In vitro evaluation of the antielastase activity of polycyclic β-lactams

Monleón, Laura M.; Díez-García, Fernando; Zamora, Héctor; Anaya, Josefa; Grande, M.; Diego, Juana Gutiérrez de; Rodríguez, Fernando Mateos

doi:10.1016/j.bioorg.2012.08.001

Cited by 8 publications

(6 citation statements)

References 72 publications

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“…The β-lactam carbonyl of the tricylic β-lactam 12 a showed a strong absorption at 1790 cm À 1 in IR spectrum due to stretching of carbonyl group. In the proton-decoupled 13 C NMR spectrum of 12 a, carbonyl carbon of the β-lactam ring appeared at δ 164.6 and 163.0 ppm for the major and the minor diastereomers respectively. The cyclization reaction of the bicyclic dichloro-β-lactam 11 a occurred in a highly regioselective manner by 5-exo-trig cyclization mode.…”

Section: Synthesis Of Another Series Of Differently Fusedtricyclic β-mentioning

confidence: 99%

“…The supporting information is available that contains all the experimental procedures and characterization data, copies of 1 H NMR, 13 C NMR spectra of all compounds, COSY NMR spectra of 7 a and 12 a, ORTEP diagram and stereostructure of 6 a and 11 d and crystallographic data of 6 a, 7 a, 11 d, 12 b and 12 h.…”

Section: Supplementary Information Summarymentioning

confidence: 99%

“…[7a] Some tricyclic β-lactams acted as inhibitors of β-lactamases [10][11][12] and other medicinally relevant mammalian enzymes implicated in many diseases. [13,14] Thus, tricyclic β-lactams constituted a new generation of β-lactam antibiotics which are resistant to a wide range of β-lactamases and exhibit improved metabolic stability.…”

Section: Introductionmentioning

confidence: 99%

“…Few more structural analogs of sanfetrinem were synthesized and are known to possess a broad spectrum of antibacterial activities . Some tricyclic β‐lactams acted as inhibitors of β‐lactamases and other medicinally relevant mammalian enzymes implicated in many diseases . Thus, tricyclic β‐lactams constituted a new generation of β‐lactam antibiotics which are resistant to a wide range of β‐lactamases and exhibit improved metabolic stability.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Chlorinated, Heteroatom‐Rich and Differently Fused Tricyclic β‐Lactams by Cu(I)‐Catalyzed Halogen Atom Transfer Radical Cyclization

Dawra¹,

Ram

Thakur

2020

ChemistrySelect

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The application of Cu (I)-catalyzed halogen atom transfer radical cyclization (ATRC) for the synthesis of two different series of chlorinated, heteroatom rich and differently fused tricyclic β-lactams has been demonstrated. N-substituted-3,4dihydropyrimidine-2(1H)-thiones synthesized by Biginelli reaction were used as starting materials for this synthetic pathway which upon S-allylation/alkylation furnished 2-allylthio/alkylthio-1,4-dihydropyrimidines (cyclic imines). Staudinger reaction of these cyclic imines with dichloroketene was employed to obtain the bicyclic dichloro-S-allyl/N-allyl-β-lactams, which upon subsequent Cu(I)-catalyzed ATRC produced two different series of tricyclic β-lactams. The difference in the relative behavior of N-allyl bicyclic dichloro-β-lactams and S-allyl bicyclic dichloro-β-lactams towards ATRC was also introspected in terms of their relative rates of cyclization, the amount of catalyst loading needed and the stabilities of tricyclic-β-lactams obtained after cyclization. To study the relative reactivity of Nallyl group and S-allyl group towards ATRC, the bicyclic dichloro-β-lactams having both S-allyl and N-allyl groups were synthesized. The intramolecular competitive experiments revealed the high reactivity of S-allyl group towards ATRC than the N-allyl group.[a] Dr. N. DawraMehr Chand Mahajan DAV College for Women Sector 36-A, Chandigarh,

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Section: Synthesis Of Another Series Of Differently Fusedtricyclic β-mentioning

confidence: 99%

Section: Supplementary Information Summarymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Chlorinated, Heteroatom‐Rich and Differently Fused Tricyclic β‐Lactams by Cu(I)‐Catalyzed Halogen Atom Transfer Radical Cyclization

Dawra¹,

Ram

Thakur

2020

ChemistrySelect

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“…Heterocyclic compounds containing [a]-fused-tetrahydro-1benzazepine systems are very important structural motifs in medicinal chemistry and such systems are often present in compounds having significant pharmacological properties (Piao et al, 2011;Monleó n et al, 2012;Zhang et al, 2012;Schmees et al, 2014). However, among [a]-fused-tetrahydro-1benzazepine heterocycles, the hexahydrobenzo[f]pyrazino-[1,2-a]azepine-1,4-diones have been very little explored and, to date, only two reports describing both the preparation and (Casara et al, 2008;Wang et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

