One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties

Abstract

In this study, hexasubstituted thiourea was carried out via reaction of isothiocyanato cyclophosphazene intermediates with a series of aromatics amines and amino acids in a one-pot reaction system. The reaction was not as straightforward as typical thiourea synthesis. Six unexpected thiourea derivatives a-f were formed in the presence of cyclotriphosphazene moieties in good yields (53-82%). The structures of a-f were characterized by elemental analysis and FTIR, 1 H, 13 C, and 31 P NMR spectroscopies. The occurrence of reverse thioureas formation in a one-pot reaction system is discussed. The possible binding interaction of the synthesised thiourea a-b in comparison to the predicted phenyl thiourea a-b and the targeted a with enzyme enoyl ACP reductase (FabI) is also discussed. Molecular docking of the targeted hexasubstituted thiourea a is able to give higher binding affinity of −7.5 kcal/mol compared to a-b (−5.9 kcal/mol and −6.3 kcal/mol) and thiourea a-b (−4.5 kcal/mol and −4.7 Kcal/mol).

Synthesis, Molecular Docking and Antimicrobial Activity of α, β‐Unsaturated Ketone Exchange Moiety for Chalcone and Pyrazoline Derivatives

“…Compound 1 d showed better activity as compare to 1 a due to the presence of hydrophilic moiety (i. e. COOH) at the favorable position. [38] Compound 2 a-d and 4 a-d, on the other hand, showed no inhibition activity against S. aureus. This could be due to the suppressing moiety of acetyl and ester groups in the molecular network, which completely indulged the activity of compound.…”

“…The pyrazoline derivatives (3 a-d) showed higher zone inhibition with range 14-17 mm compared to the standard ampicillin. The moderate to strong antimicrobial activity of 3 a-d was due to the modification of keto moiety, resonating delocalization and hydrophobic moiety to enhance lipophilicity [38] that stabilized it for favorable binding with microbial cell lines. [26] Mild antimicrobial activity for 1 a-d could be due to the nature and position of functional groups on the aromatic ring.…”

Aspirin Derivatives Exploration: A Review on Comparison Study with Parent Drug

“…This compound and its derivatives, in particular, have showed various pharmacological activities such as anti-fungal (58,59) , antiviral (58,60) , anticancer (61) , antituberculosis (62) , antimicrobial (63) and anti-inflammatory (64)(65)(66) . Thiourea has gained significant values since being studied for their application in commercial and industrial applications; plastics, textiles dyes, elastomer, herbicides, pesticides, rodenticides and catalytic (65,67,68) .…”

“…A study showed that compounds with two or more thiourea moiety hold better antimicrobial activity (67) . Moreover, it gained much attention from researchers as it contains carbon, nitrogen, hydrogen, and sulfur elements (69) .…”

Design, Synthesis, Characterization and Biological Evaluation of 6-Methoxy-2-aminobenzothioate derivatives against certain bacterial strains.

“…Recently, the number of organic researches has been expanded rapidly for preparation heterocyclic ring system containing of sulfur and nitrogen. They showed different synthetic derivatives of 2-Aminobenzothiazole and their derivatives have different biological activities and pharmacological like anti-bacterial anti-viral [ [14], antihelminthic [15], anti-tumor [16], anti-tubercular [17], antidepressant [18], anti-HIV agents [19], Antimalarial [20]and diuretic [21]., anti-pyretic properties [22]anti-proliferative [23]. Schiff's bases system an essential kind of compounds in chemistry, pharmaceutical and medicinal [24] with some biological applications which involve anti-bacterial [25], anti-tumor, anti-fungal [26], anti-inflammatory, anti-malarial [27] anti-cancer, ant tubercular [28], and herbicidal [29], activities.…”