Synthesis of Novel β‐Lactams from Phenothiazin‐10‐ylacetic Acid

Omidvari, Zahra; Zarei, Maaroof

doi:10.1002/jhet.3138

Cited by 13 publications

(5 citation statements)

References 42 publications

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“…The 1 H NMR depicted J = 5.0-5.1 Hz for cisstereoisomers because of coupling constant (J) value of H-3 and H-4, for cis isomer J À3,4 > 4 Hz and trans isomer J À3,4 ≤ 3 Hz. This confirmed the cis geometry of β-lactams synthesized [42][43][44][45]. The 13 C NMR spectra were recorded at a characteristic peak at 161.89-166.35 ppm for β-lactams carbonyl carbon.…”

Section: Resultssupporting

confidence: 67%

Stereoselective synthesis and characterization of monocyclic cis‐β‐lactams containing 5‐methyl‐1,3,4‐thiadiazole‐2‐thiol moiety

Singh

Sharma

2021

Journal of Heterocyclic Chem

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This article describes the stereoselective synthesis of monocyclic cis-β-lactams. The 2-(4-chlorophenoxy)-acetic acid or 2-phenoxy-acetic acid with a carboxylic acid activator 2-ethoxy carbonyl DCPN generate ketene in situ, which reacts with imines derived from substituted tetralone carbaldehyde yielded monocyclic cis-β-lactams having 5-methyl-1,3,4-thiadiazole-2-thiol moiety through[2+2] cyclo-addition reaction (Staudinger reaction). All structures of cisβ-lactams were elucidated by a spectral technique like FT-IR, 1 H and 13 C NMR spectra, HRMS, and single X-ray crystallography. The cis configuration of the β-lactams was determined based on coupling constant (J) value using 1 H NMR for hydrogens H-3 and H-4 of the β-lactams ring. This work presents the synthesis of β-lactams more simply with high yields. The products were simply purified by crystallization technique.

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Section: Resultssupporting

confidence: 67%

Stereoselective synthesis and characterization of monocyclic cis‐β‐lactams containing 5‐methyl‐1,3,4‐thiadiazole‐2‐thiol moiety

Singh

Sharma

2021

Journal of Heterocyclic Chem

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“…In particular, we selected methyl 5-oxomorpholine-2-carboxylate 25 derived by the application of the Castagnoli-Cushman reaction (Dar'in et al, 2015 ) between imine 23 and 1,4-dioxane-2,6-dione ( 24 ), and methyl 5-oxomorpholine-3-carboxylates 28 and 29 , obtained respectively from serine and threonine derivatives 26 - 27 after the acylation with α-bromoacetylbromide and subsequent NaH-mediated intramolecular cyclization reaction (Scheme 4 ). To improve the scaffold complexity and to install quaternary stereocenters on these compounds, we firstly studied the Staudinger reaction (Alcaide et al, 2007 ; Cossío et al, 2008 ; Omidvari and Zarei, 2018 ) with different aromatic imines to generate polycyclic spiro-β-lactams, in agreement with previous studies on 3-aza-6,8-dioxabicyclo[3.2.1]octane bicycles giving compounds 4 (Trabocchi et al, 2007 ). In particular, compounds 28 and 29 were transformed into the more reactive acyl chloride derivatives 30 – 31 in order to generate the intermediate ketene more easily and to avoid the formation of amide by-products (Scheme 4 ).…”

Section: Resultssupporting

confidence: 61%

Diversity-Oriented Synthesis and Chemoinformatic Analysis of the Molecular Diversity of sp3-Rich Morpholine Peptidomimetics

et al. 2018

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Diversity-Oriented Synthesis (DOS) consists of generating structurally diverse compounds from a complexity-generating reaction followed by cyclization steps and appendage diversity. DOS has gathered interest to systematically explore the chemical space by generating high-quality small-molecule collections as probes to investigate biological pathways. The generation of heterocycles using amino acid and sugar derivatives as building blocks is a powerful approach to access chemical and geometrical diversity thanks to the high number of stereocenters and the polyfunctionality of such compounds. Our efforts in this field are focused on the generation of diversity-oriented molecules of peptidomimetic nature as a tool addressing protein-protein interactions, taking advantage of amino acid- and sugar-derived polyfunctional building blocks to be applied in couple-pair synthetic approaches. In this paper, the combination of diversity-oriented synthesis and chemoinformatics analysis of chemical space and molecular diversity of heterocyclic peptidomimetics are reported, with particular interest toward carbohydrate- and amino acid-derived morpholine scaffolds with a higher fraction of sp3 carbon atoms. Also, the chemoinformatic analysis of chemical space and molecular diversity of 186 morpholine peptidomimetics is outlined.

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“…Stereochemical aspects of the synthesized bis-β-lactams were elucidated by 1 H NMR spectra, which showed a coupling constant (J) value, J = 5.3-5.6 Hz, for cis-stereoisomers of H-3 and H-4 in the β-lactams. These values for cis-stereoisomers J 3,4 > 4 Hz and trans isomers J 3,4 ≤ 3 Hz confirmed the cis geometry of the β-lactams [46][47][48][49]. The 13 C NMR spectra revealed characteristic peaks at 161.6-167.1 ppm showing the presence of carbonyl groups in bis-β-lactams.…”

Section: Synthetic Chemistrysupporting

confidence: 57%

Designed synthetic pathway of stereoselective novel monocyclic cis‐bis‐β‐lactams including a 1,3,4‐thiadiazole‐2,5‐dithiol constituent: Antimicrobial activity, molecular docking

Singh

Kumari

Mishra

et al. 2023

Journal of Heterocyclic Chem

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A simple synthetic method has been developed for novel monocyclic bisβ-lactams including a 1,3,4-thiadiazole-2,5-thiol constituent via [2 + 2] cycloaddition reactions, that is, Staudinger reaction (ketene-imine) of acyl chloride and numerous aromatic imines. Easily available starting materials, an easy workup, a simple purification process, no column chromatography needed, and a great yield are specific features of this work. Spectroscopic methods revealed the confirmation of synthesized products. Products were easily purified through a simple crystallization technique. The stereochemistry of bisβ-lactam derivatives at C-3 and C-4 stereocenters was validated by 1 H NMR spectra. All synthesized products exhibited good antimicrobial activities against three Gram-positive bacteria Staphylococcus aureus, Bacillus anthracis, and Clostridium perfringens, and two Gram-negative bacteria Escherichia coli, Brucella abortus. The molecular docking studies were carried out with the target receptor from E. coli, S. aureus, B. anthracis, B. abortus, and C. perfringens of PDB ID: 3T88, 4Q7G, 3Q2O, 4WJM, and 6PV4, respectively, to obtain a moderate binding interaction.

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Synthesis of Novel β‐Lactams from Phenothiazin‐10‐ylacetic Acid

Cited by 13 publications

References 42 publications

Stereoselective synthesis and characterization of monocyclic cis‐β‐lactams containing 5‐methyl‐1,3,4‐thiadiazole‐2‐thiol moiety

Stereoselective synthesis and characterization of monocyclic cis‐β‐lactams containing 5‐methyl‐1,3,4‐thiadiazole‐2‐thiol moiety

Diversity-Oriented Synthesis and Chemoinformatic Analysis of the Molecular Diversity of sp3-Rich Morpholine Peptidomimetics

Designed synthetic pathway of stereoselective novel monocyclic cis‐bis‐β‐lactams including a 1,3,4‐thiadiazole‐2,5‐dithiol constituent: Antimicrobial activity, molecular docking

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