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1.
J Org Chem ; 89(17): 12559-12575, 2024 Sep 06.
Artigo em Inglês | MEDLINE | ID: mdl-39189641

RESUMO

The catalytic atroposelective synthesis of N-N axially chiral indolylamides was established via dynamic kinetic resolution, which makes use of chiral Lewis base-catalyzed asymmetric acylation of N-acylaminoindoles as a new type of platform molecule with anhydrides. By this strategy, a series of N-N axially chiral indolylamides were synthesized in overall good yields (up to 98%) with excellent enantioselectivities (up to 99% ee). Moreover, some of these N-N axially chiral indolylamides display some extent of anticancer activity, which demonstrates their potential application in medicinal chemistry. Therefore, this work has not only provided a new strategy for the synthesis of N-N axially chiral monoaryl indoles but also offered a new member of N-N axially chiral monoaryl indoles with configurational stability and promising application, thereby solving the challenges in atroposelective synthesis and application of N-N axially chiral monoaryl indoles.

2.
Angew Chem Int Ed Engl ; 63(3): e202311053, 2024 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-37917574

RESUMO

With the rapid development of asymmetric catalysis, the demand for the enantioselective synthesis of complex and diverse molecules with different chiral elements is increasing. Owing to the unique features of atropisomerism, the catalytic asymmetric synthesis of atropisomers has attracted a considerable interest from the chemical science community. In particular, introducing additional chiral elements, such as carbon centered chirality, heteroatomic chirality, planar chirality, and helical chirality, into atropisomers provides an opportunity to incorporate new properties into axially chiral compounds, thus expanding the potential applications of atropisomers. Thus, it is important to perform catalytic asymmetric transformations to synthesize atropisomers bearing multiple chiral elements. In spite of challenges in such transformations, in recent years, chemists have devised powerful strategies under asymmetric organocatalysis or metal catalysis, synthesizing a wide range of enantioenriched atropisomers bearing multiple chiral elements. Therefore, the catalytic asymmetric synthesis of atropisomers bearing multiple chiral elements has become an emerging field. This review summarizes the rapid progress in this field and indicates challenges, thereby promoting this field to a new horizon.

3.
Angew Chem Int Ed Engl ; 62(15): e202300419, 2023 Apr 03.
Artigo em Inglês | MEDLINE | ID: mdl-36749711

RESUMO

This study establishes the first organocatalytic enantioselective synthesis of axially chiral N,N'-bisindoles via chiral phosphoric acid-catalyzed formal (3+2) cycloadditions of indole-based enaminones as novel platform molecules with 2,3-diketoesters, where de novo indole-ring formation is involved. Using this new strategy, various axially chiral N,N'-bisindoles were synthesized in good yields and with excellent enantioselectivities (up to 87 % yield and 96 % ee). More importantly, this class of axially chiral N,N'-bisindoles exhibited some degree of cytotoxicity toward cancer cells and was derived into axially chiral phosphine ligands with high catalytic activity. This study provides a new strategy for enantioselective synthesis of axially chiral N,N'-bisindoles using asymmetric organocatalysis and is the first to realize the applications of such scaffolds in medicinal chemistry and asymmetric catalysis.

4.
Angew Chem Int Ed Engl ; 60(5): 2355-2363, 2021 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-33089963

RESUMO

The regio- and enantioselective (3+3) cycloaddition of nitrones with 2-indolylmethanols was accomplished by the cooperative catalysis of hexafluoroisopropanol (HFIP) and chiral phosphoric acid (CPA). Using this approach, a series of indole-fused six-membered heterocycles were synthesized in high yields (up to 98 %), with excellent enantioselectivities (up to 96 % ee) and exclusive regiospecificity. This approach enabled not only the first organocatalytic asymmetric (3+3) cycloaddition of nitrones but also the first C3-nucleophilic asymmetric (3+3) cycloaddition of 2-indolylmethanols. More importantly, theoretical calculations elucidated the role of the cocatalyst HFIP in helping CPA control the reactivity and enantioselectivity of the reaction, demonstrating a new mode of cooperative catalysis.

