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conferenceseries.com
Volume 8, Issue 2 (Suppl) Chem Sci J 2017
ISSN: 2150-3494 CSJ, an open access journal Euro Chemistry 2017
May 11-13, 2017
May 11-13, 2017 Barcelona, Spain
4th European Chemistry Congress
Chem Sci J 2017, 8:2(Suppl)
Plant Macromolecule from different species of Boraginaceae family, its synthetic monomer and their
anticancer efficacy
V Barbakadze
Tbilisi State Medical University, Georgia
The 13C NMR experiments of water-soluble high-molecular preparations from different species of Boraginaceae family were
carried out and simulated 13C NMR spectrum was calculated for 2-hydroxy-3-(3',4'-dihydroxyphenyl)-propionic acid residue
(I) of the corresponding polyether using ACD/CNMR Version 1.1 program. Signal positions in the 13C NMR spectrum of this
hypothetical structure (I) coincided satisfactory with the experimental values. According to 13C, 1H NMR, APT, 2D heteronuclear
1H/13C HSQC and 2D DOSY experiments the main structural element of these preparations was found to be a regularly substituted
by 3,4-dihydroxyphenyl and carboxyl groups polyoxyethylene backbone, namely poly[3-(3,4-dihydroxyphenyl)glyceric acid]
(PDPGA) or poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene]. The synthesis of racemic monomer of PDPGA 2,3-dihydroxy-3-
(3,4-dihydroxyphenyl)propionic acid (DDPPA) and its enantiomers (+)-(2R,3S)-DDPPA and (–)-(2S,3R)-DDPPA was carried out via
Sharpless asymmetric dihydroxylation of trans-caffeic acid derivatives using a potassium osmate catalyst and enantiocomplementary
catalysts cinchona alkaloid derivatives (DHQ)2-PHAL and (DHQD)2-PHAL as chiral auxiliaries. The opposite configuration
of both enantiomers was confirmed by measurements of the optical rotation (+)/(–)-values and circular dichroism spectra. The
determination of enantiomeric purity was performed by HPLC analysis. PDPGA and DDPPA exerted anti-cancer efficacy in vitro
and in vivo against human prostate cancer (PCA) cells via targeting androgen receptor, cell cycle arrest and apoptosis without
any toxicity, together with a strong decrease in prostate specific antigen level in plasma. However, our results showed that
anticancer efficacy of PDPGA is more effective compared to its synthetic monomer. Overall, this study identifies PDPGA as a potent
agent against PCA without any toxicity, and supports its clinical application.
Synthesis and biological evaluation of BCP derivatives: A steadfast effort towards introducing a
contemporary lead optimization tool.
Vikrant A Adsool
ASTAR, Singapore
Potential applications of the bicyclo[1.1.1]pentane (BCP) motif, as a contemporary lead optimization tool, has generated substantial
interest in medicinal chemistry.1 However, a realistic introduction of this building-block to the mainstream medicinal chemistry
warrants a systematic and steadfast approach towards its development. In 2013, originating from an “out-of-the-box” notion to
resolve issues pertaining to an on-going medicinal chemistry study, we recognized the need to resolve the paucity of synthetic access
to BCP derivatives.2 Taking cognizance of the non-trivial chemical demeanor of the strained BCP motif, we devised contemporary
strategies to secure key BCP derivatives in a scalable fashion. As an outcome, we have now secured a robust and scalable access to a
variety of key intermediates such as the BCP amine (1) its 3-fluoro and 3-phenyl substituted counterparts 2 and 3, and 3-pyrazine
BCP carboxylic acid (4).3-6 The newly discovered synthetic know-how was deployed to generate a library of BCP-based fragments
for an ‘in-house’ FBDD initiative. Moreover, empowered by our synthetic studies we have also invested efforts to understand the
biological behavior of BCP derivatives. In this presentation, I will narrate the background, the progress, and our future objectives
related to our work on the BCP derivatives.