β‐Lactam Preparation via Staudinger Reaction with Activated Dimethylsulfoxide

Zarei, Maaroof

doi:10.1002/jhet.2685

Cited by 9 publications

(1 citation statement)

References 56 publications

(17 reference statements)

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“…The syntheses of racemic cis - and trans -oriented azetidine urea derivatives 3 and 4 are shown in Scheme . Reaction of imine 14 with 2-(1,3-dioxoisoindolin-2-yl)acetyl chloride in the presence of triethylamine gave 15 as the mixture of cis and trans isomers. Removal of the 4-methoxyphenyl group of 15 with cerium(IV) ammonium nitrate (CAN) provided cis isomer 16 .…”

Section: Chemistrymentioning

confidence: 99%

Discovery of BMS-986235/LAR-1219: A Potent Formyl Peptide Receptor 2 (FPR2) Selective Agonist for the Prevention of Heart Failure

Asahina¹,

Wurtz

K³

et al. 2020

J. Med. Chem.

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Formyl peptide receptor 2 (FPR2) agonists can stimulate resolution of inflammation and may have utility for treatment of diseases caused by chronic inflammation, including heart failure. We report the discovery of a potent and selective FPR2 agonist and its evaluation in a mouse heart failure model. A simple linear urea with moderate agonist activity served as the starting point for optimization. Introduction of a pyrrolidinone core accessed a rigid conformation that produced potent FPR2 and FPR1 agonists. Optimization of lactam substituents led to the discovery of the FPR2 selective agonist 13c, BMS-986235/LAR-1219. In cellular assays 13c inhibited neutrophil chemotaxis and stimulated macrophage phagocytosis, key end points to promote resolution of inflammation. Cardiac structure and functional improvements were observed in a mouse heart failure model following treatment with BMS-986235/LAR-1219.

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Section: Chemistrymentioning

confidence: 99%

Discovery of BMS-986235/LAR-1219: A Potent Formyl Peptide Receptor 2 (FPR2) Selective Agonist for the Prevention of Heart Failure

Asahina¹,

Wurtz

K³

et al. 2020

J. Med. Chem.

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

Omidvari

Zarei

2018

Journal of Heterocyclic Chem

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The first synthesis of 3‐phenothiazine‐β‐lactams is herein reported. Thirteen new derivatives of β‐lactams were synthesized using various Schiff bases and (phenothiazin‐10‐yl)acetic acid, which in turn was prepared starting from phenothiazine. The sole product of the Staudinger ketene–imine [2 + 2] cycloaddition reaction is the trans‐β‐lactam. All the synthesized compounds were characterized by elemental analyses and spectral (IR, 1H‐NMR, and 13C‐NMR) data.

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Organocatalyzed Annulation Cascade toward Asymmetric Functionalization of Dibenzoxazepines and Dibenzothiazepines with Vicinal Tertiary Stereogenic Centers

2019

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An efficient organocatalyzed annulation cascade has been established for the stereoselective functionalization of dibenzoxazepine and dibenzothiazepine scaffolds. The protocol used ready‐stock proline as a catalyst and a variety biologically important oxa/thiazepine based polycyclic frameworks featuring congested chiral vicinal tertiary centers were obtained in high yields and excellent diastereoselectivities (>20:1 dr) and enantioselectivities (>96:4 er). Synthetic utility was showcased through the gram‐scale reaction and diverse derivatization sequences.

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β‐Lactam Preparation via Staudinger Reaction with Activated Dimethylsulfoxide

Cited by 9 publications

References 56 publications

Discovery of BMS-986235/LAR-1219: A Potent Formyl Peptide Receptor 2 (FPR2) Selective Agonist for the Prevention of Heart Failure

Discovery of BMS-986235/LAR-1219: A Potent Formyl Peptide Receptor 2 (FPR2) Selective Agonist for the Prevention of Heart Failure

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

Organocatalyzed Annulation Cascade toward Asymmetric Functionalization of Dibenzoxazepines and Dibenzothiazepines with Vicinal Tertiary Stereogenic Centers

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