Quantum topological molecular similarity

Chaudry, U.A. and Popelier, P.L.A. (2004) Estimation of pfCa using quantum topological molecular similarity descriptors application to carboxylic acids, anilines and phenols. J. Org. Chem., 69, 233-241. 

Quantum Topological Molecular Similarity. Part 5. Further Development With An Application to the Toxicity of Polychlorinated Dibenzo-P-Dioxins (PCDDS). 

Chaudry and Popelier [281] used a method combining quantum topological molecular similarity descriptors obtained from Bader s... 

Popelier PLA (2010) Developing Quantum Topological Molecular Similarity (QTMS). In Matta CF (ed) Quantum biochemistry electronic structure and biological activity. Wiley-VCH, Weinheim, pp 669-691... 

Apparently, the concept of similarity plays an important role in the chemistry of functional groups. Motivated by the recent revival of interest in molecular similarity [7-39], we shall present a systematic approach towards a quantum chemical description of functional groups. There are two main components of the approach described in this report. The first component is shape-similarity, based on the topological shape groups and topological similarity measures of molecular electron densities[2,19-34], whereas the second component is the Density Domain approach to chemical bonding [4]. The topological Density Domain is a natural basis for a quantum... 

Molecular similarity, in turn, was expressed in the next step, directly on the topological representations of shapes, and at this level, quantum similarity is not involved directly. Using differential and algebraic topological representations of molecular shapes had several advantages when compared to the direct Quantum Similarity approach ... 

The methods applied in recent years by various groups to construct QSAR models for ART and analogues include docking calculations to heme [104, 105], CoMFA [106-109] and hologram QSAR [108] as well as the hypothetical active-site lattice (HASL) approach [107], self-organizing maps of the molecular electrostatic potential [110], quantum-similarity measures [111] and topological molecular connectivity descriptors [112]. 

A Brief Review of the QSAR Technique. Most of the 2D QSAR methods employ graph theoretic indices to characterize molecular structures, which have been extensively studied by Radic, Kier, and Hall [see 23]. Although these structural indices represent different aspects of the molecular structures, their physicochemical meaning is unclear. The successful applications of these topological indices combined with MLR analysis have been summarized recently. Similarly, the ADAPT system employs topological indices as well as other structural parameters (e.g., steric and quantum mechanical parameters) coupled with MLR method for QSAR analysis [24]. It has been extensively applied to QSAR/QSPR studies in analytical chemistry, toxicity analysis, and other biological activity prediction. On the other hand, parameters derived from various experiments through chemometric methods have also been used in the study of peptide QSAR, where partial least-squares (PLS) analysis has been employed [25]. 

Molecular Field Topology Analysis, Molecular Shape Analysis, quantum-similarity. Shannon Entropy Descriptors, Electronic-Topological method. Compass method. Comparative... 

Finally, three further studies on QSAR of artemisininoids applying a variety of quantum-chemical and conventional molecular descriptors [105], molecular quantum-similarity measures (MQSM, [111]) and topological descriptors based on molecular connectivity [112] have led to models of quite satisfactory statistical performance. However, apart from showing the applicability of the respective QSAR approaches to this type of compounds both studies offer comparatively little new information with respect to structure-activity relationships. 

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