Biheterocyclic Coumarins: A Simple Yet Versatile Resource for Futuristic Design and Applications in Bio-molecular and Material Chemistry

被引:9
作者
Anand, Ashish [1 ]
Khanapurmath, Netravati [2 ]
Kulkarni, Manohar V. [2 ]
Row, Tayur N. Guru [1 ]
机构
[1] Indian Inst Sci, Solid State & Struct Chem Unit, Bengaluru 560012, Karnataka, India
[2] Karnatak Univ, Dept Studies Chem, Dharwad 580003, Karnataka, India
关键词
Coumarin; biheterocycles; 2H-chromen-2-one; heterocycles; biomolecular and material chemistry; dyes; pigments; molecular sensors; ONE-POT SYNTHESIS; RATIOMETRIC FLUORESCENT-PROBE; AQUEOUS-SOLUTION SYNTHESIS; CATALYZED CROSS-COUPLINGS; EXCITED-STATE BEHAVIOR; BIOLOGICAL EVALUATION; ANTIMICROBIAL ACTIVITY; ANTICANCER ACTIVITY; FACILE SYNTHESIS; PHOTOPHYSICAL PROPERTIES;
D O I
10.2174/1385272826666220301124149
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Coumarin derivatives occur widely in nature and are a part of both traditional and modern advancements in synthesis and application. To date, thousands of coumarin derivatives have been synthesized in lab or isolated from plant and marine life. These are essentially 2-pyrone core fused with a benzene ring and belong to the family of aromatic oxygen heterocycles. Coumarin in conjugation with various other heterocyclic systems has provided a robust framework for tuning the properties associated with the parent structure. The frequency of reports has increased for these biheterocyclic systems from the mid twentieth century. Biheterocyclic coumarins have also attracted the attention of many organic and pharmaceutical chemists as these systems serve as useful synthetic intermediates in the synthesis of analogs of existing drugs. Their application in the design of effective organocatalysts and chemosensors has further extended their versatility. Coumarin biheterocyclic core is utilized in the rational design and tuning of complex molecular entities in molecular recognition, analytical and material chemistry. This review highlights the advancements in the synthesis and applications of coumarin-linked nitrogen, oxygen, and sulfur heterocycles. It also provides an account of five-, six-, and seven-membered heterocyclic rings linked to coumarin core. Critical physicochemical properties coupled with their application will make this review useful for synthetic chemists and drug discovery labs. A comprehensive spectrum of literature in this review will facilitate further development of biheterocycles along with their promising applications in the future.
引用
收藏
页码:444 / 506
页数:63
相关论文
共 458 条
[1]   Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives [J].
Abdelhafez, Omaima M. ;
Amin, Kamelia M. ;
Batran, Rasha Z. ;
Maher, Timothy J. ;
Nada, Somaia A. ;
Sethumadhavan, Shalini .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (10) :3371-3378
[2]   SYNTHESIS OF BENZOFURAN DERIVATIVES VIA DIFFERENT METHODS [J].
Abu-Hashem, Ameen A. ;
Hussein, Hoda A. R. ;
Aly, Ahmed S. ;
Gouda, Moustafa A. .
SYNTHETIC COMMUNICATIONS, 2014, 44 (16) :2285-2312
[3]   Synthesis and pharmacological evaluation of some novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles [J].
Aggarwal, Ranjana ;
Kumar, Sunil ;
Kaushik, Pawan ;
Kaushik, Dhirender ;
Gupta, Girish Kumar .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 62 :508-514
[4]  
Akhlaq W., 2001, INDIAN J HETEROCY CH, V11, P59
[5]   Hydrogen Peroxide Scavenging Activity of Novel Coumarins Synthesized Using Different Approaches [J].
Al-Amiery, Ahmed A. ;
Al-Majedy, Yasameen K. ;
Kadhum, Abdul Amir H. ;
Mohamad, Abu Bakar .
PLOS ONE, 2015, 10 (07)
[6]  
Al-Masoudi I., 2006, CHEM HETEROCYC COMPO, V42, P1377, DOI [DOI 10.1007/S10593-006-0255-3, 10.1007/s10593-006-0255-3]
[7]   Piperidine-iodine a dual system catalyst for synthesis of coumarin bearing pyrrolo[1,2-α]quinoxaline derivatives via a one-pot three-component reaction [J].
Alizadeh, Abdolali ;
Ghanbaripour, Rashid ;
Zhu, Long-Guan .
TETRAHEDRON, 2014, 70 (11) :2048-2053
[8]   H-bond stabilization of a tautomeric coumarin-pyrazole-pyridine triad generates a PET driven, reversible and reusable fluorescent chemosensor for anion detection [J].
Alkis, Meltem ;
Pekyilmaz, Damla ;
Yalcin, Ergin ;
Aydiner, Burcu ;
Dede, Yavuz ;
Seferoglu, Zeynel .
DYES AND PIGMENTS, 2017, 141 :493-500
[9]   Synthesis and biological evaluation of novel coumarin-pyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents [J].
Amin, Kamilia M. ;
Eissa, Amal A. M. ;
Abou-Seri, Sahar M. ;
Awadallah, Fadi M. ;
Hassan, Ghaneya S. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 60 :187-198
[10]   One pot Click chemistry: A three component reaction for the synthesis of 2-mercaptobenzimidazole linked coumarinyl triazoles as anti-tubercular agents [J].
Anand, Ashish ;
Kulkarni, Manohar V. ;
Joshi, Shrinivas D. ;
Dixit, Sheshagiri R. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (19) :4709-4713