Aqueous hydrotrope: an efficient and reusable medium for a green one-pot, diversity-oriented synthesis of quinazolinone derivatives

Patil, Ashwini; Barge, Madhuri; Rashinkar, Gajanan; Salunkhe, Rajashri

doi:10.1007/s11030-015-9580-8

Cited by 20 publications

(6 citation statements)

References 41 publications

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“…This amphiphilic molecular structure is assumed to play a role in hydrotropic drug solubilization (Li et al, 2015; Patil et al, 2015). The hydrotrope molecules are assumed to self-aggregate by a stacking mechanism, in a manner closely related to surfactants (Bauduin et al, 2005).…”

Section: Discussionmentioning

confidence: 99%

Hydrotropic Solubilization of Lipophilic Drugs for Oral Delivery: The Effects of Urea and Nicotinamide on Carbamazepine Solubility–Permeability Interplay

et al. 2016

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Hydrotropy refers to increasing the water solubility of otherwise poorly soluble compound by the presence of small organic molecules. While it can certainly increase the apparent solubility of a lipophilic drug, the effect of hydrotropy on the drugs’ permeation through the intestinal membrane has not been studied. The purpose of this work was to investigate the solubility–permeability interplay when using hydrotropic drug solubilization. The concentration-dependent effects of the commonly used hydrotropes urea and nicotinamide, on the solubility and the permeability of the lipophilic antiepileptic drug carbamazepine were studied. Then, the solubility–permeability interplay was mathematically modeled, and was compared to the experimental data. Both hydrotropes allowed significant concentration-dependent carbamazepine solubility increase (up to ∼30-fold). A concomitant permeability decrease was evident both in vitro and in vivo (∼17-fold for nicotinamide and ∼9-fold for urea), revealing a solubility–permeability tradeoff when using hydrotropic drug solubilization. A relatively simplified simulation approach based on proportional opposite correlation between the solubility increase and the permeability decrease at a given hydrotrope concentration allowed excellent prediction of the overall solubility–permeability tradeoff. In conclusion, when using hydrotropic drug solubilization it is prudent to not focus solely on solubility, but to account for the permeability as well; achieving optimal solubility–permeability balance may promote the overall goal of the formulation to maximize oral drug exposure.

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Section: Discussionmentioning

confidence: 99%

Hydrotropic Solubilization of Lipophilic Drugs for Oral Delivery: The Effects of Urea and Nicotinamide on Carbamazepine Solubility–Permeability Interplay

et al. 2016

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“…To develop new synthetic routes for the preparation of hitherto unknown heterocyclic compounds containing quinolones, quinazolinones, and aromatic thiazole moieties, the present work describes the In(III) catalyzed synthesis of quinolone‐based quinazolinones and carbamic anhydride derivatives. Many synthetic routes have been reported for the synthesis of quinazolinones [17] employing a variety of catalysts [18–27] . Some of the selected literature reports are given in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of a Series of Quinoline‐Based Quinazolinones and Carbamic Anhydride Derivatives

et al. 2023

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Quinoline-based compounds are one of the most important classes of N-heterocyclics exhibiting a wide spectrum of biological activities. There is a constant demand for the synthesis of new quinoline-based molecules suitable for therapeutic applications. Here a new strategy is developed to synthesize different quinoline-based quinazolinones catalytically using InCl 3 through a cyclocondensation reaction of isatoic anhydride and aniline with 2-substituted-quinoline-3-carbaldehyde to produce 2-(2-phenoxyquinolin-3-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives (> 90 % yields). In contrast, the reduced electrophilicity at the metal center allows the hydrazide ligand to bind In(III) and serendipitously forms benzoic(2-phenoxyquinoline-3-carbonyl) carbamic anhydride (∼ 70 % yields). The mechanistic aspects of these reactions were rationally explained. The structure and purity of all the isolated derivatives were assessed by spectroscopic and analytical data. In view of a strong correlation existing between inflammation and cancer progression, the ex-vivo anti-inflammatory effect of the ligands was established. The anti-cancer property of the proposed ligand was delineated with a specific SIRT protein family. Further, the computational docking studies on the binding abilities of 22 synthesized compounds with the Sirt1 protein were discussed in detail.

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“…2,3-Dihydroquinazolin-4(1H)-one plays an important role in the aromatic nitrogen-containing heterocycles because of their abundant pharmacological and biological activities (Kshirsagar, 2015;Zawawi et al, 2015;Dohle et al, 2018). Compounds containing this motif have shown significant biological activities which include anticancer, anticonvulsant, antidefibrillatory, analgesic, diuretic, antihistamine, antihypertensive, and many other activities (Patil et al, 2015;Zawawi et al, 2015). These heterocycles participate in physiological processes as markers or messenger molecules and a large number of pharmaceuticals based on these heterocycles have been reported in the past few decades (Saeedi et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

An Aqueous Facile Synthesis of 2,3-Dihydroquinazolin-4(1H)-One Derivatives by Reverse Zinc Oxide Micelles as Nanoreactor

et al. 2020

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A green synthetic protocol has been developed for the efficient preparation of 2,3-dihydroquinazolin−4(1H)-one derivatives with excellent yield in aqueous media. Reverse zinc oxide micelles catalyzed the reactions efficiently and selectively as the hallow nanoreactor. Moreover, the catalyst was reusable without significant loss of catalytic efficiency. The notable advantages of the procedure are high yields and mild reaction conditions, simple operation, nonchromatographic purification, environmentally friendly and good versatile substrates.

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Aqueous hydrotrope: an efficient and reusable medium for a green one-pot, diversity-oriented synthesis of quinazolinone derivatives

Cited by 20 publications

References 41 publications

Hydrotropic Solubilization of Lipophilic Drugs for Oral Delivery: The Effects of Urea and Nicotinamide on Carbamazepine Solubility–Permeability Interplay

Hydrotropic Solubilization of Lipophilic Drugs for Oral Delivery: The Effects of Urea and Nicotinamide on Carbamazepine Solubility–Permeability Interplay

Synthesis and Biological Evaluation of a Series of Quinoline‐Based Quinazolinones and Carbamic Anhydride Derivatives

An Aqueous Facile Synthesis of 2,3-Dihydroquinazolin-4(1H)-One Derivatives by Reverse Zinc Oxide Micelles as Nanoreactor

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