Abstract
Computer-aided reaction indexing has become an increasingly important tool for synthetic chemists in the past few years. New products, as well as newer versions of established products, continue to advance the state-of-the-art in areas of structural search specificity and efficiency.
The addition of atom-atom mapping to REACCS’ reaction substructure search represents another step in the efforts of our group to improve its searching capability. Related searching features, such as stereochemical transformations (inversion/retention of configuration) and exact-transformation search properties are supplied to allow the user to take better advantage of atom-atom mappings. These features also set the groundwork for the implementation of searching reaction schemes.
The REACCS program is supported by a number of large databases of reactions. To assign mappings to such a huge number of reactions with minimum time/labour costs, an automatic method of assigning mappings and reacting centres was developed. This ‘automapping’ module has the unique ability to perceive non-stoichiometric reactions, in addition to well-behaved transformations.
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References
Wipke, W. T., ‘Exploring Reactions with REACCS’ Presented at the 188th National Meeting of the American Chemical Society, Philadelphia, PA, August, 1984.
Wipke, W. T., Dill, J. D., Peacock, S., Hounshell, D. ‘Searchand Retrieval Using an Automated Molecular Access System’. Presented at the 182nd National Meeting of the American Chemical Society, New York, NY, August 1981.
Wipke, W. T., Dill, J. D., Hounshell, D., Moock, T., Grier, D. ‘Exploring Reactions with REACCS’. In Modern Approaches to Chemical Reaction Searching: Proceedings of a Conference Organised by the Chemical Structure Association at the University of York, England, July 1985; Willet, P. Ed.; Gower: Aldershot, 1986.
Other commercially available (or announced) graphical reaction indexing systems which search databases containing atom-atom mappings include ORAC, RMS-DARC and the CAS ONLINE Reaction Database. The SYNLIB program uses another approach. These programs were described in talks at the Modern Approaches to Reaction Indexing meeting, York, England, July, 1985. See reference (3).
At the time of this writing, the public databases available from Molecular Design, and their numbers of reactions are: Theilheimer 46,000 Journal of Synthetic Methods 14,000 Organic Synthesis 5,000 Current Literature File 21,000
J. Synth. Methods, 8(2), 75386X; Cassella AG, Europe, 39905.
J. Synth. Methods, 8(9), 77215X; Al-Zaudi, S., Stoodly, R. J. J. Chem. Soc. Chem. Comm. 1982, 17, 995–996.
Morgan, H. L. ‘The Generation of a Unique Machine Description for Chemical Structures — a Technique Developed at Chemical Abstracts Service’. J. Chem. Doc. 1965, 5, 107–113.
Vledutz, G. E., ‘Development of a Combined WLN/CTR Multilevel Approach to the Algorithmic Analysis of Chemical Reactions in View of Their Automatic Indexing’, British Library, Researchand Development Department Report No. 5399, 1977.
Lynch, M. F., Willet, P. ‘The Automatic Detection of Chemical Reaction Sites’, J. Chem. Inf. Comput. Sci. 1978, 18, 154–159.
J. Synth. Methods, 8(5), 76177X; Sasaki, T., Ishibashi, Y., Ohno, M. ‘Catalysed Cycloaddition Reactions of α-Silyloxy-α,ß-Unsaturated Ketone and Aldehyde’. Tetrahedron Lett. 1982, 23 (16), 1693–1696.
J. Synth. Methods, 8(4), 75842X; Yoneda, F, Koga, R., Higuchi, M. ‘A One-Step Synthesis of Purine Derivatives by the Reaction of Phenylazomalonamidamidine with Aryl Aldehydes’. Chem. Letters 1982, 3, 365–368.
J. Synth. Methods, 8(4), 75857X; Tochikawa, R., Wachi, K., Terada, A. ‘Studies on 1,3-Benzoxazines. VI. Formation of Quinazolines and 4H-3,1-Benzoxazines by the Reaction of 4-Chloro-2H-1,3-benzoxazines with Aminoacetophenone, Aminobenzophenone and Aminobenzyl Alcohol Derivatives’. Chem. Pharm. Bull. 1982, 30 (2), 559–563.
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© 1988 Springer-Verlag Berlin Heidelberg
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Moock, T.E., Nourse, J.G., Grier, D., Hounshell, W.D. (1988). The Implementation of Atom-Atom Mapping and Related Features in the Reaction Access System (REACCS). In: Warr, W.A. (eds) Chemical Structures. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-73975-0_33
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DOI: https://doi.org/10.1007/978-3-642-73975-0_33
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