Ana Milián

Universidad de Alcalá

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Trends

Author Order

Document Type

Co-Authors

Manuel A. Fernández‐Rodríguez

Universidad de Alcalá

Juan J. Vaquero

Universidad de Alcalá

Patricia García‐García

Universidad de Alcalá

Roberto Sanz

Universidad de Burgos

Estı́baliz Merino

Instituto Ramón y Cajal de Investigación Sanitaria

Adrián Pérez‐Redondo

Universidad de Alcalá

T Jakóbiec

T Zawisza

University School of Physical Education in Wroclaw

DŠ

David Šarlah

Rice University

Jaime Tostado

Universidad de Alcalá

Cooperative Institutions

Universidad de Alcalá

Instituto Ramón y Cajal de Investigación Sanitaria

Universidad Autónoma de Madrid

Instituto de Química Orgánica General

Universidad de Burgos

Hospital Universitario Fundación Jiménez Díaz

Universidad de Oviedo

University of Illinois Urbana-Champaign

Instituto de Química Médica

Spanish Clinical Research Network

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Field

Synthesis of Seven- and Eight-Membered Rings by a Brønsted Acid Catalyzed Cationic Carbocyclization of Biphenyl Embedded Enynes

Organic Letters (2024)

Jaime Tostado Ana Milián Juan J. Vaquero Manuel A. Fernández‐Rodríguez

A Brønsted acid catalyzed cyclization of o-alkenyl-o′-alkynylbiaryls for the synthesis of biologically relevant dibenzo-fused medium-sized rings has been developed. The outcome of the cyclization is determined by the nature of the substituent at the alkyne, with arenes favoring seven-membered rings and alkyl substituents producing eight-membered rings. These reactions proceed via a vinyl cation, which is captured by water and, notably, by C-nucleophiles, such as electron-rich (hetero)arenes.

Cationic polymerization

Alkyne

Biphenyl

Brønsted–Lowry acid–base theory

10.1021/acs.orglett.4c00647

Cite

Citations (1)

Derivatives of 3-p-chlorophenyl-3-oxopropane and 3-p-chlorophenyl-3-hydroxypropane-1-carboxylic acids.

PubMed (1976)

T Jakóbiec Ana Milián T Zawisza

Starting from gamma-chlorophenyltetrahydro- and gamma-chlorophenyldihydro-furan-2-ones (2 and 12), some new amides and hydrazides of the acids mentioned in the title were prepared (Table 1 and 2). Of the obtained compounds the following 10, 14, 15, 17, 20--23 show central depressant action.

Furan

Table (database)

Depressant

Source

Cite

Citations (0)

ChemInform Abstract: PYRIDOTHIAZINES. PART VI. SYNTHESES AND PROPERTIES OF PYRIDO(2,3‐C)‐1,2‐THIAZINE 1,1‐DIOXIDE DERIVATIVES

Chemischer Informationsdienst (1981)

T Zawisza Ana Milián T Jakóbiec

Abstract Ausgangsverbindungen sind die schon beschriebenen Dihydropyridothiazinone (I) und (II).

Thiazine

10.1002/chin.198117249

Cite

Citations (0)

CCDC 2011664: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Ana Milián Patricia García‐García Adrián Pérez‐Redondo Roberto Sanz Juan J. Vaquero

10.5517/ccdc.csd.cc25j9df

Cite

Citations (0)

Identification and study of new NF‐κB‐inducing kinase ligands derived from the imidazolone scaffold

Archiv der Pharmazie (2024)

Francisco Maqueda‐Zelaya Lara Valiño‐Rivas Ana Milián Sara Gutiérrez José Luis Aceña

