NMR QSAR Model for the Analysis of 4‐(5‐Arylamino‐1,3,4‐thiadiazol‐2‐yl)benzene‐1,3‐diols

Abstract

We have developed a NMR data quantitative structure-activity relationship NMR-QSAR model based on (1)H- and (13)C-NMR experimental spectral data of 4-(5-arylamino-1,3,4-thiadiazol-2-yl)benzene-1,3-diols. Compounds show in-vitro antiproliferative activity against some human cancer cell lines. Two-parameter equations obtained by the multiple linear regression procedure showed that chemical shifts of the protons of hydroxyl groups and carbon atoms of the 1,3,4-thiadiazole ring are the decisive descriptors of inhibition interactions of the compounds. The models gave leave-one-out (LOO) cross-validation ranges from 78% to 93%. The obtained NMR-QSAR equations provide a rapid, reliable, and simple way for predicting the antiproliferative activity of N-substituted 4-(5-amino-1,3,4-thiadiazol-2-yl)benzene-1,3-diols.

Synthesis and biological activity of novel benzoazoles, benzoazines and other analogs functionalized by 2,4-dihydroxyphenyl moiety

“…To extend our studies in this area, a set of new heterocyclic analogs with 2,4dihydroxyphenyl functionality were designed and obtained. Following from previous studies, this group of compounds exhibits strong antifungal and antiproliferative activity [34][35][36][37][38][39]. This paper presents the in vitro antifungal potency of compounds against the panel phytopathogenic fungi and Candida strains as well as cytotoxic potency against human cancer cell lines.…”

Synthesis of Novel 1‐(5‐(Benzylsulfinyl)‐3‐methyl‐1,3,4‐thiadiazol‐2(3H)‐ylidene)‐thiourea/urea Derivatives and Evaluation of Their Antimicrobial Activities

“…Many synthetic methods were reported in the literature for the synthesis of 1,3,4‐thiadiazole derivatives, for example, sulfuration of the corresponding 1,4‐dicarbonyl or acyl precursors using P 2 S 5 and Lawesson's reagent and also prepared from (i) carboxylic acids using propylphosphonic anhydride in one pot, (ii) from acid hydrazides under microwave irradiation in a single step , and (iii) N , N ‐diacylhydrazines in presence of P 2 S 5 and Lawesson's reagent and various other methods also reported .…”

QSAR studies of phenylhydrazine‐substituted tetronic acid derivatives based on the 1H NMR and 13C NMR chemical shifts

“…The quantitative structure–activity relationship (QSAR) is an important and common research tool in the modern bioactive molecule design . It was found that the NMR chemical shift is a good descriptor and plays a significant role in the QSAR studies of alcohols, benzene sulfonamides, and 1,3,4‐thiadiazoles …”