Identification of a chromone-based retinoid containing a polyolefinic side chain via facile synthetic routes

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 15, 2009, Pages 4339-4342

  Sun, Weilin ^a   Carroll, Patrick J ^c   Soprano, Dianne R ^b   Canney, Daniel J ^a  

^a TEMPLE UNIVERSITY   (United States)

^b TEMPLE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Polyolefinic chains; Rearrangements; Retinoids; Substituted chromones; Wittig reactions

Indexed keywords

3 BROMOMETHYL CHROMEN 4 ONE; ALDEHYDE DERIVATIVE; CHROMONE DERIVATIVE; RETINOIC ACID; RETINOID; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; CRYSTAL STRUCTURE; HORNER WADSWORTH EMMONS REACTION; WITTIG REACTION;

ALDEHYDES; ALKENES; ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; HUMANS; LIGANDS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NEOPLASMS; RETINOIDS; TRETINOIN;

EID: 67649990532     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.05.081     Document Type: Article

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15. 3): δ 8.28 (d, J = 8.0 Hz, 1H), 8.04 (s, 1H), 7.68 (t, J = 8.0 Hz, 1H), 7.33-7.56 (m, 4H), 6.67 (dd, J = 14.8, 10.8 Hz, 1H), 6.55 (d, J = 15.4 Hz, 1H), 6.47 (dd, J = 14.8, 10.8 Hz, 1H), 5.93 (d, J = 15.4 Hz, 1H), 3.76 (s, 3H).
16. 3, 400 MHz) δ: 9.65 (s, 1H), 8.21 (s, 1H), 8.19 (s, 1H), 7.52 (s, 1H), 7.41 (s, 1H), 2.01 (s, 2H), 1.75 (s, 2H), 1.37 (s, 6H), 1.35 (s, 6H).
17. Attempts to transform aldehyde 13 to a phosphorous ylide (see synthesis of 3 and 9 above) failed. Under Wittig reaction conditions, no reaction occurred between 3-formylchromones and 2-(triphenylphosphoranylidene)propionaldehyde.
18. Crystallographic data (excluding structure factors) for compounds 10 and 14 in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 283693 (for 10) and 722736 (for 14). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
19. The hydrolysis of chromone-based esters (5 and 14) under alkaline or acidic conditions was challenging due to the instability of the chromone nucleus (see: Kona, J.; Fabian, W.M.F.; Zahradnik, P. J. Chem. Soc., Perkin Trans. 2 2001, 422). No effort was made to optimize yields here but methods are available that report higher yields (for example see; He, X.; Li, Z.; You, Q. Synth. Commun. 2002, 32, 709).