Glucosamine-6-phosphate synthase inhibiting C3-β-cholesterol tethered spiro heterocyclic conjugates: Synthesis and their insight of DFT and docking study

Periyasami, Govindasami; Kamalraj, Subban; Padmanaban, R.; Kumar, Santhakumar Yeswanth; Stalin, Antony; Arumugam, Natarajan; Kumar, Raju Suresh; Rahaman, Mostafizur; Durairaju, Periyan; Alrehaili, Abdulaziz; Aldalbahi, Ali

doi:10.1016/j.bioorg.2019.102920

Cited by 5 publications

(4 citation statements)

References 23 publications

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“…9. 1,3-Dipolar cycloadditions to yield 4-benzylpyrrolidine-3-carboxylic acids 25 and 26 , synthesis of cholesterol-conjugated spiro-pyrrolidine/pyrrolizines 28–30 , and 3D/2D interaction diagrams of compound 28 with the active site of target receptor protein 1XFF [ 48 ]. Reagents and conditions: a TFA (1 M solution in DCM); b isopropyl alcohol (iPrOH), 2 h, under reflux, yields: 76% ( 28 ), 67% ( 29 ), 63% ( 30 ) …”

Section: Pyrrolidine Derivatives Obtained By Ring Synthesismentioning

confidence: 99%

“…Unlike the pyrrolidine scaffold, spiro-pyrrolidine molecules have rigid conformations that allow for easy incorporation into biological macromolecules, including cholesterol. For this purpose, Periyasami et al [ 48 ] synthesized a small set of novel spiro-pyrrolidine/pyrrolizines by one-pot three-component reactions. Stereo- and regioselective reactions based on 1,3-dipolar cycloaddition between the dipolarophile C3- β -cholesterolacrylate 27 (Fig.…”

Section: Pyrrolidine Derivatives Obtained By Ring Synthesismentioning

confidence: 99%

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Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

et al. 2021

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The five-membered pyrrolidine ring is one of the nitrogen heterocycles used widely by medicinal chemists to obtain compounds for the treatment of human diseases. The great interest in this saturated scaffold is enhanced by (1) the possibility to efficiently explore the pharmacophore space due to sp3-hybridization, (2) the contribution to the stereochemistry of the molecule, (3) and the increased three-dimensional (3D) coverage due to the non-planarity of the ring—a phenomenon called “pseudorotation”. In this review, we report bioactive molecules with target selectivity characterized by the pyrrolidine ring and its derivatives, including pyrrolizines, pyrrolidine-2-one, pyrrolidine-2,5-diones and prolinol described in the literature from 2015 to date. After a comparison of the physicochemical parameters of pyrrolidine with the parent aromatic pyrrole and cyclopentane, we investigate the influence of steric factors on biological activity, also describing the structure–activity relationship (SAR) of the studied compounds. To aid the reader’s approach to reading the manuscript, we have planned the review on the basis of the synthetic strategies used: (1) ring construction from different cyclic or acyclic precursors, reporting the synthesis and the reaction conditions, or (2) functionalization of preformed pyrrolidine rings, e.g., proline derivatives. Since one of the most significant features of the pyrrolidine ring is the stereogenicity of carbons, we highlight how the different stereoisomers and the spatial orientation of substituents can lead to a different biological profile of drug candidates, due to the different binding mode to enantioselective proteins. We believe that this work can guide medicinal chemists to the best approach in the design of new pyrrolidine compounds with different biological profiles.

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Section: Pyrrolidine Derivatives Obtained By Ring Synthesismentioning

confidence: 99%

Section: Pyrrolidine Derivatives Obtained By Ring Synthesismentioning

confidence: 99%

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

et al. 2021

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“…2 Additionally, novel cholesterol-spiropyrrolidine hybrids possessing biologically active oxindole and acenaphthylene-1-one groups have been synthesized. 3 In 2010, Waldmann et al reported the synthesis of 3,3-pyrrolidinyl spirooxoindoles through the CuI-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with 3-methylen-2-oxoindoles. 4 Shortly after, Wang et al described a silver-catalyzed version of this reaction.…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

“…13 C NMR (126 MHz, CDCl 3 ):  = 205 3. (C=O), 142.1 (CH), 138.5 (CH), 133.3 (C), 131.6 (CH), 131.6 (C), 131.3 (C), 130.3 (C), 128.8 (CH), 128.4 (CH), 128.4 (C), 127.7 (CH), 125.6 (CH), 121.6 (CH), 119.7 (CH), 93.4 (C-NO 2 ), 76.5 (C), 58.6 (CH), 55.6 (CH), 16.7 (Me).…”

mentioning

confidence: 99%

Diastereoselective Synthesis of NH-Unprotected Spiropyrrolidines via the Huisgen Reaction of Acenaphthoquinone-Derived Azomethine Ylides with β-Nitrostyrenes

Yavari,

Ghafouri

2024

Synthesis

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Abstract4′-Nitro-2H-spiro[acenaphthylene-1,2′-pyrrolidine]-2-one derivatives are prepared via [3+2] cycloaddition reactions of azomethine ylides, generated in situ from acenaphthoquinone and primary amines, with β-nitrostyrenes in the presence of ( i Pr)2NEt in methanol. Evidence for the structures of the products was obtained from single-crystal X-ray analysis. The important feature of this diastereoselective synthesis of NH-unprotected spiropyrrolidines is the formation of four contiguous stereogenic centers, one of which is quaternary, with high selectivity.

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Improving enzyme activity of glucosamine-6-phosphate synthase by semi-rational design strategy and computer analysis

et al. 2020

Biotechnol Lett

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Glucosamine-6-phosphate synthase inhibiting C3-β-cholesterol tethered spiro heterocyclic conjugates: Synthesis and their insight of DFT and docking study

Cited by 5 publications

References 23 publications

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

Diastereoselective Synthesis of NH-Unprotected Spiropyrrolidines via the Huisgen Reaction of Acenaphthoquinone-Derived Azomethine Ylides with β-Nitrostyrenes

Improving enzyme activity of glucosamine-6-phosphate synthase by semi-rational design strategy and computer analysis

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