Synthetic approaches, functionalization and therapeutic potential of quinazoline and quinazolinone skeletons: The advances continue

被引:369
作者
Khan, Imtiaz [1 ]
Ibrar, Aliya [2 ]
Ahmed, Waqas [3 ]
Saeed, Aamer [2 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[2] Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan
[3] Univ Gujrat, Off Res Innovat & Commercializat, Gujrat 50700, Pakistan
关键词
Bioactive heterocycles; Synthetic methods; Cross-coupling reactions; Inhibitors; Enzymes; Biological potential; ONE-POT SYNTHESIS; NATIONAL-CANCER-INSTITUTE; BIOLOGICAL EVALUATION; EFFICIENT SYNTHESIS; CRYSTAL-STRUCTURE; SUBSTITUTED QUINAZOLINES; HETEROGENEOUS CATALYST; OXIDATIVE SYNTHESIS; INHIBITORY-ACTIVITY; DOMINO SYNTHESIS;
D O I
10.1016/j.ejmech.2014.10.084
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The presence of N-heterocycles as an essential structural motif in a variety of biologically active substances has stimulated the development of new strategies and technologies for their synthesis. Among the various N-heterocyclic scaffolds, quinazolines and quinazolinones form a privileged class of compounds with their diverse spectrum of therapeutic potential. The easy generation of complex molecular diversity through broadly applicable, cost-effective, practical and sustainable synthetic methods in a straightforward fashion along with the importance of these motifs in medicinal chemistry, received significant attention from researchers engaged in drug design and heterocyclic methodology development. In this perspective, the current review article is an effort to recapitulate recent developments in the eco-friendly and green procedures for the construction of highly challenging and potentially bioactive quinazoline and quinazolinone compounds in order to help medicinal chemists in designing and synthesizing novel and potent compounds for the treatment of different disorders. The key mechanistic insights for the synthesis of these heterocycles along with potential applications and manipulations of the products have also been conferred. This article also aims to highlight the promising future directions for the easy access to these frameworks in addition to the identification of more potent and specific products for numerous biological targets. (C) 2014 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:124 / 169
页数:46
相关论文
共 180 条
  • [1] Novel Quinazolin-4(3H)-one/Schiff Base Hybrids as Antiproliferative and Phosphodiesterase 4 Inhibitors: Design, Synthesis, and Docking Studies
    Abdel-Rahman, Hamdy M.
    Abdel-Aziz, Mohamed
    Canzoneri, Joshua C.
    Gary, Bernard D.
    Piazza, Gary A.
    [J]. ARCHIV DER PHARMAZIE, 2014, 347 (09) : 650 - 657
  • [2] Biological effects of a new set 1,2,4-triazolo[1,5-a]quinazolines on heart rate and blood pressure
    Al-Salahi, Rashad
    El-Tahir, Kamal-Eldin
    Alswaidan, Ibrahim
    Lolak, Nabih
    Hamidaddin, Mohammed
    Marzouk, Mohamed
    [J]. CHEMISTRY CENTRAL JOURNAL, 2014, 8
  • [3] Design and synthesis of 3-(4-chlorophenyl)-2-(2-(4-substituted)-2-oxoethylthio)quinazolin-4(3H)-one as antihistamine agents
    Alagarsamy, V.
    Narendhar, B.
    Sulthana, M. T.
    Solomon, V. Raja
    [J]. MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (11) : 4692 - 4699
  • [4] 3-(3-Ethylphenyl)-2-substituted hydrazino-3H-quinazolin-4-one Derivatives: New Class of Analgesic and Anti-Inflammatory Agents
    Alagarsamy, V.
    Solomon, V. Raja
    Sheorey, R. V.
    Jayakumar, R.
    [J]. CHEMICAL BIOLOGY & DRUG DESIGN, 2009, 73 (04) : 471 - 479
  • [5] Alagarsamy V, 2008, J ENZYM INHIB MED CH, V23, P839, DOI [10.1080/14756360701746229, 10.1080/14756360701746229 ]
  • [6] Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones
    Alagarsamy, Veerachamy
    Pathak, Urvishbhai S.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (10) : 3457 - 3462
  • [7] Design, synthesis and biological evaluation of some novel substituted quinazolines as antitumor agents
    Alanazi, Amer M.
    Abdel-Aziz, Alaa A. -M.
    Al-Suwaidan, Ibrahim A.
    Abdel-Hamide, Sami G.
    Shawer, Taghreed Z.
    El-Azab, Adel S.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 79 : 446 - 454
  • [8] An Efficient Approach to the Synthesis of Coumarin-Bearing 2,3-Dihydro-4(1H)-Quinazolinone Derivatives Using a Piperidine and Molecular Iodine Dual-Catalyst System
    Alizadeh, Abdolali
    Ghanbaripour, Rashid
    Zhu, Long-Guan
    [J]. SYNLETT, 2014, 25 (11) : 1596 - 1600
  • [9] Addition of α-Lithiated Nitriles to Azaheterocycles
    Anderson, Corey
    Moreno, Jesus
    Hadida, Sabine
    [J]. SYNLETT, 2014, 25 (05) : 677 - 680
  • [10] [Anonymous], 2001, MERCK INDEX