Organic synthesis planning: Some hints from similarity

Tetrahedron

Volumn 53, Issue 10, 1997, Pages 3729-3756

  Sello, Guido ^a   Termini, Manuela ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUND;

ARTICLE; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0031562374     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00095-1     Document Type: Article

References (43)

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5. 5. For some commercial packages using molecular similarity: a) Grethe, G.; Moock, T.E.; J. Chem. Inf. Comput. Sci. 1990, 30, 511-520.
6. b) Grethe, G.; Hounshell, W.D.; Chem. Struct. 2 Proc. Int. Conf. 2nd 1990. W.A. Warr, Ed.; Springer-Verlag, Berlin, 1993; pp. 399-407.
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23. 22. Johnson, A.P.; Marshall, C.; Judson, P.N.; Recl. Trav. Chim. Pays-Bas 1992, 111, 310-316.
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28. 27. Corey, E.J.; Long, A.K.; Lotto, G.I.; Rubinstein, S.D.; Recl. Trav. Chim. Pays-Bas 1992, 111, 304-309.
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31. (b) Gasteiger, J.; Ihlenfeldt, W.D.; Rose, J.D.; J. Chem. Inf. Comput. Sci. 1992, 32, 700-712
32. TOT is the molecular complexity measured as the sum of all the atom complexity (Baumer, L.; Sala, G.; Sello, G.; Tetrahedron 1988, 44, 1195-1206).
33. 31. Baumer, L.; Sala, G.; Sello, G.; J. Am. Chem. Soc. 1991, 113, 2994-2500.
34. 32. Baumer, L.; Sala, G.; Sello, G.; Tetrahedron 1993, 49, 3367-3386.
35. 33. Leoni, B.; Sello, G. A Proposal Toward the Identification of Substructure Electronic Similarity. In Molecular Similarity and Reactivity: from Quantum Chemical to Phenomenological Approaches; Carbo', R.; Ed.; Kluwer Academic Publishers: Dordrecht, 1995. pp. 267-289.
36. 34. Sello, G. ; J. Chem. Inf. Comput. Sci., 1994, 34, 120-129.
37. 35. If we consider our second method of similarity calculation P32 and P32' result much less similar (only 12 similar atoms). A second important aspect is represented by the number of sequences containing the similar atoms. In the present case we have two sequences (7+13) that can weight differently compared with a single 20 atom sequence.
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39. 37. Blurock, E.S.; J. Chem. Inf. Comput. Sci. 1995, 35, 607-616.
40. 38. Despite of this we can, however, emphasise that bond 6-5 is a vinylogous example of bond 6-7.
41. 39. It is interesting to note that the index value for solution 6 increases going from the first to the second level. This apparently wrong result is, however, completely correct; in fact, breaking bond 9-10 the energy of atom 9 changes enough to make it different from atom 9 in the TGT.
42. 40. Corey, E. J.; Cheng, X. In The Logic of Chemical Synthesis. John Wiley & Sons, Inc.: New York, 1989; pp. 205-214.
43. 41. This number is comprehensive of two useless changes passing from the TGT to G2 to G3 for a total of 4 changes.