Novel Bisphosphonates Derived from 1H‐Indazole, 1H‐Pyrazolo[3,4‐b]Pyridine, and 1H‐Pyrazolo[3,4‐b]Quinoline

Teixeira, Fátima C.; Lucas, Carla; Curto, Manuel; Teixeira, António P. S.; Duarte, M. Teresa; André, Vânia

doi:10.1002/hc.21282

Cited by 7 publications

(1 citation statement)

References 39 publications

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“…7c During the preparation of this manuscript, a microwave-assisted aza-Michael addition of indazole to tetraethyl ethylidene-1,1-bisphosphonate was also developed. 11 With respect to enones, however, no systematic work has been described except for an example with cyclohept-2-enone. 12…”

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confidence: 99%

Highly Efficient Synthesis of N 1-Substituted 1H-Indazoles by DBU-Catalyzed Aza-Michael Reaction of Indazole with Enones

et al. 2016

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confidence: 99%

Highly Efficient Synthesis of N 1-Substituted 1H-Indazoles by DBU-Catalyzed Aza-Michael Reaction of Indazole with Enones

et al. 2016

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Chiral Magnesium(II) Complex‐Catalyzed Enantioselective Desymmetrization of meso‐Aziridines with Pyrazoles

Guo

Lin

et al. 2017

Adv Synth Catal

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A highly enantioselective catalytic protocol for the desymmetrization of meso-aziridines via ring-opening with pyrazoles is reported using an N,N'-dioxide-Mg(OTf) 2 complex as the catalyst. The corresponding trans-a-pyrazole-substituted amines were obtained in good yields and enantioselectivities (up to 99% yield and 94% ee) under mild reaction conditions. Moreover, a remarkably high asymmetric amplification was observed in the catalytic system.Enantioselective desymmetrization is a powerful strategy for the construction of complex molecules with multiple stereocentres from relatively simple meso starting materials. [1] In particular, the enantioselective desymmetrization of meso-aziridines has captured much attention for providing access to important chiral 1,2-difunctionalized molecules with vicinal stereocenters by ring opening with nucleophiles in one single step. [2] Over the past decades, many nucleophiles such as trimethylsilyl azide, [3] trimethylsilyl cyanide, [4] amines, [5] alcohols, [6] halogen, [7] etc. [8] have been demonstrated successfully for desymmetrization of meso-aziridines. As a pioneer report, Jacobsen and co-workers described the highly enantioselective ring opening of meso-aziridines, which reacted with trimethylsilyl azide to give 1,2-azidoamines in good yields with 83-94% ee under the catalysis of the chiral chromium (III)-salicylimine complex. [9] Shibasaki and co-workers subsequently provided 1,2-amidonitriles in good yields with 81-93% ee in the presence of a catalyst prepared in situ from Gd(OiPr) 3 and the chiral ligand derived from glucose in 2005. [10] Follow-ing these early reports, many excellent researches have been furnished in desymmetrization of mesoaziridines. Recently, Wang's group realized the enantioselective dearomatization reaction and [3 + 2]-cycloaddition of meso-aziridines via an in situ generated magnesium catalyst. [11] In spite of these impressive advances, there are few reports on the direct catalytic asymmetric ring-opening of meso-aziridines with pyrazoles, [12] although pyrazole motif also exists in a number of small molecules that possess diverse chemical, biological, and pharmaceutical activities. [13]

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One‐Pot Microwave‐Assisted Synthesis, in Vitro Anti‐inflammatory Evaluation and Computer‐Aided Molecular Design of Novel Sulfamide‐Containing Bisphosphonates Derivatives

et al. 2022

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An eco‐friendly and one‐step microwave‐assisted green synthesis of new functionalized bisphosphonates derivatives was described by a three‐component reaction of aromatic sulfamide with triethyl orthoformate and diethyl phosphite. The synthesized compounds were characterized by 1H, 13C, 31P NMR and IR analysis. Some of these compounds were tested for in vitro anti‐inflammatory activity and showed moderate inhibition compared to diclofenac as standard drug. Furthermore, to rationalize the observed biological data, several in silico approaches have been used to explain Structure‐Activity Relationship study (SAR) based on DFT calculation, molecular docking, pharmacodynamic, pharmacokinetic and toxicity profiles of sulfamide‐containing bisphosphonates derivatives as anti‐inflammatory drugs. The results of the in vitro and in silico activities prove that the compound 4 b have the ideal structural requirements for further development of novel anti‐inflammatory agents.

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Novel Bisphosphonates Derived from 1H‐Indazole, 1H‐Pyrazolo[3,4‐b]Pyridine, and 1H‐Pyrazolo[3,4‐b]Quinoline

Abstract: ABSTRACT:Novel tetraethyl ethylene-1,1-bisphosphonate esters derived from 1H-indazole, 1H-pyrazolo[3,4-b]pyridine, and 1H-pyrazolo[3,4-b]

Cited by 7 publications

References 39 publications

Highly Efficient Synthesis of N 1-Substituted 1H-Indazoles by DBU-Catalyzed Aza-Michael Reaction of Indazole with Enones

Highly Efficient Synthesis of N 1-Substituted 1H-Indazoles by DBU-Catalyzed Aza-Michael Reaction of Indazole with Enones

Chiral Magnesium(II) Complex‐Catalyzed Enantioselective Desymmetrization of meso‐Aziridines with Pyrazoles

One‐Pot Microwave‐Assisted Synthesis, in Vitro Anti‐inflammatory Evaluation and Computer‐Aided Molecular Design of Novel Sulfamide‐Containing Bisphosphonates Derivatives

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