Design, synthesis of novel N prenylated indole-3-carbazones and evaluation of in vitro cytotoxicity and 5-LOX inhibition activities

被引：7
作者：
Choppara, Praveen [1 ]
Prasad, Y. V. [1 ]
Rao, C. V. [2 ]
Krishna, K. Hari [2 ]
Trimoorthulu, G. [2 ]
Rao, G. U. Maheswara [2 ]
Rao, J. Venkateswara [3 ]
Bethu, M. S. [3 ]
Murthy, Y. L. N. [1 ]
机构：
[1] Andhra Univ, Dept Organ Chem Foods Drugs & Water, Visakhapatnam 530003, Andhra Pradesh, India
[2] Laila Impex, Resaearch & Dev Ctr, Vijayawada 520007, India
[3] Indian Inst Chem Technol, Biol Div, Hyderabad 500007, AP, India
来源：
ARABIAN JOURNAL OF CHEMISTRY | 2019年 / 12卷 / 08期
关键词：
Brine shrimp lethality bioassay; Cytotoxicity; 5-Lipoxygenase inhibition; N prenylated indole-3-carbazones; SHRIMP LETHALITY ASSAY; BRINE SHRIMP; ANTIPROLIFERATIVE ACTIVITY; ANTIMYCOBACTERIAL ACTIVITY; RECEPTOR ANTAGONISTS; 5-LIPOXYGENASE; SEMICARBAZONES; DERIVATIVES; DISCOVERY; INDOLES;
D O I：
10.1016/j.arabjc.2015.02.006
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A series of novel N-1 and C-3 substituted indole derivatives (5a-f) were designed, synthesized and evaluated for their cytotoxic properties, viz Brine Shrimp Lethality Bioassay (BSLB) besides 5-Lipoxygenase (5-LOX) inhibitory activities through in vitro assays. Structure Activity Relation (SAR) studies showed that compound 5d with an LC50 of 6.49 mu M and 5c with an IC50 of 33.69 mu M were found to be interesting for cytotoxicity and 5-LOX inhibitory activity respectively. (C) 2015 The Authors. Published by Elsevier B.V. on behalf of King Saud University.
引用
收藏
页码：2328 / 2335
页数：8
相关论文
共 63 条
[1]   A method of computing the effectiveness of an insecticide [J].
Abbott, WS .
JOURNAL OF ECONOMIC ENTOMOLOGY, 1925, 18 :265-267
[2]   Design, synthesis, and structure-activity relationships of indole-3-carboxamides as novel water soluble cannabinoid CB1 receptor agonists [J].
Adam, Julia M. ;
Cairns, Jim ;
Caulfield, Wilson ;
Cowley, Phillip ;
Cumming, Iain ;
Easson, Morag ;
Edwards, Darren ;
Ferguson, Morag ;
Goodwin, Richard ;
Jeremiah, Fiona ;
Kiyoi, Takao ;
Mistry, Ashvin ;
Moir, Elizabeth ;
Morphy, Richard ;
Tierney, Jason ;
York, Mark ;
Baker, James ;
Cottney, Jean E. ;
Houghton, Andrea K. ;
Westwood, Paul J. ;
Walker, Glenn .
MEDCHEMCOMM, 2010, 1 (01) :54-60
[3]  
[Anonymous], BIOASSAY TECHNIQUES
[4]  
Balkan Ayla, 2003, Current Medicinal Chemistry - Anti-Inflammatory & Anti-Allergy Agents, V2, P9, DOI 10.2174/1568014033355853
[5]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644
[6]   Thiosemicarbazole (thiacetazone-like) compound with activity against Mycobacterium avium in mice [J].
Bermudez, LE ;
Reynolds, R ;
Kolonoski, P ;
Aralar, P ;
Inderlied, CB ;
Young, LS .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2003, 47 (08) :2685-2687
[7]   DNA-DEPENDENT RNA-POLYMERASES FROM ARTEMIA EMBRYOS - CHARACTERIZATION OF POLYMERASES-1 AND POLYMERASES-2 FROM NAUPLIUS LARVAE [J].
BIRNDORF, HC ;
DALESSIO, J ;
BAGSHAW, JC .
DEVELOPMENTAL BIOLOGY, 1975, 45 (01) :34-43
[8]   A comparison between two brine shrimp assays to detect in vitrocytotoxicity in marine natural products [J].
José Luis Carballo ;
Zaira L Hernández-Inda ;
Pilar Pérez ;
María D García-Grávalos .
BMC Biotechnology, 2 (1)
[9]   Synthesis and Antiproliferative Activity of Substituted 3[2-(1H-indol-3-yl)-1,3-thiazol-4-yl]-1H-pyrrolo[3,2-b]pyridines, Marine Alkaloid Nortopsentin Analogues [J].
Carbone, A. ;
Pennati, M. ;
Barraja, P. ;
Montalbano, A. ;
Parrino, B. ;
Spano, V. ;
Lopergolo, A. ;
Sbarra, S. ;
Doldi, V. ;
Zaffaroni, N. ;
Cirrincione, G. ;
Diana, P. .
CURRENT MEDICINAL CHEMISTRY, 2014, 21 (14) :1654-1666
[10]   Synthesis and Antiproliferative Activity of 2,5-bis(3′-Indolyl)pyrroles, Analogues of the Marine Alkaloid Nortopsentin [J].
Carbone, Anna ;
Parrino, Barbara ;
Barraja, Paola ;
Spano, Virginia ;
Cirrincione, Girolamo ;
Diana, Patrizia ;
Maier, Armin ;
Kelter, Gerhard ;
Fiebig, Heinz-Herbert .
MARINE DRUGS, 2013, 11 (03) :643-654
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