New N-Mannich bases obtained from isatin and piperazine derivatives: the synthesis and evaluation of antimicrobial activity

被引：21

作者：

Bogdanov, Andrei V. ^{[1
]}

Vazykhova, Al'bina M. ^{[1
]}

Khasiyatullina, Nadezhda R. ^{[1
]}

Krivolapov, Dmitry B. ^{[1
]}

Dobrynin, Alexey B. ^{[1
]}

Voloshina, Alexandra D. ^{[1
]}

Mironov, Vladimir F. ^{[1
]}

机构：

[1] Russian Acad Sci, Kazan Sci Ctr, AE Arbuzov Organ & Phys Chem Inst, 8 Arbuzova St, Kazan 420088, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2016年 / 52卷 / 01期

基金：

俄罗斯基础研究基金会;

关键词：

isatin; piperazines; aminomethylation; antimicrobial activity; Mannich reaction; BREAST CANCER AGENTS; ANTIFUNGAL ACTIVITIES; ANTIBACTERIAL; PEPTIDOMIMETICS; ACYLISATINS; DESIGN;

D O I：

10.1007/s10593-016-1826-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Mannich reaction of isatin with monosubstituted piperazines in the presence of aqueous formaldehyde was used to synthesize new, as well as two previously described derivatives of 1-piperazinomethylisatins, which were further converted to isoindigo derivatives. The antimicrobial activity of the obtained heterocycles was evaluated.

引用

页码：25 / 30

页数：6

共 30 条

[1]

[Anonymous], 1990, ACTA CRYSTALLOGR A

[2]

[Anonymous], 1998, NATL COMMITTEE CLIN

[3] Advances in the synthesis and application of isoindigo derivatives [J].

Bogdanov, Andrei V. ;

Musin, Lenar I. ;

Mironov, Vladimir F. .

ARKIVOC, 2015, :362-392

[4] Novel 1-Aminomethylisatins: Peculiarities of the Synthesis and the Reaction with Tris(diethylamino)phosphine [J].

Bogdanov, Andrei V. ;

Musin, Lenar I. ;

Il'in, Anton V. ;

Mironov, Vladimir F. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (04) :1027-1030

[5] Synthesis of anti-bacterial peptidomimetics derived from N-acylisatins [J].

Cheah, Wai Ching ;

Black, David StC ;

Goh, Wai Kean ;

Kumar, Naresh .

TETRAHEDRON LETTERS, 2008, 49 (18) :2965-2968

[6] Facile ring-opening of N-acylisatins for the development of novel peptidomimetics [J].

Cheah, Wai Ching ;

Wood, Kasey ;

Black, David StC ;

Kumar, Naresh .

TETRAHEDRON, 2011, 67 (39) :7603-7610

[7] Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives [J].

Chiyanzu, I ;

Clarkson, C ;

Smith, PJ ;

Lehman, J ;

Gut, J ;

Rosenthal, PJ ;

Chibale, K .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (09) :3249-3261

[8]

Farrugia L.J., 1997, J. Appl. Crystallogr., V30, P565, DOI DOI 10.1107/S0021889897003117

[9] Synthesis and in vitro antimycobacterial activity of 8-OCH3 ciprofloxacin methylene and ethylene isatin derivatives [J].

Feng, Lian-Shun ;

Liu, Ming-Liang ;

Zhang, Shu ;

Chai, Yun ;

Wang, Bo ;

Zhang, Yi-Bin ;

Lv, Kai ;

Guan, Yan ;

Guo, Hui-Yuan ;

Xiao, Chun-Ling .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (01) :341-348

[10] ANTIBACTERIAL AND ANTIFUNGAL ACTIVITIES OF ISATIN N-MANNICH BASES [J].

KUPINIC, M ;

MEDICSARIC, M ;

MOVRIN, M ;

MAYSINGER, D .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1979, 68 (04) :459-462

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