Predicting anti-HIV activity of 2,3-diaryl-1,3-thiazolidin-4-ones: computational approach using reformed eccentric connectivity index

Abstract

The eccentric connectivity index, which has recently been employed successfully for the development of numerous mathematical models for the prediction of biological activities of diverse nature, has been reformed to overcome its limitations caused by degeneracy and insensitivity towards heteroatoms. The reformed eccentric connectivity index, termed the eccentric connectivity topochemical index, overcomes the limitations of the eccentric connectivity index by exhibiting very low degeneracy and displaying sensitivity to both the presence and relative position of heteroatoms without compromizing the discriminating power of the eccentric connectivity index. The relationship of the eccentric connectivity topochemical index, eccentric connectivity index and Wiener's index with regard to the anti-HIV activity of 2, 3-diaryl-1, 3-thiazolidin-4-one derivatives was subsequently investigated. The values of the eccentric connectivity topochemical index, the eccentric connectivity index and Wiener's index of each of 31 analogues comprizing the data set were computed using in-house computer program. Resultant data was analyzed and suitable models developed after identification of active ranges. Subsequently, each derivative was assigned a biological activity using these models, which was then compared with the reported anti-HIV activity. The accuracy of prediction using these models was found to vary from 81 to 90%. The proposed index offers a vast potential for virtual screening of combinatorial libraries, structure property/activity studies and drug design. [figure]. Basic structure of 2,3-diaryl-1, 3-thiazoidin-4-ones.

Predicting anti-allergic activity of 4-oxopyrimido [4,5-b]quinolines: Computational approach using topochemical indices

“…where V ic is the chemical degree of vertex i, E ic is the chemical eccentricity of vertex i, and n is the number of the vertices in graph G. The eccentric connectivity topochemical index is an improved version of an adjacency-cum-distance based topological index-the eccentric connectivity index (Sharma et al, 1997;Kumar and Madan, 2004;Lather and Madan, 2004)-and this modified index takes into consideration the presence as well as relative position of heteroatom(s) in a molecular structure.…”

On Eccentric Connectivity Index of TiO2 Nanotubes

“…The simplicity amalgamated with high correlating ability of this index can easily be exploited in QSPR/QSAR studies. [9][10][11] The prediction accuracy rate of ECI is better than the Wiener index with regard to diuretic activity 12 and anti-inflammatory activity. 13 Compare to Zagreb indices, the ECI has been shown to give a high degree of predictability in case of anticonvulsant activity.…”

Topochemical models for predicting the activity of α,γ-diketo acids as inhibitors of the hepatitis c virus NS5B RNA-dependent RNA polymerase

“…Topochemical indices are the topological parameters derived from the corresponding chemical graphs weighted with respect to the relative atomic weights of the noncarbon atom present in the given molecule. Previously, we have studied various QSARs using topochemical indices, including the atomic molecular connectivity index [20], topochemical eccentric adjacency index [21], Wiener's topochemical index [22,23], topochemical superadjacency index [24,25], topochemical Zagreb indices M c 1 and M c 2 [26], and topochemical eccentric connectivity index [27].…”