5.
Chemistry ; 26(68): 15779-15792, 2020 Dec 04.
Artigo em Inglês | MEDLINE | ID: mdl-32364633

RESUMO

Axially chiral indole-based frameworks have been recognized as a class of important five-membered heterobiaryls and developing catalytic asymmetric approaches for constructing these frameworks in an enantioselective manner is highly desirable. In recent years, synthetic chemists have paid much attention to this research field, and rapid developments have occurred. At this point, a range of axially chiral indole-based scaffolds have been constructed via various catalytic asymmetric reactions based on different strategies. Thus, the catalytic asymmetric construction of axially chiral indole-based frameworks has become an emerging area. This minireview summarizes the rapid advances in this field and gives some insights into future developments, which will help this research field to thrive.

6.
J Org Chem ; 84(6): 3214-3222, 2019 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-30777434

RESUMO

A chiral guanidine-catalyzed asymmetric [4 + 1] cyclization of benzofuran-derived azadienes with 3-chlorooxindoles has been established, which constructed chiral spirooxindole frameworks with in situ generation of a five-membered ring with high diastereoselectivities (up to >95:5 dr) and good enantioselectivities (up to 94:6 er). This reaction represents the first catalytic asymmetric [4 + 1] cyclization of benzofuran-derived azadienes, which will enrich the research field of catalytic asymmetric cyclizations of such reactants. In addition, this reaction provides a useful strategy for the enantioselective construction of five-membered ring-based chiral spirooxindole scaffolds.

7.
Org Biomol Chem ; 17(27): 6662-6670, 2019 07 21.
Artigo em Inglês | MEDLINE | ID: mdl-31241110

RESUMO

The first [4 + 2] cyclizations of para-quinone methide derivatives with isocyanates have been established under the catalysis of Brønsted acids or Brønsted bases, which efficiently constructed benzoxazin-2-one frameworks in generally high yields (up to 95%). This reaction will not only enrich the research contents of para-quinone methide-involved cyclization reactions but also provide a useful method for constructing biologically important benzoxazin-2-one frameworks.

8.
Org Lett ; 21(3): 598-602, 2019 02 01.
Artigo em Inglês | MEDLINE | ID: mdl-30645136

RESUMO

A Brønsted acid-catalyzed (4 + 3) cyclization of N, N'-cyclic azomethine imines with isatoic anhydrides has been discovered, which constructs seven-membered nitrogenous heterocyclic frameworks with overall high yields (up to 98% yield). This reaction represents a rarely reported (4 + 3) cyclization of N, N'-cyclic azomethine imines, which involves the reassembly of a C-N bond. In addition, this reaction has also accomplished the unprecedented (4 + 3) cyclization of isatoic anhydrides.

9.
Zhonghua Nan Ke Xue ; 11(2): 116-8, 123, 2005 Feb.
Artigo em Zh | MEDLINE | ID: mdl-15755030

RESUMO

OBJECTIVE: To study the effects of polychlorinated biphenyl (PCB) on bcl-2 and TGFbeta1 expression in rat testes. METHODS: Forty male Wistar rats were divided into 4 groups at random: Group A (normal control), Group B (fed on 10(-8) mol/L PBC), Group C (feb on 10(-7) mol/L) and Group D (feb on 10(-6) mol/L). After three months, all the rats were killed, the animal model established, and observations made on the expression of bcl2 and TGFbeta1 in the rat testis using the optical microscope and immunohistochemical techniques. RESULTS: The damage to the structure of the testis was related to the dosage of PCB: the higher the dodage, the more serious the damage. PCB induced the expression of bcl-2 and TGFbeta1. The TGFbeta1 expression was significantly higher in the highest dosage group than in others (P < 0.01 ), and the bcl-2 expression was dramatically higher in Group C than in other groups (P < 0.01). CONCLUSION: PCB can cause injury in rat testes.


Assuntos
Bifenilos Policlorados/toxicidade , Proteínas Proto-Oncogênicas c-bcl-2/biossíntese , Testículo/efeitos dos fármacos , Testículo/metabolismo , Fator de Crescimento Transformador beta1/biossíntese , Animais , Relação Dose-Resposta a Droga , Masculino , Distribuição Aleatória , Ratos , Ratos Wistar , Testículo/patologia
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