Applications of Personal Computer Products for Chemical Data

Chapter 6

Applications of Personal Computer Products for Chemical Data Management in the Chemist's Workstation

Downloaded by UNIV OF CALIFORNIA SAN DIEGO on March 31, 2016 | http://pubs.acs.org Publication Date: June 15, 1987 | doi: 10.1021/bk-1987-0341.ch006

Donna del Rey Molecular Design Limited, 2132 Farallon Drive, San Leandro, CA 94577 The Chemist's Personal Software Series is a family of personal computer products designed to enhance the chemist's productivity in managing chemical information - chemical structures, reactions and data - and in writing reports which integrate graphic images with text. Examples of applications demonstrating a variety of solutions and improvements to problems regarding workstation data management are provided. The IBM Personal Computer (PC) is becoming the chemical industry standard for workstation computers. To remain current with the move to workstation automation, and to continue to provide the chemical industry with structureintegrated programs, Molecular Design Limited has developed the Chemist's Personal Software Series. This family of professional software products is designed to assist individual chemists in their daily work and to increase their efficiency. The series consists of four programs: ChemBase, ChemText, ChemTalk and ChemHost. Each of these programs fills a specific need defined by the chemical community. ChemBase, the PC-based chemical database management system, enables the chemist to store and search structures, reactions and textual data, and to tailor the format and content of chemical data reports on screen and on paper. ChemText, the chemical word processor, allows the preparation and printing of documents integrating graphic images, including molecules, reactions, forms and formulas, with text. ChemTalk and ChemHost work together to fulfill the PCmainframe communication needs, including terminal emulation, error-free file transfer and streamlined access to databases created using Molecular Design Limited's MACCS software. Each PC-based program can either be used alone, or in conjunction with each other or with other programs. Together the four programs provide a complete workstation environment for the storage, retrieval, reporting and communication of chemical information. To illustrate these features, data from an article in the Journal of Medicinal Chemistry (1) are used. The article describes the syntheses and testing of a series of compounds 1 expected to have antiinflammatory and analgesic activity based on previous results with derivatives of type 2.

0097-6156/87/0341-0048$06.00/0 © 1987 American Chemical Society

Warr; Graphics for Chemical Structures ACS Symposium Series; American Chemical Society: Washington, DC, 1987.

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Personal Computer Products

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The data found in the published article will be used for the following applications of the Chemist's Personal Software Series: - ChemTalk terminal emulation to run Molecular Design Limited's reaction indexing software REACCS on a mini/mainframe computer for access to centralized structure-based synthetic information; - ChemBase data sorting to organize compounds by activity; - ChemBase structure/data manipulation for structure-activity correlation; - ChemBase data searching to identify compounds with favorable test results; - ChemBase reaction/structure searching to streamline traditional file card methods; - ChemTalk direct access to MACCS databases to retrieve centralized information regarding commercially available compounds; and - ChemText document preparation to create a status report of the project results. Applications The chemist proposed the reaction scheme (Scheme I) for synthesizing the desired compounds. The first task is to find detailed synthetic data for the individual steps by using the terminal emulator capability of ChemTalk to search mini/mainframe reaction databases. ChemTalk provides VT100 terminal emulation for non-graphic communication and a special graphics terminal emulator for Molecular Design Limited programs. It also allows access to on-line services like CAS with Tektronix 4010 emulation. The ChemTalk graphics terminal is used here to run the mini/mainframe program REACCS to search for the preparative details of a specific step in the reaction scheme. Figure 1 shows one of the search hits as seen on a REACCS screen, describing the transformation of naphthols to naphthylamines. Similarly, reaction conditions for all steps in Scheme I were found using the PC as a high resolution graphics terminal running REACCS.

Scheme I. Proposed Reaction Scheme



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Utilizing the information thus obtained, several derivatives of 1 were synthesized and subsequently tested. The following information is added to a ChemBase database dedicated to the project: structures, melting points, and L D and CE values (lethal dosage and carrageenin-induced paw edema primary testing information). ChemBase automatically calculates the formula and molecular weight when the structure is drawn. Data for the first set of compounds, consisting of twenty-five 2-arylderivatives, are shown in Figure 2. This ChemBase spreadsheet format shows compounds and associated data in the order they were entered. By viewing multiple entries, comparison of information is simple. ChemBase also provides the ability to sort a list of compounds in ascending or descending order by data fields. This feature is illustrated in Figure 3 in which the compounds are organized by descending order to rank them according to activity, allowing investigation of structure-activity correlations. Inspection of the structures for the entries in the table shows that antiinflammatory activity is increased by strong electron-donating groups in the para position of the aryl substituent, while electron-withdrawing substituents show much less activity (Scheme II).


5 0

CE = 21

CE = 8

Scheme II. Structure-Activity Observations Based on this information, it was decided that a group of 2-(4methoxyphenyl)-3//-naphth[l,2-

Applications of Personal Computer Products for Chemical Data

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