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
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
收藏
页码:536 / 545
页数:10
相关论文
共 50 条
[41]   Synthesis and Biological Evaluation of New Ibuprofen-1,3,4-oxadiazole-1,2,3-triazole Hybrids [J].
Rayam, Parsharamulu ;
Polkam, Naveen ;
Kummari, Bhaskar ;
Banothu, Venkanna ;
Gandamalla, Durgaiah ;
Yellu, Narsimha Reddy ;
Anireddy, Jaya Shree .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (01) :296-305
[42]   SYNTHESIS AND CYTOTOXIC ACTIVITY OF 1,2,3-TRIAZOLE DERIVATIVES OF EUGENOL [J].
Rodrigues Gazolla, Poliana Aparecida ;
Teixeira, Robson Ricardo ;
da Silva, Adalberto Manoel ;
Vaz, Boniek Gontijo ;
Vasconcelos, Gessica Adriana ;
Siqueira, Raoni Pais ;
Sousa Goncalves, Victor Hugo ;
Pereira, Higor Sette ;
Bressan, Gustavo Costa .
QUIMICA NOVA, 2018, 41 (05) :497-506
[43]   1,2,3-Triazole nilotinib analogues: Synthesis and Cytotoxic activity [J].
Almazan-Sanchez, Leticia ;
Ramirez-Apan, Maria Teresa ;
Morales-Morales, David ;
Garcia-Eleno, Marco A. ;
Cuevas-Yanez, Erick .
TETRAHEDRON, 2024, 167
[44]   Ferrocene conjugates linked by 1,2,3-triazole and their Zn(II) and Cu(II) complexes: Synthesis, characterization and biological activity [J].
Jakopec, Silvio ;
Juraj, Natalija Pantalon ;
Brozovic, Anamaria ;
Jadresko, Dijana ;
Peric, Berislav ;
Kirin, Srecko, I ;
Raic-Malic, Silvana .
APPLIED ORGANOMETALLIC CHEMISTRY, 2022, 36 (04)
[45]   1,2,3-Triazole tethered acetophenones: Synthesis, bioevaluation and molecular docking study [J].
Shaikh, Mubarak H. ;
Subhedar, Dnyaneshwar D. ;
Khedkar, Vijay M. ;
Jha, Prakash C. ;
Khan, Firoz A. Kalam ;
Sangshetti, Jaiprakash N. ;
Shingate, Bapurao B. .
CHINESE CHEMICAL LETTERS, 2016, 27 (07) :1058-1063
[46]   Synthesis of Dense 1,2,3-Triazole Polymers Soluble in Common Organic Solvents [J].
Yamasaki, Shota ;
Kamon, Yuri ;
Xu, Linlin ;
Hashidzume, Akihito .
POLYMERS, 2021, 13 (10)
[47]   Synthesis and evaluation of novel fluorinated pyrazolo-1,2,3-triazole hybrids as antimycobacterial agents [J].
Emmadi, Narender Reddy ;
Bingi, Chiranjeevi ;
Kotapalli, Sudha Sravanti ;
Ummanni, Ramesh ;
Nanubolu, Jagadeesh Babu ;
Atmakur, Krishnaiah .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (15) :2918-2922
[48]   Regioselective one pot synthesis of 1,2,3-triazole derivatives bearing phthalazine moiety and their pharmacological activity [J].
Shyma, P. C. ;
Kalluraya, Balakrishna ;
Peethambar, S. K. ;
Vijesh, A. M. .
MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (11) :2680-2690
[49]   Synthesis, biological evaluation, and molecular docking studies of novel 1,2,3-triazole derivatives as potent anti-inflammatory agents [J].
Kumar, A. Kishore ;
Sunitha, V. ;
Shankar, B. ;
Ramesh, M. ;
Krishna, T. Murali ;
Jalapathi, P. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2016, 86 (05) :1154-1162
[50]   Regioselective one pot synthesis of 1,2,3-triazole derivatives bearing phthalazine moiety and their pharmacological activity [J].
P. C. Shyma ;
Balakrishna Kalluraya ;
S. K. Peethambar ;
A. M. Vijesh .
Medicinal Chemistry Research, 2016, 25 :2680-2690