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1.
Org Biomol Chem ; 22(13): 2678, 2024 Mar 27.
Artigo em Inglês | MEDLINE | ID: mdl-38483197

RESUMO

Correction and removal of expression of concern for 'Total synthesis of tubulysin U and N14-desacetoxytubulysin H' by Bohua Long et al., Org. Biomol. Chem., 2020, 18, 5349-5353, https://doi.org/10.1039/D0OB01109F.

2.
Org Biomol Chem ; 21(28): 5880, 2023 07 19.
Artigo em Inglês | MEDLINE | ID: mdl-37404177

RESUMO

Expression of concern for 'Total synthesis of tubulysin U and N14-desacetoxytubulysin H' by Bohua Long et al., Org. Biomol. Chem., 2020, 18, 5349-5353, https://doi.org/10.1039/D0OB01109F.

3.
Org Biomol Chem ; 21(18): 3906, 2023 May 10.
Artigo em Inglês | MEDLINE | ID: mdl-37115103

RESUMO

Correction for 'Formal synthesis of cyclotheonellazole A' by Bohua Long et al., Org. Biomol. Chem., 2023, https://doi.org/10.1039/d3ob00038a.

4.
Org Biomol Chem ; 21(17): 3531-3536, 2023 05 03.
Artigo em Inglês | MEDLINE | ID: mdl-37039531

RESUMO

A convergent procedure for the formal synthesis of cyclotheonellazole A in high yields and excellent stereoselectivity has been developed. This synthesis features an efficient preparation of O-pivaloyl-protected α-hydroxy-ß-amino amides and a one-pot process to introduce the challenging thiazole moiety. The overall synthesis is very efficient and paves the way for the preparation of analogues for drug development.


Assuntos
Amidas , Desenvolvimento de Medicamentos
5.
Org Biomol Chem ; 18(28): 5349-5353, 2020 07 22.
Artigo em Inglês | MEDLINE | ID: mdl-32643750

RESUMO

A concise and efficient procedure for the total synthesis of tubulysin U and N14-desacetoxytubulysin H has been developed with high stereoselectivity on a gram scale. This synthesis features an elegant cascade one-pot process to install the challenging thiazole moiety and the employment of stereoselective reductions and a series of high-yield mild reactions to ensure the requisite stereochemistry, reaction scale, and yield and to avoid the vexing epimerization occurring during peptide formation.

6.
Org Biomol Chem ; 14(41): 9712-9715, 2016 Oct 18.
Artigo em Inglês | MEDLINE | ID: mdl-27714329

RESUMO

Wewakazole B is a novel cyclodecapeptide with highly potent cytotoxic activity isolated from a sample of M. producens collected from the Red Sea. It contains nine common and three modified amino acid residues. The first total synthesis of Wewakazole B was successfully achieved on a gram scale, unambiguously confirming its structure. Notable features include the careful choice of amino acid-protecting groups and the construction of three different substituted oxazoles present in this natural product.


Assuntos
Peptídeos Cíclicos/síntese química , Técnicas de Química Sintética , Oxazóis/química , Peptídeos Cíclicos/química
8.
RSC Adv ; 13(30): 20407, 2023 Jul 07.
Artigo em Inglês | MEDLINE | ID: mdl-37435387

RESUMO

Expression of concern for 'Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates' by Kehuan Sun et al., RSC Adv., 2019, 9, 32017-32020, https://doi.org/10.1039/C9RA06827A.

9.
RSC Adv ; 9(55): 32017-32020, 2019 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-35530808

RESUMO

A general and practical synthetic process for all the four diastereoisomers of Boc-protected 4-methylproline carboxylates has been developed with essentially complete stereoselectivity on the gram scale, which represents the most diastereoselective preparation of 4-methylproline derivatives to date. This synthesis features an Evans asymmetric alkylation to elegantly establish the challenging stereochemistry of the 4-methyl group, providing valuable insights for the diastereoselective preparation of 4-substituted prolines.

11.
Eur J Med Chem ; 45(3): 1181-8, 2010 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-20053481

RESUMO

The synthesis and structure-activity relationships of a series of new penems bearing ferrocenyl group attached to the C-2 position of the penem nucleus were described. The beta-lactanic derivatives obtained had been characterized as sodium salts, through (1)H NMR and IR, as well as through element analysis. Their in vitro antibacterial activities against both Gram-positive including meticillin-resistant Staphylococcus aureus (MRSA) and Gram-negative bacteria were tested. Most of the penems exhibited superior or equivalent efficacy of antibacterial activity as well as high stability to renal dehydropeptidase-I (DHP-I) compared with faropenem. In particular, the compound 14h having a heterocyclic group showed the most potent antibacterial activity.


Assuntos
Antibacterianos , Ácidos Carboxílicos , Compostos Ferrosos/química , Staphylococcus aureus/efeitos dos fármacos , Antibacterianos/síntese química , Antibacterianos/química , Antibacterianos/farmacologia , Ácidos Carboxílicos/síntese química , Ácidos Carboxílicos/química , Ácidos Carboxílicos/farmacologia , Lactamas/síntese química , Lactamas/química , Lactamas/farmacologia , Espectroscopia de Ressonância Magnética , Metalocenos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Espectroscopia de Luz Próxima ao Infravermelho , Relação Estrutura-Atividade
12.
Eur J Med Chem ; 44(6): 2572-6, 2009 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-19231037

RESUMO

In order to improve biological behavior of the retinoyl derivatives, monoarylferrocenyl alcohols 9a and 9b were synthesized by an improved Suzuki cross-coupling method and their 13-cis-retinoic acid analogues were prepared in moderate to good yields via the Mitsunobu reaction. Their structures were confirmed by IR, (1)H NMR, (13)CNMR, MS spectra and element analysis and their antiproliferative activities were determined in vitro using human cancer cell lines. The results of bioassay showed that these organometallic analogues exhibited higher antiproliferative activities than parent 13-cis-retinoic acid and other retinoyl derivatives.


Assuntos
Isotretinoína , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Desenho de Fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Compostos Ferrosos/síntese química , Compostos Ferrosos/química , Compostos Ferrosos/farmacologia , Humanos , Isotretinoína/análogos & derivados , Isotretinoína/química , Isotretinoína/farmacologia , Estrutura Molecular , Retinoides/síntese química , Retinoides/química , Retinoides/farmacologia , Estereoisomerismo
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