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Journal of Enzyme Inhibition and Medicinal Chemistry Volume 35, 2020 - Issue 1
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Short Communication

Phosphonamidates are the first phosphorus-based zinc binding motif to show inhibition of β-class carbonic anhydrases from bacteria, fungi, and protozoa

Siham A. Alissaa Chemistry Department, College of Science, Princess Nourah bint Abdulrahman University, Riyadh, Saudi ArabiaCorrespondence[email protected]
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,
Hanan A. Alghulikaha Chemistry Department, College of Science, Princess Nourah bint Abdulrahman University, Riyadh, Saudi ArabiaView further author information
,
Zeid A. Alothmanb Chemistry Department, College of Science, King Saud University, Riyadh, Saudi ArabiaView further author information
,
Sameh M. Osmanb Chemistry Department, College of Science, King Saud University, Riyadh, Saudi ArabiaView further author information
,
Sonia Del Pretec Istituto di Bioscienze e Biorisorse, CNR, Napoli, ItalyView further author information
,
Clemente Capassoc Istituto di Bioscienze e Biorisorse, CNR, Napoli, ItalyORCID Iconhttps://orcid.org/0000-0003-3314-2411View further author information
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Alessio Nocentinid NEUROFARBA Department, Sezione di Scienze Farmaceutiche e Nutraceutiche, Sezione di Scienze Farmaceutiche e Nutraceutiche, Università degli Studi di Firenze, Sesto Fiorentino (Firenze), ItalyView further author information
&
Claudiu T. Supurand NEUROFARBA Department, Sezione di Scienze Farmaceutiche e Nutraceutiche, Sezione di Scienze Farmaceutiche e Nutraceutiche, Università degli Studi di Firenze, Sesto Fiorentino (Firenze), ItalyCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0003-4262-0323View further author information
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Pages 59-64 | Received 28 Aug 2019, Accepted 10 Oct 2019, Published online: 30 Oct 2019

Figures & data

Figure 1. In silico predicted binding mode of (A) phenylphosphonic diamide 2, (B) (S)-4 and (C) (R)-4 to hCA II, as repoted in Nocentini et al.Citation28

Figure 1. In silico predicted binding mode of (A) phenylphosphonic diamide 2, (B) (S)-4 and (C) (R)-4 to hCA II, as repoted in Nocentini et al.Citation28

Scheme 1. Synthesis of benzenephosphonamidate derivatives.

Scheme 1. Synthesis of benzenephosphonamidate derivatives.

Table 1. Inhibition data of VChβ, FtuβCA, BpsCAβ, Can2, CgNce, MgCA and LdcCA with phenylphosphonic diamide 2 and alkyl phosphonamidates 3–10 and the standard sulphonamide inhibitor acetazolamide (AAZ) by a stopped flow CO2 hydrase assayCitation29.

Table 2. Selectivity index (SI) for target β-CAs over hCA II.

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