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      Isosteric design of friction-reduction and anti-wear lubricant additives with less sulfur content

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          Abstract

          To reduce harmful sulfur content in lubricant additives, making use of isosterism has been shown to be an effective strategy. When thiobenzothiazole compounds were used as templates, the exchange of sulfur atoms in the thiazole ring with oxygen atoms and NH groups produced twelve isosteres. Similarly, 2-benzothiazole- S-carboxylic acid esters were used as template molecules to produce six isosteres. About 30% of the isosteres exhibited a satisfactory deviation of ±5% relative to the template, ignoring the specific changes in the base oils, the differences in molecular structure, and the friction or wear properties. The template molecules and isosteres in triisodecyl trimellitate exhibited better tribological properties than in trimethylolpropane trioleate or bis(2- ethylhexyl) adipate. Comparative molecular field analysis (CoMFA)- and comparative molecular similarity index analysis (CoMSIA)-quantitative structure tribo-ability relationship (QSTR) models were employed to study the correlation of molecular structures between the base oils and additives. The models indicate that the higher the structural similarities of the base oils and additives are, the more synergetic the molecular force fields of the lubricating system are; the molecular force fields creating synergistic effects will improve tribological performance.

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          Most cited references 25

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          Synopsis of some recent tactical application of bioisosteres in drug design.

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            Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity.

            An alternative approach is reported to compute property fields based on similarity indices of drug molecules that have been brought into a common alignment. The fields of different physicochemical properties use a Gaussian-type distance dependence, and no singularities occur at the atomic positions. Accordingly, no arbitrary definitions of cutoff limits and deficiencies due to different slopes of the fields are encountered. The fields are evaluated by a PLS analysis similar to the CoMFA formalism. Two data sets of steroids binding to the corticosteroid-binding-globulin and thermolysin inhibitors were analyzed in terms of the conventional CoMFA method (Lennard-Jones and Coulomb potential fields) and the new comparative molecular similarity indices analysis (CoMSIA). Models of comparative statistical significance were obtained. Field contribution maps were produced for the different models. Due to cutoff settings in the CoMFA fields and the steepness of the potentials close to the molecular surface, the CoMFA maps are often rather fragmentary and not contiguously connected. This makes their interpretation difficult. The maps obtained by the new CoMSIA approach are superior and easier to interpret. Whereas the CoMFA maps denote regions apart from the molecules where interactions with a putative environment are to be expected, the CoMSIA maps highlight those regions within the area occupied by the ligand skeletons that require a particular physicochemical property important for activity. This is a more significant guide to trace the features that really matter especially with respect to the design of novel compounds.
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              Bioisosterism: A Useful Strategy for Molecular Modification and Drug Design

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                Author and article information

                Journal
                Tsinghua Science and Technology
                Friction
                Tsinghua University Press (Xueyuan Building, Tsinghua University, Beijing 100084, China )
                2223-7690
                05 June 2018
                : 06
                : 02
                : 164-182 (pp. )
                Affiliations
                [ 1 ] School of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan 430023, China
                [ 2 ] College of Pharmacy, South-Central University for Nationalities, Wuhan 430074, China
                Author notes
                * Corresponding author: Xinlei GAO, E-mail: gaoxl0131@ 123456163.com

                Xinlei GAO. She received her M.S. degree in 1996 from Huazhong Normal University in organic chemistry, and graduated from Wuhan Research Institute of Materials Protection in mechanical design and theory with Ph.D. degree in 2006. Currently she is a full professor at Wuhan Polytechnic University, member of Chinese Tribology Association. She is interested in tribology chemistry, chemical computing, and designation of lubricant.

                Article
                2223-7690-06-02-164
                10.1007/s40544-017-0162-x

                This work is licensed under a Creative Commons Attribution 4.0 Unported License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

                Page count
                Figures: 44, Tables: 4, References: 35, Pages: 19
                Categories
                Research Article

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