Synthesis and biological evaluation of a new class of 4-aminoquinoline-rhodanine hybrid as potent anti-infective agents

被引：53
作者：
Chauhan, Kuldeep [1 ]
Sharma, Moni [1 ]
Saxena, Juhi [2 ]
Singh, Shiv Vardan [3 ]
Trivedi, Priyanka [4 ]
Srivastava, Kumkum [2 ]
Puri, Sunil K. [2 ]
Saxena, J. K. [3 ]
Chaturvedi, Vinita [4 ]
Chauhan, Prem. M. S. [1 ]
机构：
[1] Cent Drug Res Inst, CSIR, Med & Proc Chem Div, Lucknow 226001, Uttar Pradesh, India
[2] Cent Drug Res Inst, CSIR, Div Parasitol, Lucknow 226001, Uttar Pradesh, India
[3] Cent Drug Res Inst, CSIR, Div Biochem, Lucknow 226001, Uttar Pradesh, India
[4] Cent Drug Res Inst, CSIR, Drug Target Discovery & Dev Div, Lucknow 226001, Uttar Pradesh, India
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 62卷
关键词：
4-Aminoquinoline; Rhodanine; Antimalarial; Antitubercular; Cytotoxicity; IN-VITRO; ANTIPLASMODIAL ACTIVITY; ANTIMALARIAL AGENTS; SIDE-CHAIN; RHODANINE; MALARIA; DISCOVERY; DESIGN; ASSAY; BURDEN;
D O I：
10.1016/j.ejmech.2013.01.017
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Synthesis of novel 4-aminoquinoline-rhodanine hybrid using inexpensive starting materials via easy to operate methodology, and their biological activity is reported. All the compounds were screened for their in vitro antimalarial activity against chloroquine-resistant (1(1) and chloroquine-sensitive (3D7) strains of Plasmodium falciparum, and their cytotoxicity toward VERO cell line. Compounds 9, 19, 21 and 23 exhibited excellent antimalarial activity with IC50 value ranging from 13.2 to 45.5 nM against chloroquine-resistant (K1) strain. Biochemical studies revealed that inhibition of hemozoin formation is the primary mechanism of action of these analogs for their antimalarial activity. Additionally, some derivatives (14, 18 and 26) of this series also exhibited the antimycobacterial activity against H(37)Rv strain of Mycobacterium tuberculosis with MIC value of 6.25 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码：693 / 704
页数：12
相关论文
共 56 条
  • [11] Sneaking in through the back entrance: the biology of malaria liver stages
    Frevert, U
    [J]. TRENDS IN PARASITOLOGY, 2004, 20 (09) : 417 - 424
  • [12] Synthesis of N1-arylidene-N2-quinolyl- and N2-acrydinylhydrazones as potent antimalarial agents active against CQ-resistant P-falciparum strains
    Gemma, Sandra
    Kukreja, Gagan
    Fattorusso, Caterina
    Persico, Marco
    Romano, Maria P.
    Altarelli, Maria
    Savini, Luisa
    Campiani, Giuseppe
    Fattorusso, Ernesto
    Basilico, Nicoletta
    Taramelli, Donatella
    Yardley, Vanessa
    Butini, Stefania
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (20) : 5384 - 5388
  • [13] Optimization of 4-Aminoquinoline/Clotrimazole-Based Hybrid Antimalarials: Further Structure-Activity Relationships, in Vivo Studies, and Preliminary Toxicity Profiling
    Gemma, Sandra
    Camodeca, Caterina
    Coccone, Salvatore Sanna
    Joshi, Bhupendra P.
    Bernetti, Matteo
    Moretti, Vittoria
    Brogi, Simone
    de Marcos, Maria Cruz Bonache
    Savini, Luisa
    Taramelli, Donatella
    Basilico, Nicoletta
    Parapini, Silvia
    Rottmann, Matthias
    Brun, Reto
    Lamponi, Stefania
    Caccia, Silvio
    Guiso, Giovanna
    Summers, Robert L.
    Martin, Rovena E.
    Saponara, Simona
    Gorelli, Beatrice
    Novellino, Ettore
    Campiani, Giuseppe
    Butini, Stefania
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (15) : 6948 - 6967
  • [14] Enone- and Chalcone-Chloroquinoline Hybrid Analogues: In Silico Guided Design, Synthesis, Antiplasmodial Activity, in Vitro Metabolism, and Mechanistic Studies
    Guantai, Eric M.
    Ncokazi, Kanyile
    Egan, Timothy J.
    Gut, Jiri
    Rosenthal, Philip J.
    Bhampidipati, Ravi
    Kopinathan, Anitha
    Smith, Peter J.
    Chibale, Kelly
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (10) : 3637 - 3649
  • [15] Synthesis and antimicrobial activity of rhodanine derivatives
    Habib, NS
    Rida, SM
    Badawey, EAM
    Fahmy, HTY
    Ghozlan, HA
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1997, 32 (09) : 759 - 762
  • [16] Landscapes of Infection INTRODUCTION
    Hurtley, Stella
    Ash, Caroline
    Roberts, Leslie
    [J]. SCIENCE, 2010, 328 (5980) : 841 - 841
  • [17] Substituted 4-methylquinolines as a new class of anti-tuberculosis agents
    Jain, R
    Vaitilingam, B
    Nayyar, A
    Palde, PB
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (06) : 1051 - 1054
  • [18] Resistance of Plasmodium falciparum field isolates to in-vitro artemether and point mutations of the SERCA-type PfATPase6
    Jambou, R
    Legrand, E
    Niang, M
    Khim, N
    Lim, P
    Volney, B
    Ekala, MT
    Bouchier, C
    Esterre, P
    Fandeur, T
    Mercereau-Puijalon, O
    [J]. LANCET, 2005, 366 (9501) : 1960 - 1963
  • [19] Quinolines and structurally related heterocycles as antimalarials
    Kaur, Kirandeep
    Jain, Meenakshi
    Reddy, Ravi P.
    Jain, Rahul
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (08) : 3245 - 3264
  • [20] Synthesis of new 4-aminoquinolines and quinoline-acridine hybrids as antimalarial agents
    Kumar, Ashok
    Srivastava, Kumkum
    Kumar, S. Raja
    Puri, S. K.
    Chauhan, Prem M. S.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (23) : 7059 - 7063
123456