Synthesis and anticancer evaluation of 6-azacyclonol-2,4,6-trimethylpyridin-3-ol derivatives: M3 muscarinic acetylcholine receptor-mediated anticancer activity of a cyclohexyl derivative in androgen-refractory prostate cancer

Karmacharya, Ujjwala; Chaudhary, Prakash; Lim, Dongchul; Dahal, Sadan; Awasthi, Bhuwan Prasad; Park, Hee Dong; Kim, Jung-Ae; Jeong, Byeong‐Seon

doi:10.1016/j.bioorg.2021.104805

Cited by 4 publications

(2 citation statements)

References 23 publications

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“…In the case of benzoylpiperidine, this role is played by the carbonyl group, which is hopefully able to establish new interactions (i.e., hydrogen bonds) with the target [1]. The bioisosteric replacement of piperazine with the benzoylpiperidine moiety is therefore used in medicinal chemistry to evaluate the structure-activity relationship (SAR) of several classes of bioactive compounds, although this chemical modification does not always lead to an improvement in terms of biological activity [2][3][4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

The Benzoylpiperidine Fragment as a Privileged Structure in Medicinal Chemistry: A Comprehensive Review

Bononi,

Lonzi,

Tuccinardi

et al. 2024

Molecules

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The phenyl(piperidin-4-yl)methanone fragment (here referred to as the benzoylpiperidine fragment) is a privileged structure in the development of new drugs considering its presence in many bioactive small molecules with both therapeutic (such as anti-cancer, anti-psychotic, anti-thrombotic, anti-arrhythmic, anti-tubercular, anti-parasitic, anti-diabetic, and neuroprotective agents) and diagnostic properties. The benzoylpiperidine fragment is metabolically stable, and it is also considered a potential bioisostere of the piperazine ring, thus making it a feasible and reliable chemical frame to be exploited in drug design. Herein, we discuss the main therapeutic and diagnostic agents presenting the benzoylpiperidine motif in their structure, covering articles reported in the literature since 2000. A specific section is focused on the synthetic strategies adopted to obtain this versatile chemical portion.

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Section: Introductionmentioning

confidence: 99%

The Benzoylpiperidine Fragment as a Privileged Structure in Medicinal Chemistry: A Comprehensive Review

Bononi,

Lonzi,

Tuccinardi

et al. 2024

Molecules

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“…Our previous synthetic strategies for lead compound discovery are summarized and illustrated in Figure 1 [ 12 , 13 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. Using an amine group of 2 at C(6)-position as a synthetic handle, amidopyridinols 3 and ureido-/thioureido-/carbamato-pyridinols 4 have been synthesized to generate a diverse set of compound collections [ 23 , 24 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pyridoxine-Derived Dimethylpyridinols Fused with Aminooxazole, Aminoimidazole, and Aminopyrrole

2022

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Described in this paper are studies on the preparation of three classes of dimethylpyridinols derived from pyridoxine fused with aminooxazole, aminoimidazole, and aminopyrrole. The key feature of this synthetic strategy is the manipulation of hydroxymethyl moiety of C(5)-position of the pyridoxine starting material along with the installation of an amino group at C(6)-position. Efficient and practical synthesis for the oxazole- and imidazole-fused targets was accomplished, while the instability of the pyrrole-fused one was observed.

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Benzbromarone Induces Targeted Degradation of HSP47 Protein and Improves Hypertrophic Scar Formation

Park,

Lim,

Park

et al. 2024

Journal of Investigative Dermatology

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Synthesis and anticancer evaluation of 6-azacyclonol-2,4,6-trimethylpyridin-3-ol derivatives: M3 muscarinic acetylcholine receptor-mediated anticancer activity of a cyclohexyl derivative in androgen-refractory prostate cancer

Cited by 4 publications

References 23 publications

The Benzoylpiperidine Fragment as a Privileged Structure in Medicinal Chemistry: A Comprehensive Review

The Benzoylpiperidine Fragment as a Privileged Structure in Medicinal Chemistry: A Comprehensive Review

Synthesis of Pyridoxine-Derived Dimethylpyridinols Fused with Aminooxazole, Aminoimidazole, and Aminopyrrole

Benzbromarone Induces Targeted Degradation of HSP47 Protein and Improves Hypertrophic Scar Formation

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