Synthesis, characterization, and pharmacological studies of ferrocene-1H-1,2,3-triazole hybrids

被引：54

作者：

Haque, Ashanul ^{[1
]}

Hsieh, Ming-Fa ^{[2
]}

Hassan, Syed Imran ^{[1
]}

Faizi, Md. Serajul Haque ^{[1
]}

Saha, Anannya ^{[3
]}

Dege, Necmi ^{[4
]}

Rather, Jahangir Ahmad ^{[1
]}

Khan, Muhammad S. ^{[1
]}

机构：

[1] Sultan Qaboos Univ, Coll Sci, Dept Chem, POB 36,Al Khod 123, Muscat, Oman

[2] Chung Yuan Christian Univ, Dept Biomed Engn, 200 Chung Pei Rd, Taoyuan 32023, Taiwan

[3] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741246, India

[4] Ondokuz Mayis Univ, Fac Arts & Sci, Dept Phys, TR-55139 Atakum, Samsun, Turkey

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2017年 / 1146卷

关键词：

Anti-inflammatory; Click-chemistry; Copper catalyzed azide alkyne cycloaddition; reaction; Ferrocene; Viability; Toxicity; FERROCENYLCHALCONE CONJUGATES SYNTHESIS; ISATIN-FERROCENE; CLICK-CHEMISTRY; DNA-BINDING; COMPLEXES; ANTICANCER; INHIBITION; SERIES; DRUG; POTENTIALS;

D O I：

10.1016/j.molstruc.2017.06.027

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A series of ferrocene-1H-1,2,3-triazole hybrids namely 1-(4-nitrophenyl)-4-ferrocenyl-1H-1,2,3-triazole (1), 1-(4,4'-dinitro-2-biphenyl)-4-ferrocenyl-1H-1,2,3-triazole (2), 1-(3-chloro-4-fluorophenyl)-4ferrocenyl-1H-1,2,3-triazole (3), 1-(4-bromopheny1)-4-ferroceny1-1H-1,2,3-triazole (4) and 1-(2nitrophenyl)-4-ferrocenyl-IH-1,2,3-triazole (5) were designed and synthesized by copper-catalyzed azide alkyne cycloaddition (CuAAC) reaction. All the new hybrids were characterized by microanalyses, NMR (H-1 and C-13), UV-vis, IR, ESI-MS and electrochemical techniques. Crystal structure of the compound (3) was solved by single crystal X-ray diffraction method. The structural (single crystal) and spectroscopic (UV Vis. and IR) properties of the compound 3 have been analyzed and compared by complementary quantum modeling. Hybrids 1-5 exhibited low toxicity and demonstrated neuroprotective effect. (C) 2017 Elsevier B.V. All rights reserved.

引用

页码：536 / 545

页数：10

共 76 条

[51] Modulation of microglial pro-inflammatory and neurotoxic activity for the treatment of Parkinson's disease [J].

Liu, Bin .

AAPS JOURNAL, 2006, 8 (03) :E606-E621

[52] ELECTROSTATIC INTERACTION OF A SOLUTE WITH A CONTINUUM - A DIRECT UTILIZATION OF ABINITIO MOLECULAR POTENTIALS FOR THE PREVISION OF SOLVENT EFFECTS [J].

MIERTUS, S ;

SCROCCO, E ;

TOMASI, J .

CHEMICAL PHYSICS, 1981, 55 (01) :117-129

[53]

Mohan J., 2004, ORGANIC SPECTROSCOPY, V2nd

[54] Experimental and theoretical studies of a pyrazole-thiazolidin-2,4-di-one hybrid [J].

Mushtaque, Md ;

Avecilla, Fernando ;

Haque, Ashanul ;

Perwez, Ahmad ;

Khan, Md Shahzad ;

Rizvi, M. Moshahid Alam .

JOURNAL OF MOLECULAR STRUCTURE, 2017, 1141 :417-427

[55] Azole-based compounds as antiamoebic agents: a perspective using theoretical calculations [J].

Mushtaque, Md. ;

Ahamad, Shahzaib ;

Jahan, Meriyam ;

Hussain, Kakul ;

Khan, Mohd Shahid .

RSC ADVANCES, 2016, 6 (01) :815-824

[56] Bioorganometallic Compounds with Antimalarial Targets: Inhibiting Hemozoin Formation [J].

Navarro, Maribel ;

Castro, William ;

Biot, Christophe .

ORGANOMETALLICS, 2012, 31 (16) :5715-5727

[57] cclib: A library for package-independent computational chemistry algorithms [J].

O'Boyle, Noel M. ;

Tenderholt, Adam L. ;

Langner, Karol M. .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 2008, 29 (05) :839-845

[58] Application of ferrocene and its derivatives in cancer research [J].

Ornelas, Catia .

NEW JOURNAL OF CHEMISTRY, 2011, 35 (10) :1973-1985

[59] Ferrocenyl Derivatives of the Anthelmintic Praziquantel: Design, Synthesis, and Biological Evaluation [J].

Patra, Malay ;

Ingram, Katrin ;

Pierroz, Vanessa ;

Ferrari, Stefano ;

Spingler, Bernhard ;

Keiser, Jennifer ;

Gasser, Gilles .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (20) :8790-8798

[60] General role of the amino and methylsulfamoyl groups in selective cyclooxygenase(COX)-1 inhibition by 1,4-diaryl-1,2,3-triazoles and validation of a predictive pharmacometric PLS model [J].

Perrone, Maria Grazia ;

Vitale, Paola ;

Panella, Andrea ;

Fortuna, Cosimo G. ;

Scilimati, Antonio .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 94 :252-264

← 1 2 3 4 5 6 7 8 →