Introduction

Vardanyan, Ruben

doi:10.1016/b978-0-12-805157-3.00001-6

Cited by 14 publications

(11 citation statements)

References 339 publications

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“…Morpholines and piperidines are common core structures of drugs and druglike molecules , that were found to be abundant in our library. For our study, compounds containing a terminal, N-substituted morpholine and piperidine, in particular, were screened for the corresponding neutral loss of a neutral morpholine and piperidine.…”

Section: Resultsmentioning

confidence: 99%

Fragmentation of Polyfunctional Compounds Recorded Using Automated High-Throughput Desorption Electrospray Ionization

Morato

Kaerner

et al. 2021

J. Am. Soc. Mass Spectrom.

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Using desorption electrospray ionization (DESI) as part of an automated high-throughput system, tandem mass spectra of the compounds in a pharmaceutical library were recorded in the positive mode under standardized conditions. Quality control filtering yielded an MS/MS library of 16 662 spectra. Fragmentation of subsets of the compounds in the library chosen to contain a single instance of a particular functional group (amide, piperazine, sulfonamide) was predicted by experts, and the results were compared with the experimental data. Expert performance was good to excellent for all the cases evaluated. Substituents on the functional groups were found to exert important secondary control over the fragmentation, with the main effect observed being product ion stabilization by aromatic substitution, which was consistent across the different groups evaluated. These substituent effects are generally explicable in terms of standard physical organic chemistry considerations of product ion stability as controlling fragmentation. A somewhat unexpected feature was the incidence of homolytic cleavages, driven by the stability of substituted amine radical cations. The findings of this study are intended to lay the groundwork for machine learning approaches to performing MS/ MS spectrum → structure and structure → MS/MS spectrum operations on the same experimental data set. The effort involved and the success achieved in computer-aided interpretation, now underway, will be compared with the expert performance as described here.

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Section: Resultsmentioning

confidence: 99%

Fragmentation of Polyfunctional Compounds Recorded Using Automated High-Throughput Desorption Electrospray Ionization

Morato

Kaerner

et al. 2021

J. Am. Soc. Mass Spectrom.

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“…As one of the most important building blocks in drugs and bioactive alkaloids,31,32 the synthesis of piperidines has drawn significant interest in the past few decades. Compared to traditional ring-closing pathways, catalytic hydrogenation of pyridines provides an atom-/step-efficient strategy to construct piperidines 33. However, there has been only a few examples of hydrogenation of pyridines using homogeneous Rh34 and Ir,35 heterogeneous Rh,36 Pd,37 and Co,38 and metal-free systems,39 as well as the semi-reduction of pyridines,40,41 likely due to strong poisoning effect of pyridines on the catalytic sites.…”

Section: Resultsmentioning

confidence: 99%

Cobalt-bridged secondary building units in a titanium metal–organic framework catalyze cascade reduction of N-heteroarenes

et al. 2019

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“…1–4 Among them, those related to pyrrolidine and piperidine are the most common five- and six-membered aliphatic N-heterocycles. 5–8 Some valuable examples are reported in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%