Multicomponent Synthesis of Antibacterial Dihydropyridin and Dihydropyran Embelin Derivatives

被引：28

作者：

Pena, Rosalyn ^{[1
,2
]}

Jimenez-Alonso, Sandra ^{[1
,2
]}

Feresin, Gabriela ^{[3
]}

Tapia, Alejandro ^{[3
]}

Mendez-Alvarez, Sebastian ^{[4
,5
]}

Machin, Felix ^{[2
,5
]}

Ravelo, Angel G. ^{[1
,2
]}

Estevez-Braun, Ana ^{[1
,2
]}

机构：

[1] Univ La Laguna, Dept Quim Organ, Inst Univ Bioorgan Antonio Gonzalez, E-38206 Tenerife, Spain

[2] ICIC, Tenerife 38204, Spain

[3] Univ Nacl San Juan, Inst Ciencias Basicas, Inst Biotecnol, San Juan, Argentina

[4] Univ La Laguna, Dept Microbiol & Biol Celular, Tenerife 38071, Spain

[5] Hosp Univ Nuestra Senora Candelaria, Unidad Invest, Santa Cruz De Tenerife 38010, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 16期

关键词：

EFFICIENT SYNTHESIS; QUINONE METHIDES; ENAMINONES; ANTITUMOR; CELLS;

D O I：

10.1021/jo401189x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of dihydropyran and dihydropyridin embelin derivatives were synthesized through a novel and straightforward one-pot protocol based on a three-component reaction with embelin, aldehydes, and cyclic enaminones as synthetic imputs. The type of substituent on the nitrogen atom of the beta-enaminone is key to obtain nitrogenated or oxygenated rings. The obtained compounds were active against Gram-positive bacteria, including multiresistant Staphylococcus aureus clinical isolates.

引用

页码：7977 / 7985

页数：9

共 45 条

[1] Enaminones as building blocks in heterocyclic syntheses: A new approach to polyfunctionally substituted cyclohexenoazines
Al-Mousawi, S
Abdelkhalik, MM
John, E
Elnagdi, MH
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 40 (04) : 689 - 695
[2] Epidemiology of methicillin-resistant Staphylococcus aureus
Boucher, Helen W.
Corey, G. Ralph
[J]. CLINICAL INFECTIOUS DISEASES, 2008, 46 : S344 - S349
[3] Achyrofuran is an antibacterial agent capable of killing methicillin-resistant vancomycin-intermediate Staphylococcus aureus in the nanomolar range
Casero, Carina
Estevez-Braun, Ana
Ravelo, Angel G.
Demo, Mirta
Mendez-Alvarez, Sebastian
Machin, Felix
[J]. PHYTOMEDICINE, 2013, 20 (02) : 133 - 138
[4] Design, synthesis, and characterization of new embelin derivatives as potent inhibitors of X-linked inhibitor of apoptosis protein
Chen, Jianyong
Nikolovska-Coleska, Zaneta
Wang, Guoping
Qiu, Su
Wang, Shaomeng
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (22) : 5805 - 5808
[5] ANTITUMOR, ANTIINFLAMMATORY AND ANALGESIC PROPERTY OF EMBELIN, A PLANT PRODUCT
CHITRA, M
SUKUMAR, E
SUJA, V
DEVI, CSS
[J]. CHEMOTHERAPY, 1994, 40 (02) : 109 - 113
[6] Sol-gel chemistry in medicinal science
Coradin, T
Boissière, M
Livage, J
[J]. CURRENT MEDICINAL CHEMISTRY, 2006, 13 (01) : 99 - 108
[7] Perspectives on Medicinal Properties of Benzoquinone Compounds
Dandawate, P. R.
Vyas, A. C.
Padhye, S. B.
Singh, M. W.
Baruah, J. B.
[J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2010, 10 (05) : 436 - 454
[8] Elassar A. Z., 2003, TETRAHEDRON, V59, P8643
[9] Bioactive alkyl phenols and embelin from Oxalis erythrorhiza
Feresin, GE
Tapia, A
Sortino, M
Zacchino, S
de Arias, AR
Inchausti, A
Yaluff, G
Rodriguez, J
Theoduloz, C
Schmeda-Hirschmann, G
[J]. JOURNAL OF ETHNOPHARMACOLOGY, 2003, 88 (2-3) : 241 - 247
[10] Ferreira ICFR, 2010, ANTI-CANCER AGENT ME, V10, P424

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