Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

• Naganna Narra,
• Shiva Shanker Kaki,
• Rachapudi Badari Narayana Prasad,
• Sunil Misra,
• Koude Dhevendar,
• Venkateshwarlu Kontham and
• Padmaja V. Korlipara

Beilstein J. Org. Chem. 2017, 13, 26–32, doi:10.3762/bjoc.13.4

• Delhi, India Biology Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500007, India 10.3762/bjoc.13.4 Abstract The synthesis of five novel methyl 10-undecenoate-based lipoconjugates of phenolic acids from undecenoic acid was carried out. Undecenoic acid was methylated to

• derivatives have been assessed by their IC50 inhibitory values in the proliferation of MDA-MB231, SKOV3, MCF7, DU 145 and HepG2 cancer cell lines. Keywords: anticancer; anti-oxidants; caffeic acid; coumaric acid; ferulic acid; phenolic lipids; sinapic acid; undecenoic acid; Introduction Phenolic compounds

• of phenolic lipids, we have synthesized novel derivatives of phenolic lipids from undecenoic acid where the phenolic acids were linked to the olefinic group of undecenoic acid via a thioamide spacer. Among the various fatty acids reported, 10-undecenoic acid is unique due to its bifunctional nature

Anodic coupling of carboxylic acids to electron-rich double bonds: A surprising non-Kolbe pathway to lactones

• Robert J. Perkins,
• Hai-Chao Xu,
• John M. Campbell and
• Kevin D. Moeller

Beilstein J. Org. Chem. 2013, 9, 1630–1636, doi:10.3762/bjoc.9.186

• (Ep/2) for 14a was measured to be +0.68 V versus Ag/AgCl. For comparison, the oxidation potential measured for 10-undecenoic acid was +1.91 V versus Ag/AgCl in DMF solvent and +1.85 V versus Ag/AgCl in acetonitrile. When 0.5 equivalents of benzyltrimethylammonium hydroxide was added to the cyclic

• voltammetry solutions in order to generate the carboxylate and mimic the preparative oxidation conditions used for the reaction originating from 14a, the oxidation potential of the 10-undecenoic acid fell to 1.36–1.40 V versus Ag/AgCl for the DMF solution and 1.38 V versus Ag/AgCl for the acetonitrile

Hoveyda–Grubbs type metathesis catalyst immobilized on mesoporous molecular sieves MCM-41 and SBA-15

• Hynek Balcar,
• Tushar Shinde,
• Naděžda Žilková and
• Zdeněk Bastl

Beilstein J. Org. Chem. 2011, 7, 22–28, doi:10.3762/bjoc.7.4

• from 10-undecenoic acid [26]. The Ru complex 3 was purchased from Zannan Pharma. Ltd., China. The synthesis of siliceous MCM-41 and SBA-15 was performed according to the procedure described in [27]. Their textural characteristics were determined for MCM-41 and SBA-15, respectively, from nitrogen

About the activity and selectivity of less well-known metathesis catalysts during ADMET polymerizations

• Hatice Mutlu,
• Lucas Montero de Espinosa,
• Oĝuz Türünç and
• Michael A. R. Meier

Beilstein J. Org. Chem. 2010, 6, 1149–1158, doi:10.3762/bjoc.6.131

• , and 10-undecenoic acid [45], a commercial derivative of castor oil (Figure 4). A set of ADMET polymerizations was used to evaluate the performance of complexes C1, C2 and C3 at four different temperatures (60, 80, 100 and 120 °C), under bulk conditions, after 5 h reaction time, and constant catalyst

• expected in the future. Experimental Materials 10-undecenoic acid (Sigma–Aldrich, 98%), 1,3-propanediol (Sigma–Aldrich, 99.6%), p-toluenesulfonic acid monohydrate (Sigma–Aldrich, 98.5%), ethyl vinyl ether (Sigma–Aldrich, 99%), sulfuric acid (Fluka, 95–97%), p-benzoquinone (Fluka, 98%), (1,3-bis(2,4,6

• mass of approximately 4 mg. The melting temperature, Tm, was recorded as the peak of the endotherm on the second heating scan unless annealing was used as a pretreatment. Synthesis of 1,3-propylene diundec-10-enoate (1) 10-Undecenoic acid (50.00 g, 0.27 mol), 1,3-propanediol (8.4 g, 0.11 mol) and p