Synthesis of aristolactam analogues and evaluation of their antitumor activity

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 11, 2009, Pages 3036-3040

  Choi, Young Lok ^a,b   Kim, Joa Kyum ^a   Choi, Sang Un ^a   Min, Yong Ki ^a   Bae, Myung Ae ^a   Kim, Bum Tae ^a   Heo, Jung Nyoung ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Sungkyunkwan University   (South Korea)

Author keywords

Anticancer; Aristolactam; Cepharanone; Cytotoxicity; Phenanthrene lactam; Piperolactam; Sauristolactam

Indexed keywords

ANTINEOPLASTIC AGENT; ARISTOLACTAM BIII; ARISTOLACTAM DERIVATIVE; ARISTOLOLACTAM; CEPHARANONE B; DOXORUBICIN; LACTAM DERIVATIVE; N METHYL PIPEROLACTAM A; PACLITAXEL; PIPEROLACTAM A; SAURISTOLACTAM; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; APORPHINES; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HUMANS; LACTAMS;

EID: 65549117281     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.04.020     Document Type: Article

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30. 3) data for 2e (80%): δ 7.33 (s, 1H), 4.23 (s, 2H), 3.93 (s, 3H), 3.91 (s, 3H), 3.67 (q, 2H, J = 7.2 Hz), 1.28 (t, 3H, J = 7.2 Hz). Compound 2f (88%): δ 7.25 (s, 1H), 4.56 (heptet, 1H, J = 6.9 Hz), 4.11 (s, 2H), 3.86 (s, 3H), 3.82 (s, 3H), 1.23 (d, 6H, J = 6.9 Hz). Compound 2g (98%): δ 7.34 (s, 1H), 4.44 (d, 2H, J = 2.5 Hz), 4.36 (s, 2H), 3.92 (s, 3H), 3.91 (s, 3H), 2.31 (t, 1H, J = 2.5 Hz). Compound 2h (88%): δ 7.34 (s, 1H), 4.37 (s, 2H), 3.93 (s, 3H), 3.91 (s, 3H), 3.80 (t, 2H, J = 4.9 Hz), 3.63 (t, 2H, J = 4.9 Hz), 3.37 (s, 3H). Compound 2i (98%): δ 7.34 (s, 1H), 4.35 (s, 2H), 3.93 (s, 3H), 3.92 (s, 3H), 3.48 (d, 2H, J = 7.1 Hz), 1.11-1.00 (m, 1H), 0.63-0.56 (m, 2H), 0.37-0.32 (m, 2H). Compound 2j (66%): δ 7.30-7.17 (m, 6H), 4.07 (s, 2H), 3.90 (s, 3H), 3.88 (s, 3H), 3.84 (t, 2H, J = 7.2 Hz), 2.97 (t, 2H, J = 7.2 Hz). Compound 2k (98%): δ 7.37 (s, 1H), 7.25 (d, 1H, J = 4.9 Hz), 7.05 (d, 1H, J = 3.3 Hz), 6.99-6.96 (dd, 1H, J = 4.9, 3.6 Hz), 4.96 (s, 2H), 4.20 (s, 2H), 3.93 (s, 3H), 3.90 (s, 3H). Compound 2l (89%): δ 7.74 (d, 2H, J = 8.7 Hz), 7.46 (d, 2H, J = 8.6 Hz), 7.40 (s, 1H), 4.68 (s, 2H), 3.96 (s, 3H), 3.94 (s, 3H), 1.34 (s, 9H). Compound 2m (90%): δ 7.73 (d, 2H, J = 9.0 Hz), 7.41 (s, 1H), 6.99 (d, 2H, J = 9.0 Hz), 4.67 (s, 2H), 3.97 (s, 3H), 3.95 (s, 3H), 3.85 (s, 3H). Compound 2n (82%): δ 8.59 (d, 2H, J = 6.6 Hz), 7.39 (s, 1H), 7.20 (d, 2H, J = 7.8 Hz), 4.80 (s, 2H), 4.16 (s, 2H), 3.954 (s, 3H), 3.951 (s, 3H). Compound 2o (98%): δ 7.33 (s, 1H), 4.32 (s, 2H), 3.92 (s, 3H), 3.90 (s, 3H), 3.72 (t, 2H, J = 6.5 Hz), 2.58 (t, 2H, J = 6.4 Hz), 2.28 (s, 6H). Compound 2p (89%): δ 7.33 (s, 1H), 4.35 (s, 2H), 3.92 (s, 3H), 3.91 (s, 3H), 3.70 (t, 2H, J = 6.6 Hz), 2.73 (t, 2H, J = 6.6 Hz), 2.60 (q, 4H, J = 7.1 Hz), 1.03 (t, 6H, J = 7.1 Hz). Compound 2q (98%): δ 7.33 (s, 1H), 4.33 (s, 2H), 3.93 (s, 3H), 3.92 (s, 3H), 3.74 (t, 2H, J = 6.3 Hz), 3.69 (t, 4H, J = 3.6 Hz), 2.64 (t, 2H, J = 6.3 Hz), 2.52 (bs, 4H). Compound 2r (99%): δ 7.33 (s, 1H), 4.35 (s, 2H), 3.92 (s, 3H), 3.90 (s, 3H), 3.72 (t, 2H, J = 6.6 Hz), 2.58 (t, 2H, J = 6.6 Hz), 2.44 (s, 4H), 1.61-1.47 (m, 4H), 1.45-1.41 (m, 2H).
31. +, 4), 336 (9), 323 (100). Compound 35: δ 8.56-8.53 (m, 2H), 8.08-8.05 (m, 2H), 7.76 (t, 1H, J = 7.8 Hz), 7.65-7.59 (m, 2H), 3.75 (s, 3H), 2.84 (s, 3H). Compound 36: δ 9.34 (dd, 1H, J = 8.0, 1.5 Hz), 8.06 (dd, 1H, J = 7.9, 1.6 Hz), 7.78 (s, 1H), 7.67-7.56 (m, 2H), 4.09 (s, 3H), 4.06 (s, 3H), 3.76 (s, 3H), 2.83 (s, 3H). Compound 37: δ 9.33 (dd, 1H, J = 6.5, 1.6 Hz), 8.09 (dd, 1H, J = 7.7, 1.6 Hz), 8.07 (s, 1H), 7.77-7.59 (m, 2H)
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