Synthesis of α,α‐Difluoro‐β‐amino Esters or <i>gem</i>‐Difluoro‐β‐lactams as Potential Metallocarboxypeptidase Inhibitors

Boyer, Nicole; Gloanec, Philippe; Nanteuil, Guillaume De; Jubault, Philippe; Quirion, J.‐C.

doi:10.1002/ejoc.200800363

Cited by 35 publications

(16 citation statements)

References 123 publications

(31 reference statements)

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“…H NMR (CDCl 3 , 400 MHz) δ 3.45 (d, J = 5.9 Hz, 2H), 3.08 (m, 2H), 2.59 (dt, J = 12.0 Hz, J = 3.0 Hz, 2H), 1.96 (br s, 1H), 1.71 (m, 2H), 1.60-1.55 (m, 1H), 1.17-1.07 (m, 2H); 13 C NMR (CDCl 3 , 100 MHz) δ 66.9, 45.9 (2C), 38.8, 29.7 (2C); IR (neat, cm -1 )  3369 , 2923, 2855, 1636, 1531, 1425, 1266, 1036. Spectral and analytical data matched with literature 46. …”

mentioning

confidence: 58%

Novel multi target-directed ligands targeting 5-HT4 receptors with in cellulo antioxidant properties as promising leads in Alzheimer's disease

Lanthier

Payan

Liparulo

et al. 2019

European Journal of Medicinal Chemistry

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confidence: 58%

Novel multi target-directed ligands targeting 5-HT4 receptors with in cellulo antioxidant properties as promising leads in Alzheimer's disease

Lanthier

Payan

Liparulo

et al. 2019

European Journal of Medicinal Chemistry

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“…Fortunately, the optimisation of this reaction using four equivalent of oxalyl chloride in dry chloroform successfully completed the conversion. 34 The 1 H NMR spectrum produced by the acid chloride 2.1.8 was consistent with the literature. 34 The Due to the unstable nature of the acid chlorides 2.1.8 -2.1.10, these compounds were used directly in the next reaction without further purification.…”

Section: 4supporting

confidence: 86%

“…34 The 1 H NMR spectrum produced by the acid chloride 2.1.8 was consistent with the literature. 34 The Due to the unstable nature of the acid chlorides 2.1.8 -2.1.10, these compounds were used directly in the next reaction without further purification. The reactions to form amide bonds were based on the method reported by Bodanszky et al 30 were successful in synthesising the coupled compound Therefore, another coupling reaction method, HBTU coupling was proposed to form the amide bond and synthesise the coupled compounds.…”

Section: 4supporting

confidence: 86%

Design, Synthesis and Testing of Novel Classes of Inhibitors Against Metallo-β-lactamases: Towards Drug Leads to Combat Antibiotic Resistance

Yusof¹

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Overprescription of antibiotics is one of the causes of the increasing incidence of antibiotic resistance. Bacteria are constantly evolving and able to develop resistance to new antibiotics by producing β-lactamases, thus causing the standard treatments to be ineffective. Furthermore, genes for antibiotic resistance can be transferred between unrelated species. β-Lactamases are classified into serine-β-lactamases (SBLs) and metallo-β-lactamases (MBLs). Clavulanic acid is a well-known inhibitor that can effectively inhibit serine β-lactamases (SBLs). Nonetheless, society is in urgent In this research, novel inhibitors against IMP-1 MBL were designed based on the excellent competitive inhibition properties of L-captopril and D-captopril, compound RS-4.2, and compound 5.1. Modelling studies were done by docking these newly designed molecules into IMP-1 enzyme (PDB code: 1JJT) using Molegro Virtual Docker (MVD) software. Thiolate group of the designed compounds was predicted to bind to both zinc ions and the carboxylate and amide carbonyl groups of the compounds were predicted to form hydrogen bond or electrostatic interactions with the amino acid residues of the IMP-1 active site. Due to these favourable interactions, the MVD software predicted that the designed compounds would have high inhibition potencies against the enzyme.Syntheses of the designed molecules were completed via esterification of the starting materials, coupling reaction and lastly hydrolysis to remove both methyl ester and thioester. Eight series of compounds were synthesised including L-and D-proline derivatives (thiols and dicarboxylic acids), D-captopril derivatives, pipecolinic acid derivatives, phenylglycine derivatives, 2-aminopyridine derivatives, 2-amino-6-picolinic acid derivatives and diaminobenzoic acid derivatives. All of the

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“…Boyer 等 [33,34] 叠氮化合物对 α,β-不饱和羧酸的 Michael 加成反应广泛地应用于 β-氨基酸的合成. Pang 等研究人员采用此方法合成 α-三氟甲基-β-氨基酸 [38] .…”

Section: Methodsunclassified

Recent Developments in the Synthesis of Fluorine-Containingβ-Amino Acids andβ-Lactams

林岱宗¹,

王江²,

柳红³

2013

Chin. J. Org. Chem.

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Fluorine-containing β-amino acids and β-lactams have attracted appreciable attention due to their wide application in organic chemistry, drug discovery, and protein biology. Accordingly, the development of efficient synthetic methods is of considerable interest in academia and industry. The synthesis and resolution are achieved. This review briefly summarizes the recent development in the methodologies for the synthesis of fluorine-containing β-amino acids and β-lactams with classification by the species of the fluorine-containing β-amino acids (α-fluorinated β-amino acids, α-trifluoromethyl β-amino acids, and β-trifluoromethyl β-amino acids). Keywords fluorine-containing β-amino acid; fluorine-containing β-lactam; synthesis β-氨基酸在天然产物、有机合成研究和生物医药等领域具有广泛应用. 氟原子以其独特的理化性质及其在药物研发中的应用吸引着研究者的目光 [1]. 近些年, 含氟小分子在药物化学研究中的比重持续增加 [2,3] , 将氟原子引入 β-氨基酸结构中而得到的含氟 β-氨基酸已成为小分子药物合成中的重要结构片段, 深受研究人员重视 [4～7] .

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Synthesis of α,α‐Difluoro‐β‐amino Esters or gem‐Difluoro‐β‐lactams as Potential Metallocarboxypeptidase Inhibitors

Cited by 35 publications

References 123 publications

Novel multi target-directed ligands targeting 5-HT4 receptors with in cellulo antioxidant properties as promising leads in Alzheimer's disease

Novel multi target-directed ligands targeting 5-HT4 receptors with in cellulo antioxidant properties as promising leads in Alzheimer's disease

Design, Synthesis and Testing of Novel Classes of Inhibitors Against Metallo-β-lactamases: Towards Drug Leads to Combat Antibiotic Resistance

Recent Developments in the Synthesis of Fluorine-Containingβ-Amino Acids andβ-Lactams

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