Medicinal chemistry perspectives of 1,2,3,4-tetrahydroisoquinoline analogs - biological activities and SAR studies

被引:55
作者
Faheem [1 ]
Karan Kumar, Banoth [1 ]
Chandra Sekhar, Kondapalli Venkata Gowri [2 ]
Chander, Subhash [3 ]
Kunjiappan, Selvaraj [4 ]
Murugesan, Sankaranarayanan [1 ]
机构
[1] Birla Inst Technol & Sci Pilani, Dept Pharm, Med Chem Res Lab, Pilani Campus, Pilani 333031, Rajasthan, India
[2] Birla Inst Technol & Sci Pilani, Dept Chem, Hyderabad Campus, Hyderabad 500078, Telangana, India
[3] Amity Univ Uttar Pradesh, Amity Inst Phytomed & Phytochem, Noida 201313, India
[4] Kalasalingam Acad Res & Educ, Dept Biotechnol, Krishnankoil 626126, Tamil Nadu, India
关键词
ANTIDEPRESSANT-LIKE ACTIVITY; IN-VITRO; PRAZIQUANTEL DERIVATIVES; ANTIBACTERIAL ACTIVITY; DOPAMINE RELEASE; ENDOGENOUS AMINE; MULTICOMPONENT REACTIONS; ANIMAL-MODEL; TETRAHYDROISOQUINOLINES; INHIBITORS;
D O I
10.1039/d1ra01480c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Isoquinoline alkaloids are a large group of natural products in which 1,2,3,4-tetrahydroisoquinolines (THIQ) form an important class. THIQ based natural and synthetic compounds exert diverse biological activities against various infective pathogens and neurodegenerative disorders. Due to these reasons, the THIQ heterocyclic scaffold has garnered a lot of attention in the scientific community which has resulted in the development of novel THIQ analogs with potent biological activity. The present review provides a much-needed update on the biological potential of THIQ analogs, their structural-activity relationship (SAR), and their mechanism of action. In addition, a note on commonly used synthetic strategies for constructing the core scaffold has also been discussed.
引用
收藏
页码:12254 / 12287
页数:34
相关论文
共 109 条
[1]   Molecular and enzymatic characterisation of Schistosoma mansoni thioredoxin [J].
Alger, HM ;
Sayed, AA ;
Stadecker, MJ ;
Williams, DL .
INTERNATIONAL JOURNAL FOR PARASITOLOGY, 2002, 32 (10) :1285-1292
[2]  
[Anonymous], 2018, Schrodinger Release 2018-3: Glide
[3]   The mechanism of 1,2,3,4-tetrahydroisoquinolines neuroprotection: the importance of free radicals scavenging properties and inhibition of glutamate-induced excitotoxicity [J].
Antkiewicz-Michaluk, L ;
Lazarewicz, JW ;
Patsenka, A ;
Kajta, M ;
Zieminska, E ;
Salinska, E ;
Wasik, A ;
Golembiowska, K ;
Vetulani, J .
JOURNAL OF NEUROCHEMISTRY, 2006, 97 (03) :846-856
[4]   Different action on dopamine catabolic pathways of two endogenous 1,2,3,4-tetrahydroisoquinolines with similar antidopaminergic properties [J].
Antkiewicz-Michaluk, L ;
Michaluk, J ;
Mokrosz, M ;
Romanska, I ;
Lorenc-Koci, E ;
Ohta, S ;
Vetulani, J .
JOURNAL OF NEUROCHEMISTRY, 2001, 78 (01) :100-108
[5]   1-Methyl-1,2,3,4-Tetrahydroisoquinoline, an Endogenous Amine with Unexpected Mechanism of Action: New Vistas of Therapeutic Application [J].
Antkiewicz-Michaluk, Lucyna ;
Wasik, Agnieszka ;
Michaluk, Jerzy .
NEUROTOXICITY RESEARCH, 2014, 25 (01) :1-12
[6]   Strategies and Synthetic Methods Directed Toward the Preparation of Libraries of Substituted Isoquinolines [J].
Awuah, Emelia ;
Capretta, Alfredo .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (16) :5627-5634
[7]   A three-component domino protocol for the facile synthesis of highly functionalized tetrahydroisoquinolines by creation of their benzene ring [J].
Balamurugan, Kamaraj ;
Jeyachandran, Veerappan ;
Perumal, Subbu ;
Carlos Menendez, J. .
TETRAHEDRON, 2011, 67 (07) :1432-1437
[8]   (+)-SJ733, a clinical candidate for malaria that acts through ATP4 to induce rapid host-mediated clearance of Plasmodium [J].
Belen Jimenez-Diaz, Maria ;
Ebert, Daniel ;
Salinas, Yandira ;
Pradhan, Anupam ;
Lehane, Adele M. ;
Myrand-Lapierre, Marie-Eve ;
O'Loughlin, Kathleen G. ;
Shackleford, David M. ;
de Almeida, Mariana Justino ;
Carrillo, Angela K. ;
Clark, Julie A. ;
Dennis, Adelaide S. M. ;
Diep, Jonathon ;
Deng, Xiaoyan ;
Duffy, Sandra ;
Endsley, Aaron N. ;
Fedewa, Greg ;
Guiguemde, W. Armand ;
Gomez, Maria G. ;
Holbrook, Gloria ;
Horst, Jeremy ;
Kim, Charles C. ;
Liu, Jian ;
Lee, Marcus C. S. ;
Matheny, Amy ;
Santos Martinez, Maria ;
Miller, Gregory ;
Rodriguez-Alejandre, Ane ;
Sanz, Laura ;
Sigal, Martina ;
Spillman, Natalie J. ;
Stein, Philip D. ;
Wang, Zheng ;
Zhu, Fangyi ;
Waterson, David ;
Knapp, Spencer ;
Shelat, Anang ;
Avery, Vicky M. ;
Fidock, David A. ;
Gamo, Francisco-Javier ;
Charman, Susan A. ;
Mirsalis, Jon C. ;
Ma, Hongshen ;
Ferrer, Santiago ;
Kirk, Kiaran ;
Angulo-Barturen, Inigo ;
Kyle, Dennis E. ;
DeRisi, Joseph L. ;
Floyd, David M. ;
Guy, R. Kiplin .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2014, 111 (50) :E5455-E5462
[9]   Synthesis and antimicrobial activity of chiral quaternary N-spiro ammonium bromides with 3′,4′-dihydro-1′H-spiro[isoindoline-2,2′-isoquinoline] skeleton [J].
Bielawski, Krzysztof ;
Leszczynska, Katarzyna ;
Kaluza, Zbigniew ;
Bielawska, Anna ;
Michalak, Olga ;
Daniluk, Tamara ;
Staszewska-Krajewska, Olga ;
Czajkowska, Anna ;
Pawlowska, Natalia ;
Gornowicz, Agnieszka .
DRUG DESIGN DEVELOPMENT AND THERAPY, 2017, 11 :2015-2028
[10]   Synthesis and activity of benzopiperidine, benzopyridine and phenyl piperazine based compounds against Leishmania infantum [J].
Chander, Subhash ;
Ashok, Penta ;
Reguera, Rosa M. ;
Yolanda Perez-Pertejo, M. ;
Carbajo-Andres, Ruben ;
Balana-Fouce, Rafael ;
Sekhar, Kondapalli Venkata Gowri Chandra ;
Sankaranarayanan, Murugesan .
EXPERIMENTAL PARASITOLOGY, 2018, 189 :49-60