Synthesis and Crystallographic Insight into the Structural Aspects of Some Novel Adamantane-Based Ester Derivatives.
Adamantyl-based compounds are commercially important in the treatments for neurological conditions and type-2 diabetes, aside from their anti-viral abilities. Their values in drug design are chronicled as multi-dimensional. In the present study, a series of 2-(adamantan-1-yl)-2-oxoethyl benzoates, 2(a-q), and 2-(adamantan-1-yl)-2-oxoethyl 2-pyridinecarboxylate, 2r, were synthesized by reacting 1-adamantyl bromomethyl ketone with various carboxylic acids using potassium carbonate in dimethylformamide medium at room temperature. Three-dimensional structures studied using X-ray diffraction suggest that the adamantyl moiety can serve as an efficient building block to synthesize 2-oxopropyl benzoate derivatives with synclinal conformation with a looser-packed crystal packing system. Compounds 2a, 2b, 2f, 2g, 2i, 2j, 2m, 2n, 2o, 2q and 2r exhibit strong antioxidant activities in the hydrogen peroxide radical scavenging test. Furthermore, three compounds, 2p, 2q and 2r, show good anti-inflammatory activities in the evaluation of albumin denaturation.
Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia. chidankumar@gmail.com.|Department of Chemistry, Alva's Institute of Engineering & Technology, Visvesvaraya Technological University, Mijar, Moodbidri 574225, India. chidankumar@gmail.com.
C S Chidan
CS
Kumar
School of Chemical Sciences, Universiti Sains Malaysia, Penang 11800, Malaysia. stonekg01@gmail.com.
Huey Chong
HC
Kwong
School of Biosciences, Taylor's University, Lakeside Campus, Subang Jaya 47500, Selangor, Malaysia. siauhui.mah@taylors.edu.my.
Siau Hui
SH
Mah
Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia. chiatzeshyang@hotmail.com.
Tze Shyang
TS
Chia
Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia. wansin_loh@live.com.
Wan-Sin
WS
Loh
Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia. ckquah@usm.my.
Ching Kheng
CK
Quah
School of Chemical Sciences, Universiti Sains Malaysia, Penang 11800, Malaysia. limgk@usm.my.
Gin Keat
GK
Lim
Department of Sugar Technology & Chemistry, University of Mysore, Sir M.V. PG Center, Mandya 571402, Karnataka, India. chandraju1@yahoo.com.
Siddegowda
S
Chandraju
Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia. hkfun@usm.my.|Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia. hkfun@usm.my.
Hoong-Kun
HK
Fun
D000218:Adamantane / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000418:Albumins / Q000737:chemistry; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis; D018360:Crystallography, X-Ray; D004952:Esters; D016166:Free Radical Scavengers / Q000138:chemical synthesis; D008968:Molecular Conformation; D011489:Protein Denaturation
D000418:Albumins; D000893:Anti-Inflammatory Agents; D004952:Esters; D016166:Free Radical Scavengers; D000218:Adamantane
adamantyl; anti-inflammatory; antioxidant; crystal packing; synclinal