Abstract Chronic kidney disease (CKD) is a growing health concern, projected to be a major cause of death by 2040, due to an increasing risk of acute kidney injury (AKI). Systems biology‐derived data suggest that the unmet need for an orally available drug to treat AKI and improve CKD outcomes may be addressed by targeting kidney inflammation and, specifically, nuclear factor κB‐inducing kinase (NIK), a key signaling molecule that activates the noncanonical nuclear factor κB (NF‐κB) pathway. We have prepared and identified a small family of imidazolone derivatives that bind NIK and inhibit the noncanonical NF‐κB activation pathway. The introduction of heterocyclic substituents in position 2 of the imidazolone core provides compounds with affinity against human NIK. Three candidates, with best affinity profile, were tested in phenotypic experiments of noncanonical NF‐κB activation, confirming that the derivative bearing the 4‐pyridyl ring can inhibit the processing of NFκB p100 to NFkB2 p52, which is NIK‐dependent in cultured kidney tubular cells. Finally, exhaustive docking calculations combined with molecular dynamics studies led us to propose a theoretical binding mode and rationalize affinity measures, in which the aminopyridine motif is a key anchoring point to the hinge region thanks to several hydrogen bonds and the interaction of heterocyclic rings in position 2 with Ser476 and Lys482. Our result will pave the way for the development of potential drug candidates targeting NIK in the context of CKD.

Docking (animal)

10.1002/ardp.202400614

Cite

Citations (1)

CCDC 2098410: Experimental Crystal Structure Determination

The Cambridge Structural Database (2022)

Ana Milián Manuel A. Fernández‐Rodríguez Estı́baliz Merino Juan J. Vaquero Patricia García‐García

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc28fkny

Cite

Citations (0)

Synthesis of Phenanthrene‐Based Polycycles by Gold(I)‐Catalyzed Cyclization of Biphenyl‐Embedded Trienynes

Advanced Synthesis & Catalysis (2022)

Ana Milián Patricia García‐García Juan J. Vaquero Roberto Sanz Manuel A. Fernández‐Rodríguez

Abstract Gold(I)‐catalyzed cyclization of o ‐alkenyl‐ o’ ‐alkynylbiaryls in the presence of external or internal nucleophiles provides a straightforward access to phenanthrene‐based polycycles, which are of considerable interest in materials science. Thus, their reactions with alcohols yield functionalized dihydrophenanthrenes, in a process that can also be carried out intramolecularly, to provide phenanthrene‐derived heteropolycyclic compounds. Moreover, benzo[ b ]triphenylenes can be synthesized from o ‐methoxyvinyl‐ o’ ‐alkynylbiaryls, in a reaction in which an (hetero)aryl substituent at the triple bond acts as an internal nucleophile. magnified image

Biphenyl

10.1002/adsc.202200887

Cite

Citations (2)

Selective Synthesis of Phenanthrenes and Dihydrophenanthrenes via Gold-Catalyzed Cycloisomerization of Biphenyl Embedded Trienynes

Organic Letters (2020)

Ana Milián Patricia García‐García Adrián Pérez‐Redondo Roberto Sanz Juan J. Vaquero

Readily available o'-alkenyl-o-alkynylbiaryls, a particular type of 1,7-enynes, undergo a selective cycloisomerization reaction in the presence of a gold(I) catalyst to give interesting phenanthrene and dihydrophenanthrene derivatives in high yields. The solvent used provokes a switch in the evolution of the gold intermediate and plays a key role in the reaction outcome.

Cycloisomerization

Phenanthrenes

Biphenyl

10.1021/acs.orglett.0c03067

Cite

Citations (17)

CCDC 2011663: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Ana Milián Patricia García‐García Adrián Pérez‐Redondo Roberto Sanz Juan J. Vaquero

10.5517/ccdc.csd.cc25j9cd

Cite

Citations (0)

Metal‐Free Temperature‐Controlled Regiodivergent Borylative Cyclizations of Enynes: BCl₃‐Promoted Skeletal Rearrangement

Angewandte Chemie International Edition (2022)

Ana Milián Manuel A. Fernández‐Rodríguez Estı́baliz Merino Juan J. Vaquero Patricia García‐García

Metal-free borylative cyclization of biphenyl-embedded 1,3,5-trien-7-ynes in the presence of simple and inexpensive BCl3 provided synthetically useful borylated building blocks. The outcome of the process depends on the reaction temperature, with borylated phenanthrenes obtained at 60 °C and phenanthrene-fused borylated cyclobutanes formed at 0 °C. Based on DFT calculations, a mechanism for these novel transformations has been proposed, which involves an uncommon skeletal rearrangement, including migration of a methyl group and alkyne fragmentation, unprecedented in BCl3 -promoted cyclization reactions.

10.1002/anie.202205651

Cite

Citations (5)