Design, synthesis and docking studies of some spiro-oxindole dihydroquinazolinones as antibacterial agents

Zhang, Jin; Zhao, Jiawen; Wang, Liangpeng; Liu, Jia; Ren, Decheng; Ma, Yangmin

doi:10.1016/j.tet.2015.12.055

Cited by 37 publications

(15 citation statements)

References 23 publications

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“…Some 2-spirooxindole dihydroquinazolinones demonstrate anti-bacterial activity in vitro. 8 Several methods have been reported for the preparation of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones, based mainly on the cyclocondensation of anthranil(onitrile)amides with aldehydes in the presence of various catalysts such as cyanuric chloride, 9 citric acid 10 , ZnCl2, 11 p-TSA 12 and sulfamic acid 13 . Moreover, many of these protocols are associated with the application of exotic catalyst systems, extended reaction times and tedious work-up procedures.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-(hetero)arylquinazolinones in aqueous media

Tmea¹,

Mikls²,

Lzr³

et al. 2017

Arkivoc

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Mechanochemical treatment of N-unsubstituted or N-methyl anthranilamide with benzaldehyde yielded their Schiff bases derivatives which could be easily cyclized to the corresponding 2-phenyl-2,3-dihydroquinazolinones via thermal rearrangement in water. On the basis of the above findings, an eco-friendly method was applied to prepare quinazolin-4(1H)-one derivatives from anthranilamides and a number of (hetero)aryl aldehydes. Heating the aqueous mixture of starting compounds to 90 °C resulted in the products in 81-94% yields. All products precipitated from the reaction mixture and were isolated by simply filtration. No further work-up or purification was necessary.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 2-(hetero)arylquinazolinones in aqueous media

Tmea¹,

Mikls²,

Lzr³

et al. 2017

Arkivoc

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“…Again, since we had seen that the compounds lost activity on human IRAP, we next tried to synthesize more soluble derivatives. However, introduction of heteroatoms in the chains (39)(40)(41) decreased the inhibition compared to 38, indicating that a lipophilic substituent in this part of the molecule is favorable but not necessary. Despite improved solubility (Table 2), these compounds lost activity on human IRAP, while retaining selectivity for IRAP versus APN.…”

Section: Resultsmentioning

confidence: 92%

“…Two and three-component reactions of structurally similar compounds have been published, typically requiring reflux for several hours. [34][35][36][37][38][39] We aimed to improve the synthetic procedures for this type of scaffold and have previously demonstrated that compound 1 can be synthesized alongside a series of analogs in a smooth and scalable way using microwave (MW) heated continuous flow synthesis (1-3, 23, 26-29, 31). [40,41] Here we show that these spiro-compounds can be obtained utilizing MW heated batch chemistry in a rapid and simple way.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Evaluation and Proposed Binding Pose of Substituted Spiro‐Oxindole Dihydroquinazolinones as IRAP Inhibitors

et al. 2020

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Insulin‐regulated aminopeptidase (IRAP) is a new potential macromolecular target for drugs aimed for treatment of cognitive disorders. Inhibition of IRAP by angiotensin IV (Ang IV) improves the memory and learning in rats. The majority of the known IRAP inhibitors are peptidic in character and suffer from poor pharmacokinetic properties. Herein, we present a series of small non‐peptide IRAP inhibitors derived from a spiro‐oxindole dihydroquinazolinone screening hit (pIC50 5.8). The compounds were synthesized either by a simple microwave (MW)‐promoted three‐component reaction, or by a two‐step one‐pot procedure. For decoration of the oxindole ring system, rapid MW‐assisted Suzuki‐Miyaura cross‐couplings (1 min) were performed. A small improvement of potency (pIC50 6.6 for the most potent compound) and an increased solubility could be achieved. As deduced from computational modelling and MD simulations it is proposed that the S‐configuration of the spiro‐oxindole dihydroquinazolinones accounts for the inhibition of IRAP.

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“…To date, many attempts have been devoted to disclose desirable protocols for the synthesis of spirooxindoles. In this line, the utilities of many catalysts, including KAl (SO 4 ) 2 ·12H 2 O (alum), 1‐methylimidazolium hydrogen sulfate, ethylenediamine diacetate and nano CeO 2 , have been evidenced, whereas some of these experimental procedures have obvious negative aspects, such as long reaction times, low yields and harsh reaction conditions. Accordingly, to avoid these limitations, the exploration of an efficient, easily available catalyst with high catalytic activity and short reaction times for the preparation of spirooxindole dihydroquinazolinone is still favored.…”

Section: Introductionmentioning

confidence: 99%

V‐N‐C catalysts anchored to mesoporous Al‐SBA‐15 with tailorable pore sizes for the synthesis of spirooxindole dihydroquinazolinones derivatives

Safaei‐Ghomi

Teymuri

2019

Applied Organom Chemis

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Heterogeneous nanoscale catalyst was successfully synthesized via anchoring of V‐bis(2‐aminobenzamide) complex on the Al‐SBA‐15. This modified mesoporous was identified by several characterization techniques, such as X‐ray diffraction, field emission‐scanning electron microscopy, Fourier transform‐infrared, Brunauer–Emmett–Teller and transmission electron microscopy. V‐Bis(2‐aminobenzamide)@Al‐SBA‐15 was found to be an efficient heterogeneous catalyst for the rapid and desirable synthesis of various spirooxindole dihydroquinazolinones derivatives. In addition, the heterogeneous nanocatalyst was chemically stabilized in organic and aqueous solutions as well as can be expeditiously reused for at least seven cycles without a significant loss in catalytic activity.

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Design, synthesis and docking studies of some spiro-oxindole dihydroquinazolinones as antibacterial agents

Cited by 37 publications

References 23 publications

Synthesis of 2-(hetero)arylquinazolinones in aqueous media

Synthesis of 2-(hetero)arylquinazolinones in aqueous media

Synthesis, Evaluation and Proposed Binding Pose of Substituted Spiro‐Oxindole Dihydroquinazolinones as IRAP Inhibitors

V‐N‐C catalysts anchored to mesoporous Al‐SBA‐15 with tailorable pore sizes for the synthesis of spirooxindole dihydroquinazolinones derivatives

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