Development of potent and selective Cathepsin C inhibitors free of aortic binding liability by application of a conformational restriction strategy

Banerjee, Abhisek; Velagaleti, Ranganadh; Patil, Saiprasad; Pawar, Mahesh Y.; Yadav, Pravin; Kadam, Pradip A.; Qadri, Mohammad Mohsin; Chakraborti, Samitabh; Saini, Jagmohan; Behera, D.; Karanjai, Keya; Iyer, Pravin S.; Gharat, Laxmikant A.; Das, Sanjib

doi:10.1016/j.bmcl.2021.128202

Cited by 3 publications

(2 citation statements)

References 27 publications

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“…Patents relating to the inhibition of dipeptidylpeptidase using methano prolines as peptide constructs in 2001 by Bristol Myers Squibb were followed by many others securing the IP for saxaglyptin . Since then, cis- and trans-4,5-methano D- or L-prolines have become prime surrogates for compounds containing proline in medicinal chemistry applications, − and covered extensively in the patent literature. − Compounds 73 – 75 are a few representative examples (Figure ).…”

Section: Medicinal Chemistry-inspired Collaborations With Industry Ma...mentioning

confidence: 80%

My 50-Plus Years of Academic Research Collaborations with Industry. A Retrospective

Hanessian

2024

J. Org. Chem.

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Section: Medicinal Chemistry-inspired Collaborations With Industry Ma...mentioning

confidence: 80%

My 50-Plus Years of Academic Research Collaborations with Industry. A Retrospective

Hanessian

2024

J. Org. Chem.

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“…The synthesis commenced from hydroxymethyloxirane and after 5 stages provided the target prolines in a low 6-12% overall yield. 35 A series of 1,3-dipolar cycloaddition protocols are known to reach the discussed framework. The reported procedures generally involve the construction of spiroisoxazoline derivatives based on exo-CH 2prolines reacting with in situ generated nitrile oxides (III).…”

mentioning

confidence: 99%

Practical Multigram Approach to Conformationally Constrained Proline-Based Building Blocks With Gamma-Spiro Conjunction

Iermolenko,

Kolosov,

Ostapchuk

et al. 2024

Preprint

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Unusual amino acids have arisen as an indispensable instrument at the disposal of modern medicinal chemistry. While extensively exploited as building blocks in the search for new pharmaceuticals, their application goes far beyond and they are currently involved in the exploration of the structure and conformational mobility of peptides, modification and amplification of peptidomimetics’ activity, and others. Herein, we communicate an effective synthetic approach to non-planar, conformationally restricted, sp3-enriched spirocyclic -prolines. The protocol employs readily available nitrile starting materials and conventional experimental procedures. The synthetic sequence is concise and includes three principal stages (one of them is a 4-step through process). The reactions proceed on a multigram scale affording the target prolines in overall good yields. The building blocks synthesized in the study are expected to have practical uses in the field of medicinal chemistry.

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Cysteine cathepsins: A long and winding road towards clinics

Biasizzo

Javoršek

Vidak

et al. 2022

Molecular Aspects of Medicine

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Development of potent and selective Cathepsin C inhibitors free of aortic binding liability by application of a conformational restriction strategy

Cited by 3 publications

References 27 publications

My 50-Plus Years of Academic Research Collaborations with Industry. A Retrospective

My 50-Plus Years of Academic Research Collaborations with Industry. A Retrospective

Practical Multigram Approach to Conformationally Constrained Proline-Based Building Blocks With Gamma-Spiro Conjunction

Cysteine cathepsins: A long and winding road towards clinics

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