,3’-methanediyl-bis-indole (3) was synthesized in a reductive cyclisation process from (E)-5-methoxy-2-nitro-β -morpholinestyrene. The solid state structure was probed by single crystal X-ray diffraction and 13C CP/MAS NMR methods. The results of the X-ray analysis indicate insignificantly different structure of both methoxyindole fragments of the molecule, and this is the main reason for the appearance of the double resonances in the solid state NMR spectrum. Interesting N-H· · ·π interactions were observed which may have a functional role in biological features of 3. 5,5’- Dimethoxy-3,3’-methanediyl-bis-indole at conc. 1 · 10−4 M reduces the growth of MCF7 (breast), NCI-H460 (lung), and SF-268 (NCS) cells to 21, 0, and 48%, respectively.
Indole derivatives R 0140Synthesis, Spectroscopic Studies and Crystal Structure of 5,5'-Dimethoxy-3,3'-methanediyl-bis-indole as the Inhibitor of Cell Proliferation of Human Tumors. -Since usual reductive cyclization procedures of 2-nitrostyrene derivatives are not very effective for the preparation of methoxyindoles, the reductive cyclization procedure for the synthesis of diindolylmethane (VII), is carried out by employing trimorpholylmethane (III) in the first step. The molecular structure of diindolylmethane (VII) is analyzed by single X-ray diffraction. NH-π Interactions are observed as for other indoles and for globular proteins, and possibly play a functional role in biological features of (VII). Diindolylmethane (VII) reduces the growth of MCF7 and NCS cells. -(MACIEJEWSKA, D.; NIEMYJSKA, M.; WOLSKA, I.; WLOSTOWSKI, M.; RASZTAWICKA, M.
Rak piersi jest najczęstszym nowotworem złośliwym u kobiet. Przyczyn jego powstawania jest wiele: genetyczne, środowiskowe, hormonalne. Chemioterapia obejmuje kilkadziesiąt leków, które mają jednak wiele niebezpiecznych działań niepożądanych, i między innymi dlatego celowe jest poszukiwanie nowych substancji leczniczych. Jednym ze związków, którego aktywność przeciwnowotworowa jest analizowana, jest 3,3’-diindolilometan (DIM), powstający w organizmie człowieka po spożyciu roślin krzyżowych takich jak kapusta, brukselka lub kalafior. Obecnie w Katedrze i Zakładzie Chemii Organicznej są prowadzone prace nad otrzymaniem analogów DIM-u, mogących znaleźć zastosowanie w lecznictwie.
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