version date: 1 December 2006 EXPERIMENTAL Drawing, conformational, and molecular analysis of drugs Drawing and 3D visualization Several easily utilized programs are available for building bidimensional molecules like Chem Window, Isis Draw, and Chem Draw. Accurate and high-quality figures and diagrams can be elaborated with the help of such programs that frequently contribute to documentation and communication in science The students learn the resources available in the main menu of chem draw and Chem3D and how to utilize the tool and template selection to design chemical structures The stereochemical aspects are discussed in depth and through exercises, they are able to correctly represent the asymmetrical carbons of drugs like benzylpenicillin(1)and estramustine(2), Fig. 1. Eventually, the structures can be drawn in perspective representing the molecules in the projections of Fisher, Newman, and Haworth 量昔 Benzylpenicillin Estramustine (1) C16HI8N2O4s Molecular weight. 334.39 C23H30CINNa2O6P C.5747:H.5.43:N.8.38 Molecular weight: 564.35 C.4895:H536:Cl.12.56:N,248 O.19.14:S.959 Na.8.15:O.17.01:P.549 Fig 1 Drug drawings showing relevant stereochemical features( ChemDraw) Several molecular properties can be calculated and/or represented in some of the programs as well as the molecular formulae, molecular weights and the theoretical elementary analysis. More sophisticated programs like ChemDraw UItra can, in addition predict H and C chemical shifts in NMR of chemical compounds, their freezing and melting points, log P, molar refractivity, and heat of formation, besides furnishing the correct chemical name (IUPAC) The students are trained to chemically recognize heterocyclic rings, frequently present in drugs, through the use of the main menu of Chem Draw by clicking on"Edit and Insert name as Structure". By introducing the English ring name in the dialog box, it is possible to visualize the corresponding chemical structure in the drawing window and the accepted IUPAC nomenclature, which helps the student build complex molecules In the Chem3D program, drugs are three-dimensionally visualized, by the grad building of bonds based on information on their length and position angles. More complex molecules can be obtained by alternating several of the available resources such as drawing <www.iupac.org/publications/cd/medicinalchemistry/>3 EXPERIMENTAL Drawing, conformational, and molecular analysis of drugs Drawing and 3D visualization Several easily utilized programs are available for building bidimensional molecules like ChemWindow, Isis Draw, and ChemDraw. Accurate and high-quality figures and diagrams can be elaborated with the help of such programs that frequently contribute to documentation and communication in science. The students learn the resources available in the main menu of ChemDraw6 and Chem3D7 and how to utilize the tool and template selection to design chemical structures. The stereochemical aspects are discussed in depth and through exercises, they are able to correctly represent the asymmetrical carbons of drugs like benzylpenicillin (1) and estramustine (2), Fig. 1. Eventually, the structures can be drawn in perspective, representing the molecules in the projections of Fisher, Newman, and Haworth. O O H N N S H H COOH N O CH3 OPO3Na2 O Cl Cl H H Benzylpenicillin (1) Estramustine phosphate (2) C16H18N2O4S Molecular weight.: 334.39 C, 57.47; H, 5.43; N, 8.38; O, 19.14; S, 9.59 C23H30Cl2NNa2O6P Molecular weight: 564.35 C, 48.95; H, 5.36; Cl, 12.56; N, 2.48; Na, 8.15; O, 17.01; P, 5.49 H Fig. 1 Drug drawings showing relevant stereochemical features (ChemDraw). Several molecular properties can be calculated and/or represented in some of the programs as well as the molecular formulae, molecular weights and the theoretical elementary analysis. More sophisticated programs like ChemDraw Ultra8 can, in addition, predict 1 H and 13C chemical shifts in NMR of chemical compounds, their freezing and melting points, log P, molar refractivity, and heat of formation, besides furnishing the correct chemical name (IUPAC). The students are trained to chemically recognize heterocyclic rings, frequently present in drugs, through the use of the main menu of ChemDraw by clicking on “Edit” and “Insert name as Structure”. By introducing the English ring name in the dialog box, it is possible to visualize the corresponding chemical structure in the drawing window and the accepted IUPAC nomenclature, which helps the student build complex molecules. In the Chem3D7 program, drugs are three-dimensionally visualized, by the gradual building of bonds based on information on their length and position angles. More complex molecules can be obtained by alternating several of the available resources such as drawing <www.iupac.org/publications/cd/medicinal_chemistry/> version date: 1 December 2006