A concise and versatile route to tetrahydro-1-benzazepines carrying [a]-fused heterocyclic units: synthetic sequence and spectroscopic characterization, and the molecular and supramolecular structures of one intermediate and two products

et al. 2019

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A concise, efficient and versatile route from simple starting materials to tricyclic tetrahydro‐1‐benzazepines carrying [a]‐fused heterocyclic units is reported. Thus, the easily accessible methyl 2‐[(2‐allyl‐4‐chlorophenyl)amino]acetate, (I), was converted, via (2RS,4SR)‐7‐chloro‐2,3,4,5‐tetrahydro‐1,4‐epoxy‐1‐benzo[b]azepine‐2‐carboxylate, (II), to the key intermediate methyl (2RS,4SR)‐7‐chloro‐4‐hydroxy‐2,3,4,5‐tetrahydro‐1H‐benzo[b]azepine‐2‐carboxylate, (III). Chloroacetylation of (III) provided the two regioisomers methyl (2RS,4SR)‐7‐chloro‐1‐(2‐chloroacetyl)‐4‐hydroxy‐2,3,4,5‐tetrahydro‐1H‐benzo[b]azepine‐2‐carboxylate, (IVa), and methyl (2RS,4SR)‐7‐chloro‐4‐(2‐chloroacetoxy)‐2,3,4,5‐tetrahydro‐1H‐benzo[b]azepine‐2‐carboxylate, C14H15Cl2NO4, (IVb), as the major and minor products, respectively, and further reaction of (IVa) with aminoethanol gave the tricyclic target compound (4aRS,6SR)‐9‐chloro‐6‐hydroxy‐3‐(2‐hydroxyethyl)‐2,3,4a,5,6,7‐hexahydrobenzo[f]pyrazino[1,2‐a]azepine‐1,4‐dione, C15H17ClN2O4, (V). Reaction of ester (III) with hydrazine hydrate gave the corresponding carbohydrazide (VI), which, with trimethoxymethane, gave a second tricyclic target product, (4aRS,6SR)‐9‐chloro‐6‐hydroxy‐4a,5,6,7‐tetrahydrobenzo[f][1,2,4]triazino[4,5‐a]azepin‐4(3H)‐one, C12H12ClN3O2, (VII). Full spectroscopic characterization (IR, 1H and 13C NMR, and mass spectrometry) is reported for each of compounds (I)–(III), (IVa), (IVb) and (V)–(VII), along with the molecular and supramolecular structures of (IVb), (V) and (VII). In each of (IVb), (V) and (VII), the azepine ring adopts a chair conformation and the six‐membered heterocyclic rings in (V) and (VII) adopt approximate boat forms. The molecules in (IVb), (V) and (VII) are linked, in each case, into complex hydrogen‐bonded sheets, but these sheets all contain a different range of hydrogen‐bond types: N—H…O, C—H…O, C—H…N and C—H…π(arene) in (IVb), multiple C—H…O hydrogen bonds in (V), and N—H…N, O—H…O, C—H…N, C—H…O and C—H…π(arene) in (VII).

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Ring‐Opening Reactions of Epoxides With Titanium(III) Reagents

RajanBabu¹,

Nugent²,

Halder³

2022

Organic Reactions

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The ring‐opening reactions of epoxides with titanium(III) reagents such as Cp 2 TiCl are critically reviewed, including the scope, limitations, and mechanism of these synthetically useful transformations. The initial reaction proceeds by single‐electron transfer to give a carbon‐centered β‐titanoxy radical. The resulting radical can be terminated by a number of different reaction pathways, including epoxide deoxygenation, reduction to the alcohol, intermolecular addition to activated olefins, and intramolecular addition (cyclization). The literature is surveyed from the first reported examples in 1988 through October, 2021.

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In vitro evaluation of the antielastase activity of polycyclic β-lactams

Cited by 8 publications

References 72 publications

Synthesis of Chlorinated, Heteroatom‐Rich and Differently Fused Tricyclic β‐Lactams by Cu(I)‐Catalyzed Halogen Atom Transfer Radical Cyclization

Synthesis of Chlorinated, Heteroatom‐Rich and Differently Fused Tricyclic β‐Lactams by Cu(I)‐Catalyzed Halogen Atom Transfer Radical Cyclization

A concise and versatile route to tetrahydro-1-benzazepines carrying [a]-fused heterocyclic units: synthetic sequence and spectroscopic characterization, and the molecular and supramolecular structures of one intermediate and two products

Ring‐Opening Reactions of Epoxides With Titanium(III) Reagents

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