C-cinnamoyl glycosides as a new class of anti-filarial agents

被引:13
|
作者
Roy, Priya [3 ]
Dhara, Debashis [1 ]
Parida, Pravat Kumar [1 ]
Kar, Rajiv Kumar [2 ]
Bhunia, Anirban [2 ]
Jana, Kuladip [1 ]
Babu, Santi P. Sinha [3 ]
Misra, Anup Kumar [1 ]
机构
[1] Bose Inst, Div Mol Med, P-1-12,CIT Scheme 7-M, Kolkata 700054, India
[2] Bose Inst, Dept Biophys, P-1-12,CIT Scheme 7-M, Kolkata 700054, India
[3] Visva Bharati Univ, Parasitol Lab, Dept Zool, Ctr Adv Studies, Santini Ketan 731235, W Bengal, India
关键词
C-glycosides; Anti-filarial; Wuchereria bancrofti; Setaria cervi; Aldol reaction; MTT reduction assay; QSAR; ANTIFILARIAL ACTIVITY; LYMPHATIC FILARIASIS; SELECTIVE INHIBITORS; APOPTOSIS; PARASITE; KETONES; IDENTIFICATION; MICROFILARIAE; DISEASE; PHASE;
D O I
10.1016/j.ejmech.2016.03.001
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of C-cinnamoyl glycosides has been synthesized in good yield by the BF3 center dot OEt2 catalyzed aldol condensation of C-glycosylated acetone derivative with a variety of aromatic aldehydes. The synthesized compounds were evaluated for their potential as anti-filarial agents against bovine filarial parasite Setaria cervi and human filariid Wuchereria bancrofti using a number of biological assays such as relative movability (RM) assessment and MTT reduction assay. Among twenty seven test compounds six compounds were found active in terms of MIC, IC50 and LC50 values. Further biological studies were carried out using three lead compounds because of their significantly low MIC values and IC50 values compared to the standard anti-filarial drug Ivermectin. In addition, structure activity relationship study of the test compounds has been carried out using 3D-QSAR analysis. (C) 2016 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:308 / 317
页数:10
相关论文
共 50 条
  • [31] Aldol reaction of β-C-glycosylic ketones:: synthesis of C-(E)-cinnamoyl glycosylic compounds as precursors for new biologically active C-glycosides
    Bisht, Surendra Singh
    Pandey, Jyoti
    Sharma, Anindra
    Tripathi, Rama Pati
    CARBOHYDRATE RESEARCH, 2008, 343 (09) : 1399 - 1406
  • [32] Brevifoliol and its Analogs: A New Class of Anti-tubercular Agents
    Bhukya, Balakishan
    Alam, Sarfaraz
    Chaturvedi, Vinita
    Trivedi, Priyanka
    Kumar, Shailesh
    Khan, Feroz
    Negi, Arvind S.
    Srivastava, Santosh Kumar
    CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2021, 21 (09) : 767 - 776
  • [33] New class of anti-inflammatory agents for colonic epithelial cells
    Walsh, JH
    GASTROENTEROLOGY, 1999, 117 (05) : 1039 - 1039
  • [34] Osmium Arenes: A New Class of Potential Anti-cancer Agents
    van Rijt, Sabine H.
    Peacock, Anna F. A.
    Sadler, Peter J.
    PLATINUM AND OTHER HEAVY METAL COMPOUNDS IN CANCER CHEMOTHERAPY, 2009, : 73 - 79
  • [35] EP 80317 a prototype of a new class of anti-atherosclerotic agents
    Ong, H.
    Harb, D.
    Bujold, K.
    Febbraio, M.
    Tremblay, A. .
    Sirois, M. G.
    Marleau, S.
    ACTA PHARMACOLOGICA SINICA, 2006, 27 : 256 - 256
  • [36] BRANCHED NITROSOUREAS AS A NEW CLASS OF POTENT ANTI-TUMOR AGENTS
    WELEBIR, AJ
    YANCEY, ST
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (SEP): : 66 - 66
  • [37] Anti-inflammatory neuropeptides: A new class of endogenous immunoregulatory agents
    Delgado, Mario
    Ganea, Doina
    BRAIN BEHAVIOR AND IMMUNITY, 2008, 22 (08) : 1146 - 1151
  • [38] Aryl ureas represent a new class of anti-trypanosomal agents
    Du, XH
    Hansell, E
    Engel, JC
    Caffrey, CR
    Cohen, FE
    McKerrow, JH
    CHEMISTRY & BIOLOGY, 2000, 7 (09): : 733 - 742
  • [39] Synthesis and molecular modeling studies of 3-chloro-4-substituted-1-(8-hydroxy-quinolin-5-yl)-azetidin-2-ones as novel anti-filarial agents
    Chhajed, Santosh S.
    Manisha, Puranik
    Bastikar, Virupaksha A.
    Animeshchandra, Haldar
    Ingle, V. N.
    Upasani, Chandrashekhar D.
    Wazalwar, Sachin S.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (12) : 3640 - 3644
  • [40] C-glycosides of dodecanoic acid: new capping/reducing agents for glyconanoparticle synthesis
    Ramana, C. V.
    Durugkar, Kulbhushan A.
    Puranik, Vedavati G.
    Narute, Sachin B.
    Prasad, B. L. V.
    TETRAHEDRON LETTERS, 2008, 49 (43) : 6227 - 6230