Simpler molecular structure as selective & sensitive ESIPT-based fluorescent probe for cysteine and Homocysteine detection with DFT studies

1,2,3-Triazoles of 8-Hydroxyquinoline and HBT: Synthesis and Studies (DNA Binding, Antimicrobial, Molecular Docking, ADME, and DFT)

“…The reaction occurs with the highly possible interaction between the HOMO of one moiety and the LUMO of another. Using HOMO and LUMO energy values for a molecule, the global chemical reactivity descriptors of molecules such as chemical hardness, chemical potential, softness, electronegativity, and electrophilicity index have been defined. − ,− …”

“…From a biological point of view, thiazole units are diversified as a core structure in many biologically important compounds and drugs. , For example, a group of xenobiotic compounds having the benzene ring fused with the thiazole unit is used worldwide for numerous therapeutic applications . Among them, hydroxyphenyl benzothiazoles (2-HBT and 4-HBT) and their analogues have attracted attention due to their wide pharmacological activities. ,− From a chemistry point of view, 2-HBT and 4-HBT are easily synthesizable, highly stable, and exhibit a fluorescence property. , For example, 2-HBT is considered one of the most common molecules that show the ESIPT (excited-state intramolecular proton transfer) mechanism, and our group recently reported it for cysteine sensing …”

“…17,23 For example, 2-HBT is considered one of the most common molecules that show the ESIPT (excited-state intramolecular proton transfer) mechanism, and our group recently reported it for cysteine sensing. 24 Quinolines are heterocyclic compounds with two fused sixmember rings and a N-atom. Nowadays, 8-hydroxyquinoline (8-HQ) has gained significant attention due to various applications in organic and inorganic chemistry for biological activity.…”

CuAAC Mediated Synthesis of 2‐HBT Linked Bioactive 1,2,3‐Triazole Hybrids: Investigations through Fluorescence, DNA Binding, Molecular Docking, ADME Predictions and DFT Study

“…[26] With the help of molecular docking, one can get such useful information for various possible interactions of the ligands with the active binding sites (pockets) of the targets to predict the binding energies of the ligands. [27] Considering the critical therapeutic properties of 2-hydroxyphenyl benzothiazoles, 1,4-disubstituted-1,2,3-triazoles, hybrid molecules containing these pharmacophores, [14][15][16][17][18][19][20][21][22] and also considering our interest in the synthesis, in vitro and in silico study of 1,4-disubstituted 1,2,3-triazole linked with other biologically significant molecules like trifluoromethyl benzoate, [28] semicarbazone, [2a] thiosemicarbazone, [3a] carbamate, [29] and N-Boc-L-Leucine. [30] We thought of designing 1,4-disubstituted 1,2,3-triazole linked with 2-hydroxyphenyl benzothiazole hybrid molecules, as shown in Figure 1, with varying degrees of alkyl linkers.…”

“…On the other end, thiazoles in the form of benzothiazole or 2‐hydroxyphenyl benzothiazole (HBT) are privileged planer heteroatomic aromatic compounds containing two pharmacophores heteroatoms N and S. Benzothiazole are important building blocks that support the discovery/construction of new drugs due to their inherent affinity to various biological receptors [13] . Interestingly, compounds containing benzothiazole unit are of much importance due to their wide spectrum pharmaceutical applications such as fluorescent probes for selective detection of amino acids, [14] as antimicrobials, [15] anti‐inflammatory, [15a,16] antiviral, [15a] antidiabetic, [17] antitubercular, [18] anticancer activities, [19] anticonvulsant, [20] anti‐allergic, [21] and as anthelmintic agents [22] . Benzothiazoles have reportedly been used as photographic sensitizers and as intermediate for dyes [23] .…”