Dataset Information

Green Protocol for the Novel Synthesis of Thiochromeno[4,3-b]pyridine and Chromeno[4,3-b]pyridine Derivatives Utilizing a High-Pressure System.

ABSTRACT: A suitable and effective Q-tube-assisted strategy for the synthesis of novel, unrivalled thiochromeno[4,3-b]pyridine and chromeno[4,3-b]pyridine derivatives has been sophisticated, which includes ammonium acetate-mediated cyclocondensation reactions between 3-oxo-2-arylhydrazonopropanals and heterobenzocyclic ketones such as thiochroman-4-one and chroman-4-one, respectively. The high-pressure Q-tube reactor was shown to be superior to conventional heating. Furthermore, this Q-tube reactor-assisted protocol is safe owing to facile pressing and sealing, a broad substrate scope, and simple work-up and purification processes, as well as being scalable and having a high atom economy. The proposed mechanistic route includes two sequential dehydrative stages. In this investigation, X-ray crystallographic analysis was performed to authenticate the targeted products.

SUBMITTER: Behbehani H

PROVIDER: S-EPMC8675170 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Green Protocol for the Novel Synthesis of Thiochromeno[4,3-b]pyridine and Chromeno[4,3-b]pyridine Derivatives Utilizing a High-Pressure System.

Behbehani Haider H Dawood Kamal M KM Aryan Fatemah A FA Ibrahim Hamada Mohamed HM

ACS omega 20211130 49

A suitable and effective Q-tube-assisted strategy for the synthesis of novel, unrivalled thiochromeno[4,3-b]pyridine and chromeno[4,3-b]pyridine derivatives has been sophisticated, which includes ammonium acetate-mediated cyclocondensation reactions between 3-oxo-2-arylhydrazonopropanals and heterobenzocyclic ketones such as thiochroman-4-one and chroman-4-one, respectively. The high-pressure Q-tube reactor was shown to be superior to conventional heating. Furthermore, this Q-tube ...[more]

PMID: 34926954

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Project description:Carbonic anhydrases (CAs, EC 4.2.1.1) catalyze the essential reaction of CO2 hydration in all living organisms, being actively involved in the regulation of a plethora of patho-/physiological conditions. A series of chromene-based sulfonamides were synthesized and tested as possible CA inhibitors. On the other hand, in microorganisms, the β- and γ- classes are expressed in addition to the α- class, showing substantial structural differences to the human isoforms. In this scenario, not only human but also bacterial CAs are of particular interest as new antibacterial agents with an alternative mechanism of action for fighting the emerging problem of extensive drug resistance afflicting most countries worldwide. Pyrazolo[4,3-c]pyridine sulfonamides were synthesized using methods of organic chemistry. Their inhibitory activity, assessed against the cytosolic human isoforms hCA I and hCA II, the transmembrane hCA IX and XII, and β- and γ-CAs from three different bacterial strains, was evaluated by a stopped-flow CO2 hydrase assay. Several of the investigated derivatives showed interesting inhibition activity towards the cytosolic associate isoforms hCA I and hCA II, as well as the 3β- and 3γ-CAs. Furthermore, computational procedures were used to investigate the binding mode of this class of compounds within the active site of hCA IX. Four compounds (1f, 1g, 1h and 1k) were more potent than AAZ against hCA I. Furthermore, compound 1f also showed better activity than AAZ against the hCA II isoform. Moreover, ten compounds out of eleven appeared to be very potent against the γ-CA from E.coli, with a Ki much lower than that of the reference drug. Most of the compounds showed better activity than AAZ against hCA I as well as the γ-CA from E.coli and the β-CA from Burkholderia pseudomallei (BpsCAβ). Compounds 1f and 1k showed a good selectivity index against hCA I and hCA XII, while 1b was selective against all 3β-CA isoforms from E.coli, BpsCA, and VhCA and all 3γ-CA isoforms from E.coli, BpsCA and PgiCA.

Dataset Information

Green Protocol for the Novel Synthesis of Thiochromeno[4,3-b]pyridine and Chromeno[4,3-b]pyridine Derivatives Utilizing a High-Pressure System.

Publications

Green Protocol for the Novel Synthesis of Thiochromeno[4,3-<i>b</i>]pyridine and Chromeno[4,3-<i>b</i>]pyridine Derivatives Utilizing a High-Pressure System.

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