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Design, Synthesis and Cytotoxicity of Novel Chalcone Analogs Derived from 1‐Cyclohexylpyrrolidin‐2‐one and 2,3‐Dihydrobenzo[f]chromen‐1‐one
Author(s) -
Brien Kimberly A.,
Bandi Ravi Kumar,
Behera Ajaya Kumar,
Mishra Bijay Kumar,
Majumdar Poulomi,
Satam Vijay,
Savagian Mia,
Tzou Samuel,
Lee Megan,
Zeller Matthias,
Robles Andrew J.,
Mooberry Susan,
Pati Hari,
Lee Moses
Publication year - 2012
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201100265
Subject(s) - chalcone , cytotoxicity , moiety , ketone , stereochemistry , chemistry , cell culture , in vitro , organic chemistry , biochemistry , biology , genetics
Two divergent series of novel chalcone analogs, one derived from 1‐cyclohexylpyrrolidin‐2‐one and the other derived from 1‐benzo[f]chromanone, were designed, synthesized and evaluated for cytotoxicity against two murine cancer cell lines. Two 1‐benzo[f]chromanone analogs, 4g and 4j yielded moderate toxicity against both melanoma B16 and lymphoma L1210 cell lines with IC 50 values between the range of 5 and 6 µM. With an IC 50 value of 3.4 µM, compound 4g was also active against human MDA‐MB‐435 melanoma cells. X‐ray structures of the β‐hydroxy ketone product ( 4a ) and the α,β‐unsaturated ketone ( 4h ) were collected, and confirm the syn ‐configuration between the carbonyl moiety and the β‐vinylic proton in 4h . X‐ray structures of two 1‐cyclohexylpyrrolidin‐2‐one derivatives were also obtained, and both showed an E‐ configuration for the double bond.