11 / 21
Page 44
Notes:
Journal of Clinical & Experimental Pathology | ISSN: 2161-0681 | Volume 8
Breast Pathology and Cancer Diagnosis
6
th
World Congress and Expo on
July 25-26, 2018 | Vancouver, Canada
Medicinal Chemistry and Rational Drugs
20
th
International Conference on
&
One-pot synthesis of oxindoles through C-H activation and evaluation of anticancer activity
Sang Hoon Han
Sungkyunkwan University, Republic of Korea
T
he oxindole skeleton has been recognized as a ubiquitous heterocycle found in bioactive natural products and synthetic
compounds with medicinal applications. In particular, 3-substituted and spiro oxindole derivatives have been implicated
in a wide spectrum of biological activities including serotonergic, anti-tumor, anti-Alzheimer’s, anti-Parkinson disease,
glycoprotein-mediated MDR inhibition, anti-bacterial and anti-inflammatory activities. Additionally, oxindoles serve as
synthetic precursors to a range of other heterocyclic compounds including indoles and isatins. Therefore, the development of
novel and highly efficient strategies for the formation of oxindole architectures is an area of great interest in organic synthesis.
With recent advances in direct and catalytic C–H functionalization, a great deal of effort has been devoted to the formation of
oxindoles via transition-metal-catalyzed or metal-free oxidative C−H functionalization events. Among reported examples, the
tandem cyclization of acrylamides has attracted much attention for the synthesis of various functionalized oxindoles. Other
routes rely on the Ir- or Cu-catalyzed intramolecular cyclization of β-keto amide derivatives. Moreover, the Ag- or Rh-catalyzed
aromatic C−H functionalization of α-diazoamides is another effective way to construct C3-functionalized oxindoles. However,
these methods require specifically functionalized starting materials and result in a special subclass of oxindoles. With a rational
design based on C−H addition and subsequent cyclization process, we herein reported efficient access to the formation of
oxindoles through Rh(III)-catalyzed site-selective alkylation of azobenzenes and internal olefins, such as maleimides, maleates
and fumarates, followed by reductive intramolecular cyclization. Particularly noteworthy was the resulting 1-amino-indolic
framework, which represents a biologically important scaffold found in various synthetic molecules. Thus, synthesized
oxindoles were evaluated for cytotoxicity against human prostate adenocarcinoma cell lines (LNCaP), human breast cancer
cell lines (MCF-7), human Ovarian Cancer Cell lines (SKOV3), human lung carcinoma cell lines (A459) and human renal
adenocarcinoma cell lines (786-O).
Biography
Sang Hoon Han is a student for Master and Ph.D combined Course in School of Pharmacy, SKKU.
Sang0306@nate.comSang Hoon Han, J Clin Exp Pathol 2018, Volume 8
DOI: 10.4172/2161-0681-C3-051