Microwave-assisted synthesis of 3'-indolyl substituted 4H-chromenes catalyzed by DMAP and their antimicrobial activity

被引：63

作者：

Kathrotiya, Harshad G. ^{[1
]}

Patel, Manish P. ^{[1
]}

机构：

[1] Sardar Patel Univ, Dept Chem, Vallabh Vidyanagar 388120, Gujarat, India

来源：

MEDICINAL CHEMISTRY RESEARCH | 2012年 / 21卷 / 11期

关键词：

4H-Chromene; Indole; DMAP; Microwave irradiation; MCR; In vitro antimicrobial activity; ONE-POT SYNTHESIS; IN-VITRO; ANTIBACTERIAL ACTIVITY; CHROMENE DERIVATIVES; BIOLOGICAL-ACTIVITY; ANTIOXIDANT; BENZIMIDAZOLES; IRRADIATION; INDOLES; BEARING;

D O I：

10.1007/s00044-011-9861-4

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new series of indole-based chromene derivatives 4a-4p has been synthesized by one pot cyclocondensation reaction of 2-phenyl-1H-indole-3-carbaldehyde 1a-1h; malononitrile 2; and 1,3-cyclohexanedione/dimedone 3a/b under microwave irradiation catalyzed by an organocatalyst 4-(N,N-dimethylamino) pyridine. Easy experimental procedure, high yield, selectivity, and shorter reaction time are the imperative features of this method. All the compounds were screened against a representative panel of bacteria and fungi. Some of the compounds are found to be equipotent or more potent than that of standard drugs as evident from SAR study.

引用

页码：3406 / 3416

页数：11

共 57 条

[1] Synthesis of substituted indole derivatives as a new class of antimalarial agents [J].

Agarwal, A ;

Srivastava, K ;

Puri, SK ;

Chauhan, PMS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (12) :3133-3136

[2] Potent antimicrobial activity of 3-(4,5-diaryl-1H-imidazol-2-yl)-1H-indole derivatives against methicillin-resistant Staphylococcus aureus [J].

Al-Qawasmeh, Raed A. ;

Huesca, Mario ;

Nedunuri, Venkata ;

Peralta, Robert ;

Wright, Jim ;

Lee, Yoon ;

Young, Aiping .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (12) :3518-3520

[3]

[Anonymous], 2021, STAND PERF STAND ANT

[4] Synthesis and in vitro anti-HIV activity of N-1,3-benzo[d]thiazol-2-yl-2-(2-oxo-2H-chromen-4-yl)acetamide derivatives using MTT method [J].

Bhavsar, Dhairya ;

Trivedi, Jalpa ;

Parekh, Shrey ;

Savant, Mahesh ;

Thakrar, Shailesh ;

Bavishi, Abhay ;

Radadiya, Ashish ;

Vala, Hardevsinh ;

Lunagariya, Jignesh ;

Parmar, Manisha ;

Paresh, Ladwa ;

Loddo, Roberta ;

Shah, Anamik .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (11) :3443-3446

[5] Novel chromene derivatives as TNF-α inhibitors [J].

Cheng, JF ;

Ishikawa, A ;

Ono, Y ;

Arrhenius, T ;

Nadzan, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (21) :3647-3650

[6] A novel class of selective anti-Helicobacter pylori agents 2-oxo-2H-chromene-3-carboxamide derivatives [J].

Chimenti, Franco ;

Bizzarri, Bruna ;

Bolasco, Adriana ;

Secci, Daniela ;

Chimenti, Paola ;

Carradori, Simone ;

Granese, Arianna ;

Rivanera, Daniela ;

Lilli, Daniela ;

Zicari, Alessandra ;

Scaltrito, M. Maddalena ;

Sisto, Francesca .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (11) :3065-3071

[7] Synthesis and pharmacological in vitro and in vivo evaluations of novel triazole derivatives as ligands of the ghrelin receptor.: 1 [J].

Demange, Luc ;

Boeglin, Damien ;

Moulin, Aline ;

Mousseaux, Delphine ;

Ryan, Joanne ;

Berge, Gilbert ;

Gagne, Didier ;

Heitz, Annie ;

Perrissoud, Daniel ;

Locatelli, Vittorio ;

Torsello, Antonio ;

Galleyrand, Jean-Claude ;

Fehrentz, Jean-Alain ;

Martinez, Jean .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (08) :1939-1957

[8] Synthesis and antiviral evaluation of benzimidazoles, quinoxalines and indoles from dehydroabietic acid [J].

Fonseca, T ;

Gigante, B ;

Marques, MM ;

Gilchrist, TL ;

De Clercq, E .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (01) :103-112

[9] Potential antimalarial activity of indole alkaloids [J].

Frederich, Michel ;

Tits, Monique ;

Angenot, Luc .

TRANSACTIONS OF THE ROYAL SOCIETY OF TROPICAL MEDICINE AND HYGIENE, 2008, 102 (01) :11-19

[10] Quercinol, an anti-inflammatory chromene from the wood-rotting fungus Daedalea quercina (Oak Mazegill) [J].

Gebhardt, P. ;

Dornberger, K. ;

Gollmick, F. A. ;

Graefe, U. ;

Haertl, A. ;

Goerls, H. ;

Schlegel, B. ;

Hertweck, C. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (09) :2558-2560

← 1 2 3 4 5 6 →