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ChemDigest – Basic bits and bolts of chemistry

Research progress of piperazine and morpholine derivatives in the discovery of agricultural chemicals

Par / 31 mai 2023 / heterocycles
Research progress of piperazine and morpholine derivatives in the discovery of agricultural chemicals

This work reviews the research progress of piperazine and morpholine derivatives in the discovery of agricultural chemicals, and discusses the structure–activity relationship and mechanism of action.

Abstract

Piperazine and morpholine are important heterocyclic structures, which are widely used in the discovery of agrochemicals. Piperazine and morpholine rings are often used as active substructures or bridges to design and synthesize new agrochemicals. In the past decade, piperazine and morpholine compounds have made rapid progress in the research and development of new pesticides, especially in the discovery of fungicides and antibacterial agents. In the future, more piperazine and morpholine pesticides may be commercialized. However, there is no comprehensive review on the use of piperazine and morpholine derivatives in the creation of new agrochemicals. Therefore, we systematically reviewed the application of piperazine and morpholine active compounds in the creation of new pesticides in the past 12 years. This paper not only summarizes the biological activities of piperazine and morpholine compounds, but also discusses the structure–activity relationship, physiological and biochemical changes, and mechanism of action. This work aims to provide inspiration and ideas for the discovery of new agrochemicals of piperazine and morpholine.

Synthesis and Structure–Activity Relationship Studies of C(13)‐Desmethylene‐(−)‐Zampanolide Analogs

Par / 30 mai 2023 / Non classé
Synthesis and Structure–Activity Relationship Studies of C(13)-Desmethylene-(−)-Zampanolide Analogs

The sponge-derived, highly unsaturated marine macrolide (−)-zampanolide is a potent antimitotic agent and cancer cell growth inhibitor. By using a convergent synthetic approach, the shown series of partially reduced and/or demethylated analogs were obtained. Depending on the site of modification, these compounds show a range of microtubule-binding affinities and cellular activities, thus providing new insights into the relative importance of specific double bonds and methyl groups for biological activity. More information can be found in the Research Article by K.-H. Altmann and co-workers (DOI: 10.1002/chem.202300703).

Wiley: Chemistry – A European Journal: Table of Contents
Authors: Tobias M. Brütsch, Etienne Cotter, Daniel Lucena‐Agell, Mariano Redondo‐Horcajo, Carolina Davies, Bernhard Pfeiffer, Sandro Pagani, Simone Berardozzi, J. Fernando Díaz, John H. Miller, Karl‐Heinz Altmann
chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202301652

Antitumor Activity and Reductive Stress by Platinum(II) N‐Heterocyclic Carbenes based on Guanosine

Par / 30 mai 2023 / Non classé
Antitumor Activity and Reductive Stress by Platinum(II) N-Heterocyclic Carbenes based on Guanosine**

Platinum(II) complexes bearing NHCs based on guanosine undergo a substantial increase in antiproliferative activity when changing the ligand trans to the NHC from bromide to hydride. Compound 6 leads to an increase in reductive stress and increase in glutathione levels in cancer cells but not in non-cancer cells.

Abstract

Platinum(II) complexes bearing N-heterocyclic carbenes based guanosine and caffeine have been synthesized by unassisted C−H oxidative addition, leading to the corresponding trans-hydride complexes. Platinum guanosine derivatives bearing triflate as counterion or bromide instead of hydride as co-ligand were also synthesized to facilitate correlation between structure and activity. The hydride compounds show high antiproliferative activity against all cell lines (TC-71, MV-4-11, U-937 and A-172). Methyl Guanosine complex 3, bearing a hydride ligand, is up to 30 times more active than compound 4, with a bromide in the same position. Changing the counterion has no significant effect in antiproliferative activity. Increasing bulkiness at N7, with an isopropyl group (compound 6), allows to maintain the antiproliferative activity while decreasing toxicity for non-cancer cells. Compound 6 leads to an increase in endoplasmic reticulum and autophagy markers on TC71 and MV-4-11 cancer cells, induces reductive stress and increases glutathione levels in cancer cells but not in non-cancer cell line HEK-293.

Wiley: Chemistry – A European Journal: Table of Contents
Authors: Maria Inês P. S. Leitão, Maria Turos‐Cabal, Ana Maria Sanchez‐Sanchez, Clara S. B. Gomes, Federico Herrera, Vanesa Martin, Ana Petronilho
chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202301078

Pnictogen Interactions with Nitrogen Acceptors

Par / 30 mai 2023 / Non classé
Pnictogen Interactions with Nitrogen Acceptors

Molecular rotors were designed to experimentally measure the transition state stabilizing abilities of nitrogen pnictogen interactions. The rotors formed intramolecular C=O⋅⋅⋅N interactions in the bond rotation transition states. Many common nitrogen functional groups were observed to form stabilizing interactions including amides, imines, and nitro groups.

Abstract

Stabilizing nitrogen pnictogen bond interactions were measured using molecular rotors. Intramolecular C=O⋅⋅⋅N interactions were formed in the bond rotation transition states which lowered the rotational barriers and increased the rates of rotation, as measured by EXSY NMR. The pnictogen interaction energies show a very strong correlation with the positive electrostatic potential on nitrogen, which was consistent with a strong electrostatic component. In contrast, the NBO perturbation and pyramidalization analyses show no correlation, suggesting that the orbital-orbital component is minor. The strongest C=O⋅⋅⋅N pnictogen interactions were comparable to C=O⋅⋅⋅C=O interactions and were stronger than C=O⋅⋅⋅Ph interactions, when measured using the same N-phenylimide rotor system. The ability of the nitrogen pnictogen interactions to stabilize transition states and enhance kinetic processes demonstrates their potential in catalysis and reaction design.

Wiley: Angewandte Chemie International Edition: Table of Contents
Authors: Binzhou Lin, Hao Liu, Ishwor Karki, Erik C. Vik, Mark D. Smith, Perry J. Pellechia, Ken D. Shimizu
onlinelibrary.wiley.com/doi/10.1002/anie.202304960

Three‐component synthesis of arene‐linked pyrazolo[1,5‐a]pyrimidines

Par / 30 mai 2023 / heterocycles
Three-component synthesis of arene-linked pyrazolo[1,5-a]pyrimidines

A regioselective method was conducted to synthesize two new series of arene-linked pyrazolo[1,5-a]pyrimidines in good yields.

Abstract

In this study, we aimed to establish an efficient method for synthesizing two new series of arene-linked pyrazolo[1,5-a]pyrimidines. This was achieved by reacting 1H-pyrazole-3,5-diamines with the respective acetophenones and benzaldehydes in a 1:1:1 ratio. To optimize this three-component reaction, various bases, and solvents were investigated. Use of two equivalents of KOH in ethanol at reflux for 4–6 h resulted in 89%–96% yields of the desired products. Structure of new products was elucidated by considering their elemental and spectral data.

TMPRSS2 Inhibitor Discovery Facilitated through an In Silico and Biochemical Screening Platform

Par / 30 mai 2023 / medchem

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ACS Medicinal Chemistry Letters

ACS Medicinal Chemistry Letters: Latest Articles (ACS Publications)
Authors: Amanda L. Peiffer, Julie M. Garlick, Yujin Wu, Jesse W. Wotring, Sahil Arora, Alexander S. Harmata, Daniel A. Bochar, Corey J. Stephenson, Matthew B. Soellner, Jonathan Z. Sexton, Charles L. Brooks, III, and Anna K. Mapp
dx.doi.org/http://dx.doi.org/10.1021/acsmedchemlett.3c00035

Wavy Graphene-Like Network Forming during Pyrolysis of Polyacrylonitrile into Carbon Fiber

Par / 30 mai 2023 / Non classé

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Journal of the American Chemical Society

Journal of the American Chemical Society: Latest Articles (ACS Publications)
Authors: Toru Ishikawa, Fumihiko Tanaka, Kosuke Kurushima, Akira Yasuhara, Ryusuke Sagawa, Tatsuya Fujita, Ryohei Yonesaki, Katsuhiko Iseki, Takayuki Nakamuro, Koji Harano, and Eiichi Nakamura
dx.doi.org/https://doi.org/10.1021/jacs.3c02504

PINK1-Dependent Mitophagy Inhibits Elevated Ubiquitin Phosphorylation Caused by Mitochondrial Damage

Par / 30 mai 2023 / medchem

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Journal of Medicinal Chemistry

Journal of Medicinal Chemistry: Latest Articles (ACS Publications)
Authors: Olivia A. Lambourne, Shane Bell, Léa P. Wilhelm, Erika B. Yarbrough, Gabriel G. Holly, Oliver M. Russell, Arwa M. Alghamdi, Azeza M. Fdel, Carmine Varricchio, Emma L. Lane, Ian G. Ganley, Arwyn T. Jones, Matthew S. Goldberg, and Youcef Mehellou
dx.doi.org/http://dx.doi.org/10.1021/acs.jmedchem.3c00555

Synergy of Single Atoms and Lewis Acid Sites for Efficient and Selective Lignin Disassembly into Monolignol Derivatives

Par / 30 mai 2023 / Non classé

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Journal of the American Chemical Society

Journal of the American Chemical Society: Latest Articles (ACS Publications)
Authors: Ge Meng, Wu Lan, Lilong Zhang, Shibin Wang, Tanhao Zhang, Shuo Zhang, Ming Xu, Yu Wang, Jian Zhang, Fengxia Yue, Yulong Wu, and Dingsheng Wang
dx.doi.org/https://doi.org/10.1021/jacs.3c04028

Approaches and Considerations for the Investigation and Synthesis of N‑Nitrosamine Drug Substance-Related Impurities (NDSRIs)

Par / 30 mai 2023 / Non classé

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Organic Process Research & Development
Organic Process Research & Development: Latest Articles (ACS Publications)

Authors: Ian W. Ashworth, Alexander Blanazs, Jonathan J. Byrne, Olivier Dirat, Jared W. Fennell, Nadine Kuhl, Stuart L. Wells, and Matthew P. Whiting
dx.doi.org/https://doi.org/10.1021/acs.oprd.3